Conformations of adducts formed between the genotoxic benzo[a]pyrene-7,8-dione and 2′-deoxycytidine

References

• Balu, N., Padgett, W. T., Lambert, G. R., Swank, A. E., Richard, A. M., & Nesnow, S. (2004). Identification and characterization of novel stable deoxyguanosine and deoxyadenosine adducts of benzo[a]pyrene-7,8-quinone from reactions at physiological pH. Chemical Research in Toxicology, 17, 827–838.10.1021/tx034207s
   PubMed Web of Science ®Google Scholar
• Balu, N., Padgett, W. T., Nelson, G. B., Lambert, G. R., Ross, J. A., & Nesnow, S. (2006). Benzo[a]pyrene-7,8-quinone-3′-mononucleotide adduct standards for 32P postlabeling analyses: Detection of benzo[a]pyrene-7,8-quinone–calf thymus DNA adducts. Analytical Biochemistry, 355, 213–223.10.1016/j.ab.2006.05.023
   PubMed Web of Science ®Google Scholar
• Becke, A. D. (1988). Density functional exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38, 3098–3100.10.1103/PhysRevA.38.3098
   PubMed Web of Science ®Google Scholar
• Becke, A. D. (1993). Density functional thermochemistry. III. The role of exact exchange. The Journal of Chemical Physics, 98, 5648–5652.10.1063/1.464913
   Web of Science ®Google Scholar
• Benamira, M., Johnson, K., Chaudhary, A., Bruner, K., Tibbetts, C., & Marnett, L. J. (1995). Induction of mutations by replication of malondialdehyde modified M13 DNA in Escherichia coli: determination of the extent of DNA modification, genetic requirements for mutagenesis, and types of mutations induced. Carcinogenesis, 16, 93–99.10.1093/carcin/16.1.93
   PubMed Web of Science ®Google Scholar
• Burak, T. (2014). Selectivity of salicylaldoxime and its derivatives. Journal of New Results in Science, 5, 67–82.
   Google Scholar
• Cavalieri, E. L., & Rogan, E. G. (1995). Central role of radical cations in metabolic activation of polycyclic aromatic hydrocarbons. Xenobiotica, 25, 677–688.10.3109/00498259509061885
   PubMed Web of Science ®Google Scholar
• Chaudhary, A. K., Nokubo, M., Reddy, G. R., Yeola, S. N., Morrow, J. D., Blair, I. A., & Marnett, L. J. (1994). Detection of endogenous malondialdehyde–deoxyguanosine adducts in human liver. Science, 265, 1580–1582.10.1126/science.8079172
   PubMed Web of Science ®Google Scholar
• Conney, A. H. (1982). Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons hydrocarbons: G.H.A. Clowes Memorial Lecture. Cancer Research, 42, 4875–4917.
   PubMed Web of Science ®Google Scholar
• Dennington II, R., Keith, T., & Millam, J. (2007). GaussView (Version 4.1). Shawnee Mission, KS: Semichem, Inc.
   Google Scholar
• Faust, W. L. (1989). Explosive Molecular Ionic Crystals. Science, 245, 37–42.10.1126/science.245.4913.37
   PubMed Web of Science ®Google Scholar
• Flowers-Geary, L., Harvey, R. G., & Penning, T. M. (1995). Identification of benzo[a]pyrene-7,8-dione as an authentic metabolite of (±)- trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene in isolated rat hepatocytes. Carcinogenesis, 16, 2707–2715.10.1093/carcin/16.11.2707
   PubMed Web of Science ®Google Scholar
• Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J., … Pople, J. A. (2004). Gaussian 03 (Revision C.02.). Pittsburgh, PA: Gaussian.
