Nucleosides and Nucleotides p. 461 - 471 (1995)
Update date:2022-08-11
Topics:
Matsuda
Azuma
The antitumor mechanism of action of 2'-C-cyano-2'-deoxy-1-β-D- arabinofuranosyl (CNDAC) has been examined. CNDAC was designed as a potentially DNA-self-strand-breaking nucleoside. It had potent antitumor effects against various solid tumors in vitro as well as in vivo. Using a chain-extension method with Vent (exo-) DNA polymerase and a short primer/template system, we found that 5'-triphosphate of CNDAC (CNDACTP) was incorporated into the primer at a site opposite a guanine residue in the template. After further chain-extension reaction of the primer containing CNDAC at the 3'-terminus, chain elongation was not observed. Therefore, CNDACTP appeared to act as a chain-terminator. Analyses of the structure of the 3'-terminus in the primer revealed 2'-C-cyano-2',3'-didehydro-2',3'- dideoxycytidine (ddCNC) together with CNDAC and 2'-C-cyano-2'-deoxy-1-β-D- ribofuranosylcytosine (CNDC). The existence of ddCNC in the 3'-end of the primer would be due to the self-strand-break by the nucleotide incorporated next to CNDAC. We also found that CNDAC was epimerized to CNDC in near- neutral to alkaline media. Therefore, CNDC found in the primer was epimerized after incorporation of CNDACTP into the primer. We also described the metabolism of CNDAC.
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