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  • 1.
    Adbo, Karina
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Håkan S.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Ankarloo, Jonas
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Norell, M C
    Olofsson, Linus
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Svenson, Johan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Örtegren, U
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Enantioselective synthetic receptors for Tröger’s base1999In: Bioorganic Chemistry, Vol. 27, no 5, p. 363-371Article in journal (Refereed)
  • 2.
    Andersson, Håkan S.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Piletsky, S A
    Koch-Schmidt, Ann-Christin
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Mosbach, K
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Influence of monomer-template ratio on selectivity and load capacity of molecularly imprinted polymers: indications of template self-association1999In: Journal of Chromatography A, Vol. 848, no 1-2, p. 39-49Article in journal (Refereed)
  • 3.
    Andersson, Håkan S.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Svenson, Johan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Can template-template self-association contribute to polymer-ligand recognition characteristics?2000Conference paper (Refereed)
  • 4.
    Chavan, Swapnil
    et al.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Abdelaziz, Ahmed
    eADMET GmbH, Germany.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Uppsala University.
    A k-nearest neighbor classification of hERG K+ channel blockers2016In: Journal of Computer-Aided Molecular Design, ISSN 0920-654X, E-ISSN 1573-4951, Vol. 30, no 3, p. 229-236Article in journal (Refereed)
    Abstract [en]

    A series of 172 molecular structures that block the hERG K+ channel were used to develop a classification model where, initially, eight types of PaDEL fingerprints were used for k-nearest neighbor model development. A consensus model constructed using Extended-CDK, PubChem and Substructure count fingerprint-based models was found to be a robust predictor of hERG activity. This consensus model demonstrated sensitivity and specificity values of 0.78 and 0.61 for the internal dataset compounds and 0.63 and 0.54 for the external (PubChem) dataset compounds, respectively. This model has identified the highest number of true positives (i.e. 140) from the PubChem dataset so far, as compared to other published models, and can potentially serve as a basis for the prediction of hERG active compounds. Validating this model against FDA-withdrawn substances indicated that it may even be useful for differentiating between mechanisms underlying QT prolongation.

  • 5.
    Elmlund, Louise
    et al.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Suriyanarayanan, Subramanian
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Aastrup, Teodor
    Attana AB, Stockholm.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Uppsala University.
    Biotin selective polymer nano-films2014In: Journal of Nanobiotechnology, ISSN 1477-3155, E-ISSN 1477-3155, Vol. 12, article id 8Article in journal (Refereed)
    Abstract [en]

    Background: The interaction between biotin and avidin is utilized in a wide range of assay and diagnostic systems. A robust material capable of binding biotin should offer scope in the development of reusable assay materials and biosensor recognition elements. Results: Biotin-selective thin (3-5 nm) films have been fabricated on hexadecanethiol self assembled monolayer (SAM) coated Au/quartz resonators. The films were prepared based upon a molecular imprinting strategy where N, N'-methylenebisacrylamide and 2-acrylamido-2-methylpropanesulfonic acid were copolymerized and grafted to the SAM-coated surface in the presence of biotin methyl ester using photoinitiation with physisorbed benzophenone. The biotinyl moiety selectivity of the resonators efficiently differentiated biotinylated peptidic or carbohydrate structures from their native counterparts. Conclusions: Molecularly imprinted ultra thin films can be used for the selective recognition of biotinylated structures in a quartz crystal microbalance sensing platform. These films are stable for periods of at least a month. This strategy should prove of interest for use in other sensing and assay systems.

  • 6.
    Elmlund, Louise
    et al.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Suriyanarayanan, Subramanian
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Wiklander, Jesper
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Uppsala University.
    Simple Strategy for Steering Polymer Film Formation on QCM Sensor SurfacesManuscript (preprint) (Other academic)
  • 7.
    Golker, Kerstin
    et al.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Bioorganic & Biophysical Chemistry Laboratory.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Rosengren, Annika M.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Uppsala university.
    Hydrogen bond diversity in the pre-polymerization stage contributes to morphology and MIP-template recognition–MAA versus MMA2015In: European Polymer Journal, ISSN 0014-3057, E-ISSN 1873-1945, Vol. 66, p. 558-568Article in journal (Refereed)
    Abstract [en]

    This report demonstrates that the diversity of hydrogen bond interactions present in molecularly imprinted polymer pre-polymerization mixtures, typically associated with binding-site heterogeneity, can also contribute to morphological characteristics that may influence polymer–template recognition. Comparisons have been made between a series of bupivacaine molecularly imprinted methacrylic acid (MAA)–ethylene glycol dimethacrylate (EGDMA) copolymers and a series of analogous methyl methacrylate (MMA)–EGDMA copolymers using comprehensive molecular dynamics studies of the respective pre-polymerization mixtures, template–polymer binding studies and detailed BET surface area and BJH porosity analyses. The role of the carboxylic acid functionality of MAA, and in particular the acidic proton, in generating morphological features conducive to analyte access (slit-like rather than ink bottle-like structures) and recognition is discussed.

