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

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• 作者：Eun-Kyoung Bang ; Giulio Gasparini ; Guillaume Molinard ; Aur茅lien Roux ; Naomi Sakai ; Stefan Matile
• 刊名：The Journal of the American Chemical Society
• 出版年：2013
• 出版时间：February 13, 2013
• 年：2013
• 卷：135
• 期：6
• 页码：2088-2091
• 全文大小：253K
• 年卷期：v.135,no.6(February 13, 2013)
• ISSN：1520-5126

文摘

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.