Cytochrome P450 family 1 inhibitors and structure-activity relationships

Molecules

Volumn 18, Issue 12, 2013, Pages 14470-14495

  Liu, Jiawang ^a   Sridhar, Jayalakshmi ^a   Foroozesh, Maryam ^a  

^a XAVIER UNIVERSITY OF LOUISIANA   (United States)

Author keywords

Cytochrome P450; Enzyme inhibitor; Flavonoids; Mechanism based inhibitor; Stilbenoids; Structure activity relationships

Indexed keywords

CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; ENZYME INHIBITOR;

ANIMAL; CHEMISTRY; DRUG ANTAGONISM; HUMAN; METABOLISM; REVIEW; STRUCTURE ACTIVITY RELATION;

ANIMALS; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP1A2; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84890919851     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181214470     Document Type: Review

References (109)

1. Walsh, A.A.; Szklarz, G.D.; Scott, E.E. Human cytochrome P450 1A1 structure and utility in understanding drug and xenobiotic metabolism. J. Biol. Chem. 2013, 288, 12932-12943.
2. Zhou, S.F.; Chan, E.; Zhou, Z.W.; Xue, C.C.; Lai, X.; Duan, W. Insights into the structure, function, and regulation of human cytochrome P450 1A2. Curr. Drug Metab. 2009, 10, 713-729.
3. Androutsopoulos, V.P.; Tsatsakis, A.M.; Spandidos, D.A. Cytochrome P450 CYP1A1: Wider roles in cancer progression and prevention. BMC Cancer 2009, 9, 187.
4. 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.; et al. CYP1A1 Ile462Val polymorphism and susceptibility to lung cancer: A meta-analysis based on 32 studies. Eur. J. Cancer Prev. 2011, 20, 445-452.
5. Surekha, D.; Sailaja, K.; Rao, D.N.; Padma, T.; Raghunadharao, D.; Vishnupriya, S. Association of CYP1A12 polymorphisms with breast cancer risk: A case control study. Indian J. Med. Sci. 2009, 63, 13-20.
6. Tan, C.; Xu, H.Y.; Zhang, C.Y.; Zhang, H.; Chen, C.M.; Zhang, W.M.; Sun, X.Y.; Jin, Y.T. Effect of CYP1A1 MSPI polymorphism on the relationship between TP53 mutation and CDKN2A hypermethylation in non-small cell lung cancer. Arch. Med. Res. 2011, 42, 669-676.
7. Zhou, S.F.; Wang, B.; Yang, L.P.; Liu, J.P. Structure, function, regulation and polymorphism and the clinical significance of human cytochrome P450 1A2. Drug Metab. Rev. 2010, 42, 268-354.
8. Kim, D.; Guengerich, F.P. Cytochrome P450 activation of arylamines and heterocyclic amines. Annu. Rev. Pharmacol. Toxicol. 2005, 45, 27-49.
9. Guengerich, F.P.; Chun, Y.J.; Kim, D.; Gillam, E.M.; Shimada, T. Cytochrome P450 1B1: A target for inhibition in anticarcinogenesis strategies. Mutat. Res. 2003, 523-524, 173-182.
10. Liehr, J.G.; Ricci, M.J. 4-Hydroxylation of estrogens as marker of human mammary tumors. Proc. Natl. Acad. Sci. USA 1996, 93, 3294-3296.
11. Takemura, H.; Itoh, T.; Yamamoto, K.; Sakakibara, H.; Shimoi, K. Selective inhibition of methoxyflavonoids on human CYP1B1 activity. Bioorg. Med. Chem. 2010, 18, 6310-6315.
12. Mikstacka, R.; Rimando, A.M.; Dutkiewicz, Z.; Stefanski, T.; Sobiak, S. Design, synthesis and evaluation of the inhibitory selectivity of novel trans-resveratrol analogues on human recombinant CYP1A1, CYP1A2 and CYP1B1. Bioorg. Med. Chem. 2012, 20, 5117-5126.
