Effects of baicalein on the pharmacokinetics of tamoxifen and its main metabolite, 4-hydroxytamoxifen, in rats: Possible role of cytochrome p450 3A4 and P-glycoprotein inhibition by baicalein

Archives of Pharmacal Research

Volumn 34, Issue 11, 2011, Pages 1965-1972

  Li, Cheng ^a,b   Kim, Minhee ^a   Choi, Hongseok ^a   Choi, Junshik ^a  

^a Chosun University   (South Korea)

^b YANBIAN UNIVERSITY   (China)

Author keywords

4 Hydroxytamoxifen; Baicalein; CYP3A4; P gp; Pharmacokinetics; Rats; Tamoxifen

Indexed keywords

AFIMOXIFENE; BAICALEIN; CYTOCHROME P450 3A4; GLYCOPROTEIN P; TAMOXIFEN;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG EFFECT; DRUG INHIBITION; MALE; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; PLASMA CONCENTRATION-TIME CURVE; RAT; SMALL INTESTINE;

ANIMALS; ANTINEOPLASTIC AGENTS, HORMONAL; BIOTRANSFORMATION; CELL LINE; CYTOCHROME P-450 CYP3A; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG INTERACTIONS; ENZYME INHIBITORS; FLAVANONES; HALF-LIFE; HUMANS; MALE; MEMBRANE TRANSPORT MODULATORS; METABOLIC CLEARANCE RATE; P-GLYCOPROTEIN; RATS; RATS, SPRAGUE-DAWLEY; RECOMBINANT PROTEINS; TAMOXIFEN;

EID: 83655203469     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-011-1117-9     Document Type: Article

References (44)

