Fluorophore-labeled S-nitrosothiols

Xi Chen, Z. Wen, M. Xian, K. Wang, N. Ramachandran, X. Tang, H. B. Schlegel, B. Mutus, P. G. Wang

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21 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)6064-6073
Number of pages10
JournalJournal of Organic Chemistry
Volume66
Issue number18
DOIs
Publication statusPublished - Sep 7 2001
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Chen, X., Wen, Z., Xian, M., Wang, K., Ramachandran, N., Tang, X., ... Wang, P. G. (2001). Fluorophore-labeled S-nitrosothiols. Journal of Organic Chemistry, 66(18), 6064-6073. https://doi.org/10.1021/jo015658p