Trapping hydrogen sulfide (H₂S) with diselenides: the application in the design of fluorescent probes.
Here we report a unique reaction between phenyl diselenide-ester substrates and H2S to form 1,2-benzothiaselenol-3-one. This reaction proceeded rapidly under mild conditions. Thiols could also react with the diselenide substrates. However, the resulted S-Se intermediate retained high reactivity toward H2S and eventually led to the same cyclized product 1,2-benzothiaselenol-3-one. Based on this reaction two fluorescent probes were developed and showed high selectivity and sensitivity for H2S. The presence of thiols was found not to interfere with the detection process.
†Department of Chemistry, Washington State University, Pullman, Washington 99164, United States.
Bo
B
Peng
†Department of Chemistry, Washington State University, Pullman, Washington 99164, United States.|‡School of Chemistry and Chemical Engineering, Center of Environmental Science and Engineering Research, Shanxi University, Taiyuan, China.
Caihong
C
Zhang
§Department of Anesthesia, Critical Care and Pain Medicine, Massachusetts General Hospital and Harvard Medical School, Boston, Massachusetts 02114, United States.
Eizo
E
Marutani
†Department of Chemistry, Washington State University, Pullman, Washington 99164, United States.
Armando
A
Pacheco
†Department of Chemistry, Washington State University, Pullman, Washington 99164, United States.
Wei
W
Chen
§Department of Anesthesia, Critical Care and Pain Medicine, Massachusetts General Hospital and Harvard Medical School, Boston, Massachusetts 02114, United States.
Fumito
F
Ichinose
†Department of Chemistry, Washington State University, Pullman, Washington 99164, United States.
Ming
M
Xian
D003500:Cyclization; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006862:Hydrogen Sulfide / Q000737:chemistry*; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry
C000600430:1,2-benzothiaselenol-3-one; D005456:Fluorescent Dyes; D016566:Organoselenium Compounds; D013438:Sulfhydryl Compounds; D006862:Hydrogen Sulfide