  • 8.
    Karlsson, Björn C. G.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    O'Mahony, John
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Bengtsson, Helen
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Eriksson, Leif A
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Structure and Dynamics of Monomer-Template Complexation: An Explanation for Molecularly Imprinted Polymer Recognition Site Heterogeneity2009In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 131, no 37, p. 13297-13304Article in journal (Refereed)
    Abstract [en]

    We here present the first simulation of a complete molecularly imprinted polymer prepolymerization system. Molecular dynamics studies were performed for a system comprising a total of 1199 discrete molecules, replicating the components and concentrations employed in the corresponding polymer synthesis. The observed interactions correlate well with results obtained from (1)H NMR spectroscopic studies. Comparison with simulations performed in the absence of cross-linking agent (ethylene dimethacrylate) demonstrated its significance in the formation of ligand recognition sites. Moreover, the influence of events such as template-template (bupivacaine) and monomer-monomer (methacrylic acid) self-association, porogen-template interactions, and template conformational variability was revealed. The template recognition capacity of the modeled polymer system was verified by synthesis of imprinted and reference polymers and subsequent radioligand binding Analysis. Collectively, through a series of statistical analyses of molecular trajectories in conjunction with spectroscopic data it was demonstrated that an ensemble of complex structures is present in the prepolymerization mixture and that this diversity is the basis for the binding site heterogeneity observed in molecularly imprinted polymers (MIPs) prepared using the noncovalent strategy.

  • 9.
    Karlsson, Björn C. G.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    O'Mahony, John
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Bengtsson, Helen
    Eriksson, Leif A
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Structure and dynamics of monomer-template complexation: can molecularly imprinted polymer recognition site heterogeneity be explained?2009Conference paper (Refereed)
  • 10.
    Karlsson, Björn
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    O'Mahony, John
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Bengtsson, Helen
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Eriksson, Leif A
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Structure and dynamics of monomer-template complexation: an explanation for molecularly imprinted polymer recognition site heterogeneity2008Conference paper (Other academic)
  • 11.
    Karlsson, Jesper G
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, L I
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Probing the molecular basis for ligand-selective recognition in molecularly imprinted polymers selective for the local anaesthetic bupivacaine2001In: Analytica Chimica Acta, Vol. 435, no 1, p. 57-64Article in journal (Refereed)
  • 12.
    Karlsson, Jesper G
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Andersson, Lars I
    Nicholls, Ian A
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Probing the molecular basis for ligand-selective recognition in molecularly imprinted polymers selective for the local anaesthetic bupivacaine.2000Conference paper (Refereed)
  • 13.
    Karlsson, Jesper G
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Lars I
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Molecular basis for recognition in bupivacaine selective imprinted polymers2001Conference paper (Refereed)
  • 14.
    Karlsson, Jesper G
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Björn
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Lars I
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    The roles of template complexation and ligand binding conditions on recognition in bupivacaine molecularly imprinted polymers2004Conference paper (Refereed)
  • 15.
    Karlsson, Jesper G
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Björn C. G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, L I
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    The roles of template complexation and ligand binding conditions on recognition in bupivacaine molecularly imprinted polymers2004In: Analyst, Vol. 129, no 5, p. 456-462Article in journal (Refereed)
  • 16.
    Karlsson, Jesper G
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Rosengren-Holmberg, Jenny
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Enantioselective synthetic thalidomide receptors based upon DNA binding motifs2006Conference paper (Refereed)
  • 17.
    Nicholls, Ian A.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Adbo, Karina
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Håkan S.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Per-Ola
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Ankarloo, Jonas
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Hedin-Dahlström, Jimmy
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Jokela, Päivi
    University of Kalmar, School of Communication and Design.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Olofsson, Linus
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Rosengren-Holmberg, Jenny
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Shoravi, Siamak
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Svenson, Johan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Wikman, Susanne
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Can we rationally design molecularly imprinted polymers?2001In: Analytica Chimica Acta, Vol. 435, no 1, p. 9-18Article in journal (Refereed)
  • 18.
    Nicholls, Ian A.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Adbo, Karina
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Per Ola
    Andersson, Håkan S.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Hedin-Dahlström, Jimmy
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Rosengren, Jenny P.
    Svenson, Johan
    Wikman, Susanne
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Molecularly imprinted polymers: unique possibilities for environmental monitoring2002In: Proceedings of Kalmar Eco-Tech'01 : conference on leachate and waste water treatment with high-tech and natural systems : the 3rd International Conference on the Establishment of Cooperation Between Companies/Institutions in the Nordic Countries and the Countries in the Baltic Sea Region : November 26 to 28, 2001 Kalmar, Sweden / [ed] William Hogland, Vilmantė Vyšniauskaitė, Högskolan i Kalmar, 2002, p. 285-288Conference paper (Other academic)
  • 19.
    Nicholls, Ian A.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Håkan S.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Charlton, Christy
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Henschel, Henning
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Björn C. G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    O'Mahony, John
    Rosengren, Annika M.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Rosengren, K. Johan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Wikman, Susanne
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Theoretical and Computational Strategies for Rational Molecularly Imprinted Polymer Design2009In: Biosensors & bioelectronics, ISSN 0956-5663, E-ISSN 1873-4235, Vol. 25, no 3, p. 543-552Article in journal (Refereed)
    Abstract [en]

    The further evolution of molecularly imprinted polymer science and technology necessitates the development of robust predictive tools capable of handling the complexity of molecular imprinting systems. A combination of the rapid growth in computer power over the past decade and significant software developments have opened new possibilities for simulating aspects of the complex molecular imprinting process. We present here a survey of the current status of the use of in silico-based approaches to aspects of molecular imprinting. Finally, we highlight areas where ongoing and future efforts should yield information critical to our understanding of the underlying mechanisms sufficient to permit the rational design of molecularly imprinted polymers. 

