• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

相似文献

1
Alkylation of deoxyribonucleic acid by carcinogens dimethyl sulphate, ethyl methanesulphonate, N-ethyl-N-nitrosourea and N-methyl-N-nitrosourea. Relative reactivity of the phosphodiester site thymidylyl(3'-5')thymidine.致癌物硫酸二甲酯、甲磺酸乙酯、N-乙基-N-亚硝基脲和N-甲基-N-亚硝基脲对脱氧核糖核酸的烷基化作用。磷酸二酯位点胸苷酰（3'-5'）胸苷的相对反应活性。
Biochem J. 1978 Jun 1;171(3):575-87. doi: 10.1042/bj1710575.
2
Alkylation of deoxyribonucleic acid in vivo in various organs of C57BL mice by the carcinogens N-methyl-N-nitrosourea, N-ethyl-N-nitrosourea and ethyl methanesulphonate in relation to induction of thymic lymphoma. Some applications of high-pressure liquid chromatography.致癌物N-甲基-N-亚硝基脲、N-乙基-N-亚硝基脲和甲磺酸乙酯对C57BL小鼠各器官脱氧核糖核酸的体内烷基化作用与胸腺淋巴瘤诱导的关系。高压液相色谱法的一些应用。
Biochem J. 1978 Sep 15;174(3):1031-44. doi: 10.1042/bj1741031.
3
Nitrosamine-induced carcinogenesis. The alkylation of N-7 of guanine of nucleic acids of the rat by diethylnitrosamine, N-ethyl-N-nitrosourea and ethyl methanesulphonate.亚硝胺诱导的致癌作用。二乙基亚硝胺、N-乙基-N-亚硝基脲和甲磺酸乙酯对大鼠核酸鸟嘌呤N-7位的烷基化作用。
Biochem J. 1971 Dec;125(3):841-7. doi: 10.1042/bj1250841.
4
In vitro reaction of N-n-butyl-N-nitrosourea and n-butyl methanesulphonate with guanine and thymine bases of DNA.N-正丁基-N-亚硝基脲和甲磺酸正丁酯与DNA的鸟嘌呤和胸腺嘧啶碱基的体外反应
Carcinogenesis. 1984 May;5(5):621-5. doi: 10.1093/carcin/5.5.621.
5
An assay for phosphotriester formation in the reaction of alkylating agents with deoxyribosenucleic acid in vitro and in vivo.一种在体外和体内测定烷基化剂与脱氧核糖核酸反应中磷酸三酯形成的方法。
Chem Biol Interact. 1976 Jun;13(3-4):223-36. doi: 10.1016/0009-2797(76)90076-4.
6
Identification of the methyl phosphotriester of thymidylyl (3',5')thymidine as a product from reaction of DNA with the carcinogen N-methyl-N-nitrosourea.鉴定胸苷酰（3'，5'）胸苷的甲基磷酸三酯为DNA与致癌物N-甲基-N-亚硝基脲反应的产物。
Chem Biol Interact. 1976 Sep;15(1):91-100. doi: 10.1016/0009-2797(76)90131-9.
7
Effect of alkylation with N-methyl-N-nitrosourea and N-ethyl-N-nitrosourea on the secondary structure of DNA.用N-甲基-N-亚硝基脲和N-乙基-N-亚硝基脲进行烷基化对DNA二级结构的影响。
Biosci Rep. 1984 Sep;4(9):729-35. doi: 10.1007/BF01128813.
8
Isolation and identification of products from alkylation of nucleic acids: ethyl- and isopropyl-purines.核酸烷基化产物的分离与鉴定：乙基嘌呤和异丙基嘌呤
Biochem J. 1975 Jan;145(1):73-84. doi: 10.1042/bj1450073.
9
Nitrosamine-induced carcinogenesis. The alklylation of nucleic acids of the rat by N-methyl-N-nitrosourea, dimethylnitrosamine, dimethyl sulphate and methyl methanesulphonate.亚硝胺诱导的致癌作用。N-甲基-N-亚硝基脲、二甲基亚硝胺、硫酸二甲酯和甲磺酸甲酯对大鼠核酸的烷基化作用。
Biochem J. 1968 Nov;110(1):39-47. doi: 10.1042/bj1100039.
10
DNA sequence dependence of guanine-O6 alkylation by the N-nitroso carcinogens N-methyl- and N-ethyl-N-nitrosourea.N-亚硝基致癌物N-甲基-N-亚硝基脲和N-乙基-N-亚硝基脲对鸟嘌呤-O6烷基化的DNA序列依赖性
Mutat Res. 1991 Sep-Oct;250(1-2):153-60. doi: 10.1016/0027-5107(91)90171-j.

