In silico studies of polyaromatic hydrocarbon inhibitors of cytochrome P450 enzymes 1A1, 1A2, 2A6, and 2B1

Chemical Research in Toxicology

Volumn 23, Issue 3, 2010, Pages 600-607

  Sridhar, Jayalakshmi ^a   Jin, Ping ^a   Liu, Jiawang ^a   Foroozesh, Maryam ^a   KleinStevens, Cheryl L ^a  

^a XAVIER UNIVERSITY OF LOUISIANA   (United States)

Author keywords

Pocket for potential

Indexed keywords

1 (1 BUTYNYL)PYRENE; 1 (1 PROPYNYL)PYRENE; 1 ETHYNYLPYRENE; 2 (1 PROPYNYL)PHENANTHRENE; 2 ETHYNYLPHENANTHRENE; 3 ETHYNYLPHENANTHRENE; 4 (1 PROPYNYL)PYRENE; 9 (1 PROPYNYL)PHENANTHRENE; 9 ETHYNYLPHENANTHRENE; ACETYLENE; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 2A6; CYTOCHROME P450 2B1; HEME; IRON; PHENYLALANINE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; COMPUTER MODEL; CRYSTAL STRUCTURE; ENZYME BINDING; HYDROGEN BOND; HYDROPHOBICITY;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; HUMANS; MODELS, MOLECULAR; POLYCYCLIC HYDROCARBONS, AROMATIC; PROTEIN BINDING; RATS;

EID: 77949356275     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx900348v     Document Type: Article

References (38)

