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Publications (10 of 24) Show all publications
Golker, K., Olsson, G. D. & Nicholls, I. A. (2017). The influence of a methyl substituent on molecularly imprinted polymer morphology and recognition – Acrylic acid versus methacrylic acid. European Polymer Journal, 92, 137-149
Open this publication in new window or tab >>The influence of a methyl substituent on molecularly imprinted polymer morphology and recognition – Acrylic acid versus methacrylic acid
2017 (English)In: European Polymer Journal, ISSN 0014-3057, E-ISSN 1873-1945, Vol. 92, p. 137-149Article in journal (Refereed) Published
Abstract [en]

In this report, we have investigated factors contributing to the morphology and template recognition of bupivacaine-imprinted copolymers of methacrylic acid (MAA) and ethyleneglycol dimethacrylate (EGDMA). To this end, MAA, the most commonly used functional monomer in non-covalent molecular imprinting protocols, was compared and contrasted with the closely related acrylic acid (AA) in terms of polymer morphologies, recognition characteristics, and molecular level events in the corresponding pre-polymerization mixtures. Two series of analogous bupivacaine-imprinted EGDMA-copolymers containing increasing fractions of either AA or MAA were studied through all-component MD simulations in the pre-polymerization phase, equilibrium binding experiments on corresponding synthesized polymers and morphology characterization by N2-sorption measurements. A higher degree of hydrogen bonding frequency between respective functional monomer and bupivacaine was recorded for the mixtures containing AA compared to those containing MAA. In contrast, results from binding experiments demonstrated higher binding capacities for the polymers prepared with MAA than for those prepared with AA, which is explained by differences in polymer morphology. The surface areas and pore volumes of the AA-polymers were higher than for the MAA-polymers and the overall pore structure in the AA-polymers was ink-bottle shaped while the pores in the MAA-polymers were slit-shaped. We suggest that the methyl substituent of MAA contributes to differences in the reaction kinetics for AA and MAA during polymerization and resulted in different morphologies, in particular pore shape, which affected mass-transfer and consequently the binding qualities of the materials. © 2017 Elsevier Ltd

Place, publisher, year, edition, pages
Elsevier, 2017
Keywords
Acrylic acid, Methacrylic acid, Molecular dynamics, Molecular recognition, Molecularly imprinted polymer, Morphology
National Category
Polymer Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-64636 (URN)10.1016/j.eurpolymj.2017.04.043 (DOI)000404315600013 ()2-s2.0-85018458746 (Scopus ID)
Available from: 2017-06-02 Created: 2017-06-02 Last updated: 2018-11-02Bibliographically approved
Shoravi, S., Olsson, G. D., Karlsson, B. C. G., Bexborn, F., Abghoui, Y., Hussain, J., . . . Nicholls, I. A. (2016). In silico screening of molecular imprinting prepolymerization systems: oseltamivir selective polymers through full-system molecular dynamics-based studies. Organic and biomolecular chemistry, 14(18), 4210-4219
Open this publication in new window or tab >>In silico screening of molecular imprinting prepolymerization systems: oseltamivir selective polymers through full-system molecular dynamics-based studies
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2016 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 14, no 18, p. 4210-4219Article in journal (Refereed) Published
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.

National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-53319 (URN)10.1039/c6ob00305b (DOI)000375610600007 ()2-s2.0-84967333692 (Scopus ID)
Available from: 2016-06-10 Created: 2016-06-10 Last updated: 2018-11-02Bibliographically approved
Olsson, G. D., Niedergall, K., Bach, M., Karlsson, B. C. G., Tovar, G. & Nicholls, I. A. (2015). Simulation of imprinted emulsion prepolymerization mixtures. Polymer journal, 47(12), 827-830
Open this publication in new window or tab >>Simulation of imprinted emulsion prepolymerization mixtures
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2015 (English)In: Polymer journal, ISSN 0032-3896, E-ISSN 1349-0540, Vol. 47, no 12, p. 827-830Article in journal (Refereed) Published
Abstract [en]

The aim of this study was to develop protocols for and evaluate the use of all-atom full system molecular dynamic (MD) simulations of emulsion systems in the development of molecularly imprinted polymers (MIPs). Here, we report on the first, to the best of our knowledge, use of all-component MD studies to simulate and evaluate MIP miniemulsion prepolymerization mixtures; in this case, the mixtures used in the synthesis of a series of MIP-nanoparticles (MIP-NPs).