引用本文的文献

1
Methyl DNA Phosphate Adduct Formation in Rats Treated Chronically with 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone and Enantiomers of Its Metabolite 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol.4-(甲基亚硝胺基)-1-(3-吡啶基)-1-丁酮及其代谢物 4-(甲基亚硝胺基)-1-(3-吡啶基)-1-丁醇对大鼠慢性处理后形成的甲基 DNA 磷酸加合物。
Chem Res Toxicol. 2018 Jan 16;31(1):48-57. doi: 10.1021/acs.chemrestox.7b00281. Epub 2017 Nov 30.
2
Analysis of DNA-phosphate adducts in vitro using miniaturized LC-ESI-MS/MS and column switching: phosphotriesters and alkyl cobalamins.使用小型化液相色谱-电喷雾串联质谱法和柱切换技术体外分析DNA-磷酸加合物：磷酸三酯和烷基钴胺素
J Am Soc Mass Spectrom. 2004 Apr;15(4):593-606. doi: 10.1016/j.jasms.2003.12.012.
3
Risk assessment of low-level chemical exposures from consumer products under the U.S. Consumer Product Safety Commission chronic hazard guidelines.根据美国消费品安全委员会的慢性危害指南对消费品低水平化学暴露进行风险评估。
Environ Health Perspect. 1998 Feb;106 Suppl 1(Suppl 1):387-90. doi: 10.1289/ehp.98106s1387.
4
Specific recognition of apurinic sites in DNA by a tryptophan-containing peptide.含色氨酸肽对DNA中脱嘌呤位点的特异性识别。
Proc Natl Acad Sci U S A. 1981 Feb;78(2):926-30. doi: 10.1073/pnas.78.2.926.
5
Inducible repair of phosphotriesters in Escherichia coli.大肠杆菌中磷酸三酯的可诱导修复
Proc Natl Acad Sci U S A. 1983 Dec;80(24):7380-4. doi: 10.1073/pnas.80.24.7380.
6
Repair and mutagenesis in Escherichia coli K-12 after exposure to various alkyl-nitrosoguanidines.大肠杆菌K-12暴露于各种烷基亚硝基胍后的修复与诱变
J Bacteriol. 1983 Oct;156(1):6-12. doi: 10.1128/jb.156.1.6-12.1983.
7
In vivo and in vitro binding of 1,2-dibromoethane and 1,2-dichloroethane to macromolecules in rat and mouse organs.1,2 - 二溴乙烷和1,2 - 二氯乙烷在大鼠和小鼠器官中与大分子的体内及体外结合
J Cancer Res Clin Oncol. 1984;108(2):204-13. doi: 10.1007/BF00402468.
8
Immunohistochemical detection of anti-(+/-)-trans-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)p yrene-bound adduct in nuclei of cultured HeLa cells and mouse lung tissue.免疫组织化学检测培养的HeLa细胞核及小鼠肺组织中抗-（+/-）-反式-7,8-二羟基-9,10-环氧-7,8,9,10-四氢苯并（a）芘结合加合物。
J Cancer Res Clin Oncol. 1988;114(3):225-30. doi: 10.1007/BF00405826.
9
Benzene adducts with rat nucleic acids and proteins: dose-response relationship after treatment in vivo.苯与大鼠核酸和蛋白质的加合物：体内处理后的剂量反应关系。
Environ Health Perspect. 1989 Jul;82:259-66. doi: 10.1289/ehp.8982259.
10
Quantitative predictability of carcinogenicity of the covalent binding index of chemicals to DNA: comparison of the in vivo and in vitro assays.化学物质与DNA共价结合指数致癌性的定量可预测性：体内和体外试验的比较。
Environ Health Perspect. 1990 Mar;84:183-92. doi: 10.1289/ehp.9084183.

