Polypeptides with Quaternary Phosphonium Side Chains: Synthesis, Characterization, and Cell-Penetrating Properties

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• 作者：Ziyuan Song ; Nan Zheng ; Xiaochu Ba ; Lichen Yin ; Rujing Zhang ; Liang Ma ; Jianjun Cheng
• 刊名：Biomacromolecules
• 出版年：2014
• 出版时间：April 14, 2014
• 年：2014
• 卷：15
• 期：4
• 页码：1491-1497
• 全文大小：385K
• 年卷期：v.15,no.4(April 14, 2014)
• ISSN：1526-4602

文摘

Polypeptides bearing quaternary phosphonium side chains were synthesized via controlled ring-opening polymerization of chlorine-functionalized amino acid N-carboxyanhydride monomers followed by one-step nucleophilic substitution reaction with triethylphosphine. The conformation of the resulting polypeptides can be controlled by modulating the side-chain length and 伪-carbon stereochemistry. The phosphonium-based poly(l-glutamate) derivatives with 11 蟽-bond backbone-to-charge distance adopt stable 伪-helical conformation against pH and ionic strength changes. These helical, quaternary phosphonium-bearing polypeptides exhibit higher cell-penetrating capability than their racemic and random-coiled analogues. They enter cells mainly via an energy-independent, nonendocytic cell membrane transduction mechanism and exhibit low cytotoxicity, substantiating their potential use as a safe and effective cell-penetrating agent.