13. Jennings, B.L.; Sahan-Firat, S.; Estes, A.M.; Das, K.; Farjana, N.; Fang, X.R.; Gonzalez, F.J.; Malik, K.U. Cytochrome P450 1B1 contributes to angiotensin II-induced hypertension and associated pathophysiology. Hypertension 2010, 56, 667-674.
14. Rendic, S.; Guengerich, F.P. Contributions of human enzymes in carcinogen metabolism. Chem. Res. Toxicol. 2012, 25, 1316-1383.
15. Bruno, R.D.; Njar, V.C. Targeting cytochrome P450 enzymes: A new approach in anti-cancer drug development. Bioorg. Med. Chem. 2007, 15, 5047-5060.
16. Tassaneeyakul, W.; Birkett, D.J.; Veronese, M.E.; McManus, M.E.; Tukey, R.H.; Quattrochi, L.C.; Gelboin, H.V.; Miners, J.O. Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J. Pharmacol. Exp. Ther. 1993, 265, 401-407.
17. Shimada, T.; Yamazaki, H.; Foroozesh, M.; Hopkins, N.E.; Alworth, W.L.; Guengerich, F.P. Selectivity of polycyclic inhibitors for human cytochrome P450s 1A1, 1A2, and 1B1. Chem. Res. Toxicol. 1998, 11, 1048-1056.
18. Shimada, T.; Murajama, N.; Tanaka, K.; Takenaka, S.; Imai, Y.; Hopkins, N.E.; Foroozesh, M.K.; Alworth, W.L.; Yamazaki, H.; Guengerich, F.P.; et al. Interaction of polycyclic aromatic hydrocarbons with human cytochrome P450 1B1 in inhibiting catalytic activity. Chem. Res. Toxicol. 2008, 21, 2313-2323.
19. Inouye, K.; Saito, A.; Orita, M.; Tonomura, B.; Imaishi, H.; Ohkawa, H. Inhibitory effects of 1,4-naphthoquinone derivatives on rat cytochrome P4501A1-dependent monooxygenase activity in recombinant yeast microsomes. J. Biochem. 2000, 127, 1041-1046.
20. Das, M.; Mukhtar, H.; Bik, D.P.; Bickers, D.R. Inhibition of epidermal xenobiotic metabolism in SENCAR mice by naturally occurring plant phenols. Cancer Res. 1987, 47, 760-766.
21. Sun, M.; Sakakibara, H.; Ashida, H.; Danno, G.; Kanazawa, K. Cytochrome P4501A1-inhibitory action of antimutagenic anthraquinones in medicinal plants and the structure-activity relationship. Biosci. Biotechnol. Biochem. 2000, 64, 1373-1378.
22. Hao, N.J.; Huang, M.P.; Lee, H. Structure-activity relationships of anthraquinones as inhibitors of 7-ethoxycoumarin O-deethylase and mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline. Mutat. Res. 1995, 328, 183-191.
23. Sridhar, J.; Liu, J.; Foroozesh, M.; Klein Stevens, C.L. Inhibition of cytochrome p450 enzymes by quinones and anthraquinones. Chem. Res. Toxicol. 2012, 25, 357-365.
24. Chun, Y.J.; Kim, M.Y.; Guengerich, F.P. Resveratrol is a selective human cytochrome P450 1A1 inhibitor. Biochem. Biophys. Res. Commun. 1999, 262, 20-24.
25. Chan, W.K.; Delucchi, A.B. Resveratrol, a red wine constituent, is a mechanism-based inactivator of cytochrome P450 3A4. Life Sci. 2000, 67, 3103-3112.
26. Casper, R.F.; Quesne, M.; Rogers, I.M.; Shirota, T.; Jolivet, A.; Milgrom, E.; Savouret, J.F. Resveratrol has antagonist activity on the aryl hydrocarbon receptor: Implications for prevention of dioxin toxicity. Mol. Pharmacol. 1999, 56, 784-790.
