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

Kyeong Im Hong; Seong Min Lee; Woo Dong Jang

doi:10.1002/open.201700144

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

Kyeong Im Hong, Seong Min Lee, Woo Dong Jang

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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 ¹H NMR study indicated the reductive elimination of the p-toluenesulfonyl group from Ts-OF in the presence of antioxidants and photo-irradiation.

Original language	English
Pages (from-to)	57-60
Number of pages	4
Journal	ChemistryOpen
Volume	7
Issue number	1
DOIs	https://doi.org/10.1002/open.201700144
Publication status	Published - 2018 Jan

Bibliographical note

Funding Information:
This work was supported by the Mid-Career Researcher Program (2014R1A2A1A10051083) funded by the National Research Foundation (NRF) of Korea, Ministry of Science, ICT & Future, Korea.

All Science Journal Classification (ASJC) codes

Chemistry(all)

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title = "Flavin-Based Light-Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids",

abstract = "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 1H NMR study indicated the reductive elimination of the p-toluenesulfonyl group from Ts-OF in the presence of antioxidants and photo-irradiation.",

author = "Hong, {Kyeong Im} and Lee, {Seong Min} and Jang, {Woo Dong}",

note = "Funding Information: This work was supported by the Mid-Career Researcher Program (2014R1A2A1A10051083) funded by the National Research Foundation (NRF) of Korea, Ministry of Science, ICT & Future, Korea.",

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AB - 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 1H 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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