Substrate-Initiated Synthesis of Cell-Penetrating Poly(disulfide)s

被引：200

作者：

Bang, Eun-Kyoung ^{[1
]}

Gasparini, Giulio ^{[1
]}

Molinard, Guillaume ^{[1
]}

Roux, Aurelien ^{[1
]}

Sakai, Naomi ^{[1
]}

Matile, Stefan ^{[1
]}

机构：

[1] Univ Geneva, Sch Chem & Biochem, Geneva, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 06期

基金：

欧洲研究理事会;

关键词：

TRANSDUCTION DOMAIN MIMICS; STACK EXCHANGE; DELIVERY; PEPTIDES; POLYMERS; POLYMERIZATION; TRANSLOCATION; PROTEINS; DESIGN; PORES;

D O I：

10.1021/ja311961k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lessons from surface-initiated polymerization are applied to grow cell-penetrating poly(disulfide)s directly on substrates of free choice. Reductive depolymerization after cellular uptake should then release the native substrates and minimize toxicity. In the presence of thiolated substrates, propagators containing a strained disulfide from asparagusic or, preferably, lipoic acid and a guanidinium cation polymerize into poly(disulfide)s in less than 5 min at room temperature at pH 7. Substrate-initiated polymerization of cationic poly(disulfide)s and their depolymerization with dithiothreitol causes the appearance and disappearance of transport activity in fluorogenic vesicles. The same process is further characterized by gel-permeation chromatography and fluorescence resonance energy transfer.

引用

页码：2088 / 2091

页数：4

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