27. Ciolino, H.P.; Daschner, P.J.; Yeh, G.C. Resveratrol inhibits transcription of CYP1A1 in vitro by preventing activation of the aryl hydrocarbon receptor. Cancer Res. 1998, 58, 5707-5712.
28. Revel, A.; Raanani, H.; Younglai, E.; Xu, J.; Rogers, I.; Han, R.; Savouret, J.F.; Casper, R.F. Resveratrol, a natural aryl hydrocarbon receptor antagonist, protects lung from DNA damage and apoptosis caused by benzo[a]pyrene. J. Appl. Toxicol. 2003, 23, 255-261.
29. Chun, Y.J.; Ryu, S.Y.; Jeong, T.C.; Kim, M.Y. Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin. Drug Metab. Dispos. 2001, 29, 389-393.
30. Chun, Y.J.; Kim, S.; Kim, D.; Lee, S.K.; Guengerich, F.P. A new selective and potent inhibitor of human cytochrome P450 1B1 and its application to antimutagenesis. Cancer Res. 2001, 61, 8164-8170.
31. Kim, S.; Ko, H.; Park, J.E.; Jung, S.; Lee, S.K.; Chun, Y.J. Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. J. Med. Chem. 2002, 45, 160-164.
32. Chun, Y.J.; Lee, S.K.; Kim, M.Y. Modulation of human cytochrome P450 1B1 expression by 2,4,3',5′-tetramethoxystilbene. Drug Metab. Dispos. 2005, 33, 1771-1776.
33. Lee, S.K.; Kim, Y.; Kim, M.Y.; Chun, Y.J.; Kim, S. Potent inhibition of recombinant human cytochrome p-450 1A1 by pentamethoxystilbene. J. Toxicol. Environ. Health A 2004, 67, 1987-2000.
34. Chun, Y.J.; Oh, Y.K.; Kim, B.J.; Kim, D.; Kim, S.S.; Choi, H.K.; Kim, M.Y. Potent inhibition of human cytochrome P450 1B1 by tetramethoxystilbene. Toxicol. Lett. 2009, 189, 84-89.
35. Mikstacka, R.; Baer-Dubowska, W.; Wieczorek, M.; Sobiak, S. Thiomethylstilbenes as inhibitors of CYP1A1, CYP1A2 and CYP1B1 activities. Mol. Nutr. Food Res. 2008, 52, S77-S83.
36. Moon, Y.J.; Wang, X.; Morris, M.E. Dietary flavonoids: Effects on xenobiotic and carcinogen metabolism. Toxicol. In Vitro 2006, 20, 187-210.
37. Zhai, S.; Dai, R.; Friedman, F.K.; Vestal, R.E. Comparative inhibition of human cytochromes P450 1A1 and 1A2 by flavonoids. Drug Metab. Dispos. 1998, 26, 989-992.
38. Sridhar, J.; Ellis, J.; Dupart, P.; Liu, J.; Stevens, C.L.; Foroozesh, M. Development of flavone propargyl ethers as potent and selective inhibitors of cytochrome P450 enzymes 1A1 and 1A2. Drug Metab. Lett. 2012, 6, 275-284.
39. Shimada, T.; Tanaka, K.; Takenaka, S.; Murayama, N.; Martin, M.V.; Foroozesh, M.K.; Yamazaki, H.; Guengerich, F.P.; Komori, M. Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. Chem. Res. Toxicol. 2010, 23, 1921-1935.
40. Shimada, T.; Tanaka, K.; Takenaka, S.; Foroozesh, M.K.; Murayama, N.; Yamazaki, H.; Guengerich, F.P.; Komori, M. Reverse type I binding spectra of human cytochrome P450 1B1 induced by flavonoid, stilbene, pyrene, naphthalene, phenanthrene, and biphenyl derivatives that inhibit catalytic activity: A structure-function relationship study. Chem. Res. Toxicol. 2009, 22, 1325-1333.
