Imperatorin is a mechanism-based inactivator of CYP2B6

Drug Metabolism and Disposition

Volumn 43, Issue 1, 2015, Pages 82-88

  Zheng, Liwei ^a   Cao, Jiaojiao ^a   Lu, Dan ^a   Ji, Lin ^a   Peng, Ying ^a   Zheng, Jiang ^a,b  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^b UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALASE; CYTOCHROME P450 1A2; CYTOCHROME P450 2A6; CYTOCHROME P450 2B6; CYTOCHROME P450 2D6; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; GLUTATHIONE; PENTOSALEN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SUPEROXIDE DISMUTASE; TICLOPIDINE; FUROCOUMARIN DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ANIMAL CELL; ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG METABOLISM; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INACTIVATION; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MALE; NONHUMAN; OXIDATION; RAT; TANDEM MASS SPECTROMETRY; ANIMAL; DRUG EFFECTS; METABOLISM; SPRAGUE DAWLEY RAT;

ANIMALS; CATALASE; CYTOCHROME P-450 CYP2B6; FUROCOUMARINS; GLUTATHIONE; MALE; MICROSOMES, LIVER; NADP; RATS; RATS, SPRAGUE-DAWLEY; SUPEROXIDE DISMUTASE; TICLOPIDINE;

EID: 84919682611     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.114.060558     Document Type: Article

References (28)

