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1
Direct-acting mutagenicity of N4-aminocytidine derivatives bearing alkyl groups at the hydrazino nitrogens.在肼基氮原子上带有烷基的N4-氨基胞苷衍生物的直接致突变性。
Nucleic Acids Res. 1985 Dec 20;13(24):8893-9. doi: 10.1093/nar/13.24.8893.
2
Mutagenicity of N4-aminocytidine and its derivatives in Chinese hamster lung V79 cells. Incorporation of N4-aminocytosine into cellular DNA.
Mutat Res. 1987 Apr;177(2):283-7. doi: 10.1016/0027-5107(87)90012-1.
3
N4-aminocytidine, a nucleoside analog that has an exceptionally high mutagenic activity.N4-氨基胞苷，一种具有极高诱变活性的核苷类似物。
Nucleic Acids Res. 1983 Aug 11;11(15):5223-33. doi: 10.1093/nar/11.15.5223.
4
Mutagenic nucleoside analog N4-aminocytidine: metabolism, incorporation into DNA, and mutagenesis in Escherichia coli.诱变核苷类似物N4-氨基胞苷：在大肠杆菌中的代谢、掺入DNA及诱变作用
J Bacteriol. 1988 Nov;170(11):5257-62. doi: 10.1128/jb.170.11.5257-5262.1988.
5
[Molecular mechanism of N4-aminocytidine mutagenesis].
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Spectrum of N4-aminocytidine mutagenesis.
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A 50 Hz, 14 mT magnetic field is not mutagenic or co-mutagenic in bacterial mutation assays.在细菌突变试验中，50赫兹、14毫特斯拉的磁场不具有致突变性或共致突变性。
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A comparison of mutation spectra detected by the Escherichia coli lac(+) reversion assay and the Salmonella typhimurium his(+) reversion assay.通过大肠杆菌乳糖（+）回复突变试验和鼠伤寒沙门氏菌组氨酸（+）回复突变试验检测到的突变谱比较。
Mutagenesis. 2000 Jul;15(4):317-23. doi: 10.1093/mutage/15.4.317.
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Mutagenesis by N4-aminocytidine: induction of AT to GC transition and its molecular mechanism.N4-氨基胞苷诱导的诱变作用：AT 到 GC 的转变及其分子机制。
Biochemistry. 1985 Dec 3;24(25):7273-8. doi: 10.1021/bi00346a038.
10
N4-aminocytidine: formation, reactivity, and mutagenicity.
Nucleic Acids Symp Ser. 1983(12):29-30.

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Ambivalent incorporation of the fluorescent cytosine analogues tC and tCo by human DNA polymerase alpha and Klenow fragment.人DNA聚合酶α和克列诺片段对荧光胞嘧啶类似物tC和tCo的矛盾掺入
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3
Mutagenic nucleoside analog N4-aminocytidine: metabolism, incorporation into DNA, and mutagenesis in Escherichia coli.诱变核苷类似物N4-氨基胞苷：在大肠杆菌中的代谢、掺入DNA及诱变作用
J Bacteriol. 1988 Nov;170(11):5257-62. doi: 10.1128/jb.170.11.5257-5262.1988.

本文引用的文献

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A new reaction useful for chemical cross-linking between nucleic acids and proteins.一种用于核酸与蛋白质之间化学交联的新反应。
FEBS Lett. 1984 Jan 23;166(1):194-8. doi: 10.1016/0014-5793(84)80071-x.
2
N4-aminocytidine, a nucleoside analog that has an exceptionally high mutagenic activity.N4-氨基胞苷，一种具有极高诱变活性的核苷类似物。
Nucleic Acids Res. 1983 Aug 11;11(15):5223-33. doi: 10.1093/nar/11.15.5223.
3
The tautomeric state of N(4)-hydroxy- and of N(4)-amino-cytosine derivatives.N(4)-羟基和N(4)-氨基胞嘧啶衍生物的互变异构状态。
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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。
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Mutagenicities of N-nitrosamines on Salmonella.N-亚硝胺对沙门氏菌的致突变性
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Reaction of cytidine with semicarbazide in the presence of bisulfite. A rapid modification specific for single-stranded polynucleotide.胞苷在亚硫酸氢盐存在下与氨基脲的反应。一种对单链多核苷酸特异的快速修饰反应。
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Reaction of the cytosine nucleus with hydrazine in the presence of bisulphite.
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在肼基氮原子上带有烷基的N4-氨基胞苷衍生物的直接致突变性。

Direct-acting mutagenicity of N4-aminocytidine derivatives bearing alkyl groups at the hydrazino nitrogens.

作者信息

Nomura A, Negishi K, Hayatsu H

出版信息

Nucleic Acids Res. 1985 Dec 20;13(24):8893-9. doi: 10.1093/nar/13.24.8893.

DOI:10.1093/nar/13.24.8893
PMID:3909110
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC318959/
Abstract

To investigate the mechanism of N4-aminocytidine-induced mutagenesis, N'-alkyl-N4-aminocytidines and N4-alkyl-N4-aminocytidines were prepared and their mutagenicity on bacteria were assayed. N'-Methyl-N4-aminocytidine, N'-(2-hydroxyethyl)-N4-aminocytidine and N',N'-dimethyl-N4-aminocytidine showed direct-acting mutagenicity on S. typhimurium TA100 and E. coli WP2 uvrA, tester strains that are sensitive to base-pair substitutions. In contrast, N4-methyl-N4-aminocytidine, N4-(2-hydroxyethyl)-N4-aminocytidine and N4,N'-dimethyl-N4-aminocytidine were not mutagenic on these bacteria. Since N'-methyl-N4-aminocytidine does not form hydrazones, the possibility that N4-aminocytidine causes mutation due to its reactivity with carbonyl compounds has been excluded. Furthermore, the fact that only those alkyl N4-aminocytidines having a hydrogen on the nitrogen at position 4 are mutagenic is consistent with the previously proposed mechanism in which the tautomerization between the amino and the imino forms of N4-aminocytosine allowing an ambiguous base pairing is the cause of the mutagenesis.

摘要

为了研究N4-氨基胞苷诱导诱变的机制，制备了N'-烷基-N4-氨基胞苷和N4-烷基-N4-氨基胞苷，并测定了它们对细菌的诱变性。N'-甲基-N4-氨基胞苷、N'-(2-羟乙基)-N4-氨基胞苷和N',N'-二甲基-N4-氨基胞苷对鼠伤寒沙门氏菌TA100和大肠杆菌WP2 uvrA（对碱基对替换敏感的测试菌株）表现出直接作用的诱变性。相比之下，N4-甲基-N4-氨基胞苷、N4-(2-羟乙基)-N4-氨基胞苷和N4,N'-二甲基-N4-氨基胞苷对这些细菌没有诱变性。由于N'-甲基-N4-氨基胞苷不会形成腙，因此排除了N4-氨基胞苷因其与羰基化合物的反应性而导致突变的可能性。此外，只有那些在4位氮上带有氢的烷基N4-氨基胞苷具有诱变性这一事实与先前提出的机制一致，即N4-氨基胞嘧啶的氨基和亚氨基形式之间的互变异构导致模糊的碱基配对是诱变的原因。