1. J. J. Bogaards M. Bertrand P. Jackson M. J. Oudshoorn R. J. Weaver P. J. van Bladeren B. Walther 2000 Determining the best animal model for human cytochrome P450 activities: a comparison of mouse, rat, rabbit, dog, micropig, monkey and man Xenobiotica 30 1131 1152 11307970 10.1080/00498250010021684 1:CAS:528:DC%2BD3MXitleksrg%3D (Pubitemid 32368013)
2. J. L. Borgna H. Rochefort 1981 Hydroxylated metabolites of tamoxifen are formed in vivo and bound to estrogen receptor in target tissues J. Biol. Chem. 256 859 868 7451477 1:CAS:528:DyaL3MXps1Kluw%3D%3D (Pubitemid 11103040)
3. M. M. Buckley K. L. Goa 1989 Tamoxifen. A reappraisal of its pharmacodynamic and pharmacokinetic properties, and therapeutic use Drugs 37 451 490 2661195 10.2165/00003495-198937040-00004 1:STN:280:DyaL1M3ovFCnug%3D%3D
4. X. Cao S. T. Gibbs L. Fang H. A. Miller C. P. Landowski H. C. Shin H. Lennernas Y. Zhong G. L. Amidon L. X. Yu D. Sun 2006 Why is it challenging to predict intestinal drug absorption and oral bioavailability in human using rat model Pharm. Res. 23 1675 1686 16841194 10.1007/s11095-006-9041-2 1:CAS:528:DC%2BD28XnvVyms7c%3D (Pubitemid 44200529)
5. Y. S. Chi H. Lim H. Park H. P. Kim 2003 Effects of wogonin, a plant flavone from Scutellaria radix, on skin inflammation: in vivo regulation of inflammation-associated gene expression Biochem. Pharmacol. 66 1271 1278 14505806 10.1016/S0006-2952(03)00463-5 1:CAS:528:DC%2BD3sXnsVamsL0%3D (Pubitemid 37130302)
6. E. Chieli N. Romiti F. Cervelli R. Tongiani 1995 Effects of flavonols on P-glycoprotein activity in cultured rat hepatocytes Life Sci. 57 1741 1751 7475916 10.1016/0024-3205(95)02152-9 1:CAS:528:DyaK2MXosVSrsLk%3D
7. E. Coezy J. L. Borgna H. Rochefort 1982 Tamoxifen and metabolites in MCF7 cells: correlation between binding to estrogen receptor and inhibition of cell growth Cancer Res. 42 317 323 7053859 1:CAS:528:DyaL38XhtFKitr8%3D (Pubitemid 12207285)
8. C. L. Crespi V. P. Miller B. W. Penman 1997 Microtiter plate assays for inhibition of human, drug-metabolizing cytochromes P450 Anal. Biochem. 248 188 190 9177742 10.1006/abio.1997.2145 1:CAS:528:DyaK2sXjsVGmtb0%3D (Pubitemid 27218241)
9. H. K. Crewe S. W. Ellis M. S. Lennard G. T. Tucker 1997 Variable contribution of cytochromes P450 2D6, 2C9 and 3A4 to the 4-hydroxylation of tamoxifen by human liver microsomes Biochem. Pharmacol. 53 171 178 9037249 10.1016/S0006-2952(96)00650-8 1:CAS:528:DyaK2sXitVSqsA%3D%3D (Pubitemid 27013472)
10. C. L. Cummins W. Jacobsen L. Z. Benet 2002 Unmasking the dynamic interplay between intestinal P-glycoprotein and CYP3A4 J. Pharmacol. Exp. Ther. 300 1036 1045 11861813 10.1124/jpet.300.3.1036 1:CAS:528:DC%2BD38XitVelsLs%3D (Pubitemid 34165010)
11. A. Di Pietro G. Conseil J. M. Pérez-Victoria G. Dayan H. Baubichon-Cortay D. Trompier E. Steinfels J. M. Jault H. de Wet M. Maitrejean G. Comte A. Boumendjel A. M. Mariotte C. Dumontet D. B. McIntosh A. Goffeau S. Castanys F. Gamarro D. Barron 2002 Modulation by flavonoids of cell multidrug resistance mediated by Pglycoprotein and related ABC transporters Cell. Mol. Life Sci. 59 307 322 11915946 10.1007/s00018-002-8424-8 (Pubitemid 34169516)
12. R. A. Dixon C. L. Steele 1999 Flavonoids and isoflavonoids -a gold mine for metabolic engineering Trends Plant Sci. 4 394 400 10498963 10.1016/S1360-1385(99)01471-5 (Pubitemid 29471622)
13. K. M. Fried I. W. Wainer 1994 Direct determination of tamoxifen and its four major metabolites in plasma using coupled column high-performance liquid chromatography J. Chromatogr. B Biomed. Appl. 655 261 268 8081472 10.1016/0378-4347(94)00054-9 1:CAS:528:DyaK2cXkslaqs7k%3D (Pubitemid 24169259)
14. T. W. Gant C. K. O'Connor R. Corbitt U. Thorgeirsson S. S. Thorgeirsson 1995 In vivo induction of liver P-glycoprotein expression by xenobiotics in monkeys Toxicol. Appl. Pharmacol. 133 269 276 7645023 10.1006/taap.1995.1151 1:CAS:528:DyaK2MXnsFGru7g%3D