National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-48813 (URN)10.1038/pj.2015.63 (DOI)000366047900008 ()2-s2.0-84949442668 (Scopus ID)
Available from: 2016-01-19 Created: 2016-01-15 Last updated: 2018-11-02Bibliographically approved
Nicholls, I. A., Chavan, S., Golker, K., Karlsson, B. C. G., Olsson, G. D., Rosengren, A. M., . . . Wiklander, J. G. (2015). Theoretical and Computational Strategies for the Study of the Molecular Imprinting Process and Polymer Performance. In: Mattiasson, B. & Ye, L. (Ed.), Molecularly Imprinted Polymers in Biotechnology: (pp. 25-50). Berlin: Springer
Open this publication in new window or tab >>Theoretical and Computational Strategies for the Study of the Molecular Imprinting Process and Polymer Performance
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2015 (English)In: 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.

Place, publisher, year, edition, pages
Berlin: Springer, 2015
Series
Advances in Biochemical Engineering-Biotechnology, ISSN 0724-6145 ; 150
National Category
Polymer Technologies
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-42600 (URN)10.1007/10_2015_318 (DOI)000365222300003 ()2-s2.0-84938411248 (Scopus ID)978-3-319-20729-2 (ISBN)978-3-319-20728-5 (ISBN)
Available from: 2015-04-15 Created: 2015-04-15 Last updated: 2018-11-02Bibliographically approved
Cleland, D., Olsson, G. D., Karlsson, B. C. G., Nicholls, I. A. & McCluskey, A. (2014). Molecular dynamics approaches to the design and synthesis of PCB targeting molecularly imprinted polymers: interference to monomer-template interactions in imprinting of 1,2,3-trichlorobenzene. Organic and biomolecular chemistry, 12(5), 844-853
Open this publication in new window or tab >>Molecular dynamics approaches to the design and synthesis of PCB targeting molecularly imprinted polymers: interference to monomer-template interactions in imprinting of 1,2,3-trichlorobenzene
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2014 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 12, no 5, p. 844-853Article in journal (Refereed) Published
Abstract [en]

The interactions between each component of the pre-polymerisation mixtures used in the synthesis of molecularly imprinted polymers (MIP) specific for 1,2,3,4,5-pentachlorobenzene (1) and 1,2,3-trichlorobenzene (2) were examined in four molecular dynamics simulations. These simulations revealed that the relative frequency of functional monomer template (FM T) interactions was consistent with results obtained by the synthesis and evaluation of the actual MIPs. The higher frequency of 1 interaction with tri-methylstyrene (TMS; 54.7%) than 1 interaction with pentafluorostyrene (PFS; 44.7%) correlated with a higher imprinting factor (IF) of 2.1 vs. 1.7 for each functional monomer respectively. The higher frequency of PFS interactions with 2 (29.6%) than TMS interactions with 2 (1.9%) also correlated well with the observed differences in IF (3.7) of 2 MIPs imprinted using PFS as the FM than the IF (2,8) of 2 MIPs imprinted using TMS as the FM. The TMS-1 interaction dominated the molecular simulation due to high interaction energies, but the weaker TMS-2 resulted in low interaction maintenance, and thus lower IF values. Examination of the other pre-polymerisation mixture components revealed that the low levels of TMS-2 interaction was, in part, due to interference caused by the cross linker (CL) ethyleneglycol dimethylacrylate (EGDMA) interactions with TMS. The main reason was, however, attributed to MeOH interactions with TMS in both a hydrogen bond and perpendicular configuration. This positioned a MeOH directly above the it-orbital of all TMS for an average of 63.8% of MD2 creating significant interference to pi-pi stacking interactions between 2 and TMS. These findings are consistent with the deviation from the 'normal' molecularly imprinted polymer synthesis ratio of 1 : 4 : 20 (T : FM : CL) of 20 : 1 : 29 and 15 : 6 : 29 observed with 2 and TMS and PFS respectively. Our molecular dynamics simulations correctly predicted the high level of interference from other MIP synthesis components. The effect on PFS-1 interaction by MeOH was significantly lower and thus this system was not adversely affected.