  • 20.
    Nicholls, Ian A.
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Andersson, Håkan S.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Golker, Kerstin
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Henschel, Henning
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Olsson, Gustaf D.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Rosengren, Annika M.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Shoravi, Siamak
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Wikman, Susanne
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Rational Design of Biomimetic Molecularly Imprinted Materials: Theoretical and Computational Strategies for Guiding Nanoscale Structured Polymer Development2011In: Analytical and Bioanalytical Chemistry, ISSN 1618-2642, E-ISSN 1618-2650, Vol. 400, p. 1771-1786Article, review/survey (Refereed)
    Abstract [en]

    In principle, molecularly imprinted polymer science and technology provides a means for ready access to nano-structured polymeric materials of predetermined selectivity. The versatility of the technique has brought it to the attention of many working with the development of nanomaterials with biological or biomimetic properties for use as therapeutics or in medical devices. Nonetheless, the further evolution of the field necessitates the development of robust predictive tools capable of handling the complexity of molecular imprinting systems. The rapid growth in computer power and software over the past decade has opened new possibilities for simulating aspects of the complex molecular imprinting process. We present here a survey of the current status of the use of in silico-based approaches to aspects of molecular imprinting. Finally, we highlight areas where ongoing and future efforts should yield information critical to our understanding of the underlying mechanisms sufficient to permit the rational design of molecularly imprinted polymers.

  • 21.
    Nicholls, Ian A.
    et al.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Andersson, Håkan S.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Golker, Kerstin
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Henschel, Henning
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Olsson, Gustaf D.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Rosengren, Annika M.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Shoravi, Siamak
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Wikman, Susanne
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Rational molecularly imprinted polymer design: theoretical and computational strategies2013In: Molecular Imprinting: Principles and Applications of Micro- and Nanostructured Polymers / [ed] Ye, L, London: Pan Stanford Publishing, 2013, p. 71-104Chapter in book (Refereed)
  • 22.
    Nicholls, Ian A.
    et al.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Uppsala Univ.
    Chavan, Swapnil
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Golker, Kerstin
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Bioorganic & Biophysical Chemistry Laboratory.
    Olsson, Gustaf D.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Rosengren, Annika M.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Suriyanarayanan, Subramanian
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Theoretical and Computational Strategies for the Study of the Molecular Imprinting Process and Polymer Performance2015In: Molecularly Imprinted Polymers in Biotechnology / [ed] Mattiasson, B. & Ye, L., Berlin: Springer, 2015, p. 25-50Chapter in book (Refereed)
    Abstract [en]

    The development of in silico strategies for the study of the molecular imprinting process and the properties of molecularly imprinted materials has been driven by a growing awareness of the inherent complexity of these systems and even by an increased awareness of the potential of these materials for use in a range of application areas. Here we highlight the development of theoretical and computational strategies that are contributing to an improved understanding of the mechanisms underlying molecularly imprinted material synthesis and performance, and even their rational design.

  • 23.
    Nicholls, Ian A.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Björn C. G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Håkan S.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Golker, Kerstin
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Henschel, Henning
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Olsson, Gustaf D.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    O'Mahony, John
    Nilsson Ekdahl, Kristina
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Orozovic, Kanita
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Rosengren, Annika M.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Rosengren-Holmberg, Jenny P.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Shoravi, Siamak
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Wiklander, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Wikman, Susanne
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Biomimetic Polymer Design2009Conference paper (Refereed)
  • 24.
    Nicholls, Ian A.
    et al.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Olsson, Gustaf D.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Suriyanarayanan, Subramanian
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Theoretical and Computational Strategies in Molecularly Imprinted Polymer Development2018In: Molecularly Imprinted Polymers for Analytical Chemistry Applications / [ed] Wlodzimierz Kutner, Piyush Sindhu Sharma, London: Royal Society of Chemistry, 2018, p. 197-226Chapter in book (Refereed)
    Abstract [en]

    Theoretical and computational studies of molecular imprinting have helped provide valuable insights concerning the nature of the molecular-level events underlying the recognition characteristics of molecularly imprinted materials. Here, we first present an overview of a thermodynamic treatment of factors governing the behaviour of these functional materials, and then a summary of the development and current status of the use of computational strategies for studying aspects of molecular imprinting and the resulting material properties.

  • 25.
    Olsson, Gustaf D.
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Shoravi, Siamak
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Mechanisms Underlying Molecularly Imprinted Polymer Molecular Memory and The Role of Crosslinker: Resolving Debate on the Nature of Template Recognition in Phenylalanine Anilide Imprinted Polymers2012In: Journal of Molecular Recognition, ISSN 0952-3499, E-ISSN 1099-1352, Vol. 25, no 2, p. 69-73Article in journal (Refereed)
    Abstract [en]

    A series of molecular dynamics simulations of prepolymerization mixtures for phenylalanine anilide imprinted co-(ethylene glycol dimethacrylate-methacrylic acid) molecularly imprinted polymers have been employed to investigate the mechanistic basis for template selective recognition in these systems. This has provided new insights on the mechanisms underlying template recognition, in particular the significant role played by the crosslinking agent. Importantly, the study supports the occurrence of template self-association events that allows us to resolve debate between the two previously proposed models used to explain this system's underlying recognition mechanisms. Moreover, the complexity of the molecular level events underlying template complexation is highlighted by this study, a factor that should be considered in rational molecularly imprinted polymer design, especially with respect to recognition site heterogeneity.

  • 26.
    Olsson, Gustaf D.
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Mechanism of Phenylalanine Anilide Molecularly Imprinted Polymer - Template Recognition: The Role of Template Dimerization2010Conference paper (Refereed)
    Abstract [en]

    It is now widely accepted that the recognition properties of a MIP are derived from molecular level events present during the prepolymerization stage.1 Studies regarding the nature and extent of template complexation during this stage should therefore yield valuable information regarding the template recognition properties of the final MIP. One method of great potential for illuminating molecular level details in this area of MIP research is molecular dynamics (MD).2 MD simulations enable studies of molecular-level events in MIP prepolymerization mixtures.

