Trapping hydrogen sulfide (H₂S) with diselenides: the application in the design of fluorescent probes

Bo Peng; Caihong Zhang; Eizo Marutani; Armando Pacheco; Wei Chen; Fumito Ichinose; Ming Xian

doi:10.1021/acs.orglett.5b00431

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Trapping hydrogen sulfide (H₂S) with diselenides: the application in the design of fluorescent probes

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Trapping hydrogen sulfide (H₂S) with diselenides: the application in the design of fluorescent probes

Bo Peng, Caihong Zhang, Eizo Marutani, Armando Pacheco, Wei Chen, Fumito Ichinose and Ming Xian

Organic letters, Vol.17(6), pp.1541-1544

03/20/2015

DOI: https://doi.org/10.1021/acs.orglett.5b00431

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https://hdl.handle.net/2376/113764

PMCID: PMC4372083

PMID: 25723840

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https://doi.org/10.1021/acs.orglett.5b00431View

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Abstract

Fluorescent Dyes - chemical synthesis

Fluorescent Dyes - chemistry

Organoselenium Compounds - chemical synthesis

Cyclization

Hydrogen Sulfide - chemistry

Sulfhydryl Compounds - chemistry

Molecular Structure

Organoselenium Compounds - chemistry

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.

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Title: Trapping hydrogen sulfide (H₂S) with diselenides: the application in the design of fluorescent probes
Creators: Bo Peng - †Department of Chemistry, Washington State University, Pullman, Washington 99164, United States
Caihong Zhang - ‡School of Chemistry and Chemical Engineering, Center of Environmental Science and Engineering Research, Shanxi University, Taiyuan, China
Eizo Marutani - §Department of Anesthesia, Critical Care and Pain Medicine, Massachusetts General Hospital and Harvard Medical School, Boston, Massachusetts 02114, United States
Armando Pacheco - †Department of Chemistry, Washington State University, Pullman, Washington 99164, United States
Wei Chen - †Department of Chemistry, Washington State University, Pullman, Washington 99164, United States
Fumito Ichinose - §Department of Anesthesia, Critical Care and Pain Medicine, Massachusetts General Hospital and Harvard Medical School, Boston, Massachusetts 02114, United States
Ming Xian - †Department of Chemistry, Washington State University, Pullman, Washington 99164, United States
Publication Details: Organic letters, Vol.17(6), pp.1541-1544
Academic Unit: Biological Systems Engineering, Department of; Chemistry, Department of
Publisher: United States
Grant note: R01 HL116571 / NHLBI NIH HHS R01 HL101930 / NHLBI NIH HHS R01HL101930 / NHLBI NIH HHS R01HL116571 / NHLBI NIH HHS
Identifiers: 99900547771401842
Language: English
Resource Type: Journal article