Enzymatic Polymerization of an Ibuprofen‐Containing Monomer and Subsequent Drug Release
Novel ibuprofen-containing monomers comprising 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 line...
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ftcdlib:oai:escholarship.org:ark:/13030/qt30t0z8c4 2023-11-05T03:36:03+01:00 Enzymatic Polymerization of an Ibuprofen‐Containing Monomer and Subsequent Drug Release Stebbins, Nicholas D Yu, Weiling Uhrich, Kathryn E 1115 - 1124 2015-08-01 application/pdf https://escholarship.org/uc/item/30t0z8c4 unknown eScholarship, University of California qt30t0z8c4 https://escholarship.org/uc/item/30t0z8c4 public Macromolecular Bioscience, vol 15, iss 8 Macromolecular and Materials Chemistry Chemical Sciences Animals Drug Liberation Fibroblasts Fungal Proteins Ibuprofen Lipase Magnetic Resonance Spectroscopy Mice Polymerization Propylene Glycols biodegradable drug delivery systems enzymes polyesters renewable resources Biomedical Engineering Chemical Engineering Polymers article 2015 ftcdlib 2023-10-09T18:06:18Z Novel ibuprofen-containing monomers comprising 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 d 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. Article in Journal/Newspaper Antarc* Antarctica University of California: eScholarship |
institution |
Open Polar |
collection |
University of California: eScholarship |
op_collection_id |
ftcdlib |
language |
unknown |
topic |
Macromolecular and Materials Chemistry Chemical Sciences Animals Drug Liberation Fibroblasts Fungal Proteins Ibuprofen Lipase Magnetic Resonance Spectroscopy Mice Polymerization Propylene Glycols biodegradable drug delivery systems enzymes polyesters renewable resources Biomedical Engineering Chemical Engineering Polymers |
spellingShingle |
Macromolecular and Materials Chemistry Chemical Sciences Animals Drug Liberation Fibroblasts Fungal Proteins Ibuprofen Lipase Magnetic Resonance Spectroscopy Mice Polymerization Propylene Glycols biodegradable drug delivery systems enzymes polyesters renewable resources Biomedical Engineering Chemical Engineering Polymers Stebbins, Nicholas D Yu, Weiling Uhrich, Kathryn E Enzymatic Polymerization of an Ibuprofen‐Containing Monomer and Subsequent Drug Release |
topic_facet |
Macromolecular and Materials Chemistry Chemical Sciences Animals Drug Liberation Fibroblasts Fungal Proteins Ibuprofen Lipase Magnetic Resonance Spectroscopy Mice Polymerization Propylene Glycols biodegradable drug delivery systems enzymes polyesters renewable resources Biomedical Engineering Chemical Engineering Polymers |
description |
Novel ibuprofen-containing monomers comprising 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 d 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 |
Article in Journal/Newspaper |
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 Release |
title_short |
Enzymatic Polymerization of an Ibuprofen‐Containing Monomer and Subsequent Drug Release |
title_full |
Enzymatic Polymerization of an Ibuprofen‐Containing Monomer and Subsequent Drug Release |
title_fullStr |
Enzymatic Polymerization of an Ibuprofen‐Containing Monomer and Subsequent Drug Release |
title_full_unstemmed |
Enzymatic Polymerization of an Ibuprofen‐Containing Monomer and Subsequent Drug Release |
title_sort |
enzymatic polymerization of an ibuprofen‐containing monomer and subsequent drug release |
publisher |
eScholarship, University of California |
publishDate |
2015 |
url |
https://escholarship.org/uc/item/30t0z8c4 |
op_coverage |
1115 - 1124 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Macromolecular Bioscience, vol 15, iss 8 |
op_relation |
qt30t0z8c4 https://escholarship.org/uc/item/30t0z8c4 |
op_rights |
public |
_version_ |
1781690741268938752 |