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Synthesis 2011(9): 1494-1500  
DOI: 10.1055/s-0030-1259991
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Coumarin Conjugates of Biological Thiols for Fluorescent Detection and Estimation

Alan R. Katritzky*a, Tarek S. Ibrahima,b, Srinivasa R. Talaa, Nader E. Abo-Dyaa,b, Zakaria K. Abdel-Samiib, Said A. El-Fekyb
a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
Fax: +1(352)3920554; e-Mail: katritzky@chem.ufl.edu;
b Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig 44519, Egypt
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Publication History

Received 2 February 2011
Publication Date:
05 April 2011 (online)

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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.

Key words

fluorescence - acylation - coumarin - thiols - benzotriazoles - peptides - amino acids - heterocycles