Hypoxia-driven elimination of thiopurines from their nitrobenzyl prodrugs

P Thomson, MA Naylor, MRL Stratford, G Lewis…

Index: Thomson, Peter; Naylor, Matthew A.; Stratford, Michael R.L.; Lewis, Gemma; Hill, Sally; Patel, Kantilal B.; Wardman, Peter; Davis, Peter D. Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 15 p. 4320 - 4322

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Citation Number: 11

Abstract

A novel bioreductive prodrug of 6-thioguanine, 2-amino-6-[2-(4-nitrophenyl) prop-2- ylsulfanyl]-9H-purine, containing a gem-dimethyl thioether linkage, was synthesised and compared with its unsubstituted analogue. In A549 whole cell experiments hypoxia selective release of 6-thioguanine was observed with the substituted prodrug only.