7-ethynylcoumarins: Selective inhibitors of human cytochrome P450s 1A1 and 1A2

Chemical Research in Toxicology

Volumn 25, Issue 5, 2012, Pages 1047-1057

  Liu, Jiawang ^a   Nguyen, Thong T ^a   Dupart, Patrick S ^a   Sridhar, Jayalakshmi ^a   Zhang, Xiaoyi ^b   Zhu, Naijue ^a   Stevens, Cheryl L Klein ^a,c   Foroozesh, Maryam ^a  

^a XAVIER UNIVERSITY OF LOUISIANA   (United States)

^b CAPITAL MEDICAL UNIVERSITY   (China)

^c WESTERN KENTUCKY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 ETHYNYL 3 PHENYLCOUMARIN; 7 ETHYNYL 3,4,8 TRIMETHYLCOUMARIN; 7 ETHYNYLCOUMARIN; COUMARIN DERIVATIVE; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 2A6; CYTOCHROME P450 2B1; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; HUMAN; IC 50; NONHUMAN; RAT; SIMULATION; X RAY CRYSTALLOGRAPHY;

CATALYTIC DOMAIN; COUMARINS; CRYSTALLOGRAPHY, X-RAY; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP1A2; ENZYME INHIBITORS; HUMANS; MODELS, MOLECULAR;

EID: 84861303753     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx300023p     Document Type: Article

References (48)

