Genistein, resveratrol, and 5-aminoimidazole-4-carboxamide-1-β-D- ribofuranoside induce cytochrome P450 4F2 expression through an AMP-activated protein kinase-dependent pathway

Journal of Pharmacology and Experimental Therapeutics

Volumn 337, Issue 1, 2011, Pages 125-136

  Hsu, Mei Hui ^a   Savas, Üzen ^a   Lasker, Jerome M ^a,b,c   Johnson, Eric F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b HACKENSACK UNIVERSITY MEDICAL CENTER   (United States)

^c Puracyp Inc   (United States)

Author keywords

hydroxylase; The expression of the human microsomal fatty acid

Indexed keywords

5 AMINO 4 IMIDAZOLECARBOXAMIDE RIBOSIDE; CYTOCHROME P450; CYTOCHROME P450 4A11; CYTOCHROME P450 4F11; CYTOCHROME P450 4F12; CYTOCHROME P450 4F2; CYTOCHROME P450 4F3; GENISTEIN; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE KINASE; MESSENGER RNA; RESVERATROL; SIRTUIN 1; UNCLASSIFIED DRUG;

ADULT; AGED; ARTICLE; CELL STRAIN HEPG2; CONTROLLED STUDY; DRUG ACTIVITY; ENZYME ACTIVATION; ENZYME INDUCTION; FEMALE; HEPATOMA CELL; HUMAN; HUMAN CELL; LIVER CELL; PRIORITY JOURNAL; PROTEIN EXPRESSION;

AGED; AMINOIMIDAZOLE CARBOXAMIDE; AMP-ACTIVATED PROTEIN KINASES; CELLS, CULTURED; CYTOCHROME P-450 ENZYME SYSTEM; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME ACTIVATION; ENZYME INDUCTION; FEMALE; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GENISTEIN; HEP G2 CELLS; HEPATOCYTES; HUMANS; MALE; MIDDLE AGED; RIBONUCLEOSIDES; SIGNAL TRANSDUCTION; STILBENES;

EID: 79953016397     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.110.175851     Document Type: Article

References (40)

