Site-specific oxidation of apolipoprotein A-I impairs cholesterol export by ABCA1, a key cardioprotective function of HDL

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1821, Issue 3, 2012, Pages 490-501

  Shao, Baohai ^a,b  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

Author keywords

3 Chlorotyrosine; Acrolein; Coronary artery disease; Dysfunctional HDL; Malondialdehyde; Myeloperoxidase

Indexed keywords

3 CHLOROTYROSINE; 3 NITROTYROSINE; ABC TRANSPORTER A1; ACROLEIN; APOLIPOPROTEIN A1; CARBONYL DERIVATIVE; HIGH DENSITY LIPOPROTEIN; LYSINE; MALONALDEHYDE; METHIONINE; MYELOPEROXIDASE; TYROSINE;

ARTERY WALL; ATHEROGENESIS; CARBOXY TERMINAL SEQUENCE; CARDIOVASCULAR DISEASE; CHOLESTEROL TRANSPORT; COVALENT BOND; HEART PROTECTION; HUMAN; IMMUNOHISTOCHEMISTRY; IN VIVO STUDY; LIPID PEROXIDATION; MACROPHAGE; MASS SPECTROMETRY; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN LOCALIZATION; PROTEIN MODIFICATION; REVIEW; TANDEM MASS SPECTROMETRY;

AMINO ACID MOTIFS; ANIMALS; APOLIPOPROTEIN A-I; ATP-BINDING CASSETTE TRANSPORTERS; CARDIOVASCULAR DISEASES; CHOLESTEROL; HALOGENATION; HUMANS; INFLAMMATION; LIPOPROTEINS, HDL; MACROPHAGES; OXIDANTS; OXIDATION-REDUCTION; PEROXIDASE;

EID: 84857633918     PISSN: 13881981     EISSN: 18792618     Source Type: Journal    
DOI: 10.1016/j.bbalip.2011.11.011     Document Type: Review

References (136)