15. F. P. Guengerich M. V. Martin P. H. Beaune P. Kremers T. Wolff D. J. Waxman 1986 Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism J. Biol. Chem. 261 5051 5060 3514607 1:CAS:528:DyaL28XktVeqtbc%3D (Pubitemid 17204301)
16. C. Y. Han K. B. Cho H. S. Choi H. K. Han K. W. Kang 2008 Role of FoxO1 activation in MDR1 expression in adriamycin-resistant breast cancer cells Carcinogenesis 29 1837 1844 18390843 10.1093/carcin/bgn092 1:CAS:528: DC%2BD1cXhtV2jsL%2FM
17. Y. Huang S. Y. Tsang X. Yao Z. Y. Chen 2005 Biological properties of baicalein in cardiovascular system Curr. Drug Targets Cardiovasc. Haematol. Disord. 5 177 184 15853750 10.2174/1568006043586206 1:CAS:528: DC%2BD2MXktlagsLc%3D (Pubitemid 40645490)
18. I. A. Jaiyesimi A. U. Buzdar D. A. Decker G. N. Hortobagyi 1995 Use of tamoxifen for breast cancer: twenty-eight years later J. Clin. Oncol. 13 513 529 7844613 1:STN:280:DyaK2M7kslSnsw%3D%3D
19. M. D. Johnson H. Zuo K. H. Lee J. P. Trebley J. M. Rae R. V. Weatherman Z. Desta D. A. Flockhart T. C. Skaar 2004 Pharmacological characterization of 4-hydroxy-Ndesmethyl tamoxifen, a novel active metabolite of tamoxifen Breast Cancer Res. Treat. 85 151 159 15111773 10.1023/B:BREA.0000025406.31193.e8 1:CAS:528:DC%2BD2cXjsVertbc%3D (Pubitemid 38987269)
20. L. S. Kaminsky M. J. Fasco 1991 Small intestinal cytochromes P450 Crit. Rev. Toxocol. 21 407 422 10.3109/10408449209089881 1:STN:280: DyaK387pvVGktA%3D%3D
21. P. A. Kelly H. Wang K. L. Napoli B. D. Kahan H. W. Strobel 1999 Metabolism of cyclosporine by cytochromes P450 3A9 and 3A4 Eur. J. Drug Metab. Pharmacokinet. 24 321 328 10892895 10.1007/BF03190040 1:CAS:528: DC%2BD3cXmsVehtLc%3D (Pubitemid 30342700)
22. C. S. Kim S. J. Choi C. Y. Park C. Li J. S. Choi 2010 Effects of silybinin on the pharmacokinetics of tamoxifen and its active metabolite, 4-hydroxytamoxifen in rats Anticancer Res. 30 79 85 20150620 1:CAS:528:DC%2BC3cXjtVymtbk%3D
23. Y. Kimura H. Okuda Z. Ogita 1997 Effects of flavonoids isolated from scutellariae radix on fibrinolytic system induced by trypsin in human umbilical vein endothelial cells J. Nat. Prod. 60 598 601 9214730 10.1021/np970035l 1:CAS:528:DyaK2sXjsFCjsL0%3D (Pubitemid 27274375)
24. H. Lee H. W. Wang H. Y. Su N. J. Hao 1994 The structureactivity relationships of flavonoids as inhibitors of cytochrome P-450 enzymes in rat liver microsomes and the mutagenicity of 2-amino-3-methyl-imidazo[4,5-f] quinoline Mutagenesis 9 101 106 8201941 10.1093/mutage/9.2.101 1:CAS:528:DyaK2cXksFajtrk%3D (Pubitemid 24090150)
25. Y. Lee H. Yeo S. H. Liu Z. Jiang R. M. Savizky D. J. Austin Y. C. Cheng 2004 Increased anti-P-glycoprotein activity of baicalein by alkylation on the A ring J. Med. Chem. 47 5555 5566 15481991 10.1021/jm049949c 1:CAS:528: DC%2BD2cXnslShsLk%3D (Pubitemid 39382802)
26. Lewis, D. F. V., Cytochrome P450. Substrate specificity and metabolism. In: Cytochromes P450. Structure, Function, and Mechanism. Taylor & Francis, Bristol, pp. 122-123, (1996).
27. M. Li-Weber 2009 New therapeutic aspects of flavones: the anticancer properties of Scutellaria and its main active constituents Wogonin, Baicalein and Baicalin Cancer Treat. Rev. 35 57 68 19004559 10.1016/j.ctrv.2008.09.005 1:CAS:528:DC%2BD1MXhtlSmur0%3D
28. C. C. Lin D. E. Shieh 1996 The anti-inflammatory activity of Scutellaria rivularis extracts and its active components, baicalin, baicalein and wogonin Am. J. Chin. Med. 24 31 36 8739179 10.1142/S0192415X96000050 1:STN:280:DyaK28zisl2gsw%3D%3D
29. S. C. Ma J. Du P. P. But X. L. Deng Y. W. Zhang V. E. Ooi H. X. Xu S. H. Lee S. F. Lee 2002 Antiviral Chinese medicinal herbs against respiratory syncytial virus J. Ethnopharmacol. 79 205 211 11801383 10.1016/S0378-8741(01) 00389-0 1:CAS:528:DC%2BD38XktFamsQ%3D%3D (Pubitemid 34136952)
30. C. Mani H. V. Gelboin S. S. Park R. Pearce A. Parkinson D. Kupfer 1993 Metabolism of the antimammary cancer antiestrogenic agent tamoxifen. I. Cytochrome P-450-catalyzed N-demethylation and 4-hydroxylation Drug Metab. Dispos. 21 645 656 8104124 1:CAS:528:DyaK3sXlslemtL0%3D (Pubitemid 23221760)
