Substrate-initiated synthesis of cell-penetrating poly(disulfide)s.
- Bang EK School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
- Gasparini G School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
- Molinard G School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
- Roux A School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
- Sakai N School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
- Matile S School of Chemistry and Biochemistry, University of Geneva, Geneva, Switzerland.
- 2013-02-01
Published in:
- Journal of the American Chemical Society. - 2013
Disulfides
Fluorescence Resonance Energy Transfer
Hydrogen-Ion Concentration
Molecular Structure
Polymerization
Polymers
Temperature
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.
- Language
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- English
- Open access status
- green
- Identifiers
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- DOI 10.1021/ja311961k
- PMID 23363440
- Persistent URL
- https://sonar.ch/global/documents/252767
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