1. E. Braunwald Biomarkers in heart failure N. Engl. J. Med. 358 2008 2148 2159
2. M.S. Brown, and J.L. Goldstein A receptor-mediated pathway for cholesterol homeostasis Science 232 1986 34 47 (Pubitemid 16037973)
3. J.A. Berliner, and J.W. Heinecke The role of oxidized lipoproteins in atherogenesis Free Radic. Biol. Med. 20 1996 707 727 (Pubitemid 26105783)
4. J.W. Heinecke Oxidants and antioxidants in the pathogenesis of atherosclerosis: implications for the oxidized low density lipoprotein hypothesis Atherosclerosis 141 1998 1 15 (Pubitemid 28539412)
5. J.L. Witztum, and D. Steinberg Role of oxidized low density lipoprotein in atherogenesis J. Clin. Invest. 88 1991 1785 1792
6. G.F. Lewis, and D.J. Rader New insights into the regulation of HDL metabolism and reverse cholesterol transport Circ. Res. 96 2005 1221 1232 (Pubitemid 40962099)
7. M.J. Haas, and A.D. Mooradian Inflammation, high-density lipoprotein and cardiovascular dysfunction Curr. Opin. Infect. Dis. 24 2011 265 272
8. C.J. Lowenstein, and S.J. Cameron High-density lipoprotein metabolism and endothelial function Curr. Opin. Endocrinol. Diabetes Obes. 17 2010 166 170
9. M. Suzuki, D.K. Pritchard, L. Becker, A.N. Hoofnagle, N. Tanimura, T.K. Bammler, R.P. Beyer, R. Bumgarner, T. Vaisar, M.C. de Beer, F.C. de Beer, K. Miyake, J.F. Oram, and J.W. Heinecke High-density lipoprotein suppresses the type I interferon response, a family of potent antiviral immunoregulators, in macrophages challenged with lipopolysaccharide Circulation 122 2010 1919 1927
10. G.A. Francis The complexity of HDL Biochim. Biophys. Acta 1801 2010 1286 1293
11. G. Assman, A. von Eckardstein, and H.B. Brewer Familial high density lipoprotein deficiency: Tangier disease C.R. Scriver, A.L. Beaudet, W.S. Sly, D. Valle, The Metabolic and Molecular Bases of Inherited Disease 1995 McGraw-Hill New York, N.Y 2053 2072
12. N. Duverger, C. Viglietta, L. Berthou, F. Emmanuel, A. Tailleux, L. Parmentier-Nihoul, B. Laine, C. Fievet, G. Castro, J.C. Fruchart, L.M. Houbebine, and P. Denefie Transgenic rabbits expressing human apolipoprotein A-I in the liver Arterioscler. Thromb. Vasc. Biol. 16 1996 1424 1429 (Pubitemid 26427594)
13. E.M. Rubin, R.M. Krauss, E.A. Spangler, J.G. Verstuyft, and S.M. Clift Inhibition of early atherogenesis in transgenic mice by human apolipoprotein AI Nature 353 1991 265 267 (Pubitemid 21896769)
14. R.K. Tangirala, K. Tsukamoto, S.H. Chun, D. Usher, E. Pure, and D.J. Rader Regression of atherosclerosis induced by liver-directed gene transfer of apolipoprotein A-I in mice Circulation 100 1999 1816 1822 (Pubitemid 29498389)
15. G.S. Getz, G.D. Wool, and C.A. Reardon Biological properties of apolipoprotein a-I mimetic peptides Curr. Atheroscler. Rep. 12 2010 96 104
16. B.J. Van Lenten, A.C. Wagner, G.M. Anantharamaiah, M. Navab, S.T. Reddy, G.M. Buga, and A.M. Fogelman Apolipoprotein A-I mimetic peptides Curr. Atheroscler. Rep. 11 2009 52 57
17. J.F. Oram, and J.W. Heinecke ATP-binding cassette transporter A1: a cell cholesterol exporter that protects against cardiovascular disease Physiol. Rev. 85 2005 1343 1372 (Pubitemid 41362273)
18. A.R. Tall, P. Costet, and N. Wang Regulation and mechanisms of macrophage cholesterol efflux J. Clin. Invest. 110 2002 899 904
19. P.G. Yancey, A.E. Bortnick, G. Kellner-Weibel, M. de la Llera-Moya, M.C. Phillips, and G.H. Rothblat Importance of different pathways of cellular cholesterol efflux Arterioscler. Thromb. Vasc. Biol. 23 2003 712 719 (Pubitemid 36566157)
20. M. Krieger Charting the fate of the "good cholesterol": identification and characterization of the high-density lipoprotein receptor SR-BI Annu. Rev. Biochem. 68 1999 523 558 (Pubitemid 29449202)
21. A.M. Gotto Jr., H.J. Pownall, and R.J. Havel Introduction to the plasma lipoproteins Methods Enzymol. 128 1986 3 41 (Pubitemid 16100885)
22. W.S. Davidson, and T.B. Thompson The structure of apolipoprotein A-I in high density lipoproteins J. Biol. Chem. 282 2007 22249 22253 (Pubitemid 47267302)