31. Y. Matsuzaki N. Kurokawa S. Terai Y. Matsumura N. Kobayashi K. Okita 1996 Cell death induced by baicalein in human hepatocellular carcinoma cell lines Jpn. J. Cancer Res. 87 170 177 8609066 10.1111/j.1349-7006.1996.tb03155.x 1:CAS:528:DyaK28XhsFCnt7g%3D (Pubitemid 26099492)
32. U. S. Rao R. L. Fine G. A. Scarborough 1994 Antiestrogens and steroid hormones: substrates of the human Pglycoprotein Biochem. Pharmacol. 48 287 292 7914405 10.1016/0006-2952(94)90099-X 1:CAS:528:DyaK2cXlt1Gmurw%3D
33. C. P. Rhoads 1947 Report on a cooperative study of nitrogen mustard (HN2) therapy of neoplastic disease Trans. Assoc. Am. Physicians 60 110 117 18917249 1:STN:280:DyaH1c%2FmtV2qtA%3D%3D
34. S. C. Shin J. S. Choi X. Li 2006 Enhanced bioavailability of tamoxifen after oral administration of tamoxifen with quercetin in rats Int. J. Pharm. 313 144 149 16516418 10.1016/j.ijpharm.2006.01.028 1:CAS:528:DC%2BD28XjtVGqtb8%3D
35. S. C. Shin J. S. Choi 2009 Effects of epigallocatechin gallate on the oral bioavailability and pharmacokinetics of tamoxifen and its main metabolite, 4-hydroxytamoxifen, in rats Anticancer Drugs 20 584 588 19491656 10.1097/CAD.0b013e32832d6834 1:CAS:528:DC%2BD1MXotFCgsbg%3D
36. V. Stearns M. D. Johnson J. M. Rae A. Morocho A. Novielli P. Bhargava D. F. Hayes Z. Desta D. A. Flockhart 2003 Active tamoxifen metabolite plasma concentrations after coadministration of tamoxifen and the selective serotonin reuptake inhibitor paroxetine J. Natl. Cancer Inst. 95 1758 1764 14652237 1:CAS:528:DC%2BD3sXpvVelsbc%3D (Pubitemid 38008898)
37. L. Sutherland T. Ebner B. Burchell 1993 The expression of UDP-glucuronosyltransferases of the UGT1 family in human liver and kidney and in response to drugs Biochem. Pharmacol. 45 295 301 8435089 10.1016/0006-2952(93) 90064-4 1:CAS:528:DyaK3sXhtl2hsrc%3D (Pubitemid 23042627)
38. D. Turgeon J. S. Carrier E. Lévesque D. W. Hum A. Bélanger 2001 Relative enzymatic activity, protein stability, and tissue distribution of human steroid-metabolizing UGT2B subfamily members Endocrinology 142 778 787 11159850 10.1210/en.142.2.778 1:CAS:528:DC%2BD3MXhtFSrt7o%3D (Pubitemid 32222427)
39. V. J. Wacher C. Y. Wu L. Z. Benet 1995 Overlapping substrate specificities and tissue distribution of cytochrome P450 3A and P-glycoprotein: implications for drug delivery and activity in cancer chemotherapy Mol. Carcinog. 13 129 134 7619215 10.1002/mc.2940130302 1:CAS:528:DyaK2MXnt1ams7k%3D
40. V. J. Wacher J. A. Silverman Y. Zhang L. Z. Benet 1998 Role of P-glycoprotein and cytochrome P450 3A in limiting oral absorption of peptides and peptidomimetics J. Pharm. Sci. 87 1322 1330 9811484 10.1021/js980082d 1:CAS:528:DyaK1cXltlyhsb0%3D (Pubitemid 28514135)
41. C. Z. Wang S. R. Mehendale C. S. Yuan 2007 Commonly used antioxidant botanicals: active constituents and their potential role in cardiovascular illness Am. J. Chin. Med. 35 543 558 17708622 10.1142/S0192415X07005053 1:CAS:528:DC%2BD2sXptFyltLw%3D (Pubitemid 47307694)
42. H. K. Wang Y. Xia Z. Y. Yang S. L. Natschke K. H. Lee 1998 Recent advances in the discovery and development of flavonoids and their analogues as antitumor and anti-HIV agents Adv. Exp. Med. Biol. 439 191 225 9781305 10.1007/978-1-4615-5335-9-15 1:CAS:528:DyaK1cXmvFKms70%3D (Pubitemid 28429018)
43. P. B. Watkins 1997 The barrier function of CYP3A4 and P-glycoprotein in the small bowel Adv. Drug Deliv. Rev. 27 161 170 10837556 10.1016/S0169-409X(97) 00041-0 1:CAS:528:DyaK2sXmtlejt74%3D (Pubitemid 27417871)
44. B. Wolozin W. Kellman P. Ruosseau G. G. Celesia G. Siegel 2000 Decreased prevalence of Alzheimer disease associated with 3-hydroxy-3-methyglutaryl coenzyme A reductase inhibitors Arch. Neurol. 57 1439 1443 11030795 10.1001/archneur.57.10.1439 1:STN:280:DC%2BD3M%2FitlGntw%3D%3D