Polypeptides with quaternary phosphonium side chains: synthesis, characterization, and cell-penetrating properties.
Polypeptides with quaternary phosphonium side chains: synthesis, characterization, and cell-penetrating properties.
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DOI：
10.1021/bm5001026
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发表时间：
2014-04-14
影响因子：
6.2
通讯作者：
Cheng, Jianjun
中科院分区：
文献类型：
--
作者：
Song, Ziyuan;Zheng, Nan;Ba, Xiaochu;Yin, Lichen;Zhang, Rujing;Ma, Liang;Cheng, Jianjun
通过氯官能化的氨基酸N-羧酸酐单体的可控开环聚合，然后与三乙基膦进行一步亲核取代反应，合成了带有季鏻侧链的多肽。所得多肽的构象可以通过调节侧链长度和α-碳立体化学来控制。具有11 σ-键的主链-电荷距离的膦基聚谷氨酸衍生物具有稳定的α-螺旋构象，对pH和离子强度的变化。这些螺旋，季膦轴承多肽表现出更高的细胞穿透能力比其外消旋和随机卷曲类似物。它们主要通过非能量依赖性、非内吞性细胞膜转导机制进入细胞，并表现出低细胞毒性，证实了它们作为安全有效的细胞穿透剂的潜在用途。
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 α-carbon stereochemistry. The phosphonium-based poly(l-glutamate) derivatives with 11 σ-bond backbone-to-charge distance adopt stable α-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.
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影响因子：
16.6
作者：
Gabrielson, Nathan P.;Lu, Hua;Yin, Lichen;Li, Dong;Wang, Fei;Cheng, Jianjun
通讯作者：
Cheng, Jianjun
影响因子：
64.8
作者：
Deming, TJ
通讯作者：
Deming, TJ
影响因子：
7.3
作者：
Floch, V;Loisel, S;Férec, C
通讯作者：
Férec, C
影响因子：
14.8
作者：
Greenfield, Norma J.
通讯作者：
Greenfield, Norma J.
影响因子：
12.4
作者：
Gabrielson, Nathan P.;Lu, Hua;Cheng, Jianjun
通讯作者：
Cheng, Jianjun