Open AccessHydrogen Sulfide Mediated Tandem Reaction of Selenenyl Sulfides and Its Application in Fluorescent Probe Development
Author(s) -
Yingying Wang,
Jinbao Liu,
Shi Xu,
Wei Chen,
Ming Xian
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b02844
Subject(s) - chemistry , hydrogen sulfide , fluorescence , cysteine , sulfide , tandem , cleavage (geology) , selectivity , combinatorial chemistry , bond cleavage , photochemistry , sulfur , organic chemistry , catalysis , enzyme , physics , materials science , geotechnical engineering , quantum mechanics , fracture (geology) , engineering , composite material
A unique reaction between H 2 S and a selenenyl sulfide containing benzoate ester template was discovered. This reaction could be specifically triggered by H 2 S and lead to ester bond cleavage. The reaction was not affected by the presence of thiols such as glutathione and cysteine. With this reaction, a series of fluorescent probes were synthesized and evaluated. The probes exhibited high sensitivity/selectivity for H 2 S in both buffers and cells.