41. Doostdar, H.; Burke, M.D.; Mayer, R.T. Bioflavonoids: Selective substrates and inhibitors for cytochrome P450 CYP1A and CYP1B1. Toxicology 2000, 144, 31-38.
42. Liu, J.; Taylor, S.F.; Dupart, P.S.; Arnold, C.L.; Sridhar, J.; Jiang, Q.; Wang, Y.; Skripnikova, E.V.; Zhao, M.; Foroozesh, M. Pyranoflavones: A group of small-molecule probes for exploring the active site cavities of cytochrome P450 enzymes 1A1, 1A2, and 1B1. J. Med. Chem. 2013, 56, 4082-4092.
43. Ciolino, H.P.; Yeh, G.C. The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor. Br. J. Cancer 1999, 79, 1340-1346.
44. Ciolino, H.P.; Daschner, P.J.; Yeh, G.C. Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially. Biochem. J. 1999, 340, 715-722.
45. Chan, H.Y.; Chen, Z.Y.; Tsang, D.S.; Leung, L.K. Baicalein inhibits DMBA-DNA adduct formation by modulating CYP1A1 and CYP1B1 activities. Biomed. Pharmacother. 2002, 56, 269-275.
46. Callero, M.A.; Suárez, G.V.; Luzzani, G.; Itkin, B.; Nguyen, B.; Loaiza-Perez, A.I. Aryl hydrocarbon receptor activation by aminoflavone: New molecular target for renal cancer treatment. Int. J. Oncol. 2012, 41, 125-134.
47. Girennavar, B.; Poulose, S.M.; Jayaprakasha, G.K.; Bhat, N.G.; Patil, B.S. Furocoumarins from grapefruit juice and their effect on human CYP 3A4 and CYP 1B1 isoenzymes. Bioorg. Med. Chem. 2006, 14, 2606-2612.
48. Baumgart, A.; Schmidt, M.; Schmitz, H.J.; Schrenk, D. Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes. Biochem. Pharmacol. 2005, 69, 657-667.
49. Olguín-Reyes, S.; Camacho-Carranza, R.; Hernández-Ojeda, S.; Elinos-Baez, M.; Espinosa-Aguirre, J.J. Bergamottin is a competitive inhibitor of CYP1A1 and is antimutagenic in the Ames test. Food Chem. Toxicol. 2012, 50, 3094-3099.
50. Cai, Y.; Bennett, D.; Nair, R.V.; Ceska, O.; Ashwood-Smith, M.J.; DiGiovanni, J. Inhibition and inactivation of murine hepatic ethoxy- and pentoxyresorufin O-dealkylase by naturally occurring coumarins. Chem. Res. Toxicol. 1993, 6, 872-879.
51. Cai, Y.; Baer-Dubowska, W.; Ashwood-Smith, M.J.; Ceska, O.; Tachibana, S.; DiGiovanni, J. Mechanism-based inactivation of hepatic ethoxyresorufin O-dealkylation activity by naturally occurring coumarins. Chem. Res. Toxicol. 1996, 9, 729-736.
52. Cai, Y.; Baer-Dubowska, W.; Ashwood-Smith, M.; DiGiovanni, J. Inhibitory effects of naturally occurring coumarins on the metabolic activation of benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene in cultured mouse keratinocytes. Carcinogenesis 1997, 18, 215-222.
53. Kleiner, H.E.; Vulimiri, S.V.; Reed, M.J.; Uberecken, A.; DiGiovanni, J. 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. 2002, 15, 226-235.
54. Liu, H.; Santostefano, M.; Lu, Y.; Safe, S. 6-substituted 3,4-benzocoumarins: A new structural class of inducers and inhibitors of CYP1A1-dependent activity. Arch. Biochem. Biophys. 1993, 306, 223-231.
