Collect. Czech. Chem. Commun. 1994, 59, 1682-1690

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


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.