A pH-triggered polymer degradation or drug delivery system by light-mediated Cis/Trans isomerization of o-hydroxy cinnamates
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hdl:2117/362014
Tipus de documentArticle
Data publicació2021-01-01
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Abstract
A new methodology for the pH-triggered degradation of polymers or for therelease of drugs under visible light irradiation based on the cyclization ofortho-hydroxy-cinnamates (oHC) to coumarins is described. The keyoHCstructural motif can be readily incorporated into the rational design of novelphotocleavable polymers via click chemistry. This main-chain moietyundergoes a fast photocleavage when irradiated with 455 nm light providedthat a suitable base is added. A series of polyethylene glycol-alt-ortho-hydroxycinnamate (polyethylene glycol (PEG)n-alt-oHC)-based polymers aresynthesized and the time-dependent visible-light initiated cleavage of thephotoactive monomer and polymer is investigated in solution by a variety ofspectroscopic and chromatographic techniques. The photo-degradationbehavior of the water-soluble poly(PEG2000-alt-oHC) is investigated within abroad 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, theneat polymer shows long-term stability under daylight conditions, thusallowing its storage without special precautions. In addition, twowater-soluble PEG-based drug-carrier molecules(mPEG2000-oHC-benzhydrol/phenol) are synthesized and used for drugdelivery studies, monitoring the process by UV–vis spectroscopy in anON/OFF intermittent manner.
CitacióAbramov, A. [et al.]. A pH-triggered polymer degradation or drug delivery system by light-mediated Cis/Trans isomerization of o-hydroxy cinnamates. "Macromolecular Rapid Communications", 1 Gener 2021, vol. 42, núm. 13, p. 2100213:1-2100213:6.
ISSN1521-3927
Versió de l'editorhttps://onlinelibrary.wiley.com/doi/10.1002/marc.202100213
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