55. Liu, J.; Nguyen, T.T.; Dupart, P.S.; Sridhar, J.; Zhang, X.; Zhu, N.; Stevens, C.L.; Foroozesh, M. 7-Ethynylcoumarins: Selective inhibitors of human cytochrome P450s 1A1 and 1A2. Chem. Res. Toxicol. 2012, 25, 1047-1057.
56. Miller, C.M.; McCarthy, F.O. Isolation, biological activity and synthesis of the natural product ellipticine and related pyridocarbazoles. RSC Adv. 2012, 2, 8883-8918.
57. Aimová, D.; Stiborová, M. Antitumor drug ellipticine inhibits the activities of rat hepatic cytochromes P450. Biomed. Pap. Med. Fac. Univ. Palacky Olomouc Czech. Repub. 2005, 149, 437-440.
58. Tarrus, E.; Cami, J.; Roberts, D.J.; Spickett, R.G.; Celdran, E.; Segura, J. Accumulation of caffeine in healthy volunteers treated with furafylline. Br. J. Clin. Pharmacol. 1987, 23, 9-18.
59. Sesardic, D.; Boobis, A.R.; Murray, B.P.; Murray, S.; Segura, J.; de la Torre, R.; Davies, D.S. Furafylline is a potent and selective inhibitor of cytochrome P450IA2 in man. Br. J. Clin. Pharmacol. 1990, 29, 651-663.
60. Kunze, K.L.; Trager, W.F. Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chem. Res. Toxicol. 1993, 6, 649-656.
61. Chang, T.K.; Chen, J.; Yang, G.; Yeung, E.Y. Inhibition of procarcinogen-bioactivating human CYP1A1, CYP1A2 and CYP1B1 enzymes by melatonin. J. Pineal Res. 2010, 48, 55-64.
62. Jahng, Y.; Kwon, O.K.; Lee, S. In vitro inhibitory effect of luotonin A on human CYP1A. Arch. Pharm. Res. 2012, 35, 2199-2203.
63. Ueng, Y.F.; Jan, W.C.; Lin, L.C.; Chen, T.L.; Guengerich, F.P.; Chen, C.F. The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes. Drug Metab. Dispos. 2002, 30, 349-353.
64. Don, M.J.; Lewis, D.F.; Wang, S.Y.; Tsai, M.W.; Ueng, Y.F. Effect of structural modification on the inhibitory selectivity of rutaecarpine derivatives on human CYP1A1, CYP1A2, and CYP1B1. Bioorg. Med. Chem. Lett. 2003, 13, 2535-2538.
65. Lo, S.N.; Chang, Y.P.; Tsai, K.C.; Chang, C.Y.; Wu, T.S.; Ueng, Y.F. Inhibition of CYP1 by berberine, palmatine, and jatrorrhizine: Selectivity, Kinetic characterization, and molecular modeling. Toxicol. Appl. Pharmacol. 2013, 272, 671-680.
66. Vrzal, R.; Zdarilová, A.; Ulrichová, J.; Bláha, L.; Giesy, J.P.; Dvorák, Z. Activation of the aryl hydrocarbon receptor by berberine in HepG2 and H4IIE cells: Biphasic effect on CYP1A1. Biochem. Pharmacol. 2005, 70, 925-936.
67. Qiu, F.; Zhang, R.; Sun, J.; Jiye, A.; Hao, H.; Peng, Y.; Ai, H.; Wang, G. Inhibitory effects of seven components of danshen extract on catalytic activity of cytochrome P450 enzyme in human liver microsomes. Drug Metab. Dispos. 2008, 36, 1308-1314.
68. Ueng, Y.F.; Kuo, Y.H.; Peng, H.C.; Chen, T.L.; Jan, W.C.; Peter Guengerich, F.; Lin, Y.L. Diterpene quinone tanshinone IIA selectively inhibits mouse and human cytochrome p4501A2. Xenobiotica 2003, 33, 603-613.
