HighlightsGrowing cells incorporate thio-iodo-deoxyuridine and thio-bromo-deoxyuridine into DNA.They are non-toxic but act as powerful UVA photosensitisers.UVA lesions include DNA-protein and DNA–DNA crosslinks.Singlet oxygen is involved in the formation of this potentially lethal damage.Thio-halo-deoxynucleosides offer a potential selective therapeutic option.

Unambiguous characterization of 5-substituted-4-thiopyrimidine nucleosides (ribonucleosides and 2'-deoxynucleosides) was performed using NMR spectroscopy. Assignments of all proton and carbon signals of 5-bromo-4-thiouridine and related nucleosides were systematically carried out and firmly established by COSY and HMQC techniques. The NMR data of various 4-thiopyrimidine nucleosides are compared, and the key contributing factors discussed. The approach presented here is applicable to other modified nucleosides and nucleotides, as well as nucleobases.

5-Substituted-4-thio-2’-deoxyuridine nucleosides have been chemically synthesized and studied by NMR and UV spectroscopy. The results have been analyzed and discussed in connection with the previous data. The imino proton signal and the carbon signal of the thiocarbonyl group in the 5-substituted-4-thio-2’-deoxyuridines were found to be at much lower field, offering a potential for monitoring these modified bases at the DNA level. All 4-thionucleosides have strong absorptions at around 340 nm and consequently would be useful as potential UVA-induced anticancer agents.

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A colorimetric probe for the detection of copper(II) ions in aqueous media by the naked eye has been developed based on a supramolecular complex comprised of a cationic polythiophene derivative and ATP with a detection limit as low as 0.05 mM.