Anandamide oxidation by wild-type and polymorphically expressed CYP2B6 and CYP2D6

Drug Metabolism and Disposition

Volumn 39, Issue 5, 2011, Pages 782-788

  Sridar, Chitra ^a   Snider, Natasha T ^a   Hollenberg, Paul F ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

14,15 EPOXYEICOSATETRAENOIC ACID ETHANOLAMIDE; 16ALPHA HYDROXYTESTOSTERONE; 16BETA HYDROXYTESTOSTERONE; 20 HYDROXYEICOSATETRAENOIC ACID ETHANOLAMIDE; ANANDAMIDE; CANNABINOID 1 RECEPTOR; CYTOCHROME P450 2B6; CYTOCHROME P450 2B6.1; CYTOCHROME P450 2B6.4; CYTOCHROME P450 2B6.6; CYTOCHROME P450 2B6.9; CYTOCHROME P450 2D6; CYTOCHROME P450 2D6.34; CYTOCHROME P450 OXYGENASE; ENDOCANNABINOID; EPOXIDE HYDROLASE; FATTY ACID AMIDASE; FATTY ACID DERIVATIVE; MUTANT PROTEIN; TESTOSTERONE DERIVATIVE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BRAIN HOMOGENATE; CONTROLLED STUDY; DRUG DEGRADATION; DRUG METABOLISM; DRUG OXIDATION; DRUG RECEPTOR BINDING; ENZYME KINETICS; ENZYME POLYMORPHISM; IN VITRO STUDY; LIGAND BINDING; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT; WILD TYPE;

8,11,14-EICOSATRIENOIC ACID; AMIDOHYDROLASES; ANIMALS; ARACHIDONIC ACIDS; ARYL HYDROCARBON HYDROXYLASES; BRAIN; CYTOCHROME P-450 CYP2D6; ENDOCANNABINOIDS; EPOXIDE HYDROLASES; HUMANS; HYDROXYEICOSATETRAENOIC ACIDS; HYDROXYLATION; MALE; OXIDATION-REDUCTION; OXIDOREDUCTASES, N-DEMETHYLATING; POLYMORPHISM, GENETIC; POLYUNSATURATED ALKAMIDES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, CANNABINOID, CB1;

RATTUS;

EID: 79955013158     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.110.036707     Document Type: Article

References (41)

