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Prodhomme, S ; Demaret, JP ; Vinogradov, S ; Asseline, U ; Morin-Allory, L ; Vigny, P

A theoretical and experimental study of two thiazole orange derivatives with single- and double-stranded oligonucleotides, polydeoxyribonucleotides and DNA

Journal of Photochemistry and Photobiology B-Biology 53 (1-3) 60-69

par Administrateur - publié le

Abstract :

The effect of interaction with DNA and oligonucleotides on the photophysical properties of two thiazole orange (TO) derivatives, with different side chains (-(CH2)(3)-N+ (CH3)(3) and -(CH2)(6)-I) linked to the nitrogen of the quinoline ring of the thiazole orange, is presented here. The first one called TO-PRO1 is a commercially available dye, whereas the second one called TO-MET has been specially synthesized for further covalent binding to oligonucleotides with the aim of being used for specific in situ detection of biomolecular interactions. Both photophysical measurements and molecular calculations have been done to assess their possible mode of interaction with DNA. When dissolved in buffered aqueous solutions both derivatives exhibit very low fluorescence quantum yields of 8 X 10(-5) and 2 X 10(-4), respectively.