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

Contributors

Bang, Eun Kyoung; Gasparini, Giulio; Molinard, Guillaume; Roux, Aurélien; Sakai, Naomi; Matile, Stefan

Published in

Journal of the American Chemical Society, vol. 135, no. 6, p. 2088-2091

Publication date

2013

Abstract

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.

UNIGE affiliation entities

Citation (ISO format)

BANG, Eun Kyoung et al. Substrate-Initiated Synthesis of Cell-Penetrating Poly(disulfide)s. In: Journal of the American Chemical Society, 2013, vol. 135, n° 6, p. 2088–2091. doi: 10.1021/ja311961k

Main files (2)

Article (Published version)
Article (Accepted version)
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Identifiers

Journal ISSN

0002-7863
739views
321downloads

Technical informations

Creation

13/02/2013 09:16:00

First validation

13/02/2013 09:16:00

Update

13/10/2025 23:42:47

Status update

14/03/2023 20:03:11

Last indexation

16/02/2026 06:56:54
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