Substrate-initiated synthesis of cell-penetrating poly(disulfide)s.
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Bang EK
School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
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Gasparini G
School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
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Molinard G
School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
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Roux A
School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
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Sakai N
School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
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Matile S
School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
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Published in:
- Journal of the American Chemical Society. - 2013
English
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.
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Language
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Open access status
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green
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Persistent URL
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https://folia.unifr.ch/global/documents/252767
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