Metabolism of bergamottin by cytochromes P450 2B6 and 3A5

Journal of Pharmacology and Experimental Therapeutics

Volumn 318, Issue 3, 2006, Pages 992-1005

  Kent, Ute M ^a   Lin, Hsia Lien ^a   Noon, Kathleen R ^a   Harris, Danni L ^b   Hollenberg, Paul F ^a,c  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^b MOLECULAR RESEARCH INSTITUTE   (United States)

^c 2301 MSRB III ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' HYDROXY BERGAMOTTIN; 5' HYDROXY BERGAMOTTIN; 6' HYDROXY BERGAMOTTIN; 6',7' DIHYDROXY BERGAMOTTIN; 7' HYDROXY BERGAMOTTIN; BERGAMOTTIN; BERGAPTOL; CYTOCHROME P450 2B6; CYTOCHROME P450 3A5; DRUG METABOLITE; EPOXIDE; FURAN; GLUTATHIONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG METABOLISM; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR MODEL; OXIDATION; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

ARYL HYDROCARBON HYDROXYLASES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; GLUTATHIONE; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; OXIDOREDUCTASES, N-DEMETHYLATING; PSORALENS;

EID: 33747616895     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.105.099887     Document Type: Article

References (41)

1. Bailey DG, Dresser GK, Kreeft JH, Munoz C Freeman DJ, and Bend JR (2000) Grapefruit-felodipine interaction: effect of unprocessed fruit and probable active ingredients. Clin Pharmacol Ther 68:468-477.
2. Blobaum AL, Harris DL, and Hollenberg PF (2005) P450 Active site architecture and reversibility: inactivation of cytochromes P450 2B4 and 2B4 T302A by tert-butyl acetylenes. Biochemistry 44:3831-3844.
3. Bumpus NN, Sridar C, Kent UM, and Hollenberg PF (2005) The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation. Drug Metab Dispos 33:795-802.
4. 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.
5. Canutescu AA, Shelenkov AA, and Dunbrack RL Jr (2003) A graph-theory algorithm for rapid protein side-chain prediction. Protein Sci 12:2001-2014.
6. Ding X and Kaminsky LS (2003) Human extrahepatic cytochromes P450: function in xenobiotic metabolism and tissue-selective chemical toxicity in the respiratory and gastrointestinal tracts. Annu Rev Pharmacol Toxicol 43:149-173.
7. Domanski TL, Finta C, Halpert JR, and Zaphiropoulos PG (2001) cDNA cloning an initial characterization of CYP3A43, a novel human cytochrome P450. Mol Pharmacol 59:386-392.
8. Evans DC, Watt AP, Nicoll-Griffith DA, and Baillie TA (2004) Drug-protein adducts: an industry perspective on minimizing the potential for drug bioactivation in drug discovery and development. Chem Res Toxicol 17:3-16.
9. 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 catalytic activity. Drug Metab Dispos 28:1222-1230.
10. Friesner RA, Banks JL, Murphy RB, Halgren TA, Klicic JJ, Mainz DT, Repasky MP, Knoll EH, Shelley M, Perry JK, et al. (2004) Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem 47:1739-1749.
11. Gerber JG, Rhodes RJ, and Gal J (2004) Stereoselective metabolism of methadone N-demethylation by cytochrome P450 2B6 and 2C19. Chirality 16:36-44.
12. Hanna IH, Roberts ES, and Hollenberg PF (1998) Molecular basis for the difference in lidocaine binding and the regioselectivity of oxidation by cytochrome P450 2B1 and 2B2. Biochemistry 37:311-318.
13. Harris DL, Park JY, Gruenke L, and Waskell L (2004) Theoretical study of the ligand-CYP2B4 complexes: effect of structure on binding free energies and heme spin state. Proteins 55:895-914.
14. He K, Iyer KR, Hayes RN, Sinz MW, Woolf TF, and Hollenberg PF (1998) Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem Res Toxicol 11:252-259.
15. Hesselink DA, van Shaik RH, van der Heiden IP, van der Werf M, Gregoor PJ, and Lindemans J (2003) Genetic polymorphisms of the CYP3A4, CYP3A5, and MDR-1 genes and pharmacokinetics of the calcineurin inhibitors cyclosporine and tacrolimus. Clin Pharmacol Ther 74:245-254.
16. Huang Z, Roy P, and Waxman DJ (2000) Role of human microsomal CYP3A4 and CYP2B6 in catalyzing N-dechlorethylation of cyclophosphamide and ifosfamide. Biochem Pharmacol 59:961-972.
17. Ingelman-Sundberg M (2004) Pharmacogenetics of cytochrome P450 and its application in drug therapy: the past, present and future. Trends Pharmacol Sci 25:193-200.
18. Jin L and Baillie TA (1997) Metabolism of the chemoprotective agent diallyl sulfide to glutathione conjugates in rats. Chem Res Toxicol 10:318-327.
19. Kabasch W and Sander C (1983) Dictionary of protein secondary structure: pattern recognition of hydrogen-bonded and geometrical features. Biopolymers 22:2577-2637.