69. Zhang, R.; Sun, J.; Ma, L.; Wu, X.; Pan, G.; Hao, H.; Zhou, F.; A, J.; Liu, C.; Ai, H.; et al. Induction of cytochromes P450 1A1 and 1A2 by tanshinones in human HepG2 hepatoma cell line. Toxicol. Appl. Pharmacol. 2011, 252, 18-27.
70. Ueng, Y.F.; Kuo, Y.H.; Wang, S.Y.; Lin, Y.L.; Chen, C.F. Induction of CYP1A by a diterpene quinone tanshinone IIA isolated from a medicinal herb Salvia miltiorrhiza in C57BL/6J but not in DBA/2J mice. Life Sci. 2004, 74, 885-896.
71. Dvorák, Z.; Vrzal, R.; Ulrichová, J. Silybin and dehydrosilybin inhibit cytochrome P450 1A1 catalytic activity: A study in human keratinocytes and human hepatoma cells. Cell Biol. Toxicol. 2006, 22, 81-90.
72. Yamaori, S.; Kushihara, M.; Yamamoto, I.; Watanabe, K. Characterization of major phytocannabinoids, cannabidiol and cannabinol, as isoform-selective and potent inhibitors of human CYP1 enzymes. Biochem. Pharmacol. 2010, 79, 1691-1698.
73. Piver, B.; Berthou, F.; Dreano, Y.; Lucas, D. Differential inhibition of human cytochrome P450 enzymes by epsilon-viniferin, the dimer of resveratrol: Comparison with resveratrol and polyphenols from alcoholized beverages. Life Sci. 2003, 73, 1199-1213.
74. Sparfel, L.; van Grevenynghe, J.; le Vee, M.; Aninat, C.; Fardel, O. Potent inhibition of carcinogen-bioactivating cytochrome P450 1B1 by the p53 inhibitor pifithrin alpha. Carcinogenesis 2006, 27, 656-663.
75. Chang, S.Y.; Chen, C.; Yang, Z.; Rodrigues, A.D. Further assessment of 17alpha-ethinyl estradiol as an inhibitor of different human cytochrome P450 forms in vitro. Drug Metab. Dispos. 2009, 37, 1667-1675.
76. Sparfel, L.; Huc, L.; le Vee, M.; Desille, M.; Lagadic-Gossmann, D.; Fardel, O. Inhibition of carcinogen-bioactivating cytochrome P450 1 isoforms by amiloride derivatives. Biochem. Pharmacol. 2004, 67, 1711-1719.
77. Rasmussen, B.B.; Maenpaa, J.; Pelkonen, O.; Loft, S.; Poulsen, H.E.; Lykkesfeldt, J.; Brøsen, K. Selective serotonin reuptake inhibitors and theophylline metabolism in human liver microsomes: Potent inhibition by fluvoxamine. Br. J. Clin. Pharmacol. 1995, 39, 151-159.
78. Konishi, H.; Morita, K.; Minouchi, T.; Yamaji, A. Preferential inhibition of CYP1A enzymes in hepatic microsomes by mexiletine. Eur. J. Drug Metab. Pharmacokinet. 1999, 24, 149-153.
79. Niwa, T.; Inoue-Yamamoto, S.; Shiraga, T.; Takagi, A. Effect of antifungal drugs on cytochrome P450 (CYP) 1A2, CYP2D6, and CYP2E1 activities in human liver microsomes. Biol. Pharm. Bull. 2005, 28, 1813-1816.
80. Langouet, S.; Furge, L.L.; Kerriguy, N.; Nakamura, K.; Guillouzo, A.; Guengerich, F.P. Inhibition of human cytochrome P450 enzymes by 1,2-dithiole-3-thione, oltipraz and its derivatives, and sulforaphane. Chem. Res. Toxicol. 2000, 13, 245-252.
81. Konwinski, R.R.; Haddad, R.; Chun, J.A.; Klenow, S.; Larson, S.C.; Haab, B.B.; Furge, L.L. Oltipraz, 3H-1,2-dithiole-3-thione, and sulforaphane induce overlapping and protective antioxidant responses in murine microglial cells. Toxicol. Lett. 2004, 153, 343-355.
