Facile Synthesis of H2O2-Cleavable Poly(ester-amide)s by Passerini Multicomponent Polymerization

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• 作者：Yang Cui ; Mei Zhang ; Fu-Sheng DuZi-Chen Li
• 刊名：ACS Macro Letters
• 出版年：2017
• 出版时间：January 17, 2017
• 年：2017
• 卷：6
• 期：1
• 页码：11-15
• 全文大小：401K
• ISSN：2161-1653

文摘

We report the straightforward synthesis of two types of H₂O₂-cleavable poly(ester-amide)s (P1 and P2) via the Passerini multicomponent polymerization (P-MCP) of 4-formylbenzeneboronic acid pinacol ester with 1,6-diisocyanohexane and 1,6-hexanedioic acid or a polyethylene glycol (PEG) dicarboxylic acid. The H₂O₂-cleavable phenylboronic acid ester was integrated into the polymer backbone by the in situ formed benzyl ester bond. GPC and ¹H NMR confirmed the complete H₂O₂-triggered degradation of these polymers in aqueous medium by a mechanism of sequential oxidation of phenylboronic acid ester and self-immolative elimination. Compared with the hydrophobic polymer P1, the PEG-based water-soluble polymer P2 degraded much faster even at a lower H₂O₂ concentration. Cytocompatible nanoparticles of polymer P1 loaded with fluorescent Nile red were fabricated, and controlled release of Nile red in response to H₂O₂ was achieved, thus, demonstrating the utility of these polymers as potential H₂O₂-responsive delivery vehicles.