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Nucleic Acids Research, 1983, Vol. 11, No. 15 5223-5233
© 1983

MOLECULAR BIOLOGY

N4-Aminocytidine, a nucleoside analog that has an exceptionally high mutagenic activity

Kazuo Negishi, Chisako Harada, Yoshiko Ohara, Kimiko Oohara, Noriko Nitta and Hikoya Hayatsu

Faculty of Pharmaceutical Sciences, Okayama University Tsushima, Okayama 700, Japan

Received June 14, 1983. Accepted July 6, 1983.

The reaction of cytidine with hydrazine to give N4-aminocytidine was greatly promoted by addition of a less-than-stoichiometric amount of bisulfite, and the product was isolated in a good yield. N4-Aminocytidine was strongly mutagenic to bacteria (Salmonella typhimurium TA100 and TA1535, and E. coli WP2 uvrA) and to phage ({varphi}X174 am3). The activity did not require the presence of mammalian microsomaT fraction 1n the system. The mutagenic potency of N4 -aminocytidine in these systems was two orders of magnitude greater than that of N4-amino-2'-deoxycytidine, and more than two orders of magnitude greater than that of N4-hydroxycyt1dine. The greater activity of the riboside than the deoxyriboside was ascribed to the lack of deoxycytidine kinase 1n these cells. This compound may be useful as a powerful mutagen to induce a transition mutation in microorganisms.


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