    Phenylalanine anilide (PA) is a molecule that has been extensively used as a template in a series of seminal molecular imprinting studies.3-5 In an effort to elucidate the origin to the imprinting effect, Sellergren, Lepistö and Mosbach proposed that selective high-affinity sites in the PA-MIP were based on functional monomer-template complexation of a 2:1 stoichiometry.3 In a follow-up study, Katz and Davis presented results that revealed further information regarding the origin of recognition in PA-MIPs.5 It was suggested that the template recognition sites were based on functional monomer-template complexes of 1:1 stoichiometry, and also that the formation of higher order template-template complexes has important effects on the final PA-MIP recognition properties. In light of this conjecture and several more recent studies highlighting the diversity of template complexation mechanisms in prepolymerization mixtures, have pointed at the complexity and diversity in the ensemble of complexes leading to the final “molecular memory”.

    Here we present the novel insights into the molecular basis for PA-MIP template recognition derived from a series of MD simulations of the PA-MIP prepolymerisation systems. Data support the presence of PA-PA complexes and that the most statistically prevalent stoichiometry functional monomer-PA complexes was 1:1. The role of cross-linker is also discussed. This study highlights the potential of all component MD studies for rational MIP design.

     

    (1)      Alexander, C.; Andersson, H.S.; Andersson, L.I.; Ansell, R.J.; Kirsch, N.; Nicholls, I.A.; O'Mahony, J.; Whitcombe, M.J.  Molecular imprinting science and technology: A survey of the literature for the years up to and including 2003. Journal of Molecular Recognition 2006, 19, 106-180.

    (2)      Nicholls, I.A.; Andersson, H.S.; Charlton, C; Henschel, H.; Karlsson, B.C.G.; Karlsson, J.G.; O’Mahony, J.; Rosengren, A.M.; Rosengren, J.K.; Wikman, S. Theoretical and computational stratgies for rational molecularly imprinted polymer design. Biosensors and Bioelectronics 2009, 25, 543-552

    (3)      Sellergren, B.; Lepistoe, M.; Mosbach, K.. Highly enantioselective and substrate-selective polymers obtained by molecular imprinting utilizing noncovalent interactions. NMR and chromatographic studies on the nature of recognition. Journal of American Chemical Society 1988, 110, 5853-5860

    (4)      Sellergren, B.. Molecular imprinting by noncovalent interactions: Tailor-made chiral stationary phases of high selectivity and sample load capacity. Chirality 1989, 1, 63-68

    (5)      Katz, A.; Davis, M.E. Investigations into the mechanism of molecular recognition with imprinted polymers. Macromolecules 1999, 32, 4113-4121

  • 27.
    Olsson, Gustaf D.
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Shoravi, Siamak
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    The nature and extent of interactions in phenylalanine anilide molecularly imprinted polymer prepolymerisation mixtures: a new model for the basis for ligand-selective recognition2010Conference paper (Refereed)
    Abstract [en]

    In this work, classical molecular dynamics (MD) simulations have been used to provide unique insights on the nature and extent of intermolecular interactions present in a phenylalanine anilide (PA) molecularly imprinted polymers (MIP) prepolymerization mixture.

    Molecular Imprinting is a technique for producing highly selective synthetic receptors for a predetermined molecular structure, and involves the formation of cavities in a synthetic polymer matrix that are of complementary functional and structural character to a template molecule.1 It is generally accepted that the recognition properties of a MIP is a product of the interactions between monomers and template during the prepolymerization stage. Accordingly, studies of the nature and extent of the interactions present in prepolymerization mixtures, in patricular those involving template, should yield information which can be related to the observed recognition properties of the final MIP.

    Phenylalanine anilide MIPs have been the subject of a significant number of studies aimed at producing an understanding of the mechanisms underlying the recognition processes. Interestingly, two different models have been proposed to explain the behaviour of PA-MIPs. Studies by Sellergren et al. proposed that template selectivity, was a consequence of  the presence of a functional monomer-template complexes of 2:1 stoichiometry.2 Later, however, Katz and Davis proposed an alternative model,3 where the template (PA) recognition sites in the MIP were suggested to arise from functional monomer-template complexes of 1:1 stoichiometry in combination with the presence of higher order template-template complexes.

    To resolve this conjecture, we performed a series of MD studies, the results of which demonstrated both the presence of PA-PA self association complexes, and that the most statistically prevalent monomer-PA complex stoichiometry was of a 1:1 nature, though differetn in character from that proposed by Katz and Davis.  Moreover, the role of cross-linker in forming recognition sites was apparnet in these studies, a fact not previously considered.

     

    References

    1. Alexander C, Andersson HS, Andersson LI, Ansell RJ, Kirsh N, Nicholls IA, O’Mahony J, Whitcombe MJ. Molecular imprinting science and technology: A survey of the literature for the years up to and including 2003. Journal of Molecular Recognition 2006;19:106-180
    2. Sellergren B, Lepistö M, Mosbach K. Highly enantioselective and substrate selective polymers obtained by molecular imprinting utilizing noncovalent interactions. NMR and chromatographic studies on the nature of recognition. Journal of the American Chemical Society 1988;110:5853-5860
    3. Katz A, Davis ME. Investigations into the mechanisms of molecular recognition with imprinted polymers. Macromolecules 1999;32:4113-4121

     

  • 28.
    Olsson, Gustaf D.
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Shoravi, Siamak
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    The Nature and Extent of Template-Template Complexation in Phenylalanine Anilide Molecularly Imprinted Polymers2010Conference paper (Refereed)
    Abstract [en]

    The molecular imprinting technique has received significant attention due to its utility in the production of synthetic polymeric materials with predetermined ligand recognition properties [1].

