Characterization of triptolide hydroxylation by cytochrome P450 in human and rat liver microsomes

Xenobiotica

Volumn 38, Issue 12, 2008, Pages 1551-1565

  Li, W ^a,e   Liu, Y ^a   He, Y Q ^b   Zhang, J W ^a   Gao, Y ^c   Ge, G B ^a,e   Liu, H X ^a,e   Huo, H ^a   Liu, H T ^a,e   Wang, L M ^c   Sun, J ^c   Wang, Q ^d   Yang, L ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b SHANGHAI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

^c DALIAN MEDICAL UNIVERSITY   (China)

^d DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^e UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Cytochrome P450; Mono hydroxylated metabolite; Triptolide

Indexed keywords

1 AMINOBENZOTRIAZOLE; CLOMETHIAZOLE; COMPLEMENTARY DNA; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2A6; CYTOCHROME P450 2C19; CYTOCHROME P450 2C8; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; FURAFYLLINE; KETOCONAZOLE; METHOXSALEN; OMEPRAZOLE; PHENACETIN O DEETHYLASE; QUERCETIN; QUINIDINE; SULFAPHENAZOLE; TRIPTERYGIUM WILFORDII EXTRACT; TRIPTOLIDE;

ADULT; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BIOTRANSFORMATION; CORRELATION ANALYSIS; DRUG MECHANISM; DRUG METABOLISM; DRUG STRUCTURE; ENZYME KINETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HUMAN TISSUE; HYDROXYLATION; INCUBATION TIME; LIQUID CHROMATOGRAPHY; LIVER CELL; LIVER CLEARANCE; MALE; MASS SPECTROMETRY; MICROSOME; NONHUMAN; RAT; SPRAGUE DAWLEY RAT; ULTRACENTRIFUGATION;

ANIMALS; CHROMATOGRAPHY, LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; DITERPENES; DNA, COMPLEMENTARY; ENZYME INHIBITORS; EPOXY COMPOUNDS; HUMANS; HYDROXYLATION; KINETICS; MASS SPECTROMETRY; MICROSOMES, LIVER; PHENANTHRENES; RATS;

RATTUS; TRIPTERYGIUM WILFORDII;

EID: 56749105762     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.1080/00498250802503359     Document Type: Article

References (28)

