Synthesis and cytostatic activity of emissive 7-thiazolyl-7-deazapurine nucleosides

Abstract

7-Functionalized 7-deazapurine fluorescent nucleosides are highly important for biotechnological applications. Here, 7-substituted 7-deaza-2′-deoxyguanosines, comprising a 4H-cyclopenta[d]thiazole ring are obtained by Hantzsch synthesis reaction of 7-thioamide-7-deaza-2′-deoxyguanosine with aromatic α-bromocarbonyl compounds (61–85%). Their photophysical properties are determined by UV and fluorescence spectroscopy, and the cytostatic activities are evaluated by MTT assay. All compounds exhibit strong solvatochromicity and pH-dependent fluorescence in aqueous solutions, indicating their promising ability to be fluorescent probes. The 7-substituted 7-deaza-2′-deoxyguanosines 5a, 5i and 5j exert cytostatic activities, which means they have the potential to be candidate for theranostics.