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

PAPER

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

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

Abstract

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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.

Key words

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

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