UNIGE document Scientific Article
previous document  unige:73190  next document
add to browser collection
Title

Ring Tension Applied to Thiol-Mediated Cellular Uptake

Authors
Published in Angewandte Chemie: International Edition. 2015, vol. 54, no. 25, p. 7328-7331
Abstract The objective of the study was to explore the potential of ring tension in cyclic disulfides for thiol-mediated cellular uptake. Fluorescent probes that cannot enter cells were equipped with cyclic disulfides of gradually increasing ring tension. As demonstrated by flow cytometry experiments, uptake into HeLa Kyoto cells increased with increasing tension. Differences in carbon-sulfur-sulfur-carbon (CSSC) dihedral angles as small as 8° caused significant changes in uptake efficiency. Uptake with high ring tension was better than with inactivated or activated linear disulfides or with thiols. Conversion of thiols on the cell surface into sulfides and disulfides decreased the uptake. Reduction of exofacial disulfides into thiols increased the uptake of transporters with disulfides and inactivated controls with thiols. These results confirm the occurrence of dynamic covalent disulfide-exchange chemistry on cell surfaces. Mechanistic and colocalization studies indicate that endocytosis does not fully account for this cellular uptake with ring tension.
Keywords Cell-penetrating peptidesCellular uptakeDihedral anglesDisulfidesRing tension
Identifiers
Full text
Article (Published version) (1.5 MB) - document accessible for UNIGE members only Limited access to UNIGE
Structures
Citation
(ISO format)
GASPARINI, Giulio et al. Ring Tension Applied to Thiol-Mediated Cellular Uptake. In: Angewandte Chemie: International Edition, 2015, vol. 54, n° 25, p. 7328-7331. https://archive-ouverte.unige.ch/unige:73190

239 hits

0 download

Update

Deposited on : 2015-06-15

Export document
Format :
Citation style :