1. Baranczewski P, Stanczak A, Sundberg K, Svensson R, Wallin A, Jansson J, Garberg P, Postlind H. 2006. Introduction to in vitro estimation of metabolic stability and drug interactions of new chemical entities in drug discovery and development. Pharmacological Reports 58(4):453-472.
2. Carter BZ, Mak DH, Schober WD, McQueen T, Harris D, Estrov Z, Evans RL, Andreeff M. 2006. Triptolide induces caspase-dependent cell death mediated via the mitochondrial pathway in leukemic cells. Blood 108(2):630-637.
3. Chen BJ. 2001. Triptolide, a novel immunosuppressive and anti-inflammatory agent purified from a Chinese herb Tripterygium wilfordii Hook F. leukemia and lymphoma 42(3):253-265.
4. Fidler JM, Ku GY, Piazza D, Xu R, Jin R, Chen Z. 2002. Immunosuppressive activity of the Chinese medicinal plant Tripterygium wilfordii. III. Suppression of graft-versus-host disease in murine allogeneic bone marrow transplantation by the PG27 extract. Transplantation 74(4):445-457.
5. Fidler JM, Li Y. 2003. Anticancer treatment using triptolide prodrugs. United States Patent No. 6620843.
6. Fidler JM, Li K, Chung C, Wei K, Ross JA, Gao M, Rosen GD. 2003. PG490-88, a derivative of triptolide, causes tumor regression and sensitizes tumors to chemotherapy. Molecular Cancer Therapeutics 2(9):855-862.
7. Gu WZ, Chen R, Brandwein S, McAlpine J, Burres N. 1995. Isolation, purification, and characterization of immunosuppressive compounds from tripterygium: Triptolide and tripdiolide. International. Immunopharmacology 17(5):351-356.
8. Guengerich FP. 2006. Cytochrome P450s and other enzymes in drug metabolism and toxicity. AAPS Journal 8(1):E101-E111.
9. Houston JB. 1994. Utility of in vitro drug metabolism data in predicting in vivo metabolic clearance. Biochemical Pharmacology 47(9):1469-1479.
10. Lasker JM, Wester MR, Aramsombatdee E, Raucy JL. 1998. Characterization of CYP2C19 and CYP2C9 from human liver: Respective roles in microsomal tolbutamide, S-mephenytoin, and omeprazole hydroxylations. Archives of Biochemistry and Biophysics 353(1):16-28.
11. Lipsky PE, Fan ZS, Tao XLC, Gustafson KR, Hess S, Penzak SR. 2005 (available at: http://nidb.nih.gov/search/searchreport.taf?ipid=35102).
12. Liu Y, Ma H, Zhang JW, Deng MC, Yang L. 2006a. Influence of ginsenoside Rh1 and F1 on human cytochrome p450 enzymes. Planta Medica 72(2):126-131.
13. Liu Y, Zhang JW, Li W, Ma H, Sun J, Deng MC, Yang L. 2006b. Ginsenoside metabolites, rather than naturally occurring ginsenosides, lead to inhibition of human cytochrome P450 enzymes. Toxicological Sciences 91(2):356-364.
14. Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. 1951. Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry 193(1):265-275.
15. Ma J, Dey M, Yang H, Poulev A, Pouleva R, Dorn R, Lipsky PE, Kennelly EJ, Raskin I. 2007. Anti-inflammatory and immunosuppressive compounds from Tripterygium wilfordii. Phytochemistry 68(8):1172-1178.
16. Matsui Y, Watanabe J, Ikegawa M, Kamoto T, Ogawa O, Nishiyama H. 2008. Cancer-specific enhancement of cisplatin-induced cytotoxicity with triptolide through an interaction of inactivated glycogen synthase kinase-3beta with p53. Oncogene 27(33):4603-4614.
17. Naritomi Y, Terashita S, Kimura S, Suzuki A, Kagayama A, Sugiyama Y. 2001. Prediction of human hepatic clearance from in vivo animal experiments and in vitro metabolic studies with liver microsomes from animals and humans. Drug Metabolism and Disposition 29(10):1316-1324.
18. Omura T, Sato R. 1964. The carbon monoxide-binding pigment of liver microsomes. Journal of Biological Chemistry 239:2370-2385.
19. Ortiz de Montellano PR, Mathews JM. 1981. Autocatalytic alkylation of the cytochrome P-450 prosthetic haem group by 1-aminobenzotriazole. Isolation of an NN-bridged benzyne-protoporphyrin IX adduct. Biochemical Journal 195(3):761-764.
20. Shao F, Wang G, Xie H, Zhu X, Sun J, A J. 2007a. Pharmacokinetic study of triptolide, a constituent of immunosuppressive Chinese herb medicine, in rats. Biological and Pharmaceutical Bulletin 30(4):702-707.
21. Shao F, Wang GJ, Sun JG, Xie HT, Zhang R, Zhu XY. 2007b. [Pharmacokinetics of triptolide in Beagle dogs]. Yao Xue Xue Bao 42(1):61-65. [in Chinese]
22. Shimada T, Yamazaki H, Mimura M, Inui Y, Guengerich FP. 1994. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians. Journal of Pharmacology and Experimental Therapeutics 270(1):414-423.
23. Tao X, Fan F, Hoffmann V, Gao CY, Longo NS, Zerfas P, Lipsky PE. 2008. Effective therapy for nephritis in (NZB NZW)F1 mice with triptolide and tripdiolide, the principal active components of the Chinese herbal remedy Tripterygium wilfordii Hook F. Arthritis and Rheumatism 58(6):1774-1783.
24. Yang S, Chen J, Guo Z, Xu XM, Wang L, Pei XF, Yang J, Underhill CB, Zhang L. 2003. Triptolide inhibits the growth and metastasis of solid tumors. Molecular Cancer Therapeutics 2(1):65-72.
25. Zhang JW, Ge GB, Liu Y, Wang LM, Liu XB, Zhang YY, Li W, He YQ, Wang ZT, Sun J, et al. 2008. Taxane's substituents at C3′ affect its regioselective metabolism: Different in vitro metabolism of cephalomannine and paclitaxel. Drug Metabolism and Disposition 36(2):418-426.
26. Zhang JW, Liu Y, Cheng J, Li W, Ma H, Liu HT, Sun J, Wang LM, He YQ, Wang Y, et al. 2007. Inhibition of human liver cytochrome P450 by star fruit juice. Journal of Pharmacy and Pharmaceutical Sciences 10(4):496-503.
27. Zhang JW, Liu Y, Li W, Hao DC, Yang L. 2006. Inhibitory effect of medroxyprogesterone acetate on human liver cytochrome P450 enzymes. European Journal of Clinical Pharmacology 62(7):497-502.
28. Zheng J. 1991. [Screening of active anti-inflammatory, immunosuppressive and antifertility components of Tripterygium wilfordii. III. A comparison of the antiinflammatory and immunosuppressive activities of seven diterpene lactone epoxide compounds in vivo]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao 13(6):391-397. [in Chinese]