1. Amemiya-Kudo M, Shimano H, Hasty AH, Yahagi N, Yoshikawa T, Matsuzaka T, Okazaki H, Tamura Y, Iizuka Y, Ohashi K, et al. (2002) Transcriptional activities of nuclear SREBP-1a, -1c, and -2 to different target promoters of lipogenic and cholesterogenic genes. J Lipid Res 43:1220-1235. (Pubitemid 34988170)
2. Bedalov A, Gatbonton T, Irvine WP, Gottschling DE, and Simon JA (2001) Identification of a small molecule inhibitor of Sir2p. Proc Natl Acad Sci USA 98:15113-15118. (Pubitemid 34013978)
3. Berasi SP, Huard C, Li D, Shih HH, Sun Y, Zhong W, Paulsen JE, Brown EL, Gimeno RE, and Martinez RV (2006) Inhibition of gluconeogenesis through transcriptional activation of EGR1 and DUSP4 by AMP-activated kinase. J Biol Chem 281:27167-27177. (Pubitemid 44401746)
4. Caldwell MD, Awad T, Johnson JA, Gage BF, Falkowski M, Gardina P, Hubbard J, Turpaz Y, Langaee TY, Eby C, et al. (2008) CYP4F2 genetic variant alters required warfarin dose. Blood 111:4106-4112.
5. Cantó C, Jiang LQ, Deshmukh AS, Mataki C, Coste A, Lagouge M, Zierath JR, and Auwerx J (2010) Interdependence of AMPK and SIRT1 for metabolic adaptation to fasting and exercise in skeletal muscle. Cell Metab 11:213-219.
6. Capdevila JH and Falck JR (2001) The CYP P450 arachidonic acid monooxygenases: from cell signaling to blood pressure regulation. Biochem Biophys Res Commun 285:571-576. (Pubitemid 32924808)
7. Dhar M, Sepkovic DW, Hirani V, Magnusson RP, and Lasker JM (2008) Omega oxidation of 3-hydroxy fatty acids by the human CYP4F gene subfamily enzyme CYP4F11. J Lipid Res 49:612-624.
8. Fava C, Montagnana M, Almgren P, Rosberg L, Lippi G, Hedblad B, Engström G, Berglund G, Minuz P, and Melander O (2008) The V433M variant of the CYP4F2 is associated with ischemic stroke in male Swedes beyond its effect on blood pressure. Hypertension 52:373-380.
9. Fogarty S and Hardie DG (2010) Development of protein kinase activators: AMPK as a target in metabolic disorders and cancer. Biochim Biophys Acta 1804:581-591.
10. Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, Ohta M, Soma M, Aoi N, Sato M, et al. (2008) A haplotype of the CYP4F2 gene is associated with cerebral infarction in Japanese men. Am J Hypertens 21:1216-1223.
11. Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, Ohta M, Soma M, Aoi N, Sato M, et al. (2009) A haplotype of the CYP4F2 gene associated with myocardial infarction in Japanese men. Mol Genet Metab 96:145-147.
12. Göransson O, McBride A, Hawley SA, Ross FA, Shpiro N, Foretz M, Viollet B, Hardie DG, and Sakamoto K (2007) Mechanism of action of A-769662, a valuable tool for activation of AMP-activated protein kinase. J Biol Chem 282:32549-32560. (Pubitemid 350159310)
13. Hardwick JP (2008) Cytochrome P450 omega hydroxylase (CYP4) function in fatty acid metabolism and metabolic diseases. Biochem Pharmacol 75:2263-2275.
14. Hart SN, Li Y, Nakamoto K, Subileau EA, Steen D, and Zhong XB (2010) A comparison of whole genome gene expression profiles of HepaRG cells and HepG2 cells to primary human hepatocytes and human liver tissues. Drug Metab Dispos 38:988-994.
15. Henin N, Vincent MF, Gruber HE, and Van den Berghe G (1995) Inhibition of fatty acid and cholesterol synthesis by stimulation of AMP-activated protein kinase. FASEB J 9:541-546.
16. Hirani V, Yarovoy A, Kozeska A, Magnusson RP, and Lasker JM (2008) Expression of CYP4F2 in human liver and kidney: assessment using targeted peptide antibodies. Arch Biochem Biophys 478:59-68.
17. Hong YH, Varanasi US, Yang W, and Leff T (2003) AMP-activated protein kinase regulates HNF4α transcriptional activity by inhibiting dimer formation and decreasing protein stability. J Biol Chem 278:27495-27501. (Pubitemid 36899932)
18. Hou X, Xu S, Maitland-Toolan KA, Sato K, Jiang B, Ido Y, Lan F, Walsh K, Wierzbicki M, Verbeuren TJ, et al. (2008) SIRT1 regulates hepatocyte lipid metabolism through activating AMP-activated protein kinase. J Biol Chem 283:20015-20026.
19. Hsu MH, Savas U, Griffin KJ, and Johnson EF (2007a) Human cytochrome p450 family 4 enzymes: function, genetic variation and regulation. Drug Metab Rev 39:515-538. (Pubitemid 47355735)
20. Hsu MH, Savas U, Griffin KJ, and Johnson EF (2007b) Regulation of human cytochrome P450 4F2 expression by sterol regulatory element-binding protein and lovastatin. J Biol Chem 282:5225-5236. (Pubitemid 47093716)