National Category
Chemical Sciences
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-31766 (URN)10.1039/c3ob42399a (DOI)000330083100018 ()2-s2.0-84891890308 (Scopus ID)
Available from: 2014-01-29 Created: 2014-01-29 Last updated: 2018-11-02Bibliographically approved
Shoravi, S., Olsson, G. D., Karlsson, B. C. G. & Nicholls, I. A. (2014). On the Influence of Crosslinker on Template Complexation in Molecularly Imprinted Polymers: A Computational Study of Prepolymerization Mixture Events with Correlations to Template-Polymer Recognition Behavior and NMR Spectroscopic Studies. International Journal of Molecular Sciences, 15(6), 10622-10634
Open this publication in new window or tab >>On the Influence of Crosslinker on Template Complexation in Molecularly Imprinted Polymers: A Computational Study of Prepolymerization Mixture Events with Correlations to Template-Polymer Recognition Behavior and NMR Spectroscopic Studies
2014 (English)In: International Journal of Molecular Sciences, ISSN 1422-0067, E-ISSN 1422-0067, Vol. 15, no 6, p. 10622-10634Article in journal (Refereed) Published
Abstract [en]

Aspects of the molecular-level basis for the function of ethylene glycol dimethacrylate and trimethylolproprane trimethacrylate crosslinked methacrylic acid copolymers molecularly imprinted with (S)-propranolol have been studied using a series of all-component and all-atom molecular dynamics studies of the corresponding prepolymerization systems. The crosslinking agents were observed to contribute to template complexation, and the results were contrasted with previously reported template-recognition behavior of the corresponding polymers. Differences in the extent to which the two crosslinkers interacted with the functional monomer were identified, and correlations were made to polymer-ligand recognition behavior and the results of nuclear magnetic resonance spectroscopic studies studies. This study demonstrates the importance of considering the functional monomer-crosslinker interaction when designing molecularly imprinted polymers, and highlights the often neglected general contribution of crosslinker to determining the nature of molecularly imprinted polymer-template selectivity.

Keywords
molecular dynamics, molecular imprinting, molecularly imprinted polymer, nuclear magnetic resonance, propranolol
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-36837 (URN)10.3390/ijms150610622 (DOI)000338639000085 ()2-s2.0-84902354509 (Scopus ID)
Available from: 2014-09-10 Created: 2014-09-10 Last updated: 2018-11-02Bibliographically approved
Nicholls, I. A., Karlsson, B. C. G., Olsson, G. D. & Rosengren, A. M. (2013). Computational Strategies for the Design and Study of Molecularly Imprinted Materials. Paper presented at 2nd Workshop of the Nano4water Cluster, APR 24-25, 2012, GREECE. Industrial & Engineering Chemistry Research, 52(39), 13900-13909
Open this publication in new window or tab >>Computational Strategies for the Design and Study of Molecularly Imprinted Materials
2013 (English)In: Industrial & Engineering Chemistry Research, ISSN 0888-5885, E-ISSN 1520-5045, Vol. 52, no 39, p. 13900-13909Article in journal (Refereed) Published
Abstract [en]

The need for materials with predetermined ligand-selectivities for use in sensing and separation technologies, e.g. membranes and chromatography, has driven the development of molecularly imprinted polymer science and technology. Over recent years, the need to develop robust predictive tools capable of handling the complexity of molecular imprinting systems has become apparent The current status of the use of in silica techniques in molecular imprinting is here presented, and we highlight areas where new developments are contributing to improvements in the rational design of molecularly imprinted polymers.

National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-31001 (URN)10.1021/ie3033119 (DOI)000326300400003 ()2-s2.0-84962377304 (Scopus ID)
Conference
2nd Workshop of the Nano4water Cluster, APR 24-25, 2012, GREECE
Available from: 2013-12-06 Created: 2013-12-06 Last updated: 2018-11-02Bibliographically approved
Karlsson, B. C. G., Olsson, G. D., Friedman, R., Rosengren, A. M., Henschel, H. & Nicholls, I. A. (2013). How warfarin’s structural diversity influences its phospholipid bilayer membrane permeation. Journal of Physical Chemistry B, 117(8), 2384-2395
Open this publication in new window or tab >>How warfarin’s structural diversity influences its phospholipid bilayer membrane permeation
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2013 (English)In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 117, no 8, p. 2384-2395Article in journal (Refereed) Published
Abstract [en]

