Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids

We have synthesized a flavin‐N(5)‐oxide derivative with a p‐toluenesulfonyl (Ts‐OF) group as a “turn‐on” fluorescent probe for the detection of several antioxidant amino acids and biothiols. Oxidized flavin was synthesized by using dithiothreitol as the reducing agent. Ts‐OF showed a light‐driven fl...

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Detalles Bibliográficos
Autores principales: Hong, Kyeong‐Im, Lee, Seong Min, Jang, Woo‐Dong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5754558/
https://www.ncbi.nlm.nih.gov/pubmed/29318097
http://dx.doi.org/10.1002/open.201700144
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author Hong, Kyeong‐Im
Lee, Seong Min
Jang, Woo‐Dong
author_facet Hong, Kyeong‐Im
Lee, Seong Min
Jang, Woo‐Dong
author_sort Hong, Kyeong‐Im
collection PubMed
description We have synthesized a flavin‐N(5)‐oxide derivative with a p‐toluenesulfonyl (Ts‐OF) group as a “turn‐on” fluorescent probe for the detection of several antioxidant amino acids and biothiols. Oxidized flavin was synthesized by using dithiothreitol as the reducing agent. Ts‐OF showed a light‐driven fluorescence enhancement in the presence of several amino acids and biothiols such as histidine (His), methionine (Met), cysteine (Cys), glutathione (GSH), and homocysteine (Hcy). The (1)H NMR study indicated the reductive elimination of the p‐toluenesulfonyl group from Ts‐OF in the presence of antioxidants and photo‐irradiation.
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spelling pubmed-57545582018-01-09 Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids Hong, Kyeong‐Im Lee, Seong Min Jang, Woo‐Dong ChemistryOpen Communications We have synthesized a flavin‐N(5)‐oxide derivative with a p‐toluenesulfonyl (Ts‐OF) group as a “turn‐on” fluorescent probe for the detection of several antioxidant amino acids and biothiols. Oxidized flavin was synthesized by using dithiothreitol as the reducing agent. Ts‐OF showed a light‐driven fluorescence enhancement in the presence of several amino acids and biothiols such as histidine (His), methionine (Met), cysteine (Cys), glutathione (GSH), and homocysteine (Hcy). The (1)H NMR study indicated the reductive elimination of the p‐toluenesulfonyl group from Ts‐OF in the presence of antioxidants and photo‐irradiation. John Wiley and Sons Inc. 2017-11-16 /pmc/articles/PMC5754558/ /pubmed/29318097 http://dx.doi.org/10.1002/open.201700144 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Hong, Kyeong‐Im
Lee, Seong Min
Jang, Woo‐Dong
Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids
title Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids
title_full Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids
title_fullStr Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids
title_full_unstemmed Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids
title_short Flavin‐Based Light‐Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids
title_sort flavin‐based light‐driven fluorescent probe for the detection of antioxidant amino acids
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5754558/
https://www.ncbi.nlm.nih.gov/pubmed/29318097
http://dx.doi.org/10.1002/open.201700144
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