23. M.J. Thomas, S. Bhat, and M.G. Sorci-Thomas Three-dimensional models of HDL apoA-I: implications for its assembly and function J. Lipid Res. 49 2008 1875 1883
24. D. Bashtovyy, M.K. Jones, G.M. Anantharamaiah, and J.P. Segrest Sequence conservation of apolipoprotein A-I affords novel insights into HDL structure-function J. Lipid Res. 52 2011 435 450
25. D.J. Gordon, and B.M. Rifkind High-density lipoprotein - the clinical implications of recent studies N. Engl. J. Med. 321 1989 1311 1316 (Pubitemid 19267219)
26. T. Gordon, W.P. Castelli, M.C. Hjortland, W.B. Kannel, and T.R. Dawber High density lipoprotein as a protective factor against coronary heart disease, the Framingham Study Am. J. Med. 62 1977 707 714 (Pubitemid 8110784)
27. A.R. Sharrett, C.M. Ballantyne, S.A. Coady, G. Heiss, P.D. Sorlie, D. Catellier, and W. Patsch Coronary heart disease prediction from lipoprotein cholesterol levels, triglycerides, lipoprotein(a), apolipoproteins A-I and B, and HDL density subfractions: the Atherosclerosis Risk in Communities (ARIC) Study Circulation 104 2001 1108 1113 (Pubitemid 32830392)
28. A.V. Khera, M. Cuchel, M. de la Llera-Moya, A. Rodrigues, M.F. Burke, K. Jafri, B.C. French, J.A. Phillips, M.L. Mucksavage, R.L. Wilensky, E.R. Mohler, G.H. Rothblat, and D.J. Rader Cholesterol efflux capacity, high-density lipoprotein function, and atherosclerosis N. Engl. J. Med. 364 2011 127 135
29. L. Yvan-Charvet, T. Pagler, E.L. Gautier, S. Avagyan, R.L. Siry, S. Han, C.L. Welch, N. Wang, G.J. Randolph, H.W. Snoeck, and A.R. Tall ATP-binding cassette transporters and HDL suppress hematopoietic stem cell proliferation Science 328 2010 1689 1693
30. X. Wang, and D.J. Rader Molecular regulation of macrophage reverse cholesterol transport Curr. Opin. Cardiol. 22 2007 368 372 (Pubitemid 46897290)
31. L. Yvan-Charvet, N. Wang, and A.R. Tall Role of HDL, ABCA1, and ABCG1 transporters in cholesterol efflux and immune responses Arterioscler. Thromb. Vasc. Biol. 30 2010 139 143
32. R.M. Lawn, D.P. Wade, T.L. Couse, and J.N. Wilcox Localization of human ATP-binding cassette transporter 1 (ABC1) in normal and atherosclerotic tissues Arterioscler. Thromb. Vasc. Biol. 21 2001 378 385 (Pubitemid 32199119)
33. C.L. Wellington, E.K. Walker, A. Suarez, A. Kwok, N. Bissada, R. Singaraja, Y.Z. Yang, L.H. Zhang, E. James, J.E. Wilson, O. Francone, B.M. McManus, and M.R. Hayden ABCA1 mRNA and protein distribution patterns predict multiple different roles and levels of regulation Lab. Invest. 82 2002 273 283 (Pubitemid 34242521)
34. M. Bodzioch, E. Orso, J. Klucken, T. Langmann, A. Bottcher, W. Diederich, W. Drobnik, S. Barlage, C. Buchler, M. Porsch-Ozcurumez, W.E. Kaminski, H.W. Hahmann, K. Oette, G. Rothe, C. Aslanidis, K.J. Lackner, and G. Schmitz The gene encoding ATP-binding cassette transporter 1 is mutated in Tangier disease Nat. Genet. 22 1999 347 351 (Pubitemid 29369524)
35. A. Brooks-Wilson, M. Marcil, S.M. Clee, L.H. Zhang, K. Roomp, M. van Dam, L. Yu, C. Brewer, J.A. Collins, H.O. Molhuizen, O. Loubser, B.F. Ouelette, K. Fichter, K.J. Ashbourne-Excoffon, C.W. Sensen, S. Scherer, S. Mott, M. Denis, D. Martindale, J. Frohlich, K. Morgan, B. Koop, S. Pimstone, J.J. Kastelein, J. Genest Jr., and M.R. Hayden Mutations in ABC1 in Tangier disease and familial high-density lipoprotein deficiency Nat. Genet. 22 1999 336 345 (Pubitemid 29369523)
36. R.M. Lawn, D.P. Wade, M.R. Garvin, X. Wang, K. Schwartz, J.G. Porter, J.J. Seilhamer, A.M. Vaughan, and J.F. Oram The Tangier disease gene product ABC1 controls the cellular apolipoprotein-mediated lipid removal pathway J. Clin. Invest. 104 1999 R25 R31
37. S. Rust, M. Rosier, H. Funke, J. Real, Z. Amoura, J.C. Piette, J.F. Deleuze, H.B. Brewer, N. Duverger, P. Denefle, and G. Assmann Tangier disease is caused by mutations in the gene encoding ATP-binding cassette transporter 1 Nat. Genet. 22 1999 352 355 (Pubitemid 29369525)
38. J.F. Oram HDL apolipoproteins and ABCA1: partners in the removal of excess cellular cholesterol Arterioscler. Thromb. Vasc. Biol. 23 2003 720 727 (Pubitemid 36566158)
