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Volumn 19, Issue 7, 2012, Pages 648-657

Molecular docking and enzyme kinetic studies of dihydrotanshinone on metabolism of a model CYP2D6 probe substrate in human liver microsomes

Author keywords

CYP2D6 activity; Danshen (Salvia miltiorrhiza); Dextromethorphan metabolism; Dihydrotanshinone; Human liver microsomes; Molecular docking

Indexed keywords

3 (3,4 DIHYDROXYPHENYL)LACTIC ACID; ASPARTIC ACID; CRYPTOTANSHINONE; CYTOCHROME P450 2D6; DEXTROMETHORPHAN; DEXTRORPHAN; DIHYDROTANSHINONE; GLUTAMINE; O DEMETHYLASE; PHENYLALANINE; QUINIDINE; SALVIA MILTIORRHIZA EXTRACT; SALVIANOLIC ACID B; TANSHINONE I; TANSHINONE IIA; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84860638612     PISSN: 09447113     EISSN: 1618095X     Source Type: Journal    
DOI: 10.1016/j.phymed.2012.01.005     Document Type: Article
Times cited : (10)

References (43)
  • 1
    • 0029025569 scopus 로고
    • The effects of Danshen (Salvia miltiorrhiza) on warfarin pharmacodynamics and pharmacokinetics of warfarin enantiomers in rats
    • K. Chan, A.C. Lo, J.H. Yeung, and K.S. Woo The effects of Danshen (Salvia miltiorrhiza) on warfarin pharmacodynamics and pharmacokinetics of warfarin enantiomers in rats J. Pharm. Pharmacol. 47 1995 402 406
    • (1995) J. Pharm. Pharmacol. , vol.47 , pp. 402-406
    • Chan, K.1    Lo, A.C.2    Yeung, J.H.3    Woo, K.S.4
  • 3
    • 38349123913 scopus 로고    scopus 로고
    • Ameliorating effects of compounds derived from Salvia miltiorrhiza root extract on microcirculatory disturbance and target organ injury by ischemia and reperfusion
    • J.Y. Han, J.Y. Fan, Y. Horie, S. Miura, D.H. Cui, H. Ishii, T. Hibi, H. Tsuneki, and I. Kimura Ameliorating effects of compounds derived from Salvia miltiorrhiza root extract on microcirculatory disturbance and target organ injury by ischemia and reperfusion Pharmacol. Ther. 117 2008 280 295
    • (2008) Pharmacol. Ther. , vol.117 , pp. 280-295
    • Han, J.Y.1    Fan, J.Y.2    Horie, Y.3    Miura, S.4    Cui, D.H.5    Ishii, H.6    Hibi, T.7    Tsuneki, H.8    Kimura, I.9
  • 4
    • 33847360957 scopus 로고    scopus 로고
    • Rapid determination of six metabolites from multiple cytochrome P450 probe substrates in human liver microsome by liquid chromatography/mass spectrometry: Application to high-throughput inhibition screening of terpenoids
    • DOI 10.1002/rcm.2881
    • F. He, H.C. Bi, Z.Y. Xie, Z. Zuo, J.K. Li, X. Li, L.Z. Zhao, X. Chen, and M. Huang Rapid determination of six metabolites from multiple cytochrome P450 probe substrates in human liver microsome by liquid chromatography/mass spectrometry: application to high-throughput inhibition screening of terpenoids Rapid Commun. Mass Spectrom. 21 2007 635 643 (Pubitemid 46340306)
    • (2007) Rapid Communications in Mass Spectrometry , vol.21 , Issue.5 , pp. 635-643
    • He, F.1    Bi, H.-C.2    Xie, Z.-Y.3    Zuo, Z.4    Li, J.-K.5    Li, X.6    Zhao, L.-Z.7    Chen, X.8    Huang, M.9
  • 6
    • 77957784497 scopus 로고    scopus 로고
    • A review of granisetron, 5-hydroxytryptamine3 receptor antagonists, and other antiemetics
    • E.S. Hsu A review of granisetron, 5-hydroxytryptamine3 receptor antagonists, and other antiemetics Am. J. Ther. 17 2010 476 486
    • (2010) Am. J. Ther. , vol.17 , pp. 476-486
    • Hsu, E.S.1
  • 7
    • 12844258387 scopus 로고    scopus 로고
    • Cardiovascular pharmacotherapy and herbal medicines: The risk of drug interaction
    • DOI 10.1016/j.ijcard.2003.06.039, PII S0167527303006272
    • A.A. Izzo, G. Di Carlo, F. Borrelli, and E. Ernst Cardiovascular pharmacotherapy and herbal medicines: the risk of drug interaction Int. J. Cardiol. 98 2005 1 14 (Pubitemid 40169845)
    • (2005) International Journal of Cardiology , vol.98 , Issue.1 , pp. 1-14
    • Izzo, A.A.1    Di Carlo, G.2    Borrelli, F.3    Ernst, E.4
  • 8
    • 79952083050 scopus 로고    scopus 로고
    • Genetic polymorphism and toxicology - With emphasis on cytochrome p450
    • I. Johansson, and M. Ingelman-Sundberg Genetic polymorphism and toxicology - with emphasis on cytochrome p450 Toxicol. Sci. 120 2011 1 13
    • (2011) Toxicol. Sci. , vol.120 , pp. 1-13
    • Johansson, I.1    Ingelman-Sundberg, M.2
  • 9
    • 7444225179 scopus 로고    scopus 로고
    • Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: Crucial role in 7-methoxy-4-(aminomethyl)- coumarin metabolism
    • DOI 10.1016/j.bcp.2004.08.013, PII S0006295204005933
    • P.H. Keizers, B.M. Lussenburg, C. de Graaf, L.M. Mentink, N.P. Vermeulen, and J.N. Commandeur Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4- (aminomethyl)-coumarin metabolism Biochem. Pharmacol. 68 2004 2263 2271 (Pubitemid 39446153)
    • (2004) Biochemical Pharmacology , vol.68 , Issue.11 , pp. 2263-2271
    • Keizers, P.H.J.1    Lussenburg, B.M.A.2    De Graaf, C.3    Mentink, L.M.4    Vermeulen, N.P.E.5    Commandeur, J.N.M.6
  • 10
    • 50049122372 scopus 로고    scopus 로고
    • Novel binding mode of the acidic CYP2D6 substrates pactimibe and its metabolite R-125528
    • M. Kotsuma, H. Hanzawa, Y. Iwata, K. Takahashi, and T. Tokui Novel binding mode of the acidic CYP2D6 substrates pactimibe and its metabolite R-125528 Drug Metab. Dispos. 36 2008 1938 1943
    • (2008) Drug Metab. Dispos. , vol.36 , pp. 1938-1943
    • Kotsuma, M.1    Hanzawa, H.2    Iwata, Y.3    Takahashi, K.4    Tokui, T.5
  • 11
    • 83655191991 scopus 로고    scopus 로고
    • Tanshinone i increases CYP1A2 protein expression and enzyme activity in primary rat hepatocytes
    • W.Y. Lee, X. Zhou, P.M. Or, Y.W. Kwan, and J.H. Yeung Tanshinone I increases CYP1A2 protein expression and enzyme activity in primary rat hepatocytes Phytomedicine 19 2012 169 176
    • (2012) Phytomedicine , vol.19 , pp. 169-176
    • Lee, W.Y.1    Zhou, X.2    Or, P.M.3    Kwan, Y.W.4    Yeung, J.H.5
  • 12
    • 0036223228 scopus 로고    scopus 로고
    • Structure-activity relationship for human cytochrome P450 substrates and inhibitors
    • DOI 10.1081/DMR-120001391
    • D.F. Lewis, S. Modi, and M. Dickins Structure-activity relationship for human cytochrome P450 substrates and inhibitors Drug Metab. Rev. 34 2002 69 82 (Pubitemid 34311089)
    • (2002) Drug Metabolism Reviews , vol.34 , Issue.1-2 , pp. 69-82
    • Lewis, D.F.V.1    Modi, S.2    Dickins, M.3
  • 13
    • 33644637320 scopus 로고    scopus 로고
    • Simultaneous determination of tanshinone IIA and its three hydroxylated metabolites by liquid chromatography/tandem mass spectrometry
    • DOI 10.1002/rcm.2367
    • P. Li, G.J. Wang, J. Li, H.P. Hao, and C.N. Zheng Simultaneous determination of tanshinone IIA and its three hydroxylated metabolites by liquid chromatography/tandem mass spectrometry Rapid Commun. Mass Spectrom. 20 2006 815 822 (Pubitemid 43326688)
    • (2006) Rapid Communications in Mass Spectrometry , vol.20 , Issue.5 , pp. 815-822
    • Li, P.1    Wang, G.-J.2    Li, J.3    Hao, H.-P.4    Zheng, C.-N.5
  • 14
    • 30544451012 scopus 로고    scopus 로고
    • High-performance liquid chromatographic determination of tanshinones in the roots of Salvia miltiorrhiza and related traditional Chinese medicinal preparations
    • A.H. Liu, Y.H. Lin, M. Yang, J.H. Sun, H. Guo, and D.A. Guo High-performance liquid chromatographic determination of tanshinones in the roots of Salvia miltiorrhiza and related traditional chinese medicinal preparations J. Pharm. Pharm. Sci. 9 2006 1 9 (Pubitemid 43078830)
    • (2006) Journal of Pharmacy and Pharmaceutical Sciences , vol.9 , Issue.1 , pp. 1-9
    • Liu, A.-H.1    Lin, Y.-H.2    Yang, M.3    Sun, J.-H.4    Guo, H.5    Guo, D.-A.6
  • 16
    • 33645222408 scopus 로고    scopus 로고
    • Determination of four water-soluble compounds in Salvia miltiorrhiza Bunge by high-performance liquid chromatography with a coulometric electrode array system
    • L. Ma, X. Zhang, H. Guo, and Y. Gan Determination of four water-soluble compounds in Salvia miltiorrhiza Bunge by high-performance liquid chromatography with a coulometric electrode array system J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 833 2006 260 263
    • (2006) J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. , vol.833 , pp. 260-263
    • Ma, L.1    Zhang, X.2    Guo, H.3    Gan, Y.4
  • 18
    • 38349110193 scopus 로고    scopus 로고
    • Nebivolol: Pharmacologic profile of an ultraselective, vasodilatory beta1-blocker
    • L.M. Prisant Nebivolol: pharmacologic profile of an ultraselective, vasodilatory beta1-blocker J. Clin. Pharmacol. 48 2008 225 239
    • (2008) J. Clin. Pharmacol. , vol.48 , pp. 225-239
    • Prisant, L.M.1
  • 19
    • 46449109055 scopus 로고    scopus 로고
    • Inhibitory effects of seven components of danshen extract on catalytic activity of cytochrome P450 enzyme in human liver microsomes
    • DOI 10.1124/dmd.108.021030
    • F. Qiu, R. Zhang, J. Sun, A. Jiye, H. Hao, Y. Peng, H. Ai, and G. Wang Inhibitory effects of seven components of danshen extract on catalytic activity of cytochrome P450 enzyme in human liver microsomes Drug Metab. Dispos. 36 2008 1308 1314 (Pubitemid 351929315)
    • (2008) Drug Metabolism and Disposition , vol.36 , Issue.7 , pp. 1308-1314
    • Qiu, F.1    Zhang, R.2    Sun, J.3    Jiye, A.4    Hao, H.5    Peng, Y.6    Ai, H.7    Wang, G.8
  • 21
    • 77953325845 scopus 로고    scopus 로고
    • Ligand docking and binding site analysis with PyMOL and Autodock/Vina
    • D. Seeliger, and B.L. de Groot Ligand docking and binding site analysis with PyMOL and Autodock/Vina J. Comput. Aided Mol. Des. 24 2010 417 422
    • (2010) J. Comput. Aided Mol. Des. , vol.24 , pp. 417-422
    • Seeliger, D.1    De Groot, B.L.2
  • 22
    • 14644442887 scopus 로고    scopus 로고
    • Simultaneous determination of cryptotanshinone, tanshinone I and tanshinone IIA in traditional Chinese medicinal preparations containing Radix salvia miltiorrhiza by HPLC
    • DOI 10.1016/j.jpba.2004.11.015
    • Z. Shi, J. He, T. Yao, W. Chang, and M. Zhao Simultaneous determination of cryptotanshinone, tanshinone I and tanshinone IIA in traditional Chinese medicinal preparations containing Radix Salvia miltiorrhiza by HPLC J. Pharm. Biomed. Anal. 37 2005 481 486 (Pubitemid 40312292)
    • (2005) Journal of Pharmaceutical and Biomedical Analysis , vol.37 , Issue.3 , pp. 481-486
    • Shi, Z.1    He, J.2    Yao, T.3    Chang, W.4    Zhao, M.5
  • 24
    • 34547208680 scopus 로고    scopus 로고
    • Profiling the metabolic difference of seven tanshinones using high-performance liquid chromatography/multi-stage mass spectrometry with data-dependent acquisition
    • DOI 10.1002/rcm.3080
    • J. Sun, M. Yang, J. Han, B. Wang, X. Ma, M. Xu, P. Liu, and D. Guo Profiling the metabolic difference of seven tanshinones using high-performance liquid chromatography/multi-stage mass spectrometry with data-dependent acquisition Rapid Commun. Mass Spectrom. 21 2007 2211 2226 (Pubitemid 47121152)
    • (2007) Rapid Communications in Mass Spectrometry , vol.21 , Issue.14 , pp. 2211-2226
    • Sun, J.1    Yang, M.2    Han, J.3    Wang, B.4    Ma, X.5    Xu, M.6    Liu, P.7    Guo, D.8
  • 27
    • 4444292394 scopus 로고    scopus 로고
    • Genetic polymorphisms in cytochrome P450 enzymes: Effect on efficacy and tolerability of HMG-CoA reductase inhibitors
    • DOI 10.2165/00129784-200404040-00005
    • A. Vermes, and I. Vermes Genetic polymorphisms in cytochrome P450 enzymes: effect on efficacy and tolerability of HMG-CoA reductase inhibitors Am. J. Cardiovasc. Drugs 4 2004 247 255 (Pubitemid 39206618)
    • (2004) American Journal of Cardiovascular Drugs , vol.4 , Issue.4 , pp. 247-255
    • Vermes, A.1    Vermes, I.2
  • 28
    • 70350044889 scopus 로고    scopus 로고
    • New insights into the structural characteristics and functional relevance of the human cytochrome P450 2D6 enzyme
    • B. Wang, L.P. Yang, X.Z. Zhang, S.Q. Huang, M. Bartlam, and S.F. Zhou New insights into the structural characteristics and functional relevance of the human cytochrome P450 2D6 enzyme Drug Metab. Rev. 41 2009 573 643
    • (2009) Drug Metab. Rev. , vol.41 , pp. 573-643
    • Wang, B.1    Yang, L.P.2    Zhang, X.Z.3    Huang, S.Q.4    Bartlam, M.5    Zhou, S.F.6
  • 29
    • 77955983219 scopus 로고    scopus 로고
    • Major tanshinones of Danshen (Salvia miltiorrhiza) exhibit different modes of inhibition on human CYP1A2, CYP2C9, CYP2E1 and CYP3A4 activities in vitro
    • 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
    • (2010) Phytomedicine , vol.17 , pp. 868-875
    • Wang, X.1    Cheung, C.M.2    Lee, W.Y.3    Or, P.M.4    Yeung, J.H.5
  • 30
    • 67349217348 scopus 로고    scopus 로고
    • Effects of major tanshinones isolated from Danshen (Salvia miltiorrhiza) on rat CYP1A2 expression and metabolism of model CYP1A2 probe substrates
    • X. Wang, W.Y. Lee, P.M. Or, and J.H. Yeung Effects of major tanshinones isolated from Danshen (Salvia miltiorrhiza) on rat CYP1A2 expression and metabolism of model CYP1A2 probe substrates Phytomedicine 16 2009 712 725
    • (2009) Phytomedicine , vol.16 , pp. 712-725
    • Wang, X.1    Lee, W.Y.2    Or, P.M.3    Yeung, J.H.4
  • 31
    • 75249084372 scopus 로고    scopus 로고
    • Pharmacokinetic interaction studies of tanshinones with tolbutamide, a model CYP2C11 probe substrate, using liver microsomes, primary hepatocytes and in vivo in the rat
    • X. Wang, W.Y. Lee, P.M. Or, and J.H. Yeung Pharmacokinetic interaction studies of tanshinones with tolbutamide, a model CYP2C11 probe substrate, using liver microsomes, primary hepatocytes and in vivo in the rat Phytomedicine 17 2010 203 211
    • (2010) Phytomedicine , vol.17 , pp. 203-211
    • Wang, X.1    Lee, W.Y.2    Or, P.M.3    Yeung, J.H.4
  • 32
    • 77955983969 scopus 로고    scopus 로고
    • A pharmacodynamic-pharmacokinetic (PD-PK) study on the effects of Danshen (Salvia miltiorrhiza) on midazolam, a model CYP3A probe substrate, in the rat
    • X. Wang, W.Y. Lee, X. Zhou, P.M. Or, and J.H. Yeung A pharmacodynamic-pharmacokinetic (PD-PK) study on the effects of Danshen (Salvia miltiorrhiza) on midazolam, a model CYP3A probe substrate, in the rat Phytomedicine 17 2010 876 883
    • (2010) Phytomedicine , vol.17 , pp. 876-883
    • Wang, X.1    Lee, W.Y.2    Zhou, X.3    Or, P.M.4    Yeung, J.H.5
  • 33
    • 33845768814 scopus 로고    scopus 로고
    • New developments in the chemistry and biology of the bioactive constituents of Tanshen
    • DOI 10.1002/med.20077
    • X. Wang, S.L. Morris-Natschke, and K.H. Lee New developments in the chemistry and biology of the bioactive constituents of Tanshen Med. Res. Rev. 27 2007 133 148 (Pubitemid 44975189)
    • (2007) Medicinal Research Reviews , vol.27 , Issue.1 , pp. 133-148
    • Wang, X.1    Morris-Natschke, S.L.2    Lee, K.-H.3
  • 34
    • 77954933481 scopus 로고    scopus 로고
    • Effects of the aqueous extract from Salvia miltiorrhiza Bunge on caffeine pharmacokinetics and liver microsomal CYP1A2 activity in humans and rats
    • X. Wang, and J.H. Yeung Effects of the aqueous extract from Salvia miltiorrhiza Bunge on caffeine pharmacokinetics and liver microsomal CYP1A2 activity in humans and rats J. Pharm. Pharmacol. 62 2010 1077 1083
    • (2010) J. Pharm. Pharmacol. , vol.62 , pp. 1077-1083
    • Wang, X.1    Yeung, J.H.2
  • 35
    • 79955473621 scopus 로고    scopus 로고
    • Inhibitory effect of tanshinones on rat CYP3A2 and CYP2C11 activity and its structure-activity relationship
    • 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
    • (2011) Fitoterapia , vol.82 , pp. 539-545
    • Wang, X.1    Yeung, J.H.2
  • 36
    • 80054910363 scopus 로고    scopus 로고
    • Effects of Salvia miltiorrhiza extract on the liver CYP3A activity in humans and rats
    • X. Wang, and J.H. Yeung Effects of Salvia miltiorrhiza extract on the liver CYP3A activity in humans and rats Phytother. Res. 25 2011 1653 1659
    • (2011) Phytother. Res. , vol.25 , pp. 1653-1659
    • Wang, X.1    Yeung, J.H.2
  • 37
    • 84857041628 scopus 로고    scopus 로고
    • Investigation of cytochrome P450 1A2 and 3A inhibitory properties of Danshen tincture
    • 10.1016/j.phymed.2011.09.075
    • X. Wang, and J.H. Yeung Investigation of cytochrome P450 1A2 and 3A inhibitory properties of Danshen tincture Phytomedicine 2011 10.1016/j.phymed.2011.09.075
    • (2011) Phytomedicine
    • Wang, X.1    Yeung, J.H.2
  • 38
    • 75249097840 scopus 로고    scopus 로고
    • Inhibition of warfarin hydroxylation by major tanshinones of Danshen (Salvia miltiorrhiza) in the rat in vitro and in vivo
    • W.W. Wu, and J.H. Yeung Inhibition of warfarin hydroxylation by major tanshinones of Danshen (Salvia miltiorrhiza) in the rat in vitro and in vivo Phytomedicine 17 2010 219 226
    • (2010) Phytomedicine , vol.17 , pp. 219-226
    • Wu, W.W.1    Yeung, J.H.2
  • 39
  • 40
    • 11144317888 scopus 로고    scopus 로고
    • Chemical fingerprint and metabolic fingerprint analysis of Danshen injection by HPLC-UV and HPLC-MS methods
    • DOI 10.1016/j.jpba.2004.09.009, PII S0731708504004303
    • J.L. Zhang, M. Cui, Y. He, H.L. Yu, and D.A. Guo Chemical fingerprint and metabolic fingerprint analysis of Danshen injection by HPLC-UV and HPLC-MS methods J. Pharm. Biomed. Anal. 36 2005 1029 1035 (Pubitemid 40037823)
    • (2005) Journal of Pharmaceutical and Biomedical Analysis , vol.36 , Issue.5 , pp. 1029-1035
    • Zhang, J.-L.1    Cui, M.2    He, Y.3    Yu, H.-L.4    Guo, D.-A.5
  • 41
    • 27844511101 scopus 로고    scopus 로고
    • Danshen: An overview of its chemistry, pharmacology, pharmacokinetics, and clinical use
    • DOI 10.1177/0091270005282630
    • L. Zhou, Z. Zuo, and M.S. Chow Danshen: an overview of its chemistry, pharmacology, pharmacokinetics, and clinical use J. Clin. Pharmacol. 45 2005 1345 1359 (Pubitemid 41643896)
    • (2005) Journal of Clinical Pharmacology , vol.45 , Issue.12 , pp. 1345-1359
    • Zhou, L.1    Zuo, Z.2    Chow, M.S.S.3
  • 42
    • 70349386728 scopus 로고    scopus 로고
    • Polymorphism of human cytochrome P450 2D6 and its clinical significance. Part i
    • S.F. Zhou Polymorphism of human cytochrome P450 2D6 and its clinical significance. Part I Clin. Pharmacokinet. 48 2009 689 723
    • (2009) Clin. Pharmacokinet. , vol.48 , pp. 689-723
    • Zhou, S.F.1
  • 43
    • 70149110672 scopus 로고    scopus 로고
    • Polymorphism of human cytochrome P450 enzymes and its clinical impact
    • S.F. Zhou, J.P. Liu, and B. Chowbay Polymorphism of human cytochrome P450 enzymes and its clinical impact Drug Metab. Rev. 41 2009 89 295
    • (2009) Drug Metab. Rev. , vol.41 , pp. 89-295
    • Zhou, S.F.1    Liu, J.P.2    Chowbay, B.3


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