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甲基重氮烷阳离子(CH3N2^+)与DNA碱基的甲基化反应 被引量:1

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摘要 在B3LYP/6-31G**和MP2/6-311G**水平上,计算了终致癌物甲基重氮烷阳离子(CH3N2+)在气相和水溶剂中与四种DNA碱基上10个亲核位发生甲基化过程的反应机理.结果表明:在气相和溶剂中,终致癌物CH3N2+对碱基上相应亲核位的甲基化反应过程,活化能都比较小(<33.5kJ/mol),是容易进行的放热反应.所以,二甲基亚硝胺一旦形成终致癌物,则很容易与碱基形成癌变物.
出处 《中国科学(B辑)》 CSCD 北大核心 2008年第12期1075-1080,共6页 Science in China(Series B)
基金 上海市教育委员会(批准号:yyy-07015)资助项目
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  • 1Lee V M, Keefer L K, Archer M C. An evaluation of the roles of metabolic denitrosation and α-hydroxylation in the heptatoxicity of N-nitrosodimethylamine. Chem Res Toxicol, 1996, 9(8): 1319-1324.
  • 2Wang M Y, Pramod U, Trieu T D, Leo E B, Stephen S H. Lactols in hydrolysates of DNA treated with α-acetoxy-N-nitrosopyrrolidine or crotonaldehyde. Chem Res Toxicol, 1998, 11, 1567-1573.
  • 3Miller J A, Miller E C. Ultimate Chemical Carcinogens as Reactive Mutagenic Electrophiles. In origins of Human Cancer, Book B, Gold Spring Harbor, New York: Cold Spring Harbor Press, 1977. 605-627.
  • 4Singer B, Grunberger D. Molecular Biology of Mutagens and Carcinogens. New York: Plenum Pres, 1983. 161-183.
  • 5Loeppky R N, Michejda C J. Nitrosamines and Related N-Nitroso Compounds Chemistry and Biochemistry, ACS Symposium Series, Vol. 553. Washington DC, 1994. 279-289.
  • 6Glaser R, Choy G S. Importance of the anisotropy of atoms in molecules for the representation of electron density distributions with Lewis structures. A case study of aliphatic diazonium ions. J Am Chem Soc, 1993, 115(6): 2340-2347.
  • 7Vincent M A, Radom L. An ab initio study of the methane- and benzene-Diazonium ions. J Am Chem Soc, 1978, 100, 3306-3311.
  • 8Reynolds C, Thomson C A. A theoretical study of N-nitrosamine metabolites: Possible alkylating species in carcinogenesis by N,N'-dimethyl nitrosamine. Int J Quant Chem, 1986, 30, 751-762.
  • 9Mohammad S N, Hopfinger A J. Chemical reactivity of a methyldiazonium ion with nucleophilic centers of DNA bases. J theor Biol, 1980, 87(2): 401-419.
  • 10Kism N S, Lebreton P R. UV photoelectron and ab ini6o quantum mechanical evaluation of nucleotide ionization potentials in water-counterion environments: π polarization effects on DNA alkylation by carcinogenic methylating agents. J Am Chem Soc, 1996, 118(15): 3694-3707.

同被引文献11

  • 1NEIDL S.Oxford hand book of nucleic acid structure[M].New York:Oxford university press Inc,1999.
  • 2KUCHINO Y,MORI F,KASAI H,et al.Misreading of DNA templates containing 8-hydroxydeoxyguanosine at the modified base and at adjacent residues[J].Nature,1987,327(6117):77-79.
  • 3YAO L S,CUKIER R I,YAN H G.Catalytic mechanism of guanine deaminase:an ONIOM and molecular dynamics study[J].Journal of Physical Chemistry B,2007,111(16):4200-4210.
  • 4ZHANG A H,YANG B H,LI Z H.Theoretical study on the hydrolytic deamination reaction mechanism of adenine-(H2O)n(n=4)[J].Journal of Molecular Structure:THEOCHEM,2007,819(1/2/3):95-101.
  • 5SPONER J E,SANZ-MIGUEL P J,SANTIAGO L R,et al.Metal-mediated deamination of cytosine:Experiment and DFT calculations[J].Angewandte Chemie International Edition,2004,43(40):5396-5399.
  • 6GOGGIN M,ANDERSON C,PARK S,et al.Quantitative high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry analysis of the adenine-guanine cross-links of 1,2,3,4-diepoxybutane in tissues of butadiene-exposed B6C3F1 mice[J].Chemical Research in Toxicology,2008,21(5):1163-1170.
  • 7LEE C,YANG W T,PARR R G.Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density[J].Physical Review.B,Condensed Matter,1988,37(2):785-789.
  • 8BARONE V,COSSI M,TOMASI J.A new definition of cavities for the computation of solvation free energies by the polarizable continuum model[J].The Journal of Chemical Physics,1997,107(8):3210-3221.
  • 9GONZALEZ C,SCHLEGEL H B.Reaction path following in mass-weighted internal coordinates[J].The Journal of Physical Chemistry,1990,94(14):5523-5527.
  • 10李澜,王竑,牛晓娟,李宗和.α-羟基化吡咯烷亚硝胺代谢及形成DNA加合物反应机理的理论研究[J].高等学校化学学报,2009,30(8):1596-1599. 被引量:3

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