The role of the structural diversity of the widely used anticoagulant drug warfarin on its distribution in 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) bilayer membranes was investigated using a series of both restrained (umbrella sampling) and unrestrained molecular dynamics simulations. Data collected from unrestrained simulations revealed favorable positions for neutral isomers of warfarin, the open side chain form (OCO), and the cyclic hemiketal (CCO), along the bilayer normal close to the polar headgroup region and even in the relatively distant nonpolar lipid tails. The deprotonated open side chain form (DCO) was found to have lower affinity for the DOPC bilayer membrane relative to the neutral forms, with only a small fraction interacting with the membrane, typically within the polar headgroup region. The conformation of OCO inside the lipid bilayer was found to be stabilized by intramolecular hydrogen bonding thereby mimicking the structure of CCO. Differences in free energies, for positions of OCO and CCO inside the bilayer membrane, as compared to positions in the aqueous phase, were −97 and −146 kJ·mol–1. Kinetic analysis based on the computed free energy barriers reveal that warfarin will diffuse through the membranes within hours, in agreement with experimental results on warfarin’s accumulation in the plasma, thus suggesting a passive diffusion mechanism. We propose that this membrane transport may be an isomerization-driven process where warfarin adapts to the various local molecular environments encountered under its journey through the membrane. Collectively, these results improve our understanding of the influence of warfarin’s structural diversity on the drug’s distribution and bioavailability, which in turn may provide insights for developing new formulations of this important pharmaceutical to better address its narrow therapeutic window.

National Category
Chemical Sciences
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-24761 (URN)10.1021/jp400264x (DOI)000315707900018 ()23373529 (PubMedID)2-s2.0-84874640546 (Scopus ID)
Available from: 2013-03-12 Created: 2013-03-12 Last updated: 2018-11-02Bibliographically approved
Golker, K., Karlsson, B. C. G., Olsson, G. D., Rosengren, A. M. & Nicholls, I. A. (2013). Influence of composition and morphology on template recognition in molecularly imprinted polymers. Macromolecules, 46(4), 1408-1414
Open this publication in new window or tab >>Influence of composition and morphology on template recognition in molecularly imprinted polymers
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2013 (English)In: Macromolecules, ISSN 0024-9297, E-ISSN 1520-5835, Vol. 46, no 4, p. 1408-1414Article in journal (Refereed) Published
Abstract [en]

A combination of theoretical and experimental studies has provided correlations between molecularly imprinted polymer composition, morphology, and recognition behavior obtained using a series of bupivacaine-imprinted methacrylic acid (MAA)–ethylene glycol dimethacrylate copolymers differing in molar ratios of the respective monomers. Results extracted from analysis of molecular dynamics (MD) trajectory data demonstrated that stability and frequency of interactions between bupivacaine and the monomers in the prepolymerization phase were strongly affected by minor changes in polymer composition, which in turn affected binding site affinity and heterogeneity of the imprinted polymers. Moreover, through the characterization of polymer morphology, we show that higher molar fractions of MAA resulted in polymeric materials with increased pore size, a feature that enhanced the binding capacity of the polymers. Furthermore, the results presented point at the strength of MD for predicting MIP-template binding capacity and affinity.

National Category
Chemical Sciences
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-24758 (URN)10.1021/ma3024238 (DOI)000315618800019 ()2-s2.0-84874402610 (Scopus ID)
Available from: 2013-03-12 Created: 2013-03-12 Last updated: 2018-11-02Bibliographically approved
Nicholls, I. A., Andersson, H. S., Golker, K., Henschel, H., Karlsson, B. C. G., Olsson, G. D., . . . Wikman, S. (2013). Rational molecularly imprinted polymer design: theoretical and computational strategies. In: Ye, L (Ed.), Molecular Imprinting: Principles and Applications of Micro- and Nanostructured Polymers (pp. 71-104). London: Pan Stanford Publishing
Open this publication in new window or tab >>Rational molecularly imprinted polymer design: theoretical and computational strategies
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2013 (English)In: Molecular Imprinting: Principles and Applications of Micro- and Nanostructured Polymers / [ed] Ye, L, London: Pan Stanford Publishing, 2013, p. 71-104Chapter in book (Refereed)
Place, publisher, year, edition, pages
London: Pan Stanford Publishing, 2013
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
urn:nbn:se:lnu:diva-8867 (URN)2-s2.0-84974679377 (Scopus ID)9789814310994 (ISBN)
Available from: 2010-10-08 Created: 2010-10-08 Last updated: 2018-11-02Bibliographically approved
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ORCID iD: ORCID iD iconorcid.org/0000-0003-4037-1992

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