20. Kivistö KT, Niemi M, Schaeffeler E, Pitkälä K, Tilvis R, Fromm MF, Schwab M, Eichelbaum M, and Strandberg T (2004) Lipid-lowering response to statins is affected by CYP3A5 polymorphism. Pharmacogenetics 14:523-525.
21. Koenigs LL and Trager WF (1998) Mechanism-based inactivation of cytochrome 2B1 by 8-methoxypsoralen and several other furanocoumarins. Biochemistry 37:13184-13193.
22. Kuehl P, Zhang J, Lin Y, Lamba J, Assem M, Schuetz J, Watkins PB, Daly A, Wrighton SA, Hall SD, et al. (2001) Sequence diversity in CYP3A promoters and characterization of the genetic basis of polymorphic CYP3A5 expression. Nat Genet 27:383-391.
23. Letteron P, Descatoire V, Larrey D, Tinel M, Geneve J, and Pessayre D (1986) Inactivation and induction of cytochrome P-450 by various psoralen derivatives in rats. J Pharmacol Exp Ther 238:685-692.
24. Lightning LK, Jones JP, Friedberg T, Pritchard MP, Shou M, Rushmore TH, and Trager WF (2000) Mechanism-based inactivation of cytochrome P450 3A4 by L-754,394. Biochemistry 39:4276-4287.
25. Lin HL, Kent UM, and Hollenberg PF (2002) Mechanism-based inactivation of cytochrome P450 3A4 by 17α-ethynylestradiol: evidence for heme destruction and covalent binding to protein. J Pharmacol Exp Ther 301:160-167.
26. Lin HL, Kent UM, and Hollenberg PF (2005) The grapefruit juice effect is not limited to P450 3A4: evidence for bergamottin-dependent inactivation, heme destruction and covalent binding to protein in P450 2B6 and 3A5. J Pharmacol Exp Ther 313:154-164.
27. Mays DC, Hilliard JB, Wong DD, Chambers MA, Park SS, Gelboin HV, and Gerber N (1990) Bioactivation of 8-methoxypsoralen and irreversible inactivation of cytochrome P 450 in mouse liver microsomes: modification by monoclonal antibodies, inhibition of drug metabolism and distribution of covalent adducts. J Pharmacol Exp Ther 254:720-731.
28. Mendes J, Nagarajaram HA, Soares CM, Blundell TL, and Carrondo MA (2001) Incorporating knowledge-based biases into an energy-based side-chain modeling method: application to comparative modeling of protein structure. Biopolymers 59:72-86.
29. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, and Olson AJ (1998) Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 19:1639-1662.
30. Paine MF, Criss AB, and Watkins PB (2004) Two major grapefruit juice components differ in intestinal CYP3A4 inhibition kinetic and binding properties. Drug Metab Dispos 32:1146-1153.
31. Park J-Y and Harris DL (2003) Construction and assessment of models of CYP2E1: predictions of metabolism from docking, molecular dynamics and density functional theoretical calculations. J Med Chem 46:1645-1660.
32. Sahali-Sahly Y, Balani S, Lin JH, and Baillie TA (1996) In vitro studies on the metabolic activation of the furanopyridine L-754,394, an highly potent and selective mechanism-based inhibitor of cytochrome P450 3A4. Chem Res Toxicol 9:1007-1012.
33. Sali A and Blundell TL (1993) Comparative protein modeling by satisfaction of spatial restraints. J Mol Biol 234:779-815.
34. Scott EE, Spatzenegger M, and Halpert JR (2001) A truncation of 2B subfamily cytochromes P450 yields increased expression levels, increased solubility, and decreased aggregation while retaining function. Arch Biochem Biophys 395:57-68.
35. Shebley M, Jushchyshyn MI, and Hollenberg PF (2006) Identification of glutathione and N-acetylcystein adducts formed by cytochrome P450 2B enzymes during the metabolism of phencyclidine and 2-phenyl-2-(1-piperidinyl)propane. Drug Metab Dispos 34:375-383.
36. Sippl MJ (1993) Recognition of errors in three-dimensional structures of proteins. Proteins 17:355-362.
37. Thompson JD and Higgins DG (1994) CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res 22:4673-4680.
38. Wangensteen H, Molden E, Christensen H, and Malterud KE (2003) Identification of epoxybergamottin as a CYP3A4 inhibitor in grapefruit peel. Eur J Clin Pharmacol 58:663-668.
39. 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.
40. Wrighton SA, Brian WR, Sari M, Iwasaki M, Guengerich FP, Raucy JL, Molowa DT, and Vandenbranden M (1990) Studies on the expression and metabolic capabilities of human liver cytochrome P450 3A5 (HLp3). Mol Pharmacol 38:207-213.
41. Zhao D, Gilfoyle DJ, Smith AT, and Loew GH (1996) Refinement of 3D models of horseradish peroxidase isoenzyme C: predictions of 2D NMR assignments and substrate binding sites. Proteins 26:204-216.