1. Guengerich, F. P. (2004) Cytochrome P450: what have we learned and what are the future issues? Drug Metab. Rev. 36, 159-197
2. Guengerich, F. P. (2001) Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity Chem. Res. Toxicol. 14, 611-650
3. Baston, E. and Leroux, F. R. (2007) Inhibitors of steroidal cytochrome p450 enzymes as targets for drug development Recent Pat. Anticancer Drug Discovery 2, 31-58
4. Chang, T. K., Chen, J., Yang, G., and Yeung, E. Y. (2010) Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin J. Pineal Res. 48, 55-64
5. Ma, Q. and Lu, A. Y. (2007) CYP1A induction and human risk assessment: an evolving tale of in vitro and in vivo studies Drug Metab. Dispos. 35, 1009-1016
6. Zhou, S. F., Chan, E., Zhou, Z. W., Xue, C. C., Lai, X., and Duan, W. (2009) Insights into the structure, function, and regulation of human cytochrome P450 1A2 Curr. Drug Metab. 10, 713-729
7. Shimada, T., Gillam, E. M., Oda, Y., Tsumura, F., Sutter, T. R., Guengerich, F. P., and 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 Chem. Res. Toxicol. 12, 623-629
8. Ueng, Y. F., Shimada, T., Yamazaki, H., and Guengerich, F. P. (1995) Oxidation of aflatoxin B1 by bacterial recombinant human cytochrome P450 enzymes Chem. Res. Toxicol. 8, 218-225
9. Van Vleet, T. R., Macé, K., and Coulombe, R. A. (2002) Comparative aflatoxin B(1) activation and cytotoxicity in human bronchial cells expressing cytochromes P450 1A2 and 3A4 Cancer Res. 62, 105-112
10. Peterson, S., Lampe, J. W., Bammler, T. K., Gross-Steinmeyer, K., and Eaton, D. L. (2006) Apiaceous vegetable constituents inhibit human cytochrome P-450 1A2 (hCYP1A2) activity and hCYP1A2-mediated mutagenicity of aflatoxin B1 Food Chem. Toxicol. 44, 1474-1484
11. Wang, J. J., Zheng, Y., Sun, L., Wang, L., Yu, P. B., Li, H. L., Tian, X. P., Dong, J. H., Zhang, L., Xu, J., Shi, W., and Ma, T. Y. (2011) CYP1A1 Ile462Val polymorphism and susceptibility to lung cancer: a meta-analysis based on 32 studies Eur. J. Cancer Prev. 20, 445-452
12. Surekha, D., Sailaja, K., Rao, D. N., Padma, T., Raghunadharao, D., and Vishnupriya, S. (2009) Association of CYP1A1*2 polymorphisms with breast cancer risk: a case control study Indian J. Med. Sci. 63, 13-20
13. Khvostova, E. P., Pustylnyak, V. O., and Gulyaeva, L. F. (2012) Genetic polymorphism of estrogen metabolizing enzymes in Siberian women with breast cancer Genet. Test. Mol. Biomarkers 16, 167-173
14. Chun, Y. J., Ryu, S. Y., Jeong, T. C., and Kim, M. Y. (2001) Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin Drug Metab. Dispos. 29, 389-393
15. Kensler, T. W., Groopman, J. D., Sutter, T. R., Curphey, T. J., and Roebuck, B. D. (1999) Development of cancer chemopreventive agents: oltipraz as a paradigm Chem. Res. Toxicol. 12, 113-126
16. Gerhäuser, C. (2005) Beer constituents as potential cancer chemopreventive agents Eur. J. Cancer 41, 1941-1954
17. 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
18. Shimada, T., Yamazaki, H., Foroozesh, M., Hopkins, N. E., Alworth, W. L., and Guengerich, F. P. (1998) Selectivity of polycyclic inhibitors for human cytochrome P450s 1A1, 1A2, and 1B1 Chem. Res. Toxicol. 11, 1048-1056
19. Sridhar, J., Jin, P., Liu, J., Foroozesh, M., and Stevens, C. L. (2010) In silico studies of polyaromatic hydrocarbon inhibitors of cytochrome P450 enzymes 1A1, 1A2, 2A6, and 2B1 Chem. Res. Toxicol. 23, 600-607
20. Shimada, T., Tanaka, K., Takenaka, S., Murayama, N., Martin, M. V., Foroozesh, M. K., Yamazaki, H., Guengerich, F. P., and Komori, M. (2010) Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives Chem. Res. Toxicol. 23, 1921-1935
21. Sridhar, J., Liu, J., Foroozesh, M., and Stevens, C. K. (2012) Inhibition of cytochrome P450 enzymes by quinones and anthraquinones Chem. Res. Toxicol. 25, 357-365
22. Li, Y., Li, N. Y., and Sellers, E. M. (1997) Comparison of CYP2A6 catalytic activity on coumarin 7-hydroxylation in human and monkey liver microsomes Eur. J. Drug Metab. Pharmacokinet. 22, 295-304
23. 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
24. Born, S. L., Caudill, D., Fliter, K. L., and Purdon, M. P. (2002) Identification of the cytochromes P450 that catalyze coumarin 3,4-epoxidation and 3-hydroxylation Drug Metab. Dispos. 30, 483-487
