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Methylation reaction for four DNA base molecules by methanediazonium ions

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Abstract

The methylation reactions at ten nucleophilic sites in four DNA base molecules with methanediazonium ions (CH3N2 +) have been theoretically investigated including solvent effects at the B3LYP/6-31G** and MP2/6-31G** levels. The results show that all the methylation reactions have relatively small activation energy (<33.5 kJ/mol), and the methylation process is exothermic reaction and easy to occur. This study shows that the ultimate carcinogen CH3N2 + by NDMA can easily methylate DNA base molecules and form carcinogenic products.

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References

  1. Lee 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

    Article  CAS  Google Scholar 

  2. Wang 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

    Article  CAS  Google Scholar 

  3. Miller J A, Miller E C, Ultimate chemical carcinogens as reactive mutagenic electrophiles. In: Origins of Human Cancer, Book B. New York: Cold Spring Harbor Press, 1977. 605–627

    Google Scholar 

  4. Singer B, Grunberger D. Molecular Biology of Mutagens and Carcinogens. New York: Plenum Pres, 1983, 161–183

    Google Scholar 

  5. Loeppky R N, Michejda C J. Nitrosamines and related N-nitroso compounds chemistry and biochemistry, ACS Symposium Series, Vol. 553. Washington DC, 1994, 279–289

    Article  Google Scholar 

  6. Glaser R and 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

    Article  CAS  Google Scholar 

  7. Vincent M A, Radom L. An ab initio study of the methane- and benzene-diazonium ions. J Am Chem Soc, 1978, 100: 3306–3311

    Article  CAS  Google Scholar 

  8. Reynolds 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

    Article  Google Scholar 

  9. Mohammad S N, Hopfinger A J. Chemical reactivity of a methyldi-azonium ion with nucleophilic centers of DNA bases. J theor Biol, 1980, 87(2): 401–419

    Article  CAS  Google Scholar 

  10. Kism N S, Lebreton P R. UV Photoelectron and ab initio 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

    Article  Google Scholar 

  11. Pullman A, Armbruster A M. On the affinity of cytosine towards electrophiles. Theor Chim Acta, 1977, 45: 249–256

    Article  CAS  Google Scholar 

  12. Li L, Zhang A H, Li Z H. Theoretical study of reaction mechanism for subsequent carcinogenic metabolites by nitrosodimethylamine. J Mole Struc: THEOCHEM, 2006, 759: 239–243

    Article  CAS  Google Scholar 

  13. Becke A D. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev, 1988, 38: 3098–3100

    Article  CAS  Google Scholar 

  14. Lee C, Yang W, Parr R G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B, 1988, 37: 785–789

    Article  CAS  Google Scholar 

  15. Head-Gordon M, Pople J A, Frisch M J. MP2 energy evaluation by direct methods. Chem Phys Lett, 1988, 153(6): 503–509

    Article  CAS  Google Scholar 

  16. Saebo S, Almlof J. Avoiding the integral storage bottleneck in LCAO calculations of electron correlation. Chem Phys Lett, 1989, 154(1): 83–89

    Article  CAS  Google Scholar 

  17. Frisch M J, Head-Gordon M, Pople J A. A direct MP2 gradient method. Chem Phys Lett, 1990, 166(3): 275–280

    Article  CAS  Google Scholar 

  18. Miertus S, Scrocco E, Tomaso J. Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Chem Phys, 1981, 55(1): 117–129

    Article  CAS  Google Scholar 

  19. Miertus S, Tomaso J. Approximate evaluations of the electrostatic free energy and internal energy changes in solution processes. Chem Phys, 1982, 65(2): 239–245

    Article  CAS  Google Scholar 

  20. Cossi M, Barone V, Cammi R, Tomasi J. Ab initio study of solvated molecules: a new implementation of the polarizable continuum model. J Chem Phys Lett. 1996, 255, 327–335

    Article  CAS  Google Scholar 

  21. Cances M T, Mennucci V and Tomaso J, A new integral equation formalism for the polarizable continuum model: Theoretical back-ground and applications to isotropic and anisotropic dielectrics. J Chem Phys, 1997, 107(8): 3032–3041

    Article  CAS  Google Scholar 

  22. Barone V, Cossi M, Tomaso J. A new definition of cavities for the computation of solvation free energies by the polarizable continuum model. J Chem Phys, 1997, 107(8): 3210–3221

    Article  CAS  Google Scholar 

  23. Cossi M, Barone V, Tomaso J. Ab initio study of ionic solutions by a polarizable continuum dielectric model. J Chem Phys Lett, 1998, 286, 253–263

    Article  CAS  Google Scholar 

  24. Barone V, Cossi M, Tomaso J. Geometry optimization of molecular structures in solution by the polarizable continuum model. J Comp Chem, 1998, 19(4): 404–417

    Article  CAS  Google Scholar 

  25. Mennucci B and Mennucci B. Analytical derivatives for geometry optimization in solvation continuum models. I. Theory. J Chem Phys, 1998, 109(1): 249–259

    Article  Google Scholar 

  26. Gonzalez C, Schlegel H B. An improved algorithm for reaction path following. J Chem Phys, 1989, 90(4): 2154–2159

    Article  CAS  Google Scholar 

  27. Gonzalez C, Schlegel H B. Reaction path following in mass-weighted internal coordinates. J Phys Chem, 1990, 94(14): 5523–5527

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Shanghai Institute of Technology, Shanghai, 200235, China

    Lan Li, ZhiHao Qu & Hong Wang

  2. College of Chemistry, Beijing Normal University, Beijing, 100875, China

    ZongHe Li

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  1. Lan Li
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  2. ZhiHao Qu
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  3. Hong Wang
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  4. ZongHe Li
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Correspondence to Lan Li.

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Supported by the Shanghai Municipal Education Commission (Grant No. YYY-07015) and Shanghai Institute of Technology (Grant No. YJ2007-36)

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Li, L., Qu, Z., Wang, H. et al. Methylation reaction for four DNA base molecules by methanediazonium ions. Sci. China Ser. B-Chem. 52, 26–30 (2009). https://doi.org/10.1007/s11426-008-0153-x

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  • DOI: https://doi.org/10.1007/s11426-008-0153-x

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