39. K. Nakamura, M.A. Kennedy, A. Baldan, D.D. Bojanic, K. Lyons, and P.A. Edwards Expression and regulation of multiple murine ATP-binding cassette transporter G1 mRNAs/isoforms that stimulate cellular cholesterol efflux to high density lipoprotein J. Biol. Chem. 279 2004 45980 45989 (Pubitemid 39491591)
40. N. Wang, D. Lan, W. Chen, F. Matsuura, and A.R. Tall ATP-binding cassette transporters G1 and G4 mediate cellular cholesterol efflux to high-density lipoproteins Proc. Natl. Acad. Sci. U.S.A. 101 2004 9774 9779 (Pubitemid 38869312)
41. A.J. Wojcik, M.D. Skaflen, S. Srinivasan, and C.C. Hedrick A critical role for ABCG1 in macrophage inflammation and lung homeostasis J. Immunol. 180 2008 4273 4282
42. -/- bone marrow Arterioscler. Thromb. Vasc. Biol. 26 2006 2301 2307 (Pubitemid 44465726)
43. R. Out, M. Hoekstra, R.B. Hildebrand, J.K. Kruit, I. Meurs, Z. Li, F. Kuipers, T.J. Van Berkel, and M. Van Eck Macrophage ABCG1 deletion disrupts lipid homeostasis in alveolar macrophages and moderately influences atherosclerotic lesion development in LDL receptor-deficient mice Arterioscler. Thromb. Vasc. Biol. 26 2006 2295 2300 (Pubitemid 44465725)
44. -/- bone marrow Arterioscler. Thromb. Vasc. Biol. 26 2006 2308 2315 (Pubitemid 44465727)
45. R. Out, M. Hoekstra, K. Habets, I. Meurs, V. de Waard, R.B. Hildebrand, Y. Wang, G. Chimini, J. Kuiper, T.J. Van Berkel, and M. Van Eck Combined deletion of macrophage ABCA1 and ABCG1 leads to massive lipid accumulation in tissue macrophages and distinct atherosclerosis at relatively low plasma cholesterol levels Arterioscler. Thromb. Vasc. Biol. 28 2008 258 264 (Pubitemid 351161197)
46. L. Yvan-Charvet, M. Ranalletta, N. Wang, S. Han, N. Terasaka, R. Li, C. Welch, and A.R. Tall Combined deficiency of ABCA1 and ABCG1 promotes foam cell accumulation and accelerates atherosclerosis in mice J. Clin. Invest. 117 2007 3900 3908 (Pubitemid 350224099)
47. P.J. Barter, S. Nicholls, K.A. Rye, G.M. Anantharamaiah, M. Navab, and A.M. Fogelman Antiinflammatory properties of HDL Circ. Res. 95 2004 764 772 (Pubitemid 39390578)
48. M. Zabalawi, S. Bhat, T. Loughlin, M.J. Thomas, E. Alexander, M. Cline, B. Bullock, M. Willingham, and M.G. Sorci-Thomas Induction of fatal inflammation in LDL receptor and ApoA-I double-knockout mice fed dietary fat and cholesterol Am. J. Pathol. 163 2003 1201 1213 (Pubitemid 37040156)
49. -/- mice J. Biol. Chem. 285 2010 36158 36169
50. L. Yvan-Charvet, C. Welch, T.A. Pagler, M. Ranalletta, M. Lamkanfi, S. Han, M. Ishibashi, R. Li, N. Wang, and A.R. Tall Increased inflammatory gene expression in ABC transporter-deficient macrophages: free cholesterol accumulation, increased signaling via toll-like receptors, and neutrophil infiltration of atherosclerotic lesions Circulation 118 2008 1837 1847
51. X. Zhu, J.Y. Lee, J.M. Timmins, J.M. Brown, E. Boudyguina, A. Mulya, A.K. Gebre, M.C. Willingham, E.M. Hiltbold, N. Mishra, N. Maeda, and J.S. Parks Increased cellular free cholesterol in macrophage-specific Abca1 knock-out mice enhances pro-inflammatory response of macrophages J. Biol. Chem. 283 2008 22930 22941
52. P. Goossens, M.J. Gijbels, A. Zernecke, W. Eijgelaar, M.N. Vergouwe, I. van der Made, J. Vanderlocht, L. Beckers, W.A. Buurman, M.J. Daemen, U. Kalinke, C. Weber, E. Lutgens, and M.P. de Winther Myeloid type I interferon signaling promotes atherosclerosis by stimulating macrophage recruitment to lesions Cell Metab. 12 2010 142 153
53. T. Vaisar, S. Pennathur, P.S. Green, S.A. Gharib, A.N. Hoofnagle, M.C. Cheung, J. Byun, S. Vuletic, S. Kassim, P. Singh, H. Chea, R.H. Knopp, J. Brunzell, R. Geary, A. Chait, X.Q. Zhao, K. Elkon, S. Marcovina, P. Ridker, J.F. Oram, and J.W. Heinecke Shotgun proteomics implicates protease inhibition and complement activation in the antiinflammatory properties of HDL J. Clin. Invest. 117 2007 746 756 (Pubitemid 46348533)
54. A. Chait, C.Y. Han, J.F. Oram, and J.W. Heinecke Thematic review series: the immune system and atherogenesis. Lipoprotein-associated inflammatory proteins: markers or mediators of cardiovascular disease? J. Lipid Res. 46 2005 389 403