    It is generally accepted that the recognition properties of a molecularly imprinted polymer (MIP) is established during the prepolymerization stage. Previous investigations on the nature and extent of template prepolymerization complexation in a phenylalanine anilide (PA) MIP pointed at the complexity and diversity in the ensemble of complexes leading to the final “molecular memory”. In particular, conflicting models have been used to explain the observed molecular memory. Sellergren, Lepistö and Mosbach [2] proposed that selective, high-affinity sites in the final MIP were based on functional monomer-PA complexation of a 2:1 stoichiometry. Later, Katz and Davis [3] proposed that the template recognition sites arose due to a 1:1 functional monomer-template complex stoichiometry and that the effect of template dimerization is critical for the observed PA-MIP recognition properties.

    In this study, we have attempted to shed new light on this as yet unresolved conflict using a series of molecular dynamics (MD) simulations. Results demonstrated the presence of PA-PA complexes and that the most statistically prevalent stoichiometry of functional monomer-PA complexes was of 1:1.

    [1]             Alexander C, Andersson HS, Andersson LI, Ansell R, Kirsch N, Nicholls IA et al. Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003, Journal of Molecular Recognition, 19, 106-180 (2006).

    [2]            Sellergren B, Lepistö M, Mosbach K. Highly enantioselective and substrate selective polymers obtained by molecular imprinting utilizing noncovalent interactions. NMR and chromatographic studies on the nature of recognition, Journal of the American Chemical Society, 110, 5853-5860 (1988).

    [3]             Katz A, Davis ME. Investigations into the mechanisms of molecular recognition with imprinted polymers, Macromolecules, 32, 4113-4121 (1999).

  • 29. Petcu, Mira
    et al.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Whitcombe, M J
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Probing the limits of molecular imprinting: strategies with a template of limited size and functionality2009In: Journal of Molecular Recognition, ISSN 0952-3499, E-ISSN 1099-1352, Vol. 22, no 1, p. 18-25Article in journal (Refereed)
    Abstract [en]

    A series of polymers molecularly imprinted with the general anaesthetic propofol were synthesized using both semi- and non-covalent approaches. The polymers were evaluated with respect to template rebinding in both aqueous and organic media. In aqueous media, the observed propofol binding in these polymer systems was largely hydrophobic and non-specific in nature. In non-polar solvents such as hexane, electrostatic (hydrogen bonding) interactions dominate resulting in some selectivity. The implication of these results, in conjunction with those obtained using structures of similar size in other studies, is that propofol, a template possessing limited functionality and size, appears to define the lower limit for template size and degree of functionalization that can be used for the creation of ligand-selective recognition sites in molecularly imprinted polymers. Furthermore, studies with alternative ligands indicate that the steric crowding of a ligand's functionality to the polymer contributes to the extent of polymer-ligand recognition.

  • 30.
    Rosengren, Annika
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, P A
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Chemometric models of template-molecularly imprinted polymer binding2005In: Analytical chemistry, Vol. 77, no 17, p. 5700-5705Article in journal (Refereed)
  • 31.
    Rosengren, Annika
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Per-Ola
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Chemometric models of synthetic receptor-ligand binding2006Conference paper (Refereed)
  • 32.
    Rosengren, Annika
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Per-Ola
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Chemometric models of synthetic receptor-ligand binding2006Conference paper (Refereed)
  • 33.
    Rosengren, Annika
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Andersson, Per-Ola
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Chemometric study of binding to bupivacaine imprinted polymer2004Conference paper (Refereed)
  • 34.
    Rosengren, Annika M.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Golker, Kerstin
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Dielectric constants are not enough: Principal component analysis of the influence of solvent properties on molecularly imprinted polymer–ligand rebinding2009In: Biosensors & bioelectronics, ISSN 0956-5663, E-ISSN 1873-4235, Vol. 25, no 3, p. 553-557Article in journal (Refereed)
    Abstract [en]

    The influence of the physical properties of incubation medium on the rebinding of template to bupivacaine molecularly imprinted and non-imprinted methacrylic acid–ethylene dimethacrylate co-polymers has been studied. Principal component analysis (PCA) was employed to identify the factors with the greatest influence on binding. While the dielectric constant (D) made a significant contribution to describing the observed binding, the influence of polarity as reflected in the Snyder polarity index (SPI) was also demonstrated to make a significant contribution. The use of solvents containing hydroxyl functionality in particular was observed to exert unique effects on recognition. The variation in solvent influence on binding at constant D motivates more complex analyses when studying MIP–ligand recognition.

  • 35.
    Rosengren, Annika M.
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Golker, Kerstin
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Identification of Solvent Properties Influencing Binding to Molecularly Imprinted Polymers2010Conference paper (Refereed)
    Abstract [en]

    In order to examine the physical mechanisms underlying molecularly imprinted polymer1 (MIP)–ligand recognition, polymers with selectivity for the local anaesthetic bupivacaine have been synthesised and their ligand-recognition characteristics examined. As several previous studies have pointed at the complexity of the rebinding characteristics and the dependence on rebinding media,2-4 we used chemometric strategies for the analysis of ligand-MIP binding in various media.5

    In a previous study we presented results from a chemometric analysis showing that rebinding of bupivacaine to the MIP in different solvent mixtures and at different temperatures follow a complicated non-linear relationship.6 The results from that analysis, motivated an investigation into the significance of the solvent physical characteristics (molecular and bulk) on rebinding properties. In this work,7 principal component analysis was employed to identify the factors with the greatest influence on binding. While the dielectric constant made a significant contribution to describing the observed binding, the influence of polarity as reflected in the Snyder polarity index was also demonstrated to also make a significant contribution. The use of solvents containing hydroxyl functionality was observed to exert unique effects on recognition. The variation in solvent influence on binding at constant dielectricity motivates more complex analyses when studying MIP-ligand recognition.