   Google Scholar
• Gece, G. (2008). The use of quantum chemical methods in corrosion inhibitor studies. Corrosion Science, 50, 2981–2992.10.1016/j.corsci.2008.08.043
   Web of Science ®Google Scholar
• Guengerich, F. P. (2000). Metabolism of chemical carcinogens. Carcinogenesis, 21, 345–351.10.1093/carcin/21.3.345
   PubMed Web of Science ®Google Scholar
• Guengerich, F., & Shimada, T. (1998). Activation of procarcinogens by human cytochrome P450 enzymes. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, 400, 201–213.10.1016/S0027-5107(98)00037-2
   PubMed Web of Science ®Google Scholar
• Gunasekaran, S., Rajalakshmi, K., & Kumaresan, S. (2013). Vibrational analysis, electronic structure and nonlinear optical properties of Levofloxacin by density functional theory. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 112, 351–363.10.1016/j.saa.2013.04.074
   PubMed Web of Science ®Google Scholar
• Gupta, V. P., Sharma, A., Virdi, A., & Ram, V. J. (2006). Structural and spectroscopic studies on some chloropyrimidine derivatives by experimental and quantum chemical methods. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 64, 57–67.10.1016/j.saa.2005.06.045
   PubMed Web of Science ®Google Scholar
• Huang, M., Blair, I. A., & Penning, T. M. (2013). Identification of stable benzo[a]pyrene-7,8-dione-DNA adducts in human lung cells. Chemical Research in Toxicology, 26, 685–692.10.1021/tx300476m
   PubMed Web of Science ®Google Scholar
• IARC. (2010). Some non-heterocyclic polycyclic aromatic hydrocarbons and some related exposures. IARC monographs on the evaluation of carcinogenic risks to humans (Vol. 92, pp. 393–423). Lyon: World Health Organization.
   Google Scholar
• Jin, B., Lee, H. M., & Kim, S. K. (2010). Conformational analysis of genotoxic benzo[a] pyrene-7,8-dione-duplex DNA adducts using a molecular dynamics method. Journal of Biomolecular Structure & Dynamics, 27, 457–464.
   PubMed Web of Science ®Google Scholar
• Kadish, K. M., Smith, K. M., & Guilard, R. (2003). The porphyrin handbook: Medical aspects of porphyrins (Vol. 14, pp. 131–133). San Diego, CA: Academic Press.
   Google Scholar
• Lee, H. M., Chae, Y.-H., Kwon, C. K.,& Kim, S. K. (2007). Conformations of adducts formed between the genotoxic benzo[a]pyrene-7,8-dione and nucleosides studied by density functional theory. Biophysical Chemistry, 125, 151–158.10.1016/j.bpc.2006.07.015
   PubMed Web of Science ®Google Scholar
• Lee, H. M., Jin, B., & Kim, S. K. (2010). Conformational analysis of genotoxic benzo[a]pyrene-7,8-dione-duplex DNA adducts using a molecular dynamics method(II). Journal of Biomolecular Structure & Dynamics, 28, 421–430.
   PubMed Web of Science ®Google Scholar
• Masoud, M. S., Awad, M. K., Shaker, M. A., & El-Tahawy, M. M. T. (2010). The role of structural chemistry in the inhibitive performance of some aminopyrimidines on the corrosion of steel. Corrosion Science, 52, 2387–2396.10.1016/j.corsci.2010.04.011
   Web of Science ®Google Scholar
• Nesnow, S., Davis, C., Nelson, G. B., Lambert, G., Padgett, W., Pimentel, M., … Ross, J. A. (2002). Comparison of the genotoxic activities of the K-region dihydrodiol of benzo[a]pyrene with benzo[a]pyrene in mammalian cells: morphological cell transformation; DNA damage; and stable covalent DNA adducts. Mutation Research/Genetic Toxicology and Environmental Mutagenesis, 521, 91–102.10.1016/S1383-5718(02)00218-8
   PubMed Web of Science ®Google Scholar
• Nesnow, S., Nelson, G., Padgett, W. T., George, M. H., Moore, T., King, L. C., … Ross, J. A. (2010). Lack of contribution of covalent benzo[a]pyrene-7,8-quinone–DNA adducts in benzo[a]pyrene-induced mouse lung tumorigenesis. Chemico-Biological Interactions, 186, 157–165.10.1016/j.cbi.2010.03.037
   PubMed Web of Science ®Google Scholar
• Ohnishi, S., & Kawanishi, S. (2002). Double base lesions of DNA by a metabolite of carcinogenic benzo[a]pyrene. Biochemical and Biophysical Research Communications, 290, 778–782.10.1006/bbrc.2001.6249
   PubMed Web of Science ®Google Scholar
• Osborne, M. R., & Crosby, N. T. (1987). Benzopyrenes. Cambridge: Cambridge University Press.
