Trapping Hydrogen Sulfide (H(2)S) with Diselenides: The Application in the Design of Fluorescent Probes

[Image: see text] Here we report a unique reaction between phenyl diselenide-ester substrates and H(2)S 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...

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Autores principales: Peng, Bo, Zhang, Caihong, Marutani, Eizo, Pacheco, Armando, Chen, Wei, Ichinose, Fumito, Xian, Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4372083/
https://www.ncbi.nlm.nih.gov/pubmed/25723840
http://dx.doi.org/10.1021/acs.orglett.5b00431
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author Peng, Bo
Zhang, Caihong
Marutani, Eizo
Pacheco, Armando
Chen, Wei
Ichinose, Fumito
Xian, Ming
author_facet Peng, Bo
Zhang, Caihong
Marutani, Eizo
Pacheco, Armando
Chen, Wei
Ichinose, Fumito
Xian, Ming
author_sort Peng, Bo
collection PubMed
description [Image: see text] Here we report a unique reaction between phenyl diselenide-ester substrates and H(2)S 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 H(2)S 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 H(2)S. The presence of thiols was found not to interfere with the detection process.
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spelling pubmed-43720832016-02-27 Trapping Hydrogen Sulfide (H(2)S) with Diselenides: The Application in the Design of Fluorescent Probes Peng, Bo Zhang, Caihong Marutani, Eizo Pacheco, Armando Chen, Wei Ichinose, Fumito Xian, Ming Org Lett [Image: see text] Here we report a unique reaction between phenyl diselenide-ester substrates and H(2)S 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 H(2)S 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 H(2)S. The presence of thiols was found not to interfere with the detection process. American Chemical Society 2015-02-27 2015-03-20 /pmc/articles/PMC4372083/ /pubmed/25723840 http://dx.doi.org/10.1021/acs.orglett.5b00431 Text en Copyright © 2015 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Peng, Bo
Zhang, Caihong
Marutani, Eizo
Pacheco, Armando
Chen, Wei
Ichinose, Fumito
Xian, Ming
Trapping Hydrogen Sulfide (H(2)S) with Diselenides: The Application in the Design of Fluorescent Probes
title Trapping Hydrogen Sulfide (H(2)S) with Diselenides: The Application in the Design of Fluorescent Probes
title_full Trapping Hydrogen Sulfide (H(2)S) with Diselenides: The Application in the Design of Fluorescent Probes
title_fullStr Trapping Hydrogen Sulfide (H(2)S) with Diselenides: The Application in the Design of Fluorescent Probes
title_full_unstemmed Trapping Hydrogen Sulfide (H(2)S) with Diselenides: The Application in the Design of Fluorescent Probes
title_short Trapping Hydrogen Sulfide (H(2)S) with Diselenides: The Application in the Design of Fluorescent Probes
title_sort trapping hydrogen sulfide (h(2)s) with diselenides: the application in the design of fluorescent probes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4372083/
https://www.ncbi.nlm.nih.gov/pubmed/25723840
http://dx.doi.org/10.1021/acs.orglett.5b00431
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