Ethynylflavones, highly potent, and selective inhibitors of cytochrome P450 1A1

Chemical Research in Toxicology

Volumn 27, Issue 8, 2014, Pages 1431-1439

  Goyal, Navneet ^a   Liu, Jiawang ^a   Lovings, Lanese ^a   Dupart, Patrick ^a   Taylor, Shannon ^a   Bellow, Sydni ^a   Mensah, Lydia ^a   McClain, Erika ^a   Dotson, Brandan ^a   Sridhar, Jayalakshmi ^a   Zhang, Xiaoyi ^b   Zhao, Ming ^b   Foroozesh, Maryam ^a  

^a XAVIER UNIVERSITY OF LOUISIANA   (United States)

^b CAPITAL MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

4' ETHYNYLFLAVONE; 5' ETHYNYLFLAVONE; 6 ETHYNYLFLAVONE; 7 ETHYNYLFLAVONE; CYTOCHROME P450 1A1; CYTOCHROME P450 INHIBITOR; ETHYNYLFLAVONE DERIVATIVE; FLAVONE DERIVATIVE; UNCLASSIFIED DRUG; ENZYME INHIBITOR; FLAVONE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ARTICLE; ENZYME ACTIVITY; ENZYME CONFORMATION; ENZYME INHIBITION; ENZYME KINETICS; ENZYME SPECIFICITY; ENZYME STRUCTURE; MOLECULAR DOCKING; PHARMACOPHORE; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMISTRY; ENZYME ACTIVE SITE; FLUOROMETRY; KINETICS; METABOLISM; MOLECULAR DYNAMICS; SYNTHESIS;

BINDING SITES; CATALYTIC DOMAIN; CYTOCHROME P-450 CYP1A1; ENZYME INHIBITORS; FLAVONES; FLUOROMETRY; KINETICS; MOLECULAR DYNAMICS SIMULATION; NADP;

EID: 84906283680     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx5001865     Document Type: Article

References (25)

1. Nebert, D. W. and Dalton, T. P. (2006) The role of cytochrome P450 enzymes in endogenous signalling pathways and environmental carcinogenesis Nat. Rev. Cancer 6, 947-960
2. Shimada, T., Sugie, A., Shindo, M., Nakajima, T., Azuma, E., Hashimoto, M., and Inoue, K. (2003) Tissue-specific induction of cytochromes P450 1A1 and 1B1 by polycyclic aromatic hydrocarbons and polychlorinated biphenyls in engineered C57BL/6J mice of arylhydrocarbon receptor gene Toxicol. Appl. Pharmacol. 187, 1-10
3. Josephy, P. D., Evans, D. H., Williamson, V., Henry, T., and Guengerich, F. P. (1999) Plasmid-mediated expression of the UmuDC mutagenesis proteins in an Escherichia coli strain engineered for human cytochrome P450 1A2-catalyzed activation of aromatic amines Mutat. Res. 429, 199-208
4. Androutsopoulos, V. P., Tsatsakis, A. M., and Spandidos, D. A. (2009) Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention BMC Cancer 9, 187
5. Shi, Z., Dragin, N., Gálvez-Peralta, M., Jorge-Nebert, L. F., Miller, M. L., Wang, B., and Nebert, D. W. (2010) Organ-specific roles of CYP1A1 during detoxication of dietary benzo[a]pyrene Mol. Pharmacol. 78, 46-57
6. Pelkonen, O. and Nebert, D. W. (1982) Metabolism of polycyclic aromatic hydrocarbons: etiologic role in carcinogenesis Pharmacol. Rev. 34, 189-222
7. Miller, K. P. and Ramos, K. S. (2001) Impact of cellular metabolism on the biological effects of benzo[a]pyrene and related hydrocarbons Drug Metab. Rev. 33, 1-35
8. Kim, D. and Guengerich, F. P. (2005) Cytochrome P450 activation of arylamines and heterocyclic amines Annu. Rev. Pharmacol. Toxicol. 45, 27-49
9. Kleiner, H. E., Reed, M. J., and DiGiovanni, J. (2003) Naturally occurring coumarins inhibit human cytochromes P450 and block benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene DNA adduct formation in MCF-7 cells Chem. Res. Toxicol. 16, 415-422
10. Kleiner, H. E., Vulimiri, S. V., Starost, M. F., Reed, M. J., and DiGiovanni, J. (2002) Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice Carcinogenesis 23, 1667-1675
11. Kleiner, H. E., Vulimiri, S. V., Reed, M. J., Uberecken, A., and DiGiovanni, J. (2002) Role of cytochrome P450 1a1 and 1b1 in the metabolic activation of 7,12-dimethylbenz[a]anthracene and the effects of naturally occurring furanocoumarins on skin tumor initiation Chem. Res. Toxicol. 15, 226-235
12. Sridhar, J., Liu, J., Foroozesh, M., and Klein Stevens, C. L. (2012) Inhibition of cytochrome p450 enzymes by quinones and anthraquinones Chem. Res. Toxicol. 25, 357-365
13. Belluti, F., Fontana, G., Dal Bo, L., Carenini, N., Giommarelli, C., and Zunino, F. (2010) Design, synthesis and anticancer activities of stilbene-coumarin hybrid compounds: Identification of novel proapoptotic agents Bioorg. Med. Chem. 18, 3543-3550
14. Mikstacka, R., Rimando, A. M., Dutkiewicz, Z., Stefański, T., and Sobiak, S. (2012) Design, synthesis and evaluation of the inhibitory selectivity of novel trans-resveratrol analogues on human recombinant CYP1A1, CYP1A2 and CYP1B1 Bioorg. Med. Chem. 20, 5117-5126
15. 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
16. 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
17. Liu, J., Nguyen, T. T., Dupart, P. S., Sridhar, J., Zhang, X., Zhu, N., Stevens, C. L., and Foroozesh, M. (2012) 7-Ethynylcoumarins: selective inhibitors of human cytochrome P450s 1A1 and 1A2 Chem. Res. Toxicol. 25, 1047-1057
18. 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
19. Liu, J., Taylor, S. F., Dupart, P. S., Arnold, C. L., Sridhar, J., Jiang, Q., Wang, Y., Skripnikova, E. V., Zhao, M., and Foroozesh, M. (2013) Pyranoflavones: a group of small-molecule probes for exploring the active site cavities of cytochrome P450 enzymes 1A1, 1A2, and 1B1 J. Med. Chem. 56, 4082-4092
20. Liu, J., Sridhar, J., and Foroozesh, M. (2013) Cytochrome P450 family 1 inhibitors and structure-activity relationships Molecules 18, 14470-14495
21. 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
22. 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
23. 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
24. Walsh, A. A., Szklarz, G. D., and Scott, E. E. (2013) Human cytochrome P450 1A1 structure and utility in understanding drug and xenobiotic metabolism J. Biol. Chem. 288, 12932-12943
25. 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