    (1)      Alexander, C.; Andersson, H.S.; Andersson, L.I.; Ansell, R.J.; Kirsch, N.; Nicholls, I.A.; O'Mahony, J.; Whitcombe, M.J. Molecular imprinting science and technology: A survey of the literature for the years up to and including 2003. Journal of Molecular Recognition 2006, 19, 106-180.

    (2)      Andersson, L.I. Efficient sample pre-concentration of bupivacaine from human plasma by solid-phase extraction on molecularly imprinted polymers. Analyst 2000, 125, 1515-1517.

    (3)      Karlsson, J.G.; Andersson, L.I.; Nicholls, I.A. Probing the molecular basis for ligand-selective recognition in molecularly imprinted polymers selective for the local anaesthetic bupivacaine. Analytica Chimica Acta 2001, 435, 57-64.

    (4)      Karlsson, J.G.; Karlsson, B.; Andersson, L.I.; Nicholls, I.A. The roles of template complexation and ligand binding conditions on recognition in bupivacaine molecularly imprinted polymers. Analyst 2004, 129, 456-462.

    (5)      Nicholls, I.A.; Andersson, H.S.; Charlton, C.; Henschel, H.; Karlsson, B.C.G.; Karlsson, J.G.; O’Mahony, J.; Rosengren, A.M.; Rosengren, K.J.; Wikman, S. Theoretical and computational strategies for rational molecularly imprinted polymer design. Biosensors and Bioelectronics 2009, 25, 543-552.

    (6)      Rosengren, A.M.; Karlsson, J.G.; Andersson, P.O.; Nicholls, I.A. Chemometric models of template-molecularly imprinted polymer binding. Analytical Chemistry 2005, 77, 5700-5705.

    (7)      Rosengren, A.M; Golker, K.; Wiklander, J.G.; Nicholls, I.A. Dielectric constants are not enough: Principal component analysis of the influence of solvent properties on molecularly imprinted polymer–ligand rebinding. Biosensors and Bioelectronics 2009, 25, 553-557.

  • 36.
    Rosengren, Annika M.
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Golker, Kerstin
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Principal component analysis of the influence of solvent properties on molecularly imprinted polymer–ligand rebinding2010Conference paper (Refereed)
    Abstract [en]

    Molecular imprinting is a technique for creating polymeric recognition materials with predetermined ligand selectivities.1 A molecularly imprinted polymer (MIP) with selectivity for the local anaesthetic bupivacaine has been synthesised in order to examine the physical mechanisms underlying MIP–ligand recognition characteristics. As rebinding characteristics has shown to be complex, we use chemometric strategies for the analysis of ligand-MIP binding in various media.2-4 The use of chemometrics simplify the selection of optimal experimental parameters as well as the extraction of significant information generated from multivariate data analysis.5

    Previously we have presented results from a chemometric analysis pointing at a complex non-linear relationship when studying binding of bupivacaine to the MIP in different solvent mixtures and at different temperatures.6 The results motivated an investigation into the significance of the solvent physical characteristics (molecular and bulk) on rebinding properties. In this work, principal component analysis was employed to identify the factors with the greatest influence on binding. While the dielectric constant made a significant contribution to describing the observed binding, the influence of polarity as reflected in the Snyder polarity index was also demonstrated to make a significant contribution. The use of solvents containing hydroxyl functionality was observed to exert unique effects on recognition. The variation in solvent influence on binding at constant dielectricity motivates more complex analyses when studying MIP-ligand recognition. Collectively, the results provided general insights concerning the complex interplay between the mechanisms controlling ligand recognition in MIPs.

     

    References

    1. Alexander, C.; Andersson, H.S.; Andersson, L.I.; Ansell, R.J.; Kirsch, N.; Nicholls, I.A.; O’Mahony, J.; Whitcombe, M.J. Journal of Molecular Recognition 2006, 19, 106-180.
    2. Andersson, L.I. Analyst 2000, 125, 1515-1517.
    3. Karlsson, J.G.; Andersson, L.I.; Nicholls, I.A. Analytica Chimica Acta 2001, 435, 57-64.
    4. Karlsson, J.G.; Karlsson, B.; Andersson, L.I.; Nicholls, I.A. Analyst 2004, 129, 456-462.
    5. Nicholls, I.A.; Andersson, H.S.; Charlton, C.; Henschel, H.; Karlsson, B.C.G.; Karlsson, J.G.; O’Mahony, J.; Rosengren, A.M.; Rosengren, K.J.; Wikman, S. Biosensors and Bioelectronics 2009, 25, 543-552.
    6. Rosengren, A.M.; Karlsson, J.G.; Andersson, P.O.; Nicholls, I.A. Analytical Chemistry 2005, 77, 5700-5705.
  • 37.
    Rosengren, Annika M.
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Golker, Kerstin
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Principal component analysis of the influence of solvent properties on molecularly imprinted polymer–ligand rebinding2010Conference paper (Refereed)
    Abstract [en]

    A molecularly imprinted polymer (MIP) is a polymeric material with selective recognition for an analyte.1 In order to examine the physical mechanisms underlying MIP–ligand recognition, polymers with selectivity for the local anaesthetic bupivacaine have been synthesised and their ligand-recognition characteristics examined. As several previous studies have pointed at the complexity of the rebinding characteristics and the dependence on rebinding media,2-4 we used chemometric strategies for the analysis of ligand-MIP binding in various media.5

    In a previous study we presented results from a chemometric analysis showing that rebinding of bupivacaine to the MIP in different solvent mixtures and at different temperatures follow a complicated non-linear relationship.6 The results from that analysis, motivated an investigation into the significance of the solvent physical characteristics (molecular and bulk) on rebinding properties. In this work, principal component analysis was employed to identify the factors with the greatest influence on binding. While the dielectric constant made a significant contribution to describing the observed binding, the influence of polarity as reflected in the Snyder polarity index was also demonstrated to also make a significant contribution. The use of solvents containing hydroxyl functionality was observed to exert unique effects on recognition. The variation in solvent influence on binding at constant dielectricity motivates more complex analyses when studying MIP-ligand recognition.

