5-iodo-4-thio-2′-deoxyuridine: synthesis, structure, and cytotoxic activity

Zhang, Xiao-Hui; Yin, Hong-Yan; Trigiante, Joseph; Brem, Reto; Karran, Peter; Pitak, Mateusz B.; Coles, Simon J. and Xu, Yao-Zhong (2015). 5-iodo-4-thio-2′-deoxyuridine: synthesis, structure, and cytotoxic activity. Chemistry Letters, 44(2) pp. 147–149.

DOI: https://doi.org/10.1246/cl.140965

URL: http://www.journal.csj.jp/cl-article/cl-44-2-147


The novel nucleoside 5-iodo-4-thio-2′-deoxyuridine (4) was synthesized and fully characterized by IR, NMR, and MS. Its structure was determined by single-crystal X-ray diffraction. Compound 4 absorbs strongly at 346 nm and is minimally toxic to human tumour cells, but its cytotoxicity is substantially enhanced by low dose UVA radiation. The combined use of 4 and UVA offers a promising route to selectively and effectively kill proliferating cells.

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