21. Hwang JT, Park IJ, Shin JI, Lee YK, Lee SK, Baik HW, Ha J, and Park OJ (2005) Genistein, EGCG, and capsaicin inhibit adipocyte differentiation process via activating AMP-activated protein kinase. Biochem Biophys Res Commun 338:694-699.
22. Kawaguchi T, Osatomi K, Yamashita H, Kabashima T, and Uyeda K (2002) Mechanism for fatty acid "sparing" effect on glucose-induced transcription: regulation of carbohydrate-responsive element-binding protein by AMP-activated protein kinase. J Biol Chem 277:3829-3835. (Pubitemid 34968632)
23. Kim YD, Park KG, Lee YS, Park YY, Kim DK, Nedumaran B, Jang WG, Cho WJ, Ha J, Lee IK, et al. (2008) Metformin inhibits hepatic gluconeogenesis through AMP-activated protein kinase-dependent regulation of the orphan nuclear receptor SHP. Diabetes 57:306-314.
24. Komen JC and Wanders RJ (2006) Identification of the cytochrome P450 enzymes responsible for the omega-hydroxylation of phytanic acid. FEBS Lett 580:3794-3798. (Pubitemid 43946863)
25. Labbe G, Pessayre D, and Fromenty B (2008) Drug-induced liver injury through mitochondrial dysfunction: mechanisms and detection during preclinical safety studies. Fundam Clin Pharmacol 22:335-353.
26. Lasker JM, Chen WB, Wolf I, Bloswick BP, Wilson PD, and Powell PK (2000) Formation of 20-hydroxyeicosatetraenoic acid, a vasoactive and natriuretic eicosanoid, in human kidney. Role of Cyp4F2 and Cyp4A11. J Biol Chem 275:4118-4126. (Pubitemid 30094644)
27. Leff T (2003) AMP-activated protein kinase regulates gene expression by direct phosphorylation of nuclear proteins. Biochem Soc Trans 31:224-227.
28. McDonald MG, Rieder MJ, Nakano M, Hsia CK, and Rettie AE (2009) CYP4F2 is a vitamin K1 oxidase: an explanation for altered warfarin dose in carriers of the V433M variant. Mol Pharmacol 75:1337-1346.
29. Miyata N and Roman RJ (2005) Role of 20-hydroxyeicosatetraenoic acid (20-HETE) in vascular system. J Smooth Muscle Res 41:175-193. (Pubitemid 41596358)
30. Mullen E, Brown RM, Osborne TF, and Shay NF (2004) Soy isoflavones affect sterol regulatory element binding proteins (SREBPs) and SREBP-regulated genes in HepG2 cells. J Nutr 134:2942-2947. (Pubitemid 39470066)
31. Nystrom GJ and Lang CH (2008) Sepsis and AMPK activation by AICAR differentially regulate FoxO-1, -3 and -4 mRNA in striated muscle. Int J Clin Exp Med 1:50-63.
32. Pérez-Andreu V, Roldán V, Antón AI, García-Barberá N, Corral J, Vicente V, and González- Conejero R (2009) Pharmacogenetic relevance of CYP4F2 V433M polymorphism on acenocoumarol therapy. Blood 113:4977-4979.
33. Reddy JK and Mannaerts GP (1994) Peroxisomal lipid metabolism. Annu Rev Nutr 14:343-370.
34. Rencurel F, Foretz M, Kaufmann MR, Stroka D, Looser R, Leclerc I, da Silva Xavier G, Rutter GA, Viollet B, and Meyer UA (2006) Stimulation of AMP-activated protein kinase is essential for the induction of drug metabolizing enzymes by phenobarbital in human and mouse liver. Mol Pharmacol 70:1925-1934. (Pubitemid 44771908)
35. Sanders RJ, Ofman R, Duran M, Kemp S, and Wanders RJ (2006) Omega-oxidation of very long-chain fatty acids in human liver microsomes. Implications for X-linked adrenoleukodystrophy. J Biol Chem 281:13180-13187. (Pubitemid 43855229)
36. Savas U, Machemer DE, Hsu MH, Gaynor P, Lasker JM, Tukey RH, and Johnson EF (2009) Opposing roles of peroxisome proliferator-activated receptor alpha and growth hormone in the regulation of CYP4A11 expression in a transgenic mouse model. J Biol Chem 284:16541-16552.
37. Stec DE, Roman RJ, Flasch A, and Rieder MJ (2007) Functional polymorphism in human CYP4F2 decreases 20-HETE production. Physiol Genomics 30:74-81. (Pubitemid 47173292)
38. Viollet B, Guigas B, Leclerc J, Hebrard S, Lantier L, Mounier R, Andreelli F, and Foretz M (2009) AMP-activated protein kinase in the regulation of hepatic energy metabolism: from physiology to therapeutic perspectives. Acta Physiol (Oxf) 196: 81-98.
39. Ward NC, Tsai IJ, Barden A, van Bockxmeer FM, Puddey IB, Hodgson JM, and Croft KD (2008) A single nucleotide polymorphism in the CYP4F2 but not CYP4A11 gene is associated with increased 20-HETE excretion and blood pressure. Hypertension 51:1393-1398. (Pubitemid 351555955)
40. Weinberg JM (2006) Lipotoxicity. Kidney Int 70:1560-1566.