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

1 Citation (Scopus)

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.

Publisher Copyright:
© 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

All Science Journal Classification (ASJC) codes

Chemistry(all)

Access to Document

10.1002/open.201700144

Cite this

@article{cf9668dd04b54987a1ca726c388b8d07,

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. Publisher Copyright: {\textcopyright} 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.",

year = "2018",

month = jan,

doi = "10.1002/open.201700144",

language = "English",

volume = "7",

pages = "57--60",

journal = "ChemistryOpen",

issn = "2191-1363",

publisher = "John Wiley and Sons Inc.",

number = "1",

}

TY - JOUR

T1 - Flavin-Based Light-Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids

AU - Hong, Kyeong Im

AU - Lee, Seong Min

AU - Jang, Woo Dong

N1 - 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. Publisher Copyright: © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

PY - 2018/1

Y1 - 2018/1

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85034078700&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85034078700&partnerID=8YFLogxK

U2 - 10.1002/open.201700144

DO - 10.1002/open.201700144

M3 - Article

AN - SCOPUS:85034078700

VL - 7

SP - 57

EP - 60

JO - ChemistryOpen

JF - ChemistryOpen

SN - 2191-1363

IS - 1

ER -

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

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this