Relationship between CYP1A2 localization and lipid microdomain formation as a function of lipid composition

Drug Metabolism and Disposition

Volumn 41, Issue 11, 2013, Pages 1896-1905

  Brignac Huber, Lauren M ^a   Reed, James R ^a   Eyer, Marilyn K ^a   Backes, Wayne L ^a  

^a LOUISIANA STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTEROL; CYTOCHROME P450 1A2; CYTOCHROME P450 REDUCTASE; LAURDAN; LIPID; PHOSPHATIDYLCHOLINE; SPHINGOMYELIN;

ARTICLE; CELL MEMBRANE; CONTROLLED STUDY; ENDOPLASMIC RETICULUM; ENZYME LOCALIZATION; FLUORESCENCE RESONANCE ENERGY TRANSFER; LIPID COMPOSITION; LIPID MICRODOMAIN; LIPID VESICLE; PRIORITY JOURNAL;

ANIMALS; CATTLE; CHICKENS; CYTOCHROME P-450 CYP1A2; CYTOCHROME P-450 ENZYME SYSTEM; ENDOPLASMIC RETICULUM; LIPIDS; MEMBRANE MICRODOMAINS; PHOSPHOLIPIDS; SWINE;

EID: 84886499832     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.113.053611     Document Type: Article

References (49)

1. Ahn T, Guengerich FP, and Yun CH (1998) Membrane insertion of cytochrome P450 1A2 promoted by anionic phospholipids. Biochemistry 37:12860-12866.
2. Ahn T and Yun CH (1998) Phase separation in phosphatidylcholine/anionic phospholipid membranes in the liquid-crystalline state revealed with fluorescent probes. J Biochem 124: 622-627.
3. Ahn T, Yun CH, and Oh DB (2005) Involvement of nonlamellar-prone lipids in the stability increase of human cytochrome P450 1A2 in reconstituted membranes. Biochemistry 44: 9188-9196.
4. Bae TJ, Kim MS, Kim JW, Kim BW, Choo HJ, Lee JW, Kim KB, Lee CS, Kim JH, and Chang SY, et al. (2004) Lipid raft proteome reveals ATP synthase complex in the cell surface. Proteomics 4:3536-3548.
5. Bagatolli LA (2006) To see or not to see: lateral organization of biological membranes and fluorescence microscopy. Biochim Biophys Acta 1758:1541-1556.
6. Barenholz Y, Suurkuusk J, Mountcastle D, Thompson TE, and Biltonen RL (1976) A calorimetric study of the thermotropic behavior of aqueous dispersions of natural and synthetic sphingomyelins. Biochemistry 15:2441-2447.
7. Baumgart T, Hunt G, Farkas ER, Webb WW, and Feigenson GW (2007) Fluorescence probe partitioning between Lo/Ld phases in lipid membranes. Biochim Biophys Acta 1768: 2182-2194.
8. Blanck J, Smettan G, Ristau O, Ingelman-Sundberg M, and Ruckpaul K (1984) Mechanism of rate control of the NADPH-dependent reduction of cytochrome P-450 by lipids in reconstituted phospholipid vesicles. Eur J Biochem 144:509-513.
9. Brignac-Huber LM, Reed JR, and Backes WL (2011) Organization of NADPH-cytochrome P450 reductase and CYP1A2 in the endoplasmic reticulum-microdomain localization affects monooxygenase function. Mol Pharmacol 79:549-557.
10. Browman DT, Resek ME, Zajchowski LD, and Robbins SM (2006) Erlin-1 and erlin-2 are novel members of the prohibitin family of proteins that define lipid-raft-like domains of the ER. J Cell Sci 119:3149-3160.
11. Brown DA and London E (1998) Functions of lipid rafts in biological membranes. Annu Rev Cell Dev Biol 14:111-136.
12. Brown RS, Brennan JD, and Krull UJ (1994) Self-quenching of nitrobenzoxadiazole labeled phospholipids in lipid membranes. J Chem Phys 100:6019-6027.
13. Carney J, East JM, and Lee AG (2007) Penetration of lipid chains into transmembrane surfaces of membrane proteins: studies with MscL. Biophys J 92:3556-3563.
14. Coon MJ, van der Hoeven TA, Dahl SB, and Haugen DA (1978) Two forms of liver microsomal cytochrome P-450, P-450lm2 and P-450LM4 (rabbit liver). Methods Enzymol 52: 109-117.
15. Crane JM and Tamm LK (2004) Role of cholesterol in the formation and nature of lipid rafts in planar and spherical model membranes. Biophys J 86:2965-2979.
16. de Almeida RF, Fedorov A, and Prieto M (2003) Sphingomyelin/ phosphatidylcholine/cholesterol phase diagram: boundaries and composition of lipid rafts. Biophys J 85:2406-2416.
17. de Almeida RF, Loura LM, Fedorov A, and Prieto M (2005) Lipid rafts have different sizes depending on membrane composition: a time-resolved fluorescence resonance energy transfer study. J Mol Biol 346:1109-1120.
18. Dietrich C, Bagatolli LA, Volovyk ZN, Thompson NL, Levi M, Jacobson K, and Gratton E (2001) Lipid rafts reconstituted in model membranes. Biophys J 80:1417-1428.
19. Dinic J, Biverstahl H, Mäler L, and Parmryd I (2011) Laurdan and di-4-ANEPPDHQ do not respond to membrane-inserted peptides and are good probes for lipid packing. Biochim Biophys Acta 1808:298-306.
20. East JM and Lee AG (1982) Lipid selectivity of the calcium and magnesium ion dependent adenosinetriphosphatase, studied with fluorescence quenching by a brominated phospholipid. Biochemistry 21:4144-4151.
21. Gigon PL, Gram TE, and Gillette JR (1969) Studies on the rate of reduction of hepatic microsomal cytochrome P-450 by reduced nicotinamide adenine dinucleotide phosphate: effect of drug substrates. Mol Pharmacol 5:109-122.
22. Hayashi T and Fujimoto M (2010) Detergent-resistant microdomains determine the localization of sigma-1 receptors to the endoplasmic reticulum-mitochondria junction. Mol Pharmacol 77: 517-528.
23. Ingelman-Sundberg M, Haaparanta T, and Rydström J (1981) Membrane charge as effector of cytochrome P-450LM2 catalyzed reactions in reconstituted liposomes. Biochemistry 20: 4100-4106.
24. Ingelman-Sundberg M, Hagbjörk AL, Ueng YF, Yamazaki H, and Guengerich FP (1996) High rates of substrate hydroxylation by human cytochrome P450 3A4 in reconstituted membranous vesicles: influence of membrane charge. Biochem Biophys Res Commun 221:318-322.
25. Jang HH, Kim DH, Ahn T, and Yun CH (2010) Functional and conformational modulation of human cytochrome P450 1B1 by anionic phospholipids. Arch Biochem Biophys 493:143-150.
