Enzymatic Polymerization of an Ibuprofen-containing Monomer and Subsequent Drug Releasea
Novel ibuprofen-containing monomers comprised of naturally occurring and biocompatible compounds were synthesized and subsequently polymerized via enzymatic methods. Through the use of a malic acid sugar backbone, ibuprofen was attached as a pendant group, and then subsequently polymerized with a li...
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ftpubmed:oai:pubmedcentral.nih.gov:4534339 2023-05-15T13:38:11+02:00 Enzymatic Polymerization of an Ibuprofen-containing Monomer and Subsequent Drug Releasea Stebbins, Nicholas D. Yu, Weiling Uhrich, Kathryn E. 2015-04-16 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4534339/ http://www.ncbi.nlm.nih.gov/pubmed/25879779 https://doi.org/10.1002/mabi.201500030 en eng http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4534339/ http://www.ncbi.nlm.nih.gov/pubmed/25879779 http://dx.doi.org/10.1002/mabi.201500030 Article Text 2015 ftpubmed https://doi.org/10.1002/mabi.201500030 2016-08-07T00:08:45Z Novel ibuprofen-containing monomers comprised of naturally occurring and biocompatible compounds were synthesized and subsequently polymerized via enzymatic methods. Through the use of a malic acid sugar backbone, ibuprofen was attached as a pendant group, and then subsequently polymerized with a linear aliphatic diol (1,3-propanediol, 1,5-pentanediol or 1,8-octanediol) as comonomer using lipase B from Candida antarctica, a greener alternative to traditional metal catalysts. Polymer structures were elucidated by nuclear magnetic resonance and infrared spectroscopies, and thermal properties and molecular weights were determined. All polymers exhibited sustained ibuprofen release, with the longer chain, more hydrophobic diols exhibiting the slowest release over the 30 day study. Polymers were deemed cytocompatible using mouse fibroblasts, when evaluated at relevant therapeutic concentrations. Additionally, ibuprofen retained its chemical integrity throughout the polymerization and in vitro hydrolytic degradation processes. This methodology of enzymatic polymerization of a drug presents a more environmentally friendly synthesis and a novel approach to bioactive polymer conjugates. Text Antarc* Antarctica PubMed Central (PMC) Macromolecular Bioscience 15 8 1115 1124 |
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Article Stebbins, Nicholas D. Yu, Weiling Uhrich, Kathryn E. Enzymatic Polymerization of an Ibuprofen-containing Monomer and Subsequent Drug Releasea |
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Article |
description |
Novel ibuprofen-containing monomers comprised of naturally occurring and biocompatible compounds were synthesized and subsequently polymerized via enzymatic methods. Through the use of a malic acid sugar backbone, ibuprofen was attached as a pendant group, and then subsequently polymerized with a linear aliphatic diol (1,3-propanediol, 1,5-pentanediol or 1,8-octanediol) as comonomer using lipase B from Candida antarctica, a greener alternative to traditional metal catalysts. Polymer structures were elucidated by nuclear magnetic resonance and infrared spectroscopies, and thermal properties and molecular weights were determined. All polymers exhibited sustained ibuprofen release, with the longer chain, more hydrophobic diols exhibiting the slowest release over the 30 day study. Polymers were deemed cytocompatible using mouse fibroblasts, when evaluated at relevant therapeutic concentrations. Additionally, ibuprofen retained its chemical integrity throughout the polymerization and in vitro hydrolytic degradation processes. This methodology of enzymatic polymerization of a drug presents a more environmentally friendly synthesis and a novel approach to bioactive polymer conjugates. |
format |
Text |
author |
Stebbins, Nicholas D. Yu, Weiling Uhrich, Kathryn E. |
author_facet |
Stebbins, Nicholas D. Yu, Weiling Uhrich, Kathryn E. |
author_sort |
Stebbins, Nicholas D. |
title |
Enzymatic Polymerization of an Ibuprofen-containing Monomer and Subsequent Drug Releasea |
title_short |
Enzymatic Polymerization of an Ibuprofen-containing Monomer and Subsequent Drug Releasea |
title_full |
Enzymatic Polymerization of an Ibuprofen-containing Monomer and Subsequent Drug Releasea |
title_fullStr |
Enzymatic Polymerization of an Ibuprofen-containing Monomer and Subsequent Drug Releasea |
title_full_unstemmed |
Enzymatic Polymerization of an Ibuprofen-containing Monomer and Subsequent Drug Releasea |
title_sort |
enzymatic polymerization of an ibuprofen-containing monomer and subsequent drug releasea |
publishDate |
2015 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4534339/ http://www.ncbi.nlm.nih.gov/pubmed/25879779 https://doi.org/10.1002/mabi.201500030 |
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Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4534339/ http://www.ncbi.nlm.nih.gov/pubmed/25879779 http://dx.doi.org/10.1002/mabi.201500030 |
op_doi |
https://doi.org/10.1002/mabi.201500030 |
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Macromolecular Bioscience |
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15 |
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8 |
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1115 |
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1124 |
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1766102322012749824 |