     

    References

    1. Alexander, C.; Andersson, H.S.; Andersson, L.I.; Ansell, R.J.; Kirsch, N.; Nicholls, I.A.; O’Mahony, J.; Whitcombe, M.J. Journal of Molecular Recognition 2006, 19, 106-180.
    2. Andersson, L.I. Analyst 2000, 125, 1515-1517.
    3. Karlsson, J.G.; Andersson, L.I.; Nicholls, I.A. Analytica Chimica Acta 2001, 435, 57-64.
    4. Karlsson, J.G.; Karlsson, B.; Andersson, L.I.; Nicholls, I.A. Analyst 2004, 129, 456-462.
    5. Nicholls, I.A.; Andersson, H.S.; Charlton, C.; Henschel, H.; Karlsson, B.C.G.; Karlsson, J.G.; O’Mahony, J.; Rosengren, A.M.; Rosengren, K.J.; Wikman, S. Biosensors and Bioelectronics 2009, 25, 543-552.
    6. Rosengren, A.M.; Karlsson, J.G.; Andersson, P.O.; Nicholls, I.A. Analytical Chemistry 2005, 77, 5700-5705.
  • 38.
    Rosengren-Holmberg, Jenny
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Enantioselective synthetic thalidomide receptors based upon DNA binding motifs2004In: Organic & Biomolecular Chemistry, Vol. 2, no 22, p. 3374-3378Article in journal (Refereed)
  • 39.
    Rosengren-Holmberg, Jenny
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Enantioselective synthetic thalidomide respectors based upon DNA binding motifs2004Conference paper (Refereed)
  • 40.
    Rosengren-Holmberg, Jenny
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Molecularly imprinted polymers for the teratogenic substance (S)-Thalidomide2002Conference paper (Refereed)
  • 41.
    Rosengren-Holmberg, Jenny
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Svenson, Johan
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Paracetamol selective synthetic antibodies2008Conference paper (Refereed)
  • 42.
    Rosengren-Holmberg, Jenny P.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Svenson, Johan
    Andersson, Håkan S.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Synthesis and ligand recognition of paracetamol selective polymers: semi-covalent versus non-covalent molecular imprinting.2009In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 7, p. 3148-3155Article in journal (Refereed)
    Abstract [en]

    Three molecular imprinting strategies, each based upon a series of ethylene glycol dimethacrylate (EGDMA) cross-linked co-polymers, have been used to produce materials selective for the commonly used analgesic and antipyretic agent paracetamol (p-acetaminophen or 4-acetamidophenol) (1). The polymers were synthesised using either a semi-covalent imprinting strategy based upon 4-acetamidophenyl-(4-vinylphenyl) carbonate (4) or a non-covalent strategy based on methacrylic acid (MAA) as the functional monomer, or by employing a combination of these strategies. Radioligand binding studies demonstrated low template affinity in polymers offering only a single electrostatic interaction point for recognition via the phenolic residue in the template, whereas binding was substantially increased upon the introduction of a second binding mode, namely interaction at the acetamide moiety. HPLC analyses revealed no imprinting effect in the purely semi-covalent system, and only a minor effect in the purely non-covalent systems. However, a pronounced imprinting effect was demonstrated for polymers prepared by a combination of semi-covalent and non-covalent imprinting. This study illustrates a limitation of both the non-covalent and the semi-covalent strategies when it comes to achieving imprinted selectivity for small and poorly functionalised templates such as paracetamol. Parallels with conclusions from studies with antibodies are discussed. 

  • 43.
    Rosengren-Holmberg, Jenny P.
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Svenson, Johan
    University of Tromsø.
    Nicholls, Ian A.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Paracetamol selective polymers prepared by semi-covalent and non-covalent imprinting2009Conference paper (Refereed)
  • 44.
    Shoravi, Siamak
    et al.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Olsson, Gustaf D.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Bexborn, Fredrik
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Abghoui, Younes
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Hussain, Javed
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Uppsala University.
    In silico screening of molecular imprinting prepolymerization systems: oseltamivir selective polymers through full-system molecular dynamics-based studies2016In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 14, no 18, p. 4210-4219Article in journal (Refereed)
    Abstract [en]

    All-component molecular dynamics studies were used to probe a library of oseltamivir molecularly imprinted polymer prepolymerization mixtures. Polymers included one of five functional monomers (acrylamide, hydroxyethylmethacrylate, methacrylic acid, 2-(triflouromethyl)acrylic acid, 4-vinylpyridine) and one of three porogens (acetonitrile, chloroform, methanol) combined with the crosslinking agent ethylene glycol dimethacrylate and initiator 2,2'-azobis(2-methylpropionitrile). Polymers were characterized by nitrogen gas sorption measurements and SEM, and affinity studies performed using radioligand binding in various media. In agreement with the predictions made from the simulations, polymers prepared in acetonitrile using either methacrylic or trifluoromethacrylic acid demonstrated the highest affinities for oseltamivir. Further, the ensemble of interactions observed in the methanol system provided an explanation for the morphology of polymers prepared in this solvent. The materials developed here offer potential for use in solid-phase extraction or for catalysis. The results illustrate the strength of this in silico strategy as a potential prognostic tool in molecularly imprinted polymer design.

