Novel natural inhibitors of CYP1A2 identified by in silico and in vitro screening

International Journal of Molecular Sciences

Volumn 12, Issue 5, 2011, Pages 3250-3262

  Zhu, Ruixin ^a,b   Hu, Liwei ^a   Li, Haiyun ^a   Su, Juan ^a   Cao, Zhiwei ^b,c   Zhang, Weidong ^a,d  

^a SECOND MILITARY MEDICAL UNIVERSITY   (China)

^b TONGJI UNIVERSITY   (China)

^c SHANGHAI CENTER FOR BIOINFORMATION TECHNOLOGY   (China)

^d SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

CYP1A2; Docking; Herb drug interaction; Pharmacophore

Indexed keywords

1,6,8 TRIHYDROXY 3,3 METHYLENEDIOXY 5 GERANYLXANTHONE; 3' HYDROXY GENKWANIN; 5 HYDROXY 7 METHOXYCOUMARIN 8 O DEXTRO GLUCOPYRANOSIDE; 5' DEMETHOXY DAPHNETICIN; ALPHA NAPHTHOFLAVONE; BIFONAZOLE; CHRYSIN; CYTOCHROME P450 1A2; DIHYDROKAEMPFEROL 3 O ALPHA DEXTRO ARABINOFURANOSE; DRACORHODIN; EDGEWORTHIN; HERBACEOUS AGENT; KAEMPFEROL 3 O ALPHA LEVO RHAMNOPYRANOSIDE; MATAIRESINOL; PICEID; PLANT MEDICINAL PRODUCT; PSORALEN; QUERCETIN 3 O ALPHA DEXTRO ARABINOFURANOSE; QUERCETIN 3 O BETA DEXTRO ARABINOPYRANOSIDE; RHAMNETIN 3 O BETA DEXTRO GALACTOPYRANOSIDE; RHAMNETIN 3 O BETA DEXTRO GLUCOPYRANOSIDE; SPINACETIN; TANSHINONE IIA; THREOGUAIACYLGLYCERO 8 O 4' ETHER; UNCLASSIFIED DRUG; CYTOCHROME P450 1A2 INHIBITOR;

ARTICLE; COMPUTER MODEL; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG SCREENING; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; HERB DRUG INTERACTION; IN VITRO STUDY; MOLECULAR DOCKING; NONHUMAN; STRUCTURE ANALYSIS; BIOLOGY; CHEMISTRY; CONFORMATION; DRUG DEVELOPMENT; ENZYME SPECIFICITY; X RAY CRYSTALLOGRAPHY;

COMPUTATIONAL BIOLOGY; CRYSTALLOGRAPHY, X-RAY; CYTOCHROME P-450 CYP1A2; CYTOCHROME P-450 CYP1A2 INHIBITORS; DRUG DISCOVERY; HERB-DRUG INTERACTIONS; MOLECULAR CONFORMATION; SUBSTRATE SPECIFICITY;

EID: 79957807265     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms12053250     Document Type: Article

References (43)

1. Kaufman, D.W.; Kelly, J.P.; Rosenberg, L.; Anderson, T.E.; Mitchell, A.A. Recent patterns of medication use in the ambulatory adult population of the United States: The Slone survey. JAMA 2002, 287, 337-344.
2. Ernst, E. Are herbal medicines effective? Int. J. Clin. Pharmacol. Ther. 2004, 42, 157-159.
3. Klepser, T.B.; Doucette, W.R.; Horton, M.R.; Buys, L.M.; Ernst, M.E.; Ford, J.K.; Hoehns, J.D.; Kautzman, H.A.; Logemann, C.D.; Swegle, J.M.; Ritho, M.; Klepser, M.E. Assessment of patients' perceptions and beliefs regarding herbal therapies. Pharmacotherapy 2000, 20, 83-87.
4. Delgoda, R.; Westlake, A.C. Herbal interactions involving cytochrome p450 enzymes: A mini review. Toxicol. Rev. 2004, 23, 239-249.
5. Saxena, A.; Tripathi, K.P.; Roy, S.; Khan, F.; Sharma, A. Pharmacovigilance: Effects of herbal components on human drugs interactions involving cytochrome P450. Bioinformation 2008, 3, 198-204.
6. Nebel, A.; Schneider, B.J.; Baker, R.K.; Kroll, D.J. Potential metabolic interaction between St. John's wort and theophylline. Ann. Pharmacother. 1999, 33, 502.
7. Ameer, B.; Weintraub, R.A. Drug interactions with grapefruit juice. Clin. Pharmacokinet. 1997, 33, 103-121.
8. Bailey, D.G.; Malcolm, J.; Arnold, O.; Spence, J.D. Grapefruit juice-drug interactions. Br. J. Clin. Pharmacol. 1998, 46, 101-110.
9. Kupferschmidt, H.H.; Fattinger, K.E.; Ha, H.R.; Follath, F.; Krahenbuhl, S. Grapefruit juice enhances the bioavailability of the HIV protease inhibitor saquinavir in man. Br. J. Clin. Pharmacol. 1998, 45, 355-359.
10. Faber, M.S.; Jetter, A.; Fuhr, U. Assessment of CYP1A2 activity in clinical practice: why, how, and when? Basic Clin. Pharmacol. Toxicol. 2005, 97, 125-134.
11. Bapiro, T.E.; Sayi, J.; Hasler, J.A.; Jande, M.; Rimoy, G.; Masselle, A.; Masimirembwa, C.M. Artemisinin and thiabendazole are potent inhibitors of cytochrome P450 1A2 (CYP1A2) activity in humans. Eur. J. Clin. Pharmacol. 2005, 61, 755-761.
12. Qiu, F.; Wang, G.; Zhao, Y.; Sun, H.; Mao, G.; A, J.; Sun, J. Effect of danshen extract on pharmacokinetics of theophylline in healthy volunteers. Br. J. Clin. Pharmacol. 2008, 65, 270-274.
13. Gorski, J.C.; Huang, S.M.; Pinto, A.; Hamman, M.A.; Hilligoss, J.K.; Zaheer, N.A.; Desai, M.; Miller, M.; Hall, S.D. The effect of echinacea (Echinacea purpurea root) on cytochrome P450 activity in vivo. Clin. Pharmacol. Ther. 2004, 75, 89-100.
14. Appiah-Opong, R.; Commandeur, J.N.; van Vugt-Lussenburg, B.; Vermeulen, N.P. Inhibition of human recombinant cytochrome P450s by curcumin and curcumin decomposition products. Toxicology 2007, 235, 83-91.
15. Tang, J.C.; Yang, H.; Song, X.Y.; Song, X.H.; Yan, S.L.; Shao, J.Q.; Zhang, T.L.; Zhang, J.N. Inhibition of cytochrome P450 enzymes by rhein in rat liver microsomes. Phytother. Res. 2009, 23, 159-164.
16. Peterson, S.; Lampe, J.W.; Bammler, T.K.; Gross-Steinmeyer, K.; Eaton, D.L. Apiaceous vegetable constituents inhibit human cytochrome P-450 1A2 (hCYP1A2) activity and hCYP1A2-mediated mutagenicity of aflatoxin B1. Food Chem. Toxicol. 2006, 44, 1474-1484.
17. Fuhr, U.; Strobl, G.; Manaut, F.; Anders, E.M.; Sorgel, F.; Lopez-de-Brinas, E.; Chu, D.T.; Pernet, A.G.; Mahr, G.; Sanz, F.; et al. Quinolone antibacterial agents: relationship between structure and in vitro inhibition of the human cytochrome P450 isoform CYP1A2. Mol. Pharmacol. 1993, 43, 191-199.
18. Sanz, F.; López-de-Briñas, E.; Rodríguez, J.; Manaut, F. Theoretical Study on the Metabolism of Caffeine by Cytochrome P-450 1A2 and its Inhibition. Quant. Struct. Act. Relatsh. 1994, 13, 281-284.
19. Lee, H.; Yeom, H.; Kim, Y.G.; Yoon, C.N.; Jin, C.; Choi, J.S.; Kim, B.R.; Kim, D.H. Structure-related inhibition of human hepatic caffeine N3-demethylation by naturally occurring flavonoids. Biochem. Pharmacol. 1998, 55, 1369-1375.
20. de Rienzo, F.; Fanelli, F.; Menziani, M.C.; De Benedetti, P.G. Theoretical investigation of substrate specificity for cytochromes P450 IA2, P450 IID6 and P450 IIIA4. J. Comput. Aided Mol. Des. 2000, 14, 93-116.
21. Lozano, J.J.; Pastor, M.; Cruciani, G.; Gaedt, K.; Centeno, N.B.; Gago, F.; Sanz, F. 3D-QSAR methods on the basis of ligand-receptor complexes. Application of COMBINE and GRID/GOLPE methodologies to a series of CYP1A2 ligands. J. Comput. Aided Mol. Des. 2000, 14, 341-353.
22. Lewis, D.F. On the recognition of mammalian microsomal cytochrome P450 substrates and their characteristics: Towards the prediction of human p450 substrate specificity and metabolism. Biochem. Pharmacol. 2000, 60, 293-306.
23. Moon, T.; Chi, M.H.; Kim, D.; Yoon, C.N.; Choi, Y. Quantitative Structure-Activity Relationships (QSAR) study of flavonoid derivatives for inhibition of cytochrome P450 1A2. Quant. Struct. Act. Relatsh. 2000, 19, 257-263.
24. Zhao, Y.; White, M.A.; Muralidhara, B.K.; Sun, L.; Halpert, J.R.; Stout, C.D. Structure of microsomal cytochrome P450 2B4 complexed with the antifungal drug bifonazole: insight into P450 conformational plasticity and membrane interaction. J. Biol. Chem. 2006, 281, 5973-5981.
25. Raychaudhuri, S.; Jain, V.; Dongre, M. Identification of a constitutively active variant of LuxO that affects production of HA/protease and biofilm development in a non-O1, non-O139 Vibrio cholerae O110. Gene 2006, 369, 126-133.
26. Vieth, M.; Hirst, J.D.; Brooks, C.R. Do active site conformations of small ligands correspond to low free-energy solution structures? J. Comput. Aided Mol. Des. 1998, 12, 563-572.
27. Chen, I.J.; Foloppe, N. Conformational sampling of druglike molecules with MOE and catalyst: implications for pharmacophore modeling and virtual screening. J. Chem. Inf. Model. 2008, 48, 1773-1791.
28. Butler, K.T.; Luque, F.J.; Barril, X. Toward accurate relative energy predictions of the bioactive conformation of drugs. J. Comput. Chem. 2009, 30, 601-610.
29. Zhu, R.X.; Zhang, X.L.; Dong, X.C.; Chen, M.B. Searching Inhibitors of Adenosine Kinase by Simulation Methods. Chin. J. Chem. 2006, 24, 1493-1497.
30. Shen, J.; Xu, X.; Cheng, F.; Liu, H.; Luo, X.; Shen, J.; Chen, K.; Zhao, W.; Shen, X.; Jiang, H. Virtual screening of natural products for discovering active compounds and target information. Curr. Med. Chem. 2003, 10, 2327-2342.
31. Krovat, E.M.; Steindl, T.; Langer, T. Recent Advances in Docking and Scoring. Curr. Comput. Aided Drug Des. 2005, 1, 93-102.
32. Sousa, S.F.; Fernandes, P.A.; Ramos, M.J. Protein-ligand docking: current status and future challenges. Proteins 2006, 65, 15-26.
33. Chen, Y.; Shoichet, B.K. Molecular docking and ligand specificity in fragment-based inhibitor discovery. Nat. Chem. Biol. 2009, 5, 358-364.
34. Cermak, R.; Wolffram, S. The potential of flavonoids to influence drug metabolism and pharmacokinetics by local gastrointestinal mechanisms. Curr. Drug Metab. 2006, 7, 729-744.
35. Hertog, M.G.L.; Hollman, P.C.H.; van de Putte, B. Content of potentially anticarcinogenic flavonoids of tea infusions wines, and fruit juices. J. Agric. Food Chem. 1993, 41, 1242-1246.
36. Peterson, J.; Dwyer, J. Taxonomic classification helps identify flavonoid-containing foods on a semiquantitative food frequency questionnaire. J. Am. Diet Assoc. 1998, 98, 677-682, 685.
37. Bravo, L. Polyphenols: chemistry, dietary sources, metabolism, and nutritional significance. Nutr. Rev. 1998, 56, 317-333.
38. State Food and Drug Administration. Catalog of the Drugs in China; State Food and Drug Administration: Beijing, China, 2008.
39. Choi, J.S.; Choi, B.C.; Choi, K.E. Effect of quercetin on the pharmacokinetics of oral cyclosporine. Am. J. Health Syst. Pharm. 2004, 61, 2406-2409.
40. Peng, W.X.; Li, H.D.; Zhou, H.H. Effect of daidzein on CYP1A2 activity and pharmacokinetics of theophylline in healthy volunteers. Eur. J. Clin. Pharmacol. 2003, 59, 237-241.
41. Rajnarayana, K.; Reddy, M.S.; Krishna, D.R. Diosmin pretreatment affects bioavailability of metronidazole. Eur. J. Clin. Pharmacol. 2003, 58, 803-807.
42. 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 P4501A2. J. Biol. Chem. 2007, 282, 14348-14355.
43. Molecular Operation Environment (MOE), version 2008.10; Chemical Computing Group Inc.: Montreal, Canada, 2008.