1. Ariyoshi N, Miyazaki M, Toide K, Sawamura Yi, and Kamataki T (2001) A single nucleotide polymorphism of CYP2b6 found in Japanese enhances catalytic activity by autoactivation. Biochem Biophys Res Commun 281:1256-1260. (Pubitemid 32924554)
2. BuczynskiMWand Parsons LH (2010) Quantification of brain endocannabinoid levels: Methods, interpretations and pitfalls. Br J Pharmacol 160:423-442.
3. Capdevila JH, Falck JR, and Estabrook RW (1992) Cytochrome P450 and the arachidonate cascade. FASEB J 6:731-736.
4. Chang TK, Weber GF, Crespi CL, and Waxman DJ (1993) Differential activation of cyclophosphamide and ifosphamide by cytochromes P-450 2B and 3A in human liver microsomes. Cancer Res 53:5629-5637. (Pubitemid 23360263)
5. Conroy JL, Fang C, Gu J, Zeitlin SO, Yang W, Yang J, VanAlstine MA, Nalwalk JW, Albrecht PJ, Mazurkiewicz JE, et al. (2010) Opioids activate brain analgesic circuits through cytochrome P450/epoxygenase signaling. Nat Neurosci 13:284-286.
6. Deutsch DG and Chin SA (1993) Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem Pharmacol 46:791-796. (Pubitemid 23272758)
7. Di Marzo V (2008) Targeting the endocannabinoid system: To enhance or reduce? Nat Rev Drug Discov 7:438-455. (Pubitemid 351649182)
8. 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.
9. Funae Y, Kishimoto W, Cho T, Niwa T, and Hiroi T (2003) CYP2D in the brain. Drug Metab Pharmacokinet 18:337-349.
10. Giang DK and Cravatt BF (1997) Molecular characterization of human and mouse fatty acid amide hydrolases. Proc Natl Acad Sci USA 94:2238-2242. (Pubitemid 27136858)
11. Hanna IH, Kim MS, and Guengerich FP (2001) Heterologous expression of cytochrome P450 2D6 mutants, electron transfer, and catalysis of bufuralol hydroxylation: The role of aspartate 301 in structural integrity. Arch Biochem Biophys 393:255-261. (Pubitemid 32907182)
12. Hanna IH, Reed JR, Guengerich FP, and Hollenberg PF (2000) Expression of human cytochrome P450 2B6 in Escherichia coli: Characterization of catalytic activity and expression levels in human liver. Arch Biochem Biophys 376:206-216. (Pubitemid 30205131)
13. Hanna IH, Teiber JF, Kokones KL, and Hollenberg PF (1998) Role of the alanine at position 363 of cytochrome P450 2B2 in influencing the NADPH- and hydroperoxide-supported activities. Arch Biochem Biophys 350:324-332. (Pubitemid 28368660)
14. Hegde VL, Hegde S, Cravatt BF, Hofseth LJ, Nagarkatti M, and Nagarkatti PS (2008) Attenuation of experimental autoimmune hepatitis by exogenous and endogenous cannabinoids: Involvement of regulatory T cells. Mol Pharmacol 74:20-33. (Pubitemid 351872155)
15. Hesse LM, He P, Krishnaswamy S, Hao Q, Hogan K, von Moltke LL, Greenblatt DJ, and Court MH (2004) Pharmacogenetic determinants of interindividual variability in bupropion hydroxylation by cytochrome P450 2B6 in human liver microsomes. Pharmacogenetics 14:225-238. (Pubitemid 38530514)
16. Hesse LM, Venkatakrishnan K, Court MH, von Moltke LL, Duan SX, Shader RI, and Greenblatt DJ (2000) CYP2B6 mediates the in vitro hydroxylation of bupropion: Potential drug interactions with other antidepressants. Drug Metab Dispos 28:1176-1183.
17. Ingelman-Sundberg M, Sim SC, Gomez A, and Rodriguez-Antona C (2007) Influence of cytochrome P450 polymorphisms on drug therapies: Pharmacogenetic, pharmacoepigenetic and clinical aspects. Pharmacol Ther 116:496-526. (Pubitemid 350116943)
18. Jenkins PM, Hurd TW, Zhang L, McEwen DP, Brown RL, Margolis B, Verhey KJ, and Martens JR (2006) Ciliary targeting of olfactory CNG channels requires the CNGB1b subunit and the kinesin-2 motor protein, KIF17. Curr Biol 16:1211-1216. (Pubitemid 43867290)
19. Kirchheiner J, Klein C, Meineke I, Sasse J, Zanger UM, Mürdter TE, Roots I, and Brockmöller J (2003) Bupropion and 4-OH-bupropion pharmacokinetics in relation to genetic polymorphisms in CYP2B6. Pharmacogenetics 13:619-626. (Pubitemid 37311148)
20. Klein K, Lang T, Saussele T, Barbosa-Sicard E, Schunck WH, Eichelbaum M, Schwab M, and Zanger UM (2005) Genetic variability of CYP2B6 in populations of African and Asian origin: Allele frequencies, novel functional variants, and possible implications for anti-HIV therapy with efavirenz. Pharmacogenet Genomics 15:861-873. (Pubitemid 41666768)