82. Langouet, S.; Mahéo, K.; Berthou, F.; Morel, F.; Lagadic-Gossman, D.; Glaise, D.; Coles, B.; Ketterer, B.; Guillouzo, A. Effects of administration of the chemoprotective agent oltipraz on CYP1A and CYP2B in rat liver and rat hepatocytes in culture. Carcinogenesis 1997, 18, 1343-1349.
83. Wójcikowski, J.; Daniel, W.A. Perazine at therapeutic drug concentrations inhibits human cytochrome P450 isoenzyme 1A2 (CYP1A2) and caffeine metabolism-an in vitro study. Pharmacol. Rep. 2009, 61, 851-858.
84. Backman, J.T.; Karjalainen, M.J.; Neuvonen, M.; Laitila, J.; Neuvonen, P.J. Rofecoxib is a potent inhibitor of cytochrome P450 1A2: Studies with tizanidine and caffeine in healthy subjects. Br. J. Clin. Pharmacol. 2006, 62, 345-357.
85. Karjalainen, M.J.; Neuvonen, P.J.; Backman, J.T. Celecoxib is a CYP1A2 inhibitor in vitro but not in vivo. Eur. J. Clin. Pharmacol. 2008, 64, 511-519.
86. Moorthy, B.; Parker, K.M.; Smith, C.V.; Bend, J.R.; Welty, S.E. Potentiation of oxygen-induced lung injury in rats by the mechanism-based cytochrome P-450 inhibitor, 1-aminobenzotriazole. J. Pharmacol. Exp. Ther. 2000, 292, 553-560.
87. Mugford, C.A.; Mortillo, M.; Mico, B.A.; Tarloff, J.B. 1-Aminobenzotriazole-induced destruction of hepatic and renal cytochromes P450 in male Sprague-Dawley rats. Fundam. Appl. Toxicol. 1992, 19, 43-49.
88. Peng, J.Z.; Remmel, R.P.; Sawchuk, R.J. Inhibition of murine cytochrome P4501A by tacrine: In vitro studies. Drug Metab. Dispos. 2004, 32, 805-812.
89. Wen, X.; Wang, J.S.; Neuvonen, P.J.; Backman, J.T. Isoniazid is a mechanism-based inhibitor of cytochrome P450 1A2, 2A6, 2C19 and 3A4 isoforms in human liver microsomes. Eur. J. Clin. Pharmacol. 2002, 57, 799-804.
90. Wei, X.; Loi, C.M.; Jarvi, E.J.; Vestal, R.E. Relative potency of mexiletine, lidocaine, and tocainide as inhibitors of rat liver CYP1A1 activity. Drug Metab. Dispos. 1995, 23, 1335-1338.
91. Lu, P.; Schrag, M.L.; Slaughter, D.E.; Raab, C.E.; Shou, M.; Rodrigues, A.D. Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. Drug Metab. Dispos. 2003, 31, 1352-1360.
92. Lee, S.K.; Kim, Y.; Kim, M.Y.; Kim, S.; Chun, Y.J. Potent inhibition of human cytochrome P450 1 enzymes by dimethoxyphenylvinyl thiophene. Arch. Pharm. Res. 2004, 27, 199-205.
93. Sienkiewicz, P.; Ciolino, H.P.; Leslie, B.J.; Hergenrother, P.J.; Singletary, K.; Yeh, G.C. A novel synthetic analogue of a constituent of Isodon excisus inhibits transcription of CYP1A1, -1A2 and -1B1 by preventing activation of the aryl hydrocarbon receptor. Carcinogenesis 2007, 28, 1052-1057.
94. Astroff, B.; Zacharewski, T.; Safe, S.; Arlotto, M.P.; Parkinson, A.; Thomas, P.; Levin, W. 6-Methyl-1,3,8-trichlorodibenzofuran as a 2,3,7,8-tetrachlorodibenzo-p-dioxin antagonist: Inhibition of the induction of rat cytochrome P-450 isozymes and related monooxygenase activities. Mol. Pharmacol. 1988, 33, 231-236.