55. A. Kontush, and M.J. Chapman Functionally defective high-density lipoprotein: a new therapeutic target at the crossroads of dyslipidemia, inflammation, and atherosclerosis Pharmacol. Rev. 58 2006 342 374 (Pubitemid 44394906)
56. B. Shao, M.N. Oda, J.F. Oram, and J.W. Heinecke Myeloperoxidase: an oxidative pathway for generating dysfunctional high-density lipoprotein Chem. Res. Toxicol. 23 2010 447 454
57. J. Heinecke HDL and cardiovascular-disease risk - time for a new approach? N. Engl. J. Med. 364 2011 170 171
58. C. Bergt, S. Pennathur, X. Fu, J. Byun, K. O'Brien, T.O. McDonald, P. Singh, G.M. Anantharamaiah, A. Chait, J. Brunzell, R.L. Geary, J.F. Oram, and J.W. Heinecke The myeloperoxidase product hypochlorous acid oxidizes HDL in the human artery wall and impairs ABCA1-dependent cholesterol transport Proc. Natl. Acad. Sci. U.S.A. 101 2004 13032 13037 (Pubitemid 39167578)
59. S. Pennathur, C. Bergt, B. Shao, J. Byun, S.Y. Kassim, P. Singh, P.S. Green, T.O. McDonald, J. Brunzell, A. Chait, J.F. Oram, K. O'Brien, R.L. Geary, and J.W. Heinecke Human atherosclerotic intima and blood of patients with established coronary artery disease contain high density lipoprotein damaged by reactive nitrogen species J. Biol. Chem. 279 2004 42977 42983 (Pubitemid 39372190)
60. L. Zheng, B. Nukuna, M.L. Brennan, M. Sun, M. Goormastic, M. Settle, D. Schmitt, X. Fu, L. Thomson, P.L. Fox, H. Ischiropoulos, J.D. Smith, M. Kinter, and S.L. Hazen Apolipoprotein A-I is a selective target for myeloperoxidase- catalyzed oxidation and functional impairment in subjects with cardiovascular disease J. Clin. Invest. 114 2004 529 541 (Pubitemid 39572103)
61. A. Daugherty, J.L. Dunn, D.L. Rateri, and J.W. Heinecke Myeloperoxidase, a catalyst for lipoprotein oxidation, is expressed in human atherosclerotic lesions J. Clin. Invest. 94 1994 437 444 (Pubitemid 24218123)
62. J.P. Henderson Myeloperoxidase and eosinophil peroxidase: phagocytosis and microbial killing H.B. Dunford, Heme Peroxidases 1999 New York John Wiley & Sons, Inc 349 385
63. J.K. Hurst, and W.C. Barrette Jr. Leukocytic oxygen activation and microbicidal oxidative toxins Crit. Rev. Biochem. Mol. Biol. 24 1989 271 328
64. S.J. Klebanoff Oxygen metabolism and the toxic properties of phagocytes Ann. Intern. Med. 93 1980 480 489 (Pubitemid 10055919)
65. J.W. Heinecke Pathways for oxidation of low density lipoprotein by myeloperoxidase: tyrosyl radical, reactive aldehydes, hypochlorous acid and molecular chlorine Biofactors 6 1997 145 155 (Pubitemid 27487819)
66. N.M. Domigan, T.S. Charlton, M.W. Duncan, C.C. Winterbourn, and A.J. Kettle Chlorination of tyrosyl residues in peptides by myeloperoxidase and human neutrophils J. Biol. Chem. 270 1995 16542 16548
67. S.L. Hazen, F.F. Hsu, D.M. Mueller, J.R. Crowley, and J.W. Heinecke Human neutrophils employ chlorine gas as an oxidant during phagocytosis J. Clin. Invest. 98 1996 1283 1289 (Pubitemid 26322052)
68. J.P. Gaut, G.C. Yeh, H.D. Tran, J. Byun, J.P. Henderson, G.M. Richter, M.L. Brennan, A.J. Lusis, A. Belaaouaj, R.S. Hotchkiss, and J.W. Heinecke Neutrophils employ the myeloperoxidase system to generate antimicrobial brominating and chlorinating oxidants during sepsis Proc. Natl. Acad. Sci. U.S.A. 98 2001 11961 11966 (Pubitemid 32959809)
69. S.L. Hazen, and J.W. Heinecke 3-Chlorotyrosine, a specific marker of myeloperoxidase-catalyzed oxidation, is markedly elevated in low density lipoprotein isolated from human atherosclerotic intima J. Clin. Invest. 99 1997 2075 2081 (Pubitemid 27203762)
70. C.E. Cooper, R.P. Patel, P.S. Brookes, and V.M. Darley-Usmar Nanotransducers in cellular redox signaling: modification of thiols by reactive oxygen and nitrogen species Trends Biochem. Sci. 27 2002 489 492 (Pubitemid 35279586)
71. S. Moncada, R.M. Palmer, and E.A. Higgs Nitric oxide: physiology, pathophysiology, and pharmacology Pharmacol. Rev. 43 1991 109 142
72. J.S. Beckman, J. Chