Cholesterol, an essential molecule: Diverse roles involving cytochrome P450 enzymes

Biochemical Society Transactions

Volumn 40, Issue 3, 2012, Pages 587-593

  McLean, Kirsty J ^a   Hans, Marcus ^b   Munro, Andrew W ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b DSM BIOTECHNOLOGY CENTER   (Netherlands)

Author keywords

Cholesterol; Cholesterol homoeostasis; Cytochrome P450; Statin; Steroid; Tuberculosis

Indexed keywords

CHOLESTANETRIOL 26 MONOOXYGENASE; CHOLESTEROL; CHOLESTEROL 7ALPHA MONOOXYGENASE; CHOLESTEROL MONOOXYGENASE (SIDE CHAIN CLEAVING); CYTOCHROME P450; CYTOCHROME P450 125; CYTOCHROME P450 142; CYTOCHROME P450 46A1; EZETIMIBE; FIBRIC ACID DERIVATIVE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; MEVINOLIN; NICOTINAMIDE; NICOTINIC ACID; PRAVASTATIN; PYRROLE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; STEROID HORMONE; STEROL 14ALPHA DEMETHYLASE; UNCLASSIFIED DRUG;

APOPTOSIS; BLOOD BRAIN BARRIER; CATABOLISM; CHOLESTEROL METABOLISM; CHOLESTEROL SYNTHESIS; CONFERENCE PAPER; DEGRADATION; ENERGY RESOURCE; ENZYME ACTIVITY; GENETIC TRANSCRIPTION; HEART INFARCTION; HUMAN; HYDROXYLATION; IMMUNE SYSTEM; ISCHEMIC HEART DISEASE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN DEGRADATION; SIGNAL TRANSDUCTION;

ANIMALS; CHOLESTEROL; CYTOCHROME P-450 ENZYME SYSTEM; HOMEOSTASIS; HUMANS; HYDROXYMETHYLGLUTARYL-COA REDUCTASE INHIBITORS; MYCOBACTERIUM TUBERCULOSIS;

EUKARYOTA; MYCOBACTERIUM TUBERCULOSIS;

EID: 84861521100     PISSN: 03005127     EISSN: 14708752     Source Type: Journal    
DOI: 10.1042/BST20120077     Document Type: Conference Paper

References (50)

1. Rezen, T., Rozman, D., Pascussi, J.-M. and Monostory, K. (2011) Interplay between cholesterol and drug metabolism. Biochim. Biophys. Acta 1814, 146-160
2. Ikonen, E. (2008) Cellular cholesterol trafficking and compartmentalization. Nat. Rev. Mol. Cell Biol. 9, 125-138
3. Pikuleva, I.A. (2006) Cytochrome P450s and cholesterol homeostasis. Pharmacol. Ther. 112, 761-773
4. Saher, G., Quintes, S. and Nave, K.-A. (2011) Cholesterol: a novel regulatory role in myelin formation. Neuroscientist 17, 79-93
5. Jeitner, T.M., Voloshyna, I. and Reiss, A.B. (2011) Oxysterol derivatives of cholesterol in neurodegenerative disorders. Curr. Med. Chem. 18, 1515-1525
6. Valenza, M. and Cattaneo, E. (2011) Emerging roles for cholesterol in Huntington's disease. Trends Neurosci. 34, 474-486
7. Rezen, T. (2011) The impact of cholesterol and its metabolites on drug metabolism. Expert Opin. Drug Metab. Toxicol. 7, 387-398
8. Olkkonen, V.M. and Hynynen, R. (2009) Interactions of oxysterols with membranes and proteins. Mol. Aspects Med. 30, 123-133
9. Javitt, N.B. (2008) Oxysterols: novel biologic roles for the 21st century. Steroids 73, 149-157
10. Norlin, M. and Wikvall, K. (2007) Enzymes in the conversion of cholesterol into bile acids. Curr. Mol. Med. 7, 199-218 (Pubitemid 46488191)
11. Hylemon, P.B., Zhou, H.P., Pandak, W.M., Ren, S.L., Gil, G. and Dent, P. (2009) Bile acids as regulatory molecules. J. Lipid Res. 50, 1509-1520
12. Jansen, P.L.M. (2010) A new life for bile acids. J. Hepatol. 52, 937-938
13. Makishima, M., Okamoto, A.Y., Repa, J.J., Tu, H., Learned, R.M., Luk, A., Hull, M.V., Lustig, K.D., Mangelsdorf, D.J. and Shan, B. (1999) Identification of a nuclear receptor for bile acids. Science 284, 1362-1365 (Pubitemid 29289663)
14. Russell, D.W. (2003) The enzymes, regulation, and genetics of bile acid synthesis. Annu. Rev. Biochem. 72, 137-174
15. Philipp, B. (2011) Bacterial degradation of bile salts. Appl. Microbiol. Biotechnol. 89, 903-915
16. Russell, D.W. (2009) Fifty years of advances in bile acid synthesis and metabolism. J. Lipid Res. 50, S120-S125
17. Mast, N., Charvet, C., Pikuleva, I.A. and Stout, C.D. (2010) Structural basis of drug binding to CYP46A1, an enzyme that controls cholesterol turnover in the brain. J. Biol. Chem. 285, 31783-31795
18. Lorbek, G., Lewinska, M. and Rozman, D. (2012) Cytochrome P450s in the synthesis of cholesterol and bile acids: from mouse models to human diseases. FEBS J. 279, 1516-1533
19. Miller, W.L. and Bose, H.S. (2011) Early steps in steroidogenesis: intracellular cholesterol trafficking. J. Lipid Res. 52, 2111-2135
20. Li, J., Brown, G., Ailion, M., Lee, S. and Thomas, J.H. (2004) NCR-1 and NCR-2, the C. elegans homologs of the human Niemann-Pick type C1 disease protein, function upstream of DAF-9 in the dauer formation pathways. Development 131, 5741-5752 (Pubitemid 39625216)
21. Keber, R., Motaln, H., Wagner, K.D., Debeljak, N., Rassoulzadegan, M., Acimovic, J., Rozman, D. and Horvat, S. (2011) Mouse knockout of the cholesterogenic cytochrome P450 lanosterol 14α-demethylase (CYP51) resembles Antley-Bixler syndrome. J. Biol. Chem. 286, 29086-29097
22. Katragadda, S., Rai, F. and Arora, R. (2010) Dual inhibition, newer paradigms for cholesterol lowering. Am. J. Ther. 17, E88-E99
23. Manghat, P. and Wierzbicki, A.S. (2008) Colesevelam hydrochloride: a specifically engineered bile acid sequestrant. Future Lipidol. 3, 237-255 (Pubitemid 352015399)
24. Pahan, K. (2006) Lipid-lowering drugs. Cell. Mol. Life Sci. 63, 1165-1178
25. Preiss, D. and Sattar, N. (2009) Lipids, lipid modifying agents and cardiovascular risk: a review of the evidence. Clin. Endocrinol. 70, 815-828
26. Rozman, D. and Monostory, K. (2010) Perspectives of the non-statin hypolipidemic agents. Pharmacol. Ther. 127, 19-40
27. Abd, T.T. and Jacobson, T.A. (2011) Statin-induced myopathy: a review and update. Expert Opin. Drug Saf. 10, 373-387
28. Corsini, A. and Ceska, R. (2011) Drug-drug interactions with statins: will pitavastatin overcome the statins' Achilles' heel? Curr. Med. Res. Opin. 27, 1551-1562
29. Feidt, D.M., Klein, K., Hofmann, U., Riedmaier, S., Knobeloch, D., Thasler, W.E., Weiss, T.S., Schwab, M. and Zanger, U.M. (2010) Profiling induction of cytochrome P450 enzyme activity by statins using a new liquid chromatography-tandem mass spectrometry cocktail assay in human hepatocytes. Drug Metab. Dispos. 38, 1589-1597
30. Barrios-Gonzalez, J. and Miranda, R.U. (2010) Biotechnological production and applications of statins. Appl. Microbiol. Biotechnol. 85, 869-883
31. Munro, A.W., Girvan, H.M. and McLean, K.J. (2007) Cytochrome p450: redox partner fusion enzymes. Biochim. Biophys. Acta 1770, 345-359 (Pubitemid 46136745)
32. Munro, A.W., Girvan, H.M. and McLean, K.J. (2007) Variations on a (t)heme: novel mechanisms, redox partners and catalytic functions in the cytochrome p450 superfamily. Nat. Prod. Rep. 24, 585-609 (Pubitemid 46848711)
33. Waterman, M.R. and Lepesheva, G.I. (2005) Sterol 14α-demethylase, an abundant and essential mixed-function oxidase. Biochem. Biophys. Res. Commun. 338, 418-422 (Pubitemid 41540584)
34. Lepesheva, G.I., Ott, R.D., Hargrove, T.Y., Kleshchenko, Y.Y., Schuster, I., Nes, W.D., Hill, G.C., Villalta, F. and Waterman, M.R. (2007) Sterol 14α-demethylase as a potential target for antitrypanosomal therapy: enzyme inhibition and parasite cell growth. Chem. Biol. 14, 1283-1293 (Pubitemid 350102245)
35. Lepesheva, G.I. and Waterman, M.R. (2011) Structural basis for conservation in the CYP51 family. Biochim. Biophys. Acta 1814, 88-93
36. Strushkevich, N., Usanov, S.A. and Park, H.-W. (2010) Structural basis of human CYP51 inhibition by antifungal azoles. J. Mol. Biol. 397, 1067-1078
37. Mast, N., Whitet, M.A., Bjorkhem, I., Johnson, E.F., Stout, C.D. and Pikuleva, I.A. (2008) Crystal structures of substrate-bound and substrate-free cytochrome P450 46A1, the principal cholesterol hydroxylase in the brain. Proc. Natl. Acad. Sci. U.S.A. 105, 9546-9551 (Pubitemid 352031338)
38. Strott, C.A. and Higashi, Y. (2003) Cholesterol sulfate in human physiology: what's it all about? J. Lipid Res. 44, 1268-1278 (Pubitemid 37279607)
39. Pikuleva, I.A. (2008) Cholesterol-metabolizing cytochromes P450: implications for cholesterol lowering. Expert Opin. Drug Metab. Toxicol. 4, 1403-1414
40. Umetani, M., Domoto, H., Gormley, A.K., Yuhanna, I.S., Cummins, C.L., Javitt, N.B., Korach, K.S., Shaul, P.W. and Mangelsdorf, D.J. (2007) 27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen. Nat. Med. 13, 1185-1192 (Pubitemid 47530633)
41. n analysis. J. Chromatogr. B 879, 1384-1392
42. Strushkevich, N., MacKenzie, F., Cherkesova, T., Grabovec, I., Usanov, S. and Park, H.-W. (2011) Structural basis for pregnenolone biosynthesis by the mitochondrial monooxygenase system. Proc. Natl. Acad. Sci. U.S.A. 108, 10139-10143
43. Mast, N., Annalora, A.J., Lodowski, D.T., Palczewski, K., Stout, C.D. and Pikuleva, I.A. (2011) Structural basis for three-step sequential catalysis by the cholesterol side chain cleavage enzyme CYP11A1. J. Biol. Chem. 286, 5607-5613
44. McLean, K.J. and Munro, A.W. (2008) Structural biology and biochemistry of cytochrome P450 systems in Mycobacterium tuberculosis. Drug Metab. Rev. 40, 427-446 (Pubitemid 352019962)
45. Chang, J.C., Miner, M.D., Pandey, A.K., Gill, W.P., Harik, N.S., Sassetti, C.M. and Sherman, D.R. (2009) Igr genes and Mycobacterium tuberculosis cholesterol metabolism. J. Bacteriol. 191, 5232-5239
46. McLean, K.J., Lafite, P., Levy, C., Cheesman, M.R., Mast, N., Pikuleva, I.A., Leys, D. and Munro, A.W. (2009) The structure of Mycobacterium tuberculosis CYP125: molecular basis for cholesterol binding in a P450 needed for host infection. J. Biol. Chem. 284, 35524-35533
47. Johnston, J.B., Ouellet, H. and de Montellano, P.R.O. (2010) Functional redundancy of steroid C26-monooxygenase activity in Mycobacterium tuberculosis revealed by biochemical and genetic analyses. J. Biol. Chem. 285, 36352-36360
48. Thomas, S.T., VanderVen, B.C., Sherman, D.R., Russell, D.G. and Sampson, N.S. (2011) Pathway profiling in Mycobacterium tuberculosis elucidation of cholesterol-derived catabolite and enzymes that catalyze its metabolism. J. Biol. Chem. 286, 43668-43678
49. Manzoni, M. and Rollini, N. (2002) Biosynthesis and biotechnological production of statins by filamentous fungi and application of these cholesterol-lowering drugs. Appl. Microbiol. Biotechnol. 58, 555-564 (Pubitemid 34299219)
50. Watanabe, I. and Serizawa, N. (1998) Molecular approaches for production of pravastatin, a HMG-CoA reductase inhibitor: transcriptional regulation of the cytochrome P450sca gene from Streptomyces carbophilus by ML-236B sodium salt and phenobarbital. Gene 210, 109-116 (Pubitemid 28156393)