5-Iodo-4-thio-2 '-deoxyuridine: Synthesis, Structure, and Cytotoxic Activity

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 substa...

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Published inChemistry letters Vol. 44; no. 2; pp. 147 - 149
Main Authors Zhang, Xiao-Hui, Yin, Hong-Yan, Trigiante, Giuseppe, Brem, Reto, Karran, Peter, Pitak, Mateusz B., Coles, Simon J., Xu, Yao-Zhong
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.02.2015
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
THYMIDINE
OXIDATION
REPLICATION
HUMAN-CELLS
UVA LIGHT
CRYSTAL
PHOTOACTIVATION
6-THIOGUANINE
SPECTRA
DNA LESIONS
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Summary: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.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.140965