Enzyme kinetic and molecular docking studies for the inhibitions of miltirone on major human cytochrome P450 isozymes

Phytomedicine

Volumn 20, Issue 3-4, 2013, Pages 367-374

  Zhou, Xuelin ^a   Wang, Yan ^a   Hu, Tao ^a   Or, Penelope M Y ^a   Wong, John ^b   Kwan, Yiu Wa ^a   Wan, David C C ^a   Hoi, Pui Man ^c   Lai, Paul B S ^a   Yeung, John H K ^a  

^a and Hong Kong Branch of CAS Center for Excellence in Animal Evolution and Genetics   (Hong Kong)

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^c University of Macau   (Macao)

Author keywords

Cytochrome P450; Miltirone; Molecular docking; Probe substrates; Salvia miltiorrhiza

Indexed keywords

ABIETANE DERIVATIVE; CYTOCHROME P450 1A2; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; CYTOCHROME P450 ISOENZYME; MILTIRONE; TANSHINONE; UNCLASSIFIED DRUG;

ARTICLE; CLINICAL ARTICLE; DRUG BINDING; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME KINETICS; FEMALE; HERB DRUG INTERACTION; HUMAN; HUMAN TISSUE; HYDROXYLATION; LIVER MICROSOME; MALE; MOLECULAR DOCKING; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

CYTOCHROME P-450 ENZYME SYSTEM; DEXTROMETHORPHAN; DRUGS, CHINESE HERBAL; HERB-DRUG INTERACTIONS; HUMANS; KINETICS; MICROSOMES, LIVER; MOLECULAR DOCKING SIMULATION; PHENACETIN; PHENANTHRENES; SALVIA MILTIORRHIZA; TESTOSTERONE; TOLBUTAMIDE;

RATTUS; SALVIA MILTIORRHIZA;

EID: 84873724973     PISSN: 09447113     EISSN: 1618095X     Source Type: Journal    
DOI: 10.1016/j.phymed.2012.09.021     Document Type: Article

References (36)

1. J.D. Adams, R. Wang, J. Yang, and E.J. Lien Preclinical and clinical examinations of Salvia miltiorrhiza and its tanshinones in ischemic conditions Chinese Medicine 1 2006 3
2. P. Baranczewski, A. Stanczak, K. Sundberg, R. Svensson, A. Wallin, J. Jansson, P. Garberg, and H. Postlind Introduction to in vitro estimation of metabolic stability and drug interactions of new chemical entities in drug discovery and development Pharmacological Reports 58 2006 453 472
3. J. Cao, Y.J. Wei, L.W. Qi, P. Li, Z.M. Qian, H.W. Luo, J. Chen, and J. Zhao Determination of fifteen bioactive components in Radix et Rhizoma Salviae Miltiorrhizae by high-performance liquid chromatography with ultraviolet and mass spectrometric detection Biomedical Chromatography 22 2008 164 172
4. H.M. Chang, K.Y. Chui, F.W. Tan, Y. Yang, Z.P. Zhong, C.M. Lee, H.L. Sham, and H.N. Wong Structure-activity relationship of miltirone, an active central benzodiazepine receptor ligand isolated from Salvia miltiorrhiza Bunge (Danshen) Journal of Medicinal Chemistry 34 1991 1675 1692
5. G. Colombo, S. Serra, G. Vacca, A. Orru, P. Maccioni, P. Morazzoni, E. Bombardelli, A. Riva, G.L. Gessa, and M.A. Carai Identification of miltirone as active ingredient of Salvia miltiorrhiza responsible for the reducing effect of root extracts on alcohol intake in rats Alcoholism, Clinical and Experimental Research 30 2006 754 762
6. C.P. Comission Chinese Pharmacopoeia Version 2010 2010 China Medical Science Press Beijing
7. Y. Dong, S.L. Morris-Natschke, and K.H. Lee Biosynthesis, total syntheses, and antitumor activity of tanshinones and their analogs as potential therapeutic agents Natural Products Reports 28 2011 529 542
8. T. Efferth, S. Kahl, K. Paulus, M. Adams, R. Rauh, H. Boechzelt, X. Hao, B. Kaina, and R. Bauer Phytochemistry and pharmacogenomics of natural products derived from traditional Chinese medicine and Chinese materia medica with activity against tumor cells Molecular Cancer Therapeutics 7 2008 152 161
9. R. Feng, X. Zhou, P.M.Y. Or, J.-Y. Ma, X.-S. Tan, J. Fu, C. Ma, J.-G. Shi, C.-T. Che, Y. Wang, and J.H.K. Yeung Enzyme kinetic and molecular docking studies on the metabolic interactions of 1-hydroxy-2,3,5-trimethoxy-xanthone, isolated from Halenia elliptica D. Don, with model probe substrates of human cytochrome P450 enzymes Phytomedicine 2012 10.1016/j.phymed.2012.1006.1009
10. W.G. Huang, Y.F. Li, W. Lu, and H.A. Aisa Total synthesis of miltirone Chemistry of Natural Compounds 42 2006 665 667
11. Y. Ito, H. Kondo, P.S. Goldfarb, and D.F. Lewis Analysis of CYP2D6 substrate interactions by computational methods Journal of Molecular Graphics and Modelling 26 2008 947 956
12. F.F. Lam, J.H. Yeung, K.M. Chan, and P.M. Or Dihydrotanshinone, a lipophilic component of Salvia miltiorrhiza (danshen), relaxes rat coronary artery by inhibition of calcium channels Journal of Ethnopharmacology 119 2008 318 321
13. F.F. Lam, J.H. Yeung, K.M. Chan, and P.M. Or Mechanisms of the dilator action of cryptotanshinone on rat coronary artery European Journal of Pharmacology 578 2008 253 260
14. W.Y. Lee, C.C. Cheung, K.W. Liu, K.P. Fung, J. Wong, P.B. Lai, and J.H. Yeung Cytotoxic effects of tanshinones from Salvia miltiorrhiza on doxorubicin-resistant human liver cancer cells Journal of Natural Products 73 2010 854 859
15. L.A. McLaughlin, M.J. Paine, C.A. Kemp, J.D. Marechal, J.U. Flanagan, C.J. Ward, M.J. Sutcliffe, G.C. Roberts, and C.R. Wolf Why is quinidine an inhibitor of cytochrome P450 2D6? The role of key active-site residues in quinidine binding Journal of Biological Chemistry 280 2005 38617 38624
16. M.C. Mostallino, M.P. Mascia, M.G. Pisu, F. Busonero, G. Talani, and G. Biggio Inhibition by miltirone of up-regulation of GABAA receptor alpha4 subunit mRNA by ethanol withdrawal in hippocampal neurons European Journal of Pharmacology 494 2004 83 90
17. T. Polgar, D.K. Menyhard, and G.M. Keseru Effective virtual screening protocol for CYP2C9 ligands using a screening site constructed from flurbiprofen and S-warfarin pockets Journal of Computer-Aided Molecular Design 21 2007 539 548
18. K. Purnapatre, S.K. Khattar, and K.S. Saini Cytochrome P450s in the development of target-based anticancer drugs Cancer Letters 259 2008 1 15
19. S. Sansen, J.K. Yano, R.L. Reynald, G.A. Schoch, K.J. Griffin, C.D. Stout, and E.F. Johnson Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2 Journal of Biological Chemistry 282 2007 14348 14355
20. J.H. Segel Enzyme Kinetics 1975 John Wiley & Sons New York
21. M. Shou, Y. Lin, P. Lu, C. Tang, Q. Mei, D. Cui, W. Tang, J.S. Ngui, C.C. Lin, R. Singh, B.K. Wong, J.A. Yergey, J.H. Lin, P.G. Pearson, T.A. Baillie, A.D. Rodrigues, and T.H. Rushmore Enzyme kinetics of cytochrome P450-mediated reactions Current Drug Metabolism 2 2001 17 36
22. A. Sun, Y. Zhang, A. Li, Z. Meng, and R. Liu Extraction and preparative purification of tanshinones from Salvia miltiorrhiza Bunge by high-speed counter-current chromatography Journal of Chromatography B 879 2011 1899 1904
23. O. Trott, and A.J. Olson AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading Journal of Computational Chemistry 31 2010 455 461
24. A. Wang, U. Savas, M.H. Hsu, C.D. Stout, and E.F. Johnson Crystal structure of human cytochrome P450 2D6 with prinomastat bound Journal of Biological Chemistry 287 2012 10834 10843
25. X. Wang, C.M. Cheung, W.Y. Lee, P.M. Or, and J.H. Yeung Major tanshinones of Danshen (Salvia miltiorrhiza) exhibit different modes of inhibition on human CYP1A2, CYP2C9, CYP2E1 and CYP3A4 activities in vitro Phytomedicine 17 2010 868 875
26. X. Wang, S.L. Morris-Natschke, and K.H. Lee New developments in the chemistry and biology of the bioactive constituents of Tanshen Medicinal Research Reviews 27 2007 133 148
27. X. Wang, and J.H. Yeung Effects of Salvia miltiorrhiza extract on the liver CYP3A activity in humans and rats Phytotherapy Research 25 2011 1653 1659
28. X. Wang, and J.H. Yeung Inhibitory effect of tanshinones on rat CYP3A2 and CYP2C11 activity and its structure-activity relationship Fitoterapia 82 2011 539 545
29. X. Wang, and J.H. Yeung Investigation of cytochrome P450 1A2 and 3A inhibitory properties of Danshen tincture Phytomedicine 19 2012 348 354
30. X.C. Weng, and M.H. Gordon Antioxidant activity of quinones extracted from tanshen (Salvia miltiorrhiza Bunge) Journal of Agricultural and Food Chemistry 40 1992 1331 1336
31. M.R. Wester, J.K. Yano, G.A. Schoch, C. Yang, K.J. Griffin, C.D. Stout, and E.F. Johnson The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A resolution Journal of Biological Chemistry 279 2004 35630 35637
32. P.A. Williams, J. Cosme, D.M. Vinkovic, A. Ward, H.C. Angove, P.J. Day, C. Vonrhein, I.J. Tickle, and H. Jhoti Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone Science 305 2004 683 686
33. P.A. Williams, J. Cosme, A. Ward, H.C. Angove, D. Matak Vinkovic, and H. Jhoti Crystal structure of human cytochrome P450 2C9 with bound warfarin Nature 424 2003 464 468
34. L.P. Yang, Z.W. Zhou, X.W. Chen, C.G. Li, K.B. Sneed, J. Liang, and S.F. Zhou Computational and in vitro studies on the inhibitory effects of herbal compounds on human cytochrome P450 1A2 Xenobiotica 42 2012 238 255
35. X. Zhou, K. Chan, and J.H.K. Yeung Herb-drug interactions with Danshen (Salvia miltiorrhiza): a review on the role of cytochrome P450 enzymes Drug Metabolism and Drug Interactions 27 2012 9 18
36. X. Zhou, Y. Wang, P.M. Or, D.C. Wan, Y.W. Kwan, and J.H. Yeung Molecular docking and enzyme kinetic studies of dihydrotanshinone on metabolism of a model CYP2D6 probe substrate in human liver microsomes Phytomedicine 19 2012 648 657