25. Regal, K. A., Schrag, M. L., Kent, U. M., Wienkers, L. C., and Hollenberg, P. F. (2000) Mechanism-based inactivation of cytochrome P450 2B1 by 7-ethynylcoumarin: verification of apo-P450 adduction by electrospray ion trap mass spectrometry Chem. Res. Toxicol. 13, 262-270
26. Sridar, C., Kent, U. M., Noon, K., McCall, A., Alworth, B., Foroozesh, M., and Hollenberg, P. F. (2008) Differential inhibition of cytochromes P450 3A4 and 3A5 by the newly synthesized coumarin derivatives 7-coumarin propargyl ether and 7-(4-trifluoromethyl)coumarin propargyl ether Drug Metab. Dispos. 36, 2234-2243
27. 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
28. 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
29. 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
30. 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
31. Shimada, T., Murayama, N., Tanaka, K., Takenaka, S., Guengerich, F. P., Yamazaki, H., and Komori, M. (2011) Spectral modification and catalytic inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2A6, and 2A13 by four chemopreventive organoselenium compounds Chem. Res. Toxicol. 24, 1327-1337
32. Wu, J., Cui, G., Zhao, M., Cui, C., and Peng, S. (2007) Novel N-(3-carboxyl-9-benzyl-carboline-1-yl)ethylamino acids: synthesis, anti-proliferation activity and two-step-course of intercalation with calf thymus DNA Mol. Biosyst. 3, 855-861
33. 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
34. Venkatachalam, C. M., Jiang, X., Oldfield, T., and Waldman, M. (2003) LigandFit: a novel method for the shape-directed rapid docking of ligands to protein active sites J. Mol. Graphics Modell. 21, 289-307
35. Sharma, P. and Ghoshal, N. (2006) Exploration of a binding mode of benzothiazol-2-yl acetonitrile pyrimidine core based derivatives as potent c-Jun N-terminal kinase-3 inhibitors and 3D-QSAR analyses J. Chem. Inf. Model. 46, 1763-1774
36. Hu, L., Chen, G., and Chau, R. M. (2006) A neural networks-based drug discovery approach and its application for designing aldose reductase inhibitors J. Mol. Graphics Modell. 24, 244-253
37. Shrestha, A. R., Shindo, T., Ashida, N., and Nagamatsu, T. (2008) Synthesis, biological active molecular design, and molecular docking study of novel deazaflavin-cholestane hybrid compounds Bioorg. Med. Chem. 16, 8685-8696
38. Krovat, E. M. and Langer, T. (2004) Impact of scoring functions on enrichment in docking-based virtual screening: an application study on renin inhibitors J. Chem. Inf. Comput. Sci. 44, 1123-1129
39. Sakkiah, S., Thangapandian, S., John, S., Kwon, Y. J., and Lee, K. W. (2010) 3D QSAR pharmacophore based virtual screening and molecular docking for identification of potential HSP90 inhibitors Eur. J. Med. Chem. 45, 2132-2140
40. 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
41. 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
42. Zhu, N., Lightsey, D., Liu, J., Foroozesh, M., Morgan, K. M., Stevens, E. D., and Klein Stevens, C. L. (2010) Ethynyl and propynylpyrene inhibitors of cytochrome P450 J. Chem. Crystallogr. 40, 343-352
43. Androutsopoulos, V. P., Papakyriakou, A., Vourloumis, D., and Spandidos, D. A. (2011) Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids Bioorg. Med. Chem. 19, 2842-2849
44. Yamazaki, K., Suzuki, M., Itoh, T., Yamamoto, K., Kanemitsu, M., Matsumura, C., Nakano, T., Sakaki, T., Fukami, Y., Imaishi, H., and Inui, H. (2011) Structural basis of species differences between human and experimental animal CYP1A1s in metabolism of 3,3′,4,4′,5-pentachlorobiphenyl J. Biochem. 149, 487-494
45. Rosales-Hernández, M. C., Mendieta-Wejebe, J. E., Trujillo-Ferrara, J. G., and Correa-Basurto, J. (2010) Homology modeling and molecular dynamics of CYP1A1 and CYP2B1 to explore the metabolism of aryl derivatives by docking and experimental assays Eur. J. Med. Chem. 45, 4845-4855
46. Liu, J., Ericksen, S. S., Besspiata, D., Fisher, C. W., and Szklarz, G. D. (2003) Characterization of substrate binding to cytochrome P450 1A1 using molecular modeling and kinetic analyses: case of residue 382 Drug Metab. Dispos. 31, 412-420
47. Itoh, T., Takemura, H., Shimoi, K., and Yamamoto, K. (2010) A 3D model of CYP1B1 explains the dominant 4-hydroxylation of estradiol J. Chem. Inf. Model. 50, 1173-1178
48. Lewis, B. C., Mackenzie, P. I., and Miners, J. O. (2011) Application of homology modeling to generate CYP1A1 mutants with enhanced activation of the cancer chemotherapeutic prodrug dacarbazine Mol. Pharmacol. 80, 879-888