Quantum chemical simulation of cytochrome P450 catalyzed aromatic oxidation: Metabolism, toxicity, and biodegradation of benzene derivatives

International Journal of Quantum Chemistry

Volumn 107, Issue 13, 2007, Pages 2454-2478

  D'Yachkov, P N ^a   Kharchevnikova, N V ^b   Dmitriev, A V ^b   Kuznetsov, A V ^a   Poroikov, V V ^b  

^a KURNAKOV INSTITUTE OF GENERAL AND INORGANIC CHEMISTRY   (Russian Federation)

^b INSTITUTE OF BIOMEDICAL CHEMISTRY   (Russian Federation)

Author keywords

Benzene derivatives; Biological oxidation; Chlorinated biphenyls; Metabolism; MO LCAO MNDO approach; P450 monooxygenase system; Toxicity

Indexed keywords

AROMATIC COMPOUNDS; COMPUTER SIMULATION; METABOLISM; OXIDATION; PROTEINS; TOXICITY;

BENZENE DERIVATIVES; BIOLOGICAL OXIDATION; CHLORINATED BIPHENYLS; MO LCAO MNDO APPROACH; P450 MONOOXYGENASE SYSTEM;

QUANTUM CHEMISTRY;

EID: 34548562171     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.21416     Document Type: Article

References (70)

