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An Artificial Estrogen Receptor through Combinatorial Imprinting
Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences. (BBCL)ORCID iD: 0000-0003-4037-1992
Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences. (BBCL)ORCID iD: 0000-0002-0407-6542
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2012 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 46, 14773-14783 p.Article in journal (Refereed) Published
Abstract [en]

Polymeric sorbents targeting endocrine-disrupting estrogen active compounds (EAC) were prepared by terpolymer imprinting using 17 beta-estradiol (E2) as template. From a group of eight functional monomers representing Bronsted acids, bases, hydrogen-bond donors and acceptors, as well as pi-interacting monomers, a terpolymer library that comprises all possible binary combinations of the functional monomers was prepared. Binding tests revealed that imprinted polymers exhibit a markedly higher affinity for E2 compared to nonimprinted polymers (NIPs) or polymers prepared by using single functional monomers. A combination of methacrylic acid (MAA) and p-vinylbenzoic acid offered a particularly promising lead polymer, displaying an imprinting factor of 17 versus 2.4 for a benchmark polymer prepared by using only MAA as functional monomer. The saturation capacities ascribed to imprinted sites were four to five times higher for this polymer compared to previously reported imprinted polymers. NMR titrations and molecular dynamics simulations corroborated these results, indicating an orthogonal preference of the two functional monomers with respect to the E2 3-OH and 17-OH groups. The optimized polymer exhibited a retentivity for EACs that correlates with their inhibitory effect on the natural receptor. By using the optimized molecularly imprinted polymers (MIPs) in a model water-purification system, they were capable of completely removing ppb levels of a small group of EACs from water. This is in contrast to the performance of nonimprinted polymers and well-established sorbents for water purification (e.g., active carbon), which still contained detectable amounts of the compounds after treatment.

Place, publisher, year, edition, pages
2012. Vol. 18, no 46, 14773-14783 p.
Keyword [en]
endocrine disruptor, estrogen, imprinting, receptors, recognition, water treatment
National Category
Organic Chemistry
Research subject
Chemistry, Organic Chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-22792DOI: 10.1002/chem.201201428ISI: 000310800200028OAI: oai:DiVA.org:lnu-22792DiVA: diva2:576104
Available from: 2012-12-12 Created: 2012-12-12 Last updated: 2017-02-07Bibliographically approved

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Olsson, Gustaf D.Nicholls, Ian A.
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CiteExportLink to record
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