1. Nelson, D. R., Koymans, L., Kamataki, T., Stegeman, J. J., Feyereisen, R., Waxman, D. J., Waterman, M. R., Gotoh, O., Coon, M. J., Estabrook, R. W., Gunsalus, I. C., and Nebert, D. W. (1996) P450 superfamily: Update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 6, 1-42.
2. Nelson, D. R., Kamataki, T., Waxman, D. J., Guengerich, F. P., Estabrook, R. W., Feyereisen, R., Gonzalez, F. J., Coon, M. J., Gunsalus, I. C., Gotoh, O., et al. (1993) The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature. DNA Cell Biol. 12, 1-51.
3. Guengerich, F. P. (2004) Cytochrome P450: What have we learned and what are the future issues? Drug Metab. ReV. 36, 159-197.
4. Agundez, J. A. (2004) Cytochrome P450 gene polymorphism and cancer. Curr. Drug Metab. 5, 211-224.
5. Shimada, T., Oda, Y., Gillam, E. M., Guengerich, F. P., and 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 Metab. Dispos. 29, 1176-1182.
6. Shimada, T., and Guengerich, F. P. (2006) Inhibition of human cytochrome P450 1A1-, 1A2-, and 1B1-mediated activation of procarcinogens to genotoxic metabolites by polycyclic aromatic hydrocarbons. Chem. Res. Toxicol. 19, 288-294.
7. Guengerich, F. P., and Shimada, T. (1998) Activation of procarcinogens by human cytochrome P450 enzymes. Mutat. Res./Fundam. Mol. Mech. Mutagen. 400, 201-213.
8. Conney, A. H. (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture. Cancer Res. 42, 4875-4917.
9. Bruno, R. D., and Njar, V. C. (2007) Targeting cytochrome P450 enzymes: A new approach in anti-cancer drug development. Bioorg. Med. Chem. 15, 5047-5060.
10. Foroozesh, M., Primrose, G., Guo, Z., Bell, L. C., Alworth, W. L., and Guengerich, F. P. (1997) Aryl acetylenes as mechanism-based inhibitors of cytochrome P450-dependent monooxygenase enzymes. Chem. Res. Toxicol. 10, 91-102.
11. Shimada, T., Murajama, N., Tanaka, K., Takenaka, S., Imai, Y., Hopkins, N. E., Foroozesh, M. K., Alworth, W. L., Yamazaki, H., Guengerich, F. P., and Komori, M. (2008) Interaction of polycyclic aromatic hydrocarbons with human cytochrome P450 1B1 in inhibiting catalytic activity. Chem. Res. Toxicol. 21, 2313-2323.
12. Alexander, D. L., Zhang, L., Foroozesh, M., Alworth, W. L., and Jefcoate, C. R. (1999) Metabolism-based polycyclic aromatic acetylene inhibition of CYP1B1 in 10T1/2 cells potentiates aryl hydrocarbon receptor activity. Toxicol. Appl. Pharmacol. 161, 123-139.
13. Roberts, E. S., Hopkins, N. E., Foroozesh, M., Alworth, W. L., Halpert, J. R., and Hollenberg, P. F. (1997) Inactivation of cytochrome P450s 2B1, 2B4, 2B6, and 2B11 by arylalkynes. Drug Metab. Dispos. 25, 1242-1248.
14. Hopkins, N. E., Foroozesh, M. K., and Alworth, W. L. (1992) Suicide inhibitors of cytochrome P450 1A1 and P450 2B1. Biochem. Pharmacol. 44, 787-796.
15. Courter, L. A., Musafia-Jeknic, T., Fischer, K., Bildfell, R., Giovanini, J., Pereira, C., and Baird, W. M. (2007) Urban dust particulate matter alters PAH-induced carcinogenesis by inhibition of CYP1A1 and CYP1B1. Toxicol. Sci. 95, 63-73.
16. Ortiz de Montellano, P. R., and Kunze, K. L. (1980) Self-catalyzed inactivation of hepatic cytochrome P-450 by ethynyl substrates. J. Biol. Chem. 255, 5578-5585.
17. Ortiz de Montellano, P. R. (1991) Mechanism-based inactivation of cytochrome P450: Isolation and characterization of N-alkyl heme adducts. Methods Enzymol. 206, 533-540.
18. Burke, M. D., Thompson, S., Weaver, R. J., Wolf, C. R., and Mayer, R. T. (1994) Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem. Pharmacol. 48, 923-936.
19. Buters, J. T., Schiller, C. D., and Chou, R. C. (1993) A highly sensitive tool for the assay of cytochrome P450 enzyme activity in rat, dog and man. Direct fluorescence monitoring of the deethylation of 7-ethoxy-4- trifluoromethylcoumarin. Biochem. Pharmacol. 46, 1577-1584.
20. Deluca, J. G., Dysaft, G. R., Rasnick, D., and Bradley, M. O. (1989) A direct, highly sensitive assay for cytochrome P-450 catalyzed O-deethylation using a novel coumarin analog. Biochem. Pharmacol. 37, 1731-1739.
21. O'Donovan, C., Martin, M. J., Gattiker, A., Gasteiger, E., Bairoch, A., and Apweiler, R. (2002) High-quality protein knowledge resource: SWISS-PROT and TrEMBL. Brief Bioinform. 3, 275-284.
22. Needleman, S. B., and Wunsch, C. D. (1970) A general method applicable to the search for similarities in the amino acid sequence of two proteins. J. Mol. Biol. 48, 443-453.
23. Laskowski, R. A., Rullmannn, J. A., MacArthur, M. W., Kaptein, R., and Thornton, J. M. (1996) AQUA and PROCHECK-NMR: Programs for checking the quality of protein structures solved by NMR. J. Biomol. NMR 8, 477-486.
24. Sippl, M. J. (1993) Recognition of errors in three-dimensional structures of proteins. Proteins 17, 355-362.
25. Oda, A., Yamaotsu, N., and Hirono, S. (2005) New AMBER force field parameters of heme iron for cytochrome P450s determined by quantum chemical calculations of simplified models. J. Comput. Chem. 26, 818-826.
26. Gill, P. E., Murray, W., and Wright, M. H. (1981) Practical Optimization, Academic Press, London.
27. Sansen, S., Yano, J. K., Reynald, R. L., Schoch, G. A., Griffin, K. J., Stout, C. D., and Johnson, E. F. (2007) Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2. J. Biol. Chem. 282, 14348-14355.
28. Yano, J. K., Hsu, M. H., Griffin, K. J., Stout, C. D., and Johnson, E. F. (2005) Structures of human microsomal cytochrome P450 2A6 complexed with coumarin and methoxsalen. Nat. Struct. Mol. Biol. 12, 822-823.
29. Dawson, J. H., Holm, R. H., Trudell, J. R., Barth, G., Linder, R. E., Bunnenberg, E., Djerassi, C., and Tang, S. C. (1976) Letter: Oxidized cytochrome P-450. Magnetic circular dichroism evidence for thiolate ligation in the substrate-bound form. Implications for the catalytic mechanism. J. Am. Chem. Soc. 98, 3707-3708.
30. Ortiz de Montellano, P. R., and Komives, E. A. (1985) Branchpoint for heme alkylation and metabolite formation in the oxidation of arylacetylenes by cytochrome P-450. J. Biol. Chem. 260, 3330-3336.
31. Ortiz de Montellano, P. R. (1991) Mechanism-based inactivation of cytochrome P450: Isolation and characterization of N-alkyl heme adducts. Methods Enzymol. 206, 533-540.
32. Roberts, E. S., Hopkins, N. E., Alworth, W. L., and Hollenberg, P. F. (1993) Mechanism-based inactivation of cytochrome P450 2B1 by 2-ethynylnaphthalene: identification of an active-site peptide. Chem. Res. Toxicol. 6, 470-479.
33. Chan, W. K., Sui, Z., and Ortiz de Montellano, P. R. (1993) Determinants of protein modification versus heme alkylation: inactivation of cytochrome P450 1A1 by 1-ethynylpyrene and phenylacetylene. Chem. Res. Toxicol. 6, 38-45.
34. Sinnokrot, M. O., and Sherrill, C. D. (2006) High-accuracy quantum mechanical studies of pi-pi interactions in benzene dimers. J. Phys. Chem. A 110, 10656-10668.
35. Grimme, S. (2008) Do special noncovalent pi-pi stacking interactions really exist. Angew. Chem., Int. Ed. Engl. 47, 3430-3434.
36. Zimmerman, S. C., VanZyl, C. M., and Hamilton, G. S. (1989) Rigid molecular tweezers: Preorganized hosts for electron donor-acceptor complexation in organic solvents. J. Am. Chem. Soc. 111, 1373-1381.
37. Hunter, C. A., Singh, J., and Thornton, J. M. (1991) Pi-pi interactions: The geometry and energetics of phenylalanine-phenylalanine interactions in proteins. J. Mol. Biol. 218, 837-846.
38. Hunter, C. A., and Sanders, J. K. M. (1990) The nature of π-π interactions. J. Am. Chem. Soc. 112, 5525-5534.