1. Goldstein, J. A.; Faletto, M. B. Environ Health Persp 1993, 100, 169.
2. Guengerich, F. P. Chem Res Toxicol 2001, 14, 612.
3. Guengerich, F. P.; Shimada, T. Chem Res Toxicol 1991, 4, 391.
4. Miller, E. C.; Miller, J. A. Pharmacol Rev 1966, 18, 805.
5. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327.
6. McKinney, J. D. Environ Health Persp 1996, 104, 810.
7. Lag, M.; Omichinski, J. G.; Dybing, E. Chem-Biol Interact 1994, 93, 73.
8. Loew, G. H.; Spangler, D.; Spanggord, R. J. In QSAR in Toxicology and Xenobiochemistry; Tichy, M., Ed.; Pharmacochem Library; Elsevier: Amsterdam, 1985, 8, 111.
9. Ford, G. P. J Mol Struct (Theochem) 1997, 401, 253.
10. Grogan, J.; De Vito, S. C.; Korzekwa, K. R. Chem Res Toxicol 1992, 5, 548.
11. Von Szenpaly, S. V. J. J Am Chem Soc 1984, 106, 6021.
12. Lehner, A. F.; Horn, J.; Flesher, J. W. J Mol Struct (Theochem) 1996, 366, 203.
13. Flesher, J. W.; Horn, J.; Lehner, A. F. J Mol Struct (Theochem) 1996, 362, 29.
14. Noor Mohammad, S. Indian J Biochem Biophys 1984, 21, 269.
15. Braga, R. S.; Barone, P. M.; Galvao, D. S. J Mol Struct (Theochem) 1999, 464, 257.
16. Rabinowitz, J.; Little, S.; Brown, K. Int J Quant Chem 2002, 88, 99.
17. Silverman, B. D. Cancer Biochem Biophys 1981, 5, 207.
18. Maynard, A. T.; Pedersen, L. G.; Posner, H. S.; McKinney, J. D. Mol Pharmacol 1986, 9, 629.
19. Loew, G. H. Sudhidra, B. S.; Burt, S. Int J Quant Chem: Quant Biol Symp 1979, 6, 259.
20. Sabbioni, G.; Wild, D. Carcinogenesis 1992, 13, 709.
21. Wild, D. Environ Health Persp 1993, 88, 27.
22. Ford, G. P.; Herman, P. S. Chem-Biol Interact 1992, 9, 81.
23. Hatch, F. T.; Colvin, M. E.; Seidl, E. T. Environ Mol Mutagen 1996, 27, 314.
24. Benigni, R.; Passerini, L. Mutat Res 2002, 511, 191.
25. Benigni, R.; Andreoli, C. Environ Mol Mutag 1994, 24, 208.
26. Sasaki, J. C.; Fellers, R. S.; Colvin, M. E. Mutat Res 2002, 506, 79.
27. Pudzanowski, A. T.; Loew, G. H.; Mico, B. A. J Am Chem Soc 1983, 105, 3434.
28. Quanhuan, D. J Mol Struct (Theochem) 1987, 149, 167.
29. Loew, G. H.; Rebagliati, M.; Poulsen, M. Biochem Biophys 1984, 7, 109.
30. Korzekwa, K. R.; Jones, J. P.; Gilette, J. R. J Am Chem Soc 1990, 112, 7046.
31. Yin, H.; Anders, M.; Korsekwa, K.; Higgins, L. A.; Thummel, K. E. Proc Natl Acad Sci USA 1995, 92, 11076.
32. Parke, D. V. The Biochemistry of Foreign Compounds; Pergamon Press: Oxford, 1968; p 120.
33. Rickert, D. E. Drug Metabol Rev 1987, 18, 23.
34. Hata, M.; Hoshino, T.; Tsuda, M. Chem Commun 2000, 2037.
35. Hata, M.; Hirano, Y.; Hoshino, T.; Nishida, R.; Tsuda, M. J Mol Struct (Theochem) 2005, 722, 133.
36. de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. J Am Chem Soc 2002, 124, 11809.
37. de Visser, S. P.; Shaik, S. J Am Chem Soc 2003, 125, 7413.
38. Bathelt, C. M.; Ridder, L.; Mulholland, A. J.; Harvey, J. N. J Am Chem Soc 2003, 125, 15004.
39. Bathelt, C. M.; Ridder, L.; Mulholland, A. J.; Harvey, J. N. Org Biomol Chem 2004, 2, 2998.
40. Dowers, T. S.; Rock, D. A.; Rock, D. A.; Perkins, B. N.; Jones, J. P. Drug Metabol Dispos 2004, 32, 328.
41. Yuan, Z. X.; Kumar, S.; Sikka, H. C. Chem Res Toxicol 2004, 17, 672.
42. Korsekwa, K.; Trager, W.; Gouterman, M.; Spangler, D.; Loew, G. H. J Am Chem Soc 1985, 107, 4273.
43. Burka, L. T.; Plucinski, T. M.; McDonald, T. L. Proc Nati Acad Sci USA 1983, 80, 6680.
44. Pudzianowski, A. T.; Loew, G. H. J Mol Catal 1982, 17, 1.
45. Pudzianowski, A. T.; Loew, G. H. Int J Quantum Chem 1983, 23, 1257.
46. Kuznetsov, A. V. Molekulyarnaya Biologiya (Molecular Biology) 1990, 24, 1373 [in Russian].
47. Daly, J.; Jerina, D.; Witkop, B. Arch Biochem Biophys 1968, 128, 517.
48. Novikov, S. M.; Poroikov, V. V.; Tertychnikov, S. N. Gygiena i Sanitariya (Hygiene and Sanitary) 1995, 1, 29 [in Russian].
49. Hanch, C.; Leo, A. J. Substituents Constants for Correlation Analysis in Chemistry and Biology. Wiley: New York, 1979.
50. Bedarl, D. L.; Haberl, M. L. Microbiol Ecol 1990, 20, 87.
51. Bedarl, D. L.; Haberl, M. L. Appl Environ Microbiol 1987, 53, 1103.
52. Chakrabarty, A. M. Biodegradation and Detoxication of Environmental Pollutants, CRC Press: Boca Raton, FL, 1982; p 39.
53. Williams, R. T. Detoxication Mechanisms. The Metabolism and Detoxication of Drugs, Toxic Substances and Other Organic Compounds. Chapman & Hall: London, 1959.
54. Rusvai, E.; Vedh, M.; Kramer, M. Biochem Pharmacol 1988, 37, 4574.
55. Loew, G. H.; Sudhindra, B. S.; Walker, J. M. J Environ Pathol Toxicol 1979, 2, 106.
56. Inoue, O.; Seiji, K.; Ikeda, M. Bull Environ Contam Toxicol 1989, 43, 220.
57. Gorrod, J. W. Xenobiotica 1980, 10, 603.
58. Nechiporenko, S. P.; Rotenberg, Yu. S. Toksikologiya (Toxicology) 1981, 12, 118 [in Russian].
59. Bakke, O. M.; Scheline, R. R. Toxicol Appl Pharmacol 1970, 691.
60. Woiwode, W.; Wadarz, R.; Drysch, K.; Weichardt, H. Arch Toxicol 1979, 43, 93.
61. Woiwode, W.; Drysch, K. Br J Ind Med 1981, 38, 194.
62. Kondo, K. Yoshido, Y.; Yamadata, H. Ind Health 1985, 23, 37.
63. Hanzlik, R. P.; Hogberg, K.; Judson, C. M. Biochemistry 1984, 23, 3048.
64. Inoue, O.; Seigi, K.; Nakotsuka, H. Bull Environ Contam Toxocol 1989, 43, 74.
65. Ohtsuji, H.; Ikeda, M. Toxicol Appl Pharmacol 1971, 16, 321.
66. Ogata, M.; Shimada, Y. Int Arch Occup Environ Health 1983, 53, 51.
67. Selander, H. G.; Jerina, D. M.; Daly, J. W. Arch Biochem Biophys 1975, 168, 309.
68. Rickert, D. E. Drug Metabol Rev 1987, 18, 23.
69. Pathiratne, A.; Puyear, R. L.; Brammer, J. D. Drug Metal Dispos 1984, 14, 386.
70. Yoshida, M.; Hara, I. Ind Health 1985, 23, 239.