21. Lang T, Klein K, Fischer J, Nüssler AK, Neuhaus P, Hofmann U, Eichelbaum M, Schwab M, and Zanger UM (2001) Extensive genetic polymorphism in the human CYP2B6 gene with impact on expression and function in human liver. Pharmacogenetics 11:399-415. (Pubitemid 32656581)
22. Mackie K (2008) Cannabinoid receptors: Where they are and what they do. J Neuroendocrinol 20 (Suppl 1):10-14. (Pubitemid 351552670)
23. Marez D, Legrand M, Sabbagh N, Lo Guidice JM, Spire C, Lafitte JJ, Meyer UA, and Broly F (1997) Polymorphism of the cytochrome P450 CYP2D6 gene in a European population: Characterization of 48 mutations and 53 alleles, their frequencies and evolution. Pharmacogenetics 7:193-202. (Pubitemid 27290633)
24. Matsuda LA, Lolait SJ, Brownstein MJ, Young AC, and Bonner TI (1990) Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346:561-564.
25. Miksys S, Lerman C, Shields PG, Mash DC, and Tyndale RF (2003) Smoking, alcoholism and genetic polymorphisms alter CYP2B6 levels in human brain. Neuropharmacology 45:122-132. (Pubitemid 36700458)
26. 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. (Pubitemid 38802491)
27. Muthian S, Rademacher DJ, Roelke CT, Gross GJ, and Hillard CJ (2004) Anandamide content is increased and CB1 cannabinoid receptor blockade is protective during transient, focal cerebral ischemia. Neuroscience 129:743-750. (Pubitemid 39487125)
28. Niwa T, Hiroi T, Tsuzuki D, Yamamoto S, Narimatsu S, Fukuda T, Azuma J, and Funae Y (2004) Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res 129:117-123. (Pubitemid 39304255)
29. Pertwee RG (2005) Pharmacological actions of cannabinoids. Handb Exp Pharmacol 168:1-51.
30. Rockwell CE and Kaminski NE (2004) A cyclooxygenase metabolite of anandamide causes inhibition of interleukin-2 secretion in murine splenocytes. J Pharmacol Exp Ther 311:683-690. (Pubitemid 39391556)
31. Rotger M, Colombo S, Furrer H, Bleiber G, Buclin T, Lee BL, Keiser O, Biollaz J, Dícosterd L, Telenti A, et al. (2005) Influence of CYP2B6 polymorphism on plasma and intracellular concentrations and toxicity of efavirenz and nevirapine in HIV-infected patients. Pharmacogenet Genomics 15:1-5. (Pubitemid 43205520)
32. Schlosburg JE, Kinsey SG, and Lichtman AH (2009) Targeting fatty acid amide hydrolase (FAAH) to treat pain and inflammation. AAPS J 11:39-44.
33. 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. (Pubitemid 33030143)
34. Snider NT, Kornilov AM, Kent UM, and Hollenberg PF (2007) Anandamide metabolism by human liver and kidney microsomal cytochrome P450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther 321:590-597. (Pubitemid 46624513)
35. Snider NT, Nast JA, Tesmer LA, and Hollenberg PF (2009) A cytochrome P450-derived epoxygenated metabolite of anandamide is a potent cannabinoid receptor 2-selective agonist. Mol Pharmacol 75:965-972.
36. Snider NT, Sikora MJ, Sridar C, Feuerstein TJ, Rae JM, and Hollenberg PF (2008) The endocannabinoid anandamide is a substrate for the human polymorphic cytochrome P450 2D6. J Pharmacol Exp Ther 327:538-545.
37. Snider NT, Walker VJ, and Hollenberg PF (2010) Oxidation of the endogenous cannabinoid arachidonoyl ethanolamide by the cytochrome P450 monooxygenases: Physiological and pharmacological implications. Pharmacol Rev 62:136-154.
38. van der Stelt M and Di Marzo V (2005) Anandamide as an intracellular messenger regulating ion channel activity. Prostaglandins Other Lipid Mediat 77:111-122. (Pubitemid 41133420)
39. Zanger UM, Klein K, Saussele T, Blievernicht J, Hofmann MH, and Schwab M (2007) Polymorphic CYP2B6: Molecular mechanisms and emerging clinical significance. Pharmacogenomics 8:743-759. (Pubitemid 47288975)
40. Zeldin DC, Plitman JD, Kobayashi J, Miller RF, Snapper JR, Falck JR, Szarek JL, Philpot RM, and Capdevila JH (1995) The rabbit pulmonary cytochrome P450 arachidonic acid metabolic pathway: Characterization and significance. J Clin Invest 95:2150-2160.
41. Zhang W, Koerner IP, Noppens R, Grafe M, Tsai HJ, Morisseau C, Luria A, Hammock BD, Falck JR, and Alkayed NJ (2007) Soluble epoxide hydrolase: A novel therapeutic target in stroke. J Cereb Blood Flow Metab 27:1931-1940. (Pubitemid 350129162)