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Nucleic Acids Research, 1990, Vol. 18, No. 7 1833-1838
© 1990

GENOME STRUCTURE AND MAPPING

2-(p-Nitrophenyl)-2'-deoxyadenosine, a new type of mutagenic nucleoside

Akira Matsuda*, Yoshiko Ohara1, Toshifumi Kakutani1, Kazuo Negishi1, Yusuke Wataya1, Hikoya Hayatsu1 and Tohru Ueda

Faculty of Pharmaceutical Sciences, Hokkaido University Kita-12 Nishi-6, Kita-ku, Sapporo 060 1Faculty of Pharmaceutical Sciences, Okayama University Tsushimanaka 1-1-1, Okayama 700, Japan

* To whom correspondence should be addressed

Received November 28, 1989. Revised January 4, 1990. Accepted January 4, 1990.

A crude preparation of 2-phenyladenosine was found to be mutagenlc in the Ames Salmonella assay. In the purification of this preparation, it was revealed that 2-phenyladenosine itself was nonmutagenic but that 2-(m- and p-nitrophenyl)-adenosines (5m,p) contaminating the sample were the mutagenic principles. A structure-activity relationship study was carried out, and it was found that 5p, 2-(p-nitrophenyl)- adenine (7p), and 2-(p-nitrophenyl)-2'-deoxyadenosine (15p) were strongly mutagenic toward S. typhimurium TA98 and TA100 without metabolic activation, the potency being in the order 15p > 7p > 5p. The potency of 15p in TA98 was one order of magnitude greater than that of 4-nitroquinoline N-oxide. 15p also showed mutagenicity in the mouse cell line FM3A in culture.


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