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2-(对硝基苯基)-2'-脱氧腺苷,一种新型诱变核苷。

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

作者信息

Matsuda A, Ohara Y, Kakutani T, Negishi K, Wataya Y, Hayatsu H, Ueda T

机构信息

Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.

出版信息

Nucleic Acids Res. 1990 Apr 11;18(7):1833-8. doi: 10.1093/nar/18.7.1833.

Abstract

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.

摘要

在艾姆斯沙门氏菌试验中,发现2-苯基腺苷的粗制品具有致突变性。在该制品的纯化过程中,发现2-苯基腺苷本身无致突变性,但污染样品的2-(间硝基苯基)腺苷和2-(对硝基苯基)腺苷(5m,p)是致突变成分。开展了构效关系研究,发现5p、2-(对硝基苯基)腺嘌呤(7p)和2-(对硝基苯基)-2'-脱氧腺苷(15p)在无代谢活化的情况下对鼠伤寒沙门氏菌TA98和TA100具有强烈的致突变性,效力顺序为15p大于7p大于5p。15p在TA98中的效力比4-硝基喹啉N-氧化物高一个数量级。15p在培养的小鼠细胞系FM3A中也表现出致突变性。

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本文引用的文献

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N(4)-amino-and N(4)-hydroxycytosines as base analogue mutagens.
Mutat Res. 1974 May;23(2):267-73. doi: 10.1016/0027-5107(74)90147-x.
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Chem Pharm Bull (Tokyo). 1975 Apr;23(4):759-74. doi: 10.1248/cpb.23.759.
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