1. Baek NI, Ahn EM, Kim HY, and Park YD (2000) Furanocoumarins from the root of Angelica dahurica. Arch Pharm Res 23:467-470.
2. Baumgart A, Schmidt M, Schmitz HJ, and Schrenk D (2005) Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes. Biochem Pharmacol 69: 657-667.
3. Cai Y, Bennett D, Nair RV, Ceska O, Ashwood-Smith MJ, and DiGiovanni J (1993) Inhibition and inactivation of murine hepatic ethoxy- and pentoxyresorufin O-dealkylase by naturally occurring coumarins. Chem Res Toxicol 6:872-879.
4. Edwards DJ, Bellevue FH, 3rd, and Woster PM (1996) Identification of 69,79-dihydroxybergamottin, a cytochrome P450 inhibitor, in grapefruit juice. Drug Metab Dispos 24:1287-1290.
5. Faucette SR, Hawke RL, Lecluyse EL, Shord SS, Yan B, Laethem RM, and Lindley CM (2000) Validation of bupropion hydroxylation as a selective marker of human cytochrome P450 2B6 catalytic activity. Drug Metab Dispos 28:1222-1230.
6. García-Argáez AN, Ramírez Apan TO, Parra Delgado H, Velázquez G, and Martínez-Vázquez M (2000) Anti-inflammatory activity of coumarins from Decatropis bicolor on TPA ear mice model. Planta Med 66:279-281.
7. Gerber JG, Rhodes RJ, and Gal J (2004) Stereoselective metabolism of methadone N-demethylation by cytochrome P4502B6 and 2C19. Chirality 16:36-44.
8. He JY, Zhang W, He LC, and Cao YX (2007) Imperatorin induces vasodilatation possibly via inhibiting voltage dependent calcium channel and receptor-mediated Ca2+ influx and release. Eur J Pharmacol 573:170-175.
9. Huang Z, Roy P, and Waxman DJ (2000) Role of human liver microsomal CYP3A4 and CYP2B6 in catalyzing N-dechloroethylation of cyclophosphamide and ifosfamide. Biochem Pharmacol 59:961-972.
10. Kent UM, Juschyshyn MI, and Hollenberg PF (2001) Mechanism-based inactivators as probes of cytochrome P450 structure and function. Curr Drug Metab 2:215-243.
11. Kim YK, Kim YS, and Ryu SY (2007) Antiproliferative effect of furanocoumarins from the root of Angelica dahurica on cultured human tumor cell lines. Phytother Res 21:288-290.
12. Klaassen CD, Amdur MO, and Doull J (1986) Biotransformation of xenobiotics, in Casarett and Doull's Toxicology, the Basic Science of Poisons (Klaassen CD ed) pp 113-186, McGraw-Hill, New York.
13. Koenigs LL and Trager WF (1998) Mechanism-based inactivation of cytochrome P450 2B1 by 8-methoxypsoralen and several other furanocoumarins. Biochemistry 37:13184-13193.
14. Lia HB and Chen F (2004) Preparative isolation and purification of bergapten and imperatorin from the medicinal plant Cnidium monnieri using high-speed counter-current chromatography by stepwise increasing the flow-rate of the mobile phase. J Chromatogr A 1061:51-54.
15. Lin G, Tang J, Liu XQ, Jiang Y, and Zheng J (2007) Deacetylclivorine: A gender-selective metabolite of clivorine formed in female Sprague-Dawley rat liver microsomes. Drug Metab Dispos 35:607-613.
16. Lin HL, Kent UM, and Hollenberg PF (2005) The grapefruit juice effect is not limited to cytochrome P450 (P450) 3A4: Evidence for bergamottin-dependent inactivation, heme destruction, and covalent binding to protein in P450s 2B6 and 3A5. J Pharmacol Exp Ther 313: 154-164.
17. Marumoto S and Miyazawa M (2010) b-secretase inhibitory effects of furanocoumarins from the root of Angelica dahurica. Phytother Res 24:510-513.
18. Miksys S and Tyndale RF (2004) The unique regulation of brain cytochrome P450 2 (CYP2) family enzymes by drugs and genetics. Drug Metab Rev 36:313-333.
19. Rosselli S, Maggio A, Bellone G, Formisano C, Basile A, Cicala C, Alfieri A, Mascolo N, and Bruno M (2007) Antibacterial and anticoagulant activities of coumarins isolated from the flowers of Magydaris tomentosa. Planta Med 73:116-120.
20. Silverman RB (1996) Mechanism-based enzyme inactivation, in Contemporary Enzyme Kinetics and Mechanisms (Purich DL ed) pp 291-335, Academic Press, San Diego, CA.
21. Stresser DM and Kupfer D (1999) Monospecific antipeptide antibody to cytochrome P-450 2B6. Drug Metab Dispos 27:517-525.
22. Talakad JC, Shah MB, Walker GS, Xiang C, Halpert JR, and Dalvie D (2011) Comparison of in vitro metabolism of ticlopidine by human cytochrome P450 2B6 and rabbit cytochrome P450 2B4. Drug Metab Dispos 39:539-550.
23. Tang CH, Yang RS, Chien MY, Chen CC, and Fu WM (2008) Enhancement of bone morphogenetic protein-2 expression and bone formation by coumarin derivatives via p38 and ERKdependent pathway in osteoblasts. Eur J Pharmacol 579:40-49.
24. Thum T and Borlak J (2000) Gene expression in distinct regions of the heart. Lancet 355: 979-983.
25. Ward BA, Gorski JC, Jones DR, Hall SD, Flockhart DA, and Desta Z (2003) The cytochrome P450 2B6 (CYP2B6) is the main catalyst of efavirenz primary and secondary metabolism: Implication for HIV/AIDS therapy and utility of efavirenz as a substrate marker of CYP2B6 catalytic activity. J Pharmacol Exp Ther 306:287-300.
26. Zhang QY, Qin LP, Huang BK, Zheng HC, Wang Y, Wang H, and Chen L (2003) Study on effects of total coumarines from the fruits of Cnidium monnieri on osteoporosis in ovariectomized rats. Chin Pharm J 38:101-103.
27. Zhang Y, Cao Y, Zhan Y, Duan H, and He L (2010) Furanocoumarins-imperatorin inhibits myocardial hypertrophy both in vitro and in vivo. Fitoterapia 81:1188-1195.
28. Zhuang XM, Zhong YH, Xiao WB, Li H, and Lu C (2013) Identification and characterization of psoralen and isopsoralen as potent CYP1A2 reversible and time-dependent inhibitors in human and rat preclinical studies. Drug Metab Dispos 41:1914-1922.