26. Jin L, Millard AC, Wuskell JP, Dong X, Wu D, Clark HA, and Loew LM (2006) Characterization and application of a new optical probe for membrane lipid domains. Biophys J 90:2563-2575.
27. Kim KH, Ahn T, and Yun CH (2003) Membrane properties induced by anionic phospholipids and phosphatidylethanolamine are critical for the membrane binding and catalytic activity of human cytochrome P450 3A4. Biochemistry 42:15377-15387.
28. Kim KH, Kim DH, Jang HH, Kim M, Kim DH, Kim JS, Kim JI, Chae HZ, Ahn T, and Yun CH (2007) Lateral segregation of anionic phospholipids in model membranes induced by cytochrome P450 2B1: bi-directional coupling between CYP2B1 and anionic phospholipid. Arch Biochem Biophys 468:226-233.
29. Lingwood D, Ries J, Schwille P, and Simons K (2008) Plasma membranes are poised for activation of raft phase coalescence at physiological temperature. Proc Natl Acad Sci USA 105: 10005-10010.
30. Loura LM, Fedorov A, and Prieto M (2001) Fluid-fluid membrane microheterogeneity: a fluorescence resonance energy transfer study. Biophys J 80:776-788.
31. Nelson DR (2003) Comparison of P450s from human and fugu: 420 million years of vertebrate P450 evolution. Arch Biochem Biophys 409:18-24.
32. Niu SL and Litman BJ (2002) Determination of membrane cholesterol partition coefficient using a lipid vesicle-cyclodextrin binary system: effect of phospholipid acyl chain unsaturation and headgroup composition. Biophys J 83:3408-3415.
33. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J Biol Chem 239:2370-2378.
34. Ozols J (1986) Complete amino acid sequence of a cytochrome P-450 isolated from betanaphthoflavone- induced rabbit liver microsomes. Comparison with phenobarbital-induced and constitutive isozymes and identification of invariant residues. J Biol Chem 261:3965-3979.
35. Parasassi T, Conti F, and Gratton E (1986) Time-resolved fluorescence emission spectra of Laurdan in phospholipid vesicles by multifrequency phase and modulation fluorometry. Cell Mol Biol 32:103-108.
36. Parasassi T, De Stasio G, Ravagnan G, Rusch RM, and Gratton E (1991) Quantitation of lipid phases in phospholipid vesicles by the generalized polarization of Laurdan fluorescence. Biophys J 60:179-189.
37. Pathak P and London E (2011) Measurement of lipid nanodomain (raft) formation and size in sphingomyelin/POPC/cholesterol vesicles shows TX-100 and transmembrane helices increase domain size by coalescing preexisting nanodomains but do not induce domain formation. Biophys J 101:2417-2425.
38. Pielsticker LK, Mann KJ, Lin WL, and Sevlever D (2005) Raft-like membrane domains contain enzymatic activities involved in the synthesis of mammalian glycosylphosphatidylinositol anchor intermediates. Biochem Biophys Res Commun 330:163-171.
39. Pike LJ (2004) Lipid rafts: heterogeneity on the high seas. Biochem J 378:281-292.
40. Quinn PJ and Wolf C (2009) The liquid-ordered phase in membranes. Biochim Biophys Acta 1788:33-46.
41. Reed JR (2010) The use of liposomes in the study of drug metabolism: a method to incorporate the enzymes of the cytochrome p450 monooxygenase system into phospholipid, bilayer vesicles. Methods Mol Biol 606:11-20.
42. Reed JR, Brignac-Huber LM, and Backes WL (2008) Physical incorporation of NADPHcytochrome P450 reductase and cytochrome P450 into phospholipid vesicles using glycocholate and Bio-Beads. Drug Metab Dispos 36:582-588.
43. Reed JR, Kelley RW, and Backes WL (2006) An evaluation of methods for the reconstitution of cytochromes P450 and NADPH P450 reductase into lipid vesicles. Drug Metab Dispos 34: 660-666.
44. Rodgers W and Glaser M (1991) Characterization of lipid domains in erythrocyte membranes. Proc Natl Acad Sci USA 88:1364-1368.
45. Sansen S, Yano JK, Reynald RL, Schoch GA, Griffin KJ, Stout CD, and Johnson EF (2007) Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2. J Biol Chem 282:14348-14355.
46. Sengupta P, Hammond A, Holowka D, and Baird B (2008) Structural determinants for partitioning of lipids and proteins between coexisting fluid phases in giant plasma membrane vesicles. Biochim Biophys Acta 1778:20-32.
47. Sevlever D, Pickett S, Mann KJ, Sambamurti K, Medof ME, and Rosenberry TL (1999) Glycosylphosphatidylinositol-anchor intermediates associate with triton-insoluble membranes in subcellular compartments that include the endoplasmic reticulum. Biochem J 343:627-635.
48. Strobel HW, Lu AYH, Heidema J and Coon MJ (1970) Phosphatidylcholine requirement in the enzymatic reduction of hemoprotein P-450 and in fatty acid, hydrocarbon, and drug hydroxylation. J Biol Chem 245:4851-4854.
49. van Meer G, Voelker DR, and Feigenson GW (2008) Membrane lipids: where they are and how they behave. Nat Rev Mol Cell Biol 9:112-124.