| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1401959 | European Polymer Journal | 2013 | 8 Pages |
•Selective transformation of PHB crotonate into PHB glyoxylate via ozonolysis.•Model drug delivery system – conjugate of PHB glyoxylate with primary amine.•pH-controlled release of amine from the model conjugate.
Synthetic route to prepare model PHB-amine conjugate containing hydrolysable imine bond is reported. Short-chain PHB crotonate is converted into PHB glyoxylate via clean and efficient ozonolysis followed by reductive decomposition of peroxidic products with dimethylsulfide. Aldehyde-functionalized PHB is obtained quantitatively without polymer backbone degradation while PHB-amine conjugate is synthesized with very high yield. Release properties of such-prepared conjugate is confirmed in hydrolysis experiment revealing pH-dependent kinetics of amine release. Simplicity of the protocol in conjunction with unique properties of PHB carrier are believed to be powerful tool for development of novel drug conjugates.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
