Cysteine-specific blue fluorescence probe

Gondi Sudershan Reddy; Hsuan Ying Chen; I. Jy Chang

doi:10.1002/jccs.200600174

Cysteine-specific blue fluorescence probe

Gondi Sudershan Reddy, Hsuan Ying Chen, I. Jy Chang

Department of Chemistry

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

2 Citations (Scopus)

Abstract

A strong fluorescence probe has been designed to investigate cytochrome c folding kinetics. The cysteine specific modifier, 2-[(-Iodo-acetyl)-methyl- amino]-6-methylaminobenzoic acid methyl ester (1), has been prepared, and the reaction with cysteine can be performed in aqueous solution to ensure its application to protein modification. The model compound, 2-{[2-(2-Acetylamino-2- methyoxycarbonylethylsulfanyl)-acetyl]-methyl-amino}-6-methyl amino-benzoic acid methyl ester (2), resulting from the reaction of 1 with N-acetyl cysteine has emission quantum yields of 0.627 and 0.185 in nonaqueous and aqueous buffer solutions, respectively. The lifetime of 4.6 ns for compound 2 manifests a singlet excited-state. The Förster energy transfer distance of compound 2 and cytochrome c is calculated to be 45 Å.

Original language	English
Pages (from-to)	1303-1308
Number of pages	6
Journal	Journal of the Chinese Chemical Society
Volume	53
Issue number	6
DOIs	https://doi.org/10.1002/jccs.200600174
Publication status	Published - 2006 Jan 1

Keywords

Cysteine-specific
Energy-transfer
Fluorescence
Heme protein

ASJC Scopus subject areas

Chemistry(all)

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10.1002/jccs.200600174

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title = "Cysteine-specific blue fluorescence probe",

abstract = "A strong fluorescence probe has been designed to investigate cytochrome c folding kinetics. The cysteine specific modifier, 2-[(-Iodo-acetyl)-methyl- amino]-6-methylaminobenzoic acid methyl ester (1), has been prepared, and the reaction with cysteine can be performed in aqueous solution to ensure its application to protein modification. The model compound, 2-{[2-(2-Acetylamino-2- methyoxycarbonylethylsulfanyl)-acetyl]-methyl-amino}-6-methyl amino-benzoic acid methyl ester (2), resulting from the reaction of 1 with N-acetyl cysteine has emission quantum yields of 0.627 and 0.185 in nonaqueous and aqueous buffer solutions, respectively. The lifetime of 4.6 ns for compound 2 manifests a singlet excited-state. The F{\"o}rster energy transfer distance of compound 2 and cytochrome c is calculated to be 45 {\AA}.",

keywords = "Cysteine-specific, Energy-transfer, Fluorescence, Heme protein",

author = "Reddy, {Gondi Sudershan} and Chen, {Hsuan Ying} and Chang, {I. Jy}",

year = "2006",

month = jan,

day = "1",

doi = "10.1002/jccs.200600174",

language = "English",

volume = "53",

pages = "1303--1308",

journal = "Journal of the Chinese Chemical Society",

issn = "0009-4536",

publisher = "Chinese Chemical Society",

number = "6",

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TY - JOUR

T1 - Cysteine-specific blue fluorescence probe

AU - Reddy, Gondi Sudershan

AU - Chen, Hsuan Ying

AU - Chang, I. Jy

PY - 2006/1/1

Y1 - 2006/1/1

N2 - A strong fluorescence probe has been designed to investigate cytochrome c folding kinetics. The cysteine specific modifier, 2-[(-Iodo-acetyl)-methyl- amino]-6-methylaminobenzoic acid methyl ester (1), has been prepared, and the reaction with cysteine can be performed in aqueous solution to ensure its application to protein modification. The model compound, 2-{[2-(2-Acetylamino-2- methyoxycarbonylethylsulfanyl)-acetyl]-methyl-amino}-6-methyl amino-benzoic acid methyl ester (2), resulting from the reaction of 1 with N-acetyl cysteine has emission quantum yields of 0.627 and 0.185 in nonaqueous and aqueous buffer solutions, respectively. The lifetime of 4.6 ns for compound 2 manifests a singlet excited-state. The Förster energy transfer distance of compound 2 and cytochrome c is calculated to be 45 Å.

AB - A strong fluorescence probe has been designed to investigate cytochrome c folding kinetics. The cysteine specific modifier, 2-[(-Iodo-acetyl)-methyl- amino]-6-methylaminobenzoic acid methyl ester (1), has been prepared, and the reaction with cysteine can be performed in aqueous solution to ensure its application to protein modification. The model compound, 2-{[2-(2-Acetylamino-2- methyoxycarbonylethylsulfanyl)-acetyl]-methyl-amino}-6-methyl amino-benzoic acid methyl ester (2), resulting from the reaction of 1 with N-acetyl cysteine has emission quantum yields of 0.627 and 0.185 in nonaqueous and aqueous buffer solutions, respectively. The lifetime of 4.6 ns for compound 2 manifests a singlet excited-state. The Förster energy transfer distance of compound 2 and cytochrome c is calculated to be 45 Å.

KW - Cysteine-specific

KW - Energy-transfer

KW - Fluorescence

KW - Heme protein

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DO - 10.1002/jccs.200600174

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JO - Journal of the Chinese Chemical Society

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Cysteine-specific blue fluorescence probe

Abstract

Keywords

ASJC Scopus subject areas

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