References
- Endo , Y. and Tsurugi , K. 1988 . J. Biol. Chem. , 263 : 7917 – 7920 .
- Monzingo , A. F. and Robertus , J. D. 1992 . J. Mol. Biol. , 227 : 1136 – 1145 .
- Lewis , A. F. and Townsend , L. B. 1982 . J. Amer. Chem. Soc. , 104 : 1073 – 1077 . The biological activity (i.e., cytotoxicity) of nucleosides is commonly thought to result from their conversion to the corresponding 5′-phosphates, cf. Blocking this conversion might be accomplished by conversion of the 5′-hydroxy group to a halo group or a hydrogen atom. Thus, we observed that the nucleoside antibiotic tubercidin, had an IC50 of 50 ng/mL against EL4 mouse leukemia cells in culture, while 5′-chloro-5′-deoxytubercidin lacked toxicity at 10. μg/mL. A similar effect was observed for formycin-A, which also had an IC50, of 50 ng/mL, while the 5′-chloro-5′-deoxy derivative was non-toxic at 100 μg/mL.
- Kissman , H. M. and Baker , B. R. 1957 . J. Amer. Chem. Soc. , 79 : 5534 – 55440 .
- Wagner , O. W. , Lee , H. A. Jr. , Frey , P. A. and Abeles , R. H. 1966 . J. Biol. Chem. , 241 : 1751 – 1762 .
- Wang , Y. , Hogenkamp , H. P. C. , Long , R. A. , Revenkar , G. R. and Robins , R. K. 1977 . Carbohydr. Res. , 59 : 449 – 457 .
- Robbins , M. J. , Hansske , F. , Wnuk , S. F. and Kanai , T. 1991 . Can. J. Chem. , 69 : 1468 – 1474 .