本文引用的文献

1
[Desoxyribonucleic acids in some fish spermatozoa].[某些鱼类精子中的脱氧核糖核酸]
Hoppe Seylers Z Physiol Chem. 1956 Mar 17;303(3-6):140-52.
2
Determination of the rate constants for alkylation of DNA in vitro with methanesulfonic esters.体外测定甲磺酸酯对DNA进行烷基化反应的速率常数。
Acta Chem Scand. 1969;23(3):1080-2. doi: 10.3891/acta.chem.scand.23-1080.
3
Reaction rates and biological action of N-methyl- and N-ethyl-N-nitrosourea.N-甲基-和N-乙基-N-亚硝基脲的反应速率及生物学作用
Mutat Res. 1970 Sep;10(3):169-74. doi: 10.1016/0027-5107(70)90113-2.
4
Methylation of deoxyribonucleic acid in cultured mammalian cells by N-methyl-N'-nitro-N-nitrosoguanidine. The influence of cellular thiol concentrations on the extent of methylation and the 6-oxygen atom of guanine as a site of methylation.N-甲基-N'-硝基-N-亚硝基胍对培养的哺乳动物细胞中脱氧核糖核酸的甲基化作用。细胞内硫醇浓度对甲基化程度的影响以及鸟嘌呤的6-氧原子作为甲基化位点的情况。
Biochem J. 1970 Feb;116(4):693-707. doi: 10.1042/bj1160693.
5
Syntheses and properties of adenine and thymine nucleoside alkyl phosphotriesters, the neutral analogs of dinucleoside monophosphates.腺嘌呤和胸腺嘧啶核苷烷基磷酸三酯（二核苷单磷酸的中性类似物）的合成与性质
J Am Chem Soc. 1971 Dec;93(24):6657-65. doi: 10.1021/ja00753a054.
6
Reaction products from N-methyl-N-nitrosourea and deoxyribonucleic acid containing thymidine residues. Synthesis and identification of a new methylation product, O4-methylthymidine.N-甲基-N-亚硝基脲与含胸苷残基的脱氧核糖核酸的反应产物。一种新的甲基化产物O4-甲基胸苷的合成与鉴定。
Biochem J. 1973 Sep;135(1):193-201. doi: 10.1042/bj1350193.
7
The alkylation of 2'-deoxyguanosine and of thymidine with diazoalkanes. Some observations on o-alkylation.重氮烷与2'-脱氧鸟苷和胸腺嘧啶核苷的烷基化反应。关于邻位烷基化的一些观察结果。
Biochem J. 1973 Sep;135(1):203-13. doi: 10.1042/bj1350203.
8
Hydrogen-bonded complexes of adenine and thymine nucleoside alkyl phosphotriesters in deuteriochloroform.腺嘌呤与胸腺嘧啶核苷烷基磷酸三酯在氘代氯仿中的氢键复合物。
Biochemistry. 1973 Feb;12(4):720-6. doi: 10.1021/bi00728a023.
9
Methylation of ribonucleic acid by the carcinogens dimethyl sulphate, N-methyl-N-nitrosourea and N-methyl-N'-nitro-N-nitrosoguanidine. Comparisons of chemical analyses at the nucleoside and base levels.致癌物质硫酸二甲酯、N-甲基-N-亚硝基脲和N-甲基-N'-硝基-N-亚硝基胍对核糖核酸的甲基化作用。核苷和碱基水平化学分析的比较。
Biochem J. 1972 Jun;128(1):117-32. doi: 10.1042/bj1280117.
10
Reaction of N-methyl-N-nitrosourea (MNUA) with 32P-labelled DNA: evidence for formation of phosphotriesters.N-甲基-N-亚硝基脲（MNUA）与32P标记的DNA的反应：磷酸三酯形成的证据。
Chem Biol Interact. 1973 Aug;7(2):127-30. doi: 10.1016/0009-2797(73)90022-7.

致癌物硫酸二甲酯、甲磺酸乙酯、N-乙基-N-亚硝基脲和N-甲基-N-亚硝基脲对脱氧核糖核酸的烷基化作用。磷酸二酯位点胸苷酰（3'-5'）胸苷的相对反应活性。

Alkylation of deoxyribonucleic acid by carcinogens dimethyl sulphate, ethyl methanesulphonate, N-ethyl-N-nitrosourea and N-methyl-N-nitrosourea. Relative reactivity of the phosphodiester site thymidylyl(3'-5')thymidine.

