Synthesis and biological evaluation of 3′-carboranyl thymidine analogues

Junhua Yan, Charlotta Naeslund, Ashraf Al Madhoun, Jianghai Wang, Weihua Ji, Guirec Y. Cosquer, Jayaseharan Johnsamuel, Stefan Sjöberg, Staffan Eriksson, Werner Tjarks

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)


Boron neutron capture therapy (BNCT) is a chemoradio-therapeutic method for the treatment of cancer. It depends on the selective targeting of tumor cells by boron-containing compounds. One category of BNCT agents with potential to selectively target tumor cells may be thymidine derivatives substituted at the 3′-position with appropriate boron moieties. Thus, several thymidine analogues were synthesized with a carborane cluster bound to the 3′-position either through an ether or a carbon linkage. The latter are the first reported carborane-containing nucleosides in which the carboranyl entity is directly linked to the carbohydrate portion of the nucleoside by a carbon-carbon bond. Low but significant phosphorylation rates in the range of 0.18% that of thymidine were observed for the carbon-linked 3′-carboranyl thymidine analogues in phosphoryl transfer assays using recombinant preparations of thymidine kinases 1 (TK1) and thymidine kinases 2 (TK2). Some of the ether-linked 3′-carboranyl thymidine analogues appeared to be slightly unstable under acidic as well as phosphoryl transfer assay conditions and were, if at all, poor substrates for TK1.

Original languageEnglish
Pages (from-to)2209-2212
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Issue number16
Publication statusPublished - 19 Aug 2002


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