95. Monostory, K.; Tamási, V.; Vereczkey, L.; Perjési, P. A study on CYP1A inhibitory action of E-2-(4′-methoxybenzylidene)-1- benzosuberone and some related chalcones and cyclic chalcone analogues. Toxicology 2003, 184, 203-210.
96. Hollenberg, P.F.; Kent, U.M.; Bumpus, N.N. Mechanism-based inactivation of human cytochromes p450s: Experimental characterization, reactive intermediates, and clinical implications. Chem. Res. Toxicol. 2008, 21, 189-205.
97. Wright, A.T.; Song, J.D.; Cravatt, B.F. A suite of activity-based probes for human cytochrome P450 enzymes. J. Am. Chem. Soc. 2009, 131, 10692-10700.
98. Ortiz de Montellano, P.R. Mechanism-based inactivation of cytochrome P450: Isolation and characterization of N-alkyl heme adducts. Methods Enzymol. 1991, 206, 533-540.
99. Ortiz de Montellano, P.R.; Komives, E.A. Branchpoint for heme alkylation and metabolite formation in the oxidation of arylacetylenes by cytochrome P-450. J. Biol. Chem. 1985, 260, 3330-3336.
100. Ortiz de Montellano, P.R.; Kunze, K.L. Self-catalyzed inactivation of hepatic cytochrome P-450 by ethynyl substrates. J. Biol. Chem. 1980, 255, 5578-5585.
101. Chan, W.K.; Sui, Z.; Ortiz de Montellano, P.R. Determinants of protein modification versus heme alkylation: Inactivation of cytochrome P450 1A1 by 1-ethynylpyrene and phenylacetylene. Chem. Res. Toxicol. 1993, 6, 38-45.
102. Roberts, E.S.; Hopkins, N.E.; Alworth, W.L.; Hollenberg, P.F. Mechanism-based inactivation of cytochrome P450 2B1 by 2-ethynylnaphthalene: Identification of an active-site peptide. Chem. Res. Toxicol. 1993, 6, 470-479.
103. Foroozesh, M.; Primrose, G.; Guo, Z.; Bell, L.C.; Alworth, W.L.; Guengerich, F.P. Aryl acetylenes as mechanism-based inhibitors of cytochrome P450-dependent monooxygenase enzymes. Chem. Res. Toxicol. 1997, 10, 91-102.
104. Shimada, T.; Murayama, N.; Okada, K.; Funae, Y.; Yamazaki, H.; Guengerich, F.P. Different mechanisms for inhibition of human cytochromes P450 1A1, 1A2, and 1B1 by polycyclic aromatic inhibitors. Chem. Res. Toxicol. 2007, 20, 489-496.
105. Sansen, S.; Yano, J.K.; Reynald, R.L.; Schoch, G.A.; Griffin, K.J.; Stout, C.D.; Johnson, E.F. Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2. J. Biol. Chem. 2007, 282, 14348-14355.
106. Wang, A.; Savas, U.; Stout, C.D.; Johnson, E.F. Structural characterization of the complex between alpha-naphthoflavone and human cytochrome P450 1B1. J. Biol. Chem. 2011, 286, 5736-5743.
107. Nebert, D.W.; Dalton, T.P. The role of cytochrome P450 enzymes in endogenous signalling pathways and environmental carcinogenesis. Nat. Rev. Cancer 2006, 6, 947-960.
108. Shimada, T.; Sugie, A.; Shindo, M.; Nakajima, T.; Azuma, E.; Hashimoto, M.; Inoue, K. 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. 2003, 187, 1-10.
109. Josephy, P.D.; Evans, D.H.; Williamson, V.; Henry, T.; Guengerich, F.P. 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. 1999, 429, 199-208.