作者信息

Swenson D H, Lawley P D

出版信息

Biochem J. 1978 Jun 1;171(3):575-87. doi: 10.1042/bj1710575.

DOI:10.1042/bj1710575
PMID:208508
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1184002/
Abstract
  1. The ethyl phosphotriester of thymidylyl(3'-5')thymidine, dTp(Et)dT, was identified as a product from reaction of DNA with N-ethyl-N-nitrosourea, by procedures parallel to those reported previously for the methyl homologue produced by N-methyl-N-nitrosourea. 2. Enzymic degradation to yield alkyl phosphotriesters from DNA alkylated by these carcinogens and by dimethyl sulphate and ethyl methanesulphonate was studied quantitatively, and the relative yields of the triesters dTp(Alk)dT were determined. The relative reactivity of the phosphodiester group dTpdT to each of the four carcinogens was thus obtained, and compared with that of DNA overall, or with that of the N-7 atom of guanine in DNA. Relative reactivity of the phosphodiester group was lowest towards dimethyl sulphate, the least electrophilic of the reagents used, and was highest towards N-ethyl-N-nitrosourea, the most electrophilic reagent. 3. The nature of the alkyl group transferred also influenced reactivity of the phosphodiester site, since this site was relatively more reactive towards ethylation than would be predicted simply from the known Swain-Scott s values of the alkylating agents. It was therefore suggested that the steric accessibility of the weakly nucleophilic phosphodiester group on the outside of the DNA macromolecule favours its reaction with ethylating, as opposed to methylating, reagents. 4. Taking a value of the Swain-Scott nucleophilicity (n) of 2.5 for an average DNA nucleotide unit [Walles & Ehrenberg (1969) Acta Chem. Scand. 23, 1080-1084], a value of n of about 1 for the phosphodiester group was deduced, and this value was found to be 2-3 units less than that for the N-7 atom of guanine in DNA. 5. The reactivity of DNA overall was markedly high towards the alkylnitrosoureas, despite their relatively low s values. This was ascribed to an electrostatic factor that favoured reaction of the negatively charged polymer with alkyldiazonium cation intermediates.
摘要
  1. 通过与之前报道的由N-甲基-N-亚硝基脲产生的甲基同系物的方法平行的程序，胸苷酰基（3'-5'）胸苷的乙基磷酸三酯dTp(Et)dT被鉴定为DNA与N-乙基-N-亚硝基脲反应的产物。2. 对由这些致癌物以及硫酸二甲酯和甲磺酸乙酯烷基化的DNA进行酶促降解以产生烷基磷酸三酯进行了定量研究，并测定了三酯dTp(Alk)dT 的相对产率。由此获得了磷酸二酯基团dTpdT对四种致癌物中每一种致癌物的相对反应活性，并将其与DNA整体的反应活性或与DNA中鸟嘌呤的N-7原子的反应活性进行了比较。磷酸二酯基团的相对反应活性对硫酸二甲酯最低，硫酸二甲酯是所用试剂中亲电性最弱的，而对N-乙基-N-亚硝基脲最高，N-乙基-N-亚硝基脲是亲电性最强的试剂。3. 转移的烷基的性质也影响了磷酸二酯位点的反应活性，因为该位点对乙基化的反应活性相对较高，这比仅根据烷基化剂已知的斯温-斯科特s值所预测的要高。因此有人提出，DNA大分子外部亲核性较弱的磷酸二酯基团的空间可及性有利于其与乙基化试剂而非甲基化试剂反应。4. 假设平均DNA核苷酸单元的斯温-斯科特亲核性（n）值为2.5 [瓦莱斯和埃伦贝格（1969年）《化学学报》23卷，1080 - 1084页]，推断出磷酸二酯基团的n值约为1，并且发现该值比DNA中鸟嘌呤的N-7原子的n值小2 - 3个单位。5. 尽管烷基亚硝基脲的s值相对较低，但DNA整体对其反应活性明显较高。这归因于一个静电因素，该因素有利于带负电荷的聚合物与烷基重氮阳离子中间体反应。