   Google Scholar
• Palackal, N. T., Burczynski, M. E., Harvey, R. G., & Penning, T. M. (2001). The ubiquitous aldehyde reductase (AKR1A1) oxidizes proximate carcinogen trans-dihydrodiols to o-quinones: Potential role in polycyclic aromatic hydrocarbon activation. Biochemistry, 40, 10901–10910.10.1021/bi010872t
   PubMed Web of Science ®Google Scholar
• Palackal, N. T., Lee, S. H., Harvey, R. G., Blair, I. A., & Penning, T. M. (2002). Activation of polycyclic aromatic hydrocarbontrans-dihydrodiol proximate carcinogens by human aldo-keto reductase (AKR1C) enzymes and their functional overexpression in human lung carcinoma (A549) cells. Journal of Biological Chemistry, 277, 24799–24808.10.1074/jbc.M112424200
   PubMed Web of Science ®Google Scholar
• Pearson, R. G. (1989). Absolute electronegativity and hardness: Applications to organic chemistry. Journal of Organic Chemistry, 54, 1423–1430.10.1021/jo00267a034
   Web of Science ®Google Scholar
• Pearson, R. G. (2005). Chemical hardness and density functional theory. Journal of Chemical Sciences, 117, 369–377.10.1007/BF02708340
   Web of Science ®Google Scholar
• Reed, M., Monske, M., Lauer, F., Meserole, S., Born, J., & Burchiel, S. (2003). Benzo[a]pyrene diones are produced by photochemical and enzymatic oxidation and induce concentration-dependent decreases in the proliferative state of human pulmonary epithelial cells. Journal of Toxicology and Environmental Health, Part A, 66, 1189–1205.10.1080/15287390306409
   PubMed Web of Science ®Google Scholar
• Rothman, N., Poirier, M. C., Baser, M. E., Hansen, J. A., Gentile, C., Bowman, E. D., & Strickland, P. T. (1990). Formation of polycyclic aromatic hydrocarbon–DNA adducts in peripheral white blood cells during consumption of charcoal-broiled beef. Carcinogenesis, 11, 1241–1243.10.1093/carcin/11.7.1241
   PubMed Web of Science ®Google Scholar
• Shimada, T., Gillam, E. M., Oda, Y., Tsumura, F., Sutter, T. R., Guengerich, F. P., & Inoue, K. (1999). Metabolism of benzo[a]-pyrene to trans-7,8-dihydroxy-7,8-dihydrobenzo [a]pyrene by recombinant human cytochrome P450 1B1 and purified liver epoxide hydrolase. Chemical Research in Toxicology, 12, 623–629.10.1021/tx990028s
   PubMed Web of Science ®Google Scholar
• Shimada, T., Oda, Y., Gillam, E. M., Guengerich, F. P., & Inoue, K. (2001). Metabolic activation of polycyclic aromatic hydrocarbons and other procarcinogens by cytochromes P450 1A1 and P450 1B1 allelic variants and other human cytochromes P450 in Salmonella typhimurium NM2009. Drug Metabolism and Disposition, 29, 1176–1182.
   PubMed Web of Science ®Google Scholar
• Shou, M., Harvey, R. G., & Penning, T. M. (1993). Reactivity of benzo[a]pyrene-7,8-dione with DNA. Evidence for the formation of deoxyguanosine adducts. Carcinogenesis, 14, 475–482.10.1093/carcin/14.3.475
   PubMed Web of Science ®Google Scholar
• Zhang, G., & Musgrave, C. B. (2007). Comparison of DFT methods for molecular orbital eigenvalue calculations. Journal of Physical Chemistry A, 111, 1554–1561.10.1021/jp061633o
   PubMed Web of Science ®Google Scholar
• Zhou, Z., & Parr, R. G. (1990). Activation hardness: New index for describing the orientation of electrophilic aromatic substitution. Journal of the American Chemical Society, 112, 5720–5724.10.1021/ja00171a007
   Web of Science ®Google Scholar