Synthesis of coumarin conjugates of biological thiols for fluorescent detection and estimation

Alan R. Katritzky; Tarek S. Ibrahim; Srinivasa R. Tala; Nader E. Abo-Dya; Zakaria K. Abdel-Samii; Said A. El-Feky

doi:10.1055/s-0030-1259991

Synthesis of coumarin conjugates of biological thiols for fluorescent detection and estimation

Alan R. Katritzky, Tarek S. Ibrahim, Srinivasa R. Tala, Nader E. Abo-Dya, Zakaria K. Abdel-Samii, Said A. El-Feky

Medicinal Chemistry

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18 Scopus citations

Abstract

Coumarin-labeled thioesters are efficiently prepared from biological thiols using N-coumarin-3-carbonyl benzotriazoles. Absorption (λ_abs) , fluorescence (λ_em) wavelength maxima and quantum yields (φ) for the thioesters are measured in buffer solution at physiological pH 7.4. Quantum yields (φ = 0.0318-0.1068) of four of the products are higher than their precursor 7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-one (φ = 0.0195), suggesting that derivatives of this type could be suitable for quantitative thiol assays.

Original language	English (US)
Article number	M16611SS
Pages (from-to)	1494-1500
Number of pages	7
Journal	Synthesis
Issue number	9
DOIs	https://doi.org/10.1055/s-0030-1259991
State	Published - 2011

Keywords

acylation
amino acids
benzotriazoles
coumarin
fluorescence
heterocycles
peptides
thiols

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10.1055/s-0030-1259991

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title = "Synthesis of coumarin conjugates of biological thiols for fluorescent detection and estimation",

abstract = "Coumarin-labeled thioesters are efficiently prepared from biological thiols using N-coumarin-3-carbonyl benzotriazoles. Absorption (λabs) , fluorescence (λem) wavelength maxima and quantum yields (φ) for the thioesters are measured in buffer solution at physiological pH 7.4. Quantum yields (φ = 0.0318-0.1068) of four of the products are higher than their precursor 7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-one (φ = 0.0195), suggesting that derivatives of this type could be suitable for quantitative thiol assays.",

keywords = "acylation, amino acids, benzotriazoles, coumarin, fluorescence, heterocycles, peptides, thiols",

author = "Katritzky, {Alan R.} and Ibrahim, {Tarek S.} and Tala, {Srinivasa R.} and Abo-Dya, {Nader E.} and Abdel-Samii, {Zakaria K.} and El-Feky, {Said A.}",

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language = "English (US)",

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journal = "Synthesis",

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TY - JOUR

T1 - Synthesis of coumarin conjugates of biological thiols for fluorescent detection and estimation

AU - Katritzky, Alan R.

AU - Ibrahim, Tarek S.

AU - Tala, Srinivasa R.

AU - Abo-Dya, Nader E.

AU - Abdel-Samii, Zakaria K.

AU - El-Feky, Said A.

PY - 2011

Y1 - 2011

N2 - Coumarin-labeled thioesters are efficiently prepared from biological thiols using N-coumarin-3-carbonyl benzotriazoles. Absorption (λabs) , fluorescence (λem) wavelength maxima and quantum yields (φ) for the thioesters are measured in buffer solution at physiological pH 7.4. Quantum yields (φ = 0.0318-0.1068) of four of the products are higher than their precursor 7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-one (φ = 0.0195), suggesting that derivatives of this type could be suitable for quantitative thiol assays.

AB - Coumarin-labeled thioesters are efficiently prepared from biological thiols using N-coumarin-3-carbonyl benzotriazoles. Absorption (λabs) , fluorescence (λem) wavelength maxima and quantum yields (φ) for the thioesters are measured in buffer solution at physiological pH 7.4. Quantum yields (φ = 0.0318-0.1068) of four of the products are higher than their precursor 7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-one (φ = 0.0195), suggesting that derivatives of this type could be suitable for quantitative thiol assays.

KW - acylation

KW - amino acids

KW - benzotriazoles

KW - coumarin

KW - fluorescence

KW - heterocycles

KW - peptides

KW - thiols

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DO - 10.1055/s-0030-1259991

M3 - Article

AN - SCOPUS:79955022459

SN - 0039-7881

SP - 1494

EP - 1500

JO - Synthesis

JF - Synthesis

IS - 9

M1 - M16611SS

ER -

Synthesis of coumarin conjugates of biological thiols for fluorescent detection and estimation

Abstract

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