Collect. Czech. Chem. Commun. 1994, 59, 1682-1690
https://doi.org/10.1135/cccc19941682

Fluorescence Reagents for Labelling of Biomolecules. Part III. Study of the Reactions of 2- and 4-Substituted 9-Isothiocyanatoacridines with Glycine

Danica Sabolováa, Dana Mazagováb, Pavol Kristianb, Marián Antalíka, Dušan Podhradskýa and Ján Imrichb

a Department of Biochemistry, P. J. Šafárik University, 041 54 Košice, Slovak Republic
b Department of Organic Chemistry, P. J. Šafárik University, 041 54 Košice, Slovak Republic

This article is part of serial Fluorescence Reagents for Labelling of Biomolecules.

Abstract

Kinetics of nucleophilic addition reaction of 2- and 4-substituted 9-isothiocyanatoacridines I - VII with glycine in buffered aqueous dimethylformamide has been studied. The addition products, N-(9-acridinylthiocarbamoyl)glycines VIII - XIV, were characterized by IR, UV, 1H NMR, mass and fluorescence spectra. Derivatives VIII, X and XII exhibited higher fluorescence intensity than the starting isothiocyanates; the highest fluorescence was found for the unsubstituted compound X. The reaction mechanism is discussed on the basis of properties of the reaction products and kinetic characteristics.