Abramov, Alex and Maiti, Binoy and Keridou, Ina and Puiggali, Jordi and Reiser, Oliver and Diaz Diaz, David (2021) A pH-Triggered Polymer Degradation or Drug Delivery System by Light-Mediated Cis/Trans Isomerization of o-Hydroxy Cinnamates. MACROMOLECULAR RAPID COMMUNICATIONS, 42 (13): 2100213. ISSN 1022-1336, 1521-3927
Full text not available from this repository. (Request a copy)Abstract
A new methodology for the pH-triggered degradation of polymers or for the release of drugs under visible light irradiation based on the cyclization of ortho-hydroxy-cinnamates (oHC) to coumarins is described. The key oHC structural motif can be readily incorporated into the rational design of novel photocleavable polymers via click chemistry. This main-chain moiety undergoes a fast photocleavage when irradiated with 455 nm light provided that a suitable base is added. A series of polyethylene glycol-alt-ortho-hydroxy cinnamate (polyethylene glycol (PEG)(n)-alt-oHC)-based polymers are synthesized and the time-dependent visible-light initiated cleavage of the photoactive monomer and polymer is investigated in solution by a variety of spectroscopic and chromatographic techniques. The photo-degradation behavior of the water-soluble poly(PEG(2000)-alt-oHC) is investigated within a broad pH range (pH = 2.1-11.8), demonstrating fast degradation at pH 11.8, while the stability of the polymer is greatly enhanced at pH 2.1. Moreover, the neat polymer shows long-term stability under daylight conditions, thus allowing its storage without special precautions. In addition, two water-soluble PEG-based drug-carrier molecules (mPEG(2000)-oHC-benzhydrol/phenol) are synthesized and used for drug delivery studies, monitoring the process by UV-vis spectroscopy in an ON/OFF intermittent manner.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | COUMARIN DERIVATIVES; ANTIOXIDANT ACTIVITY; RESPONSIVE POLYMERS; PARTICLES; ANTITUMOR; HYDROGELS; FILMS; coumarins; drug delivery; E/Z-double bond isomerization; o-hydroxy cinnamates; polymer degradation; visible light photocatalysis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. David Díaz Díaz |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Sep 2022 09:49 |
| Last Modified: | 14 Sep 2022 09:49 |
| URI: | https://pred.uni-regensburg.de/id/eprint/47458 |
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