دورية أكاديمية
Release-Modulated Antioxidant Activity of a Composite Curcumin-Chitosan Polymer.
| العنوان: | Release-Modulated Antioxidant Activity of a Composite Curcumin-Chitosan Polymer. |
|---|---|
| المؤلفون: | O'Toole MG; Department of Bioengineering and ‡Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States., Soucy PA; Department of Bioengineering and ‡Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States., Chauhan R; Department of Bioengineering and ‡Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States., Raju MV; Department of Bioengineering and ‡Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States., Patel DN; Department of Bioengineering and ‡Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States., Nunn BM; Department of Bioengineering and ‡Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States., Keynton MA; Department of Bioengineering and ‡Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States., Ehringer WD; Department of Bioengineering and ‡Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States., Nantz MH; Department of Bioengineering and ‡Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States., Keynton RS; Department of Bioengineering and ‡Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States., Gobin AS; Department of Bioengineering and ‡Department of Chemistry, University of Louisville , Louisville, Kentucky 40292, United States. |
| المصدر: | Biomacromolecules [Biomacromolecules] 2016 Apr 11; Vol. 17 (4), pp. 1253-60. Date of Electronic Publication: 2016 Mar 04. |
| نوع المنشور: | Journal Article; Research Support, U.S. Gov't, Non-P.H.S. |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 100892849 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1526-4602 (Electronic) Linking ISSN: 15257797 NLM ISO Abbreviation: Biomacromolecules Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: Washington, DC : American Chemical Society, c2000- |
| مواضيع طبية MeSH: | Antioxidants/*pharmacology , Chitosan/*chemistry , Curcumin/*chemistry , Drug Carriers/*pharmacology , Polymers/*chemical synthesis, Carbonic Anhydrases/metabolism ; Drug Carriers/chemical synthesis ; Drug Carriers/chemistry ; Glucosamine/chemistry ; Mass Spectrometry ; Polymers/chemistry ; Spectrum Analysis |
| مستخلص: | Curcumin is known to have immense therapeutic potential but is hindered by poor solubility and rapid degradation in solution. To overcome these shortcomings, curcumin has been conjugated to chitosan through a pendant glutaric anhydride linker using amide bond coupling chemistry. The hybrid polymer has been characterized by UV-visible, fluorescence, and infrared spectroscopies as well as zeta potential measurements and SEM imaging. The conjugation reactivity was confirmed through gel permeation chromatography and quantification of unconjugated curcumin. An analogous reaction of curcumin with glucosamine, a small molecule analogue for chitosan, was performed and the purified product characterized by mass spectrometry, UV-visible, fluorescence, and infrared spectroscopies. Conjugation of curcumin to chitosan has greatly improved curcumin aqueous solubility and stability, with no significant curcumin degradation detected after one month in solution. The absorbance and fluorescence properties of curcumin are minimally perturbed (λmax shifts of 2 and 5 nm, respectively) by the conjugation reaction. This conjugation strategy required use of one out of two curcumin phenols (one of the main antioxidant functional groups) for covalent linkage to chitosan, thus temporarily attenuating its antioxidant capacity. Hydrolysis-based release of curcumin from the polymer, however, is accompanied by full restoration of curcumin's antioxidant potential. Antioxidant assays show that curcumin radical scavenging potential is reduced by 40% after conjugation, but that full antioxidant potential is restored upon hydrolytic release from chitosan. Release studies show that curcumin is released over 19 days from the polymer and maintains a concentration of 0.23 ± 0.12 μM curcumin/mg polymer/mL solution based on 1% curcumin loading on the polymer. Release studies in the presence of carbonic anhydrase, an enzyme with known phenolic esterase activity, show no significant difference from nonenzymatic release studies, implying that simple ester hydrolysis is the dominant release mechanism. Conjugation of curcumin to chitosan through a phenol ester modification provides improved stability and solubility to curcumin, with ester hydrolysis restoring the full antioxidant potential of curcumin. |
| المشرفين على المادة: | 0 (Antioxidants) 0 (Drug Carriers) 0 (Polymers) 9012-76-4 (Chitosan) EC 4.2.1.1 (Carbonic Anhydrases) IT942ZTH98 (Curcumin) N08U5BOQ1K (Glucosamine) |
| تواريخ الأحداث: | Date Created: 20160225 Date Completed: 20170109 Latest Revision: 20170110 |
| رمز التحديث: | 20231215 |
| DOI: | 10.1021/acs.biomac.5b01019 |
| PMID: | 26908114 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1526-4602 |
|---|---|
| DOI: | 10.1021/acs.biomac.5b01019 |