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Research article2004Peer reviewed

The synthesis and biochemical evaluation of thymidine analogues substituted with nido carborane at the N-3 position

Byun Y, Yan J, Al-Madhoun AS, Johnsamuel J, Yang WL, Barth RF, Staffan E, Tjarks W


Several thymidine analogues substituted with closo- and nido-carborane at the N-3 position were synthesized. The nido-carboranyl thymidine analogues were designed to be effective substrates for human thymidine kinase I in combination with an increased water solubility sufficient for clinical application in boron neutron capture therapy. This was done because N-3 substituted closo-carboranyl thymidine analogues previously synthesized in our laboratories were good TK1 substrates but were poorly water-soluble. Newly synthesized zwitterionic amino nido- and the corresponding neutral closo-m-carboranyl thymidine analogues exhibited excellent TK1 phosphorylation rates up to 75% relative to thymidine, indicating that these compounds were good substrates for thymidine kinase 1. Thin layer chromatographic studies were indicative of increased hydrophilicity of the synthesized nido-carboranyl thymidine analogues compared with their closo-carboranyl counterparts and previously reported closo-carboranyl thymidine analogues. (C) 2004 Elsevier Ltd. All rights reserved

Published in

Applied Radiation and Isotopes
2004, Volume: 61, number: 5, pages: 1125-1130

      SLU Authors

    • Eriksson, Staffan

      • Department of Molecular Biosciences, Swedish University of Agricultural Sciences

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