Journal article
Fluorophore-Labeled S-Nitrosothiols
Journal of organic chemistry, Vol.66(18), pp.6064-6073
09/07/2001
Handle:
https://hdl.handle.net/2376/116211
PMID: 11529732
Abstract
A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the “overlap” between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.
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Details
- Title
- Fluorophore-Labeled S-Nitrosothiols
- Creators
- Xinchao ChenZhong WenMing XianKun WangNiroshan RamachandranXiaoping TangH. Bernhard SchlegelBulent MutusPeng George Wang
- Publication Details
- Journal of organic chemistry, Vol.66(18), pp.6064-6073
- Academic Unit
- Chemistry, Department of
- Publisher
- American Chemical Society
- Identifiers
- 99900548267401842
- Language
- English
- Resource Type
- Journal article