2-(p-Nitrophenyl)-2′-deoxyadenosine, a new type of mutagenic nucleoside | Zendy

Akira Matsuda | Zendy; Yoshiko Ohara | Zendy; Toshifumi Kakutani | Zendy; Kazuo Negishi | Zendy; Yusuke Wataya | Zendy; Hikoya Hayatsu | Zendy; Tohru Ueda | Zendy

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

Author(s) -

Akira Matsuda,

Yoshiko Ohara,

Toshifumi Kakutani,

Kazuo Negishi,

Yusuke Wataya,

Hikoya Hayatsu,

Tohru Ueda

Publication year - 1990

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/18.7.1833

Subject(s) - deoxyadenosine , biology , potency , nucleoside , salmonella , ames test , biochemistry , microbiology and biotechnology , dna , genetics , in vitro , bacteria

A crude preparation of 2-phenyladenosine was found to be mutagenic 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 greater than 7p greater than 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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