2'-O-nitro-1-beta-D-arabinofuranosylcytosine. A new derivative of 1-beta-D-arabinofuranosylcytosine that resists enzymatic deamination and has antileukemic activity.
To overcome the susceptibility of the anticancer drug 1-beta-D-arabinofuranosylcytosine (ara-C) to enzymatic deamination, and hence deactivation, we prepared the 2'-O-nitro-1-beta-D-arabinofuranosylcytosine (termed nitrara-C) and evaluated it for biological activity. Nitrara-C was resistant to enzymatic deamination and inhibited the proliferation of several strains of human leukemic T and B lymphoblasts grown in culture. Moreover, it substantially extended the life spans of mice with L1210 leukemia. Studies with ara-C-resistant human leukemic lymphoblasts deficient in deoxycytidine kinase activity disclosed that the inhibitory activity of the new compound depends on its phosphorylation.
D000818:Animals; D000964:Antimetabolites, Antineoplastic / Q000138:chemical synthesis*; D003561:Cytarabine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use; D004353:Drug Evaluation, Preclinical; D005260:Female; D007939:Leukemia L1210 / Q000188:drug therapy*; D051379:Mice; D008815:Mice, Inbred Strains
D000964:Antimetabolites, Antineoplastic; D003561:Cytarabine; C037434:1-(2-O-nitro-beta-D-arabinofuranosyl)cytosine