  • 45.
    Shoravi, Siamak
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Orozovic, Kanita
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Wiklander, Jesper G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Towards Synthetic Neuraminidases2010Conference paper (Refereed)
    Abstract [en]

    Influenza endemics and pandemics have been a menace to humanity through the ages and pose ominous threats and with dire consequences for humanity [1]. A better understanding of the virus, the epidemiology of the disease, and its structure and function is essential for creating new therapies and even for better understanding resistance to existing treatments. At the molecular level the two capside proteins Neuraminidase and Hemagglutinin are engaged in interactions with host cell surface sialic acid residues, and are critical for contagion and budding off of the virus into and from the cell, and have been the  targets for drug development strategies [2]. The rise of strains of the virus resistant to drugs targeting Neuraminidase make it crucial to develop techniques for better understanding of the virus and hence design of better antiviral agents [3].

    In this study a combination of molecular dynamics (MD) and NMR spectroscopy [4-7] is been utilised in order to screen some 60 polymers for candidate systems [8] for use in the preparation of synthetic polymer neauraminidase mimics.  Progress in the design, synthesis and evaluation of these materials shall be presented.

    References

    1. Webster et al., Microbiol. Rev., 56, 152-175 (1992).

    2. von Itzstein et al., Nature, 263, 418-423 (1993).

    3. Lindberg et al., Chemosphere, 57, 1479-1488. (2004).

    4. Svensson et al., J. Chromatogr. A, 1024, 39-44 (2004).

    5. O’Mahony et al., Analyst, 23, 1147-1115 (2007).

    6. Karlsson et al., J. Am. Chem. Soc., 131, 13297-13304 (2009).

    7. Nicholls et al., Biosens. Bioelectron., 25, 553-557 (2009).

    8. Shoravi et al., unpublished results (2010).

     

  • 46. Svenson, Johan
    et al.
    Karlsson, Jesper G
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Craik, David C
    Nicholls, Ian A
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Nuclear magnetic resonance studies of the molecular imprinting of (-)-nicotine.2001Conference paper (Refereed)
  • 47.
    Svenson, Johan
    et al.
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Karlsson, Jesper G
    University of Kalmar, School of Pure and Applied Natural Sciences.
    Nicholls, Ian Alan
    University of Kalmar, School of Pure and Applied Natural Sciences.
    1H-nuclear magnetic resonance study of the molecular imprinting of (-)-nicotine: template self-association, a molecular basis for cooperative ligand binding2004In: Journal of Chromatography A, ISSN 0021-9673, E-ISSN 1873-3778, Vol. 1024, no 1-2, p. 39-44Article in journal (Refereed)
    Abstract [en]

    In the present study, the interactions of components in a (−)-nicotine molecular imprinting polymerization mixture have been studied by NMR spectroscopy. The dissociation constants for complexation of template by a functional monomer analogue, acetic acid, have been determined. Nicotine was shown to self-associate at concentrations comparable to those used in previous molecular imprinting studies (app Kdiss=0.082 M in CDCl3 at 298 K). The extent of self-association was enhanced by the presence of acetic acid. Previous studies on (−)-nicotine–imprinted methacrylic acid–ethylene dimethacrylate co-polymers suggested the involvement of recognition sites for template–template complexes. Collectively these results provide the first direct evidence for the presence of template–template complexes, and support the previously hypothesized basis for cooperative ligand recognition events in this polymer system.

  • 48.
    Wiklander, Jesper
    University of Kalmar, Department of Chemistry and Biomedical Sciences.
    Molecular Imprinting: A Study of the Mechanisms Underlying Polymer-Ligand Recognition2004Doctoral thesis, monograph (Other academic)
  • 49.
    Wiklander, Jesper G.
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Aastrup, Teodor
    Attana AB, Stockholm.
    Nicholls, Ian A.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    A synthetic polymer with avidin-like binding properties2010Conference paper (Refereed)
    Abstract [en]

    A series of streptavidin mimicking molecularly imprinted polymers has been developed and evaluated for their biotin binding characteristics. A combination of molecular dynamics and NMR spectroscopy was used to examine potential polymer systems, in particular with the functional monomers methacrylic acid and 2-acrylamidopyridine. Synthesis of co-polymers of ethylene dimethacrylate and one or both of these functional monomers was performed. A combination of radioligand binding studies and surface area analyses (BET, SEM) demonstrated the presence of selectivity in polymers prepared using methacrylic acid as functional monomer. This correlated well with the molecular dynamics studies, showing the power of this methodology as a prognostic tool for predicting the behaviour of molecularly imprinted polymers.

  • 50.
    Wiklander, Jesper G.
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Karlsson, Björn C. G.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Aastrup, Teodor
    Nicholls, Ian A.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Towards a synthetic avidin mimic2011In: Analytical and Bioanalytical Chemistry, ISSN 1618-2642, E-ISSN 1618-2650, Vol. 400, no 5, p. 1397-1404Article in journal (Refereed)
    Abstract [en]

    A series of streptavidin-mimicking molecularly imprinted polymers has been developed and evaluated for their biotin binding characteristics. A combination of molecular dynamics and NMR spectroscopy was used to examine potential polymer systems, in particular with the functional monomers methacrylic acid and 2-acrylamidopyridine. The synthesis of copolymers of ethylene dimethacrylate and one or both of these functional monomers was performed. A combination of radioligand binding studies and surface area analyses demonstrated the presence of selectivity in polymers prepared using methacrylic acid as the functional monomer. This was predicted by the molecular dynamics studies showing the power of this methodology as a prognostic tool for predicting the behavior of molecularly imprinted polymers.

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