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N4-氨基胞苷,一种具有极高诱变活性的核苷类似物。

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

作者信息

Negishi K, Harada C, Ohara Y, Oohara K, Nitta N, Hayatsu H

出版信息

Nucleic Acids Res. 1983 Aug 11;11(15):5223-33. doi: 10.1093/nar/11.15.5223.

Abstract

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 (phi X174 am3). The activity did not require the presence of mammalian microsomal fraction in 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-hydroxycytidine. The greater activity of the riboside than the deoxyriboside was ascribed to the lack of deoxycytidine kinase in these cells. This compound may be useful as a powerful mutagen to induce a transition mutation in microorganisms.

摘要

通过加入化学计量比不足的亚硫酸氢盐,胞苷与肼反应生成N4-氨基胞苷的反应得到极大促进,且产物以良好产率分离出来。N4-氨基胞苷对细菌(鼠伤寒沙门氏菌TA100和TA1535以及大肠杆菌WP2 uvrA)和噬菌体(phi X174 am3)具有强烈的致突变性。该活性在系统中不需要哺乳动物微粒体部分的存在。N4-氨基胞苷在这些系统中的致突变效力比N4-氨基-2'-脱氧胞苷高两个数量级,比N4-羟基胞苷高两个多数量级。核糖核苷比脱氧核糖核苷具有更高活性归因于这些细胞中缺乏脱氧胞苷激酶。该化合物可用作强大的诱变剂以在微生物中诱导转换突变。

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本文引用的文献

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Bisulfite-catalyzed transamination of cytosine and cytidine.亚硫酸氢盐催化的胞嘧啶和胞苷转氨作用。
Biochem Biophys Res Commun. 1970 Aug 24;40(4):839-43. doi: 10.1016/0006-291x(70)90979-4.
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Biochem Biophys Res Commun. 1974 Jan 23;56(2):459-66. doi: 10.1016/0006-291x(74)90864-x.
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Mutagenic action of N4-hydroxycytidine on Escherichia coli B cyt-.
Mutat Res. 1973 Oct;20(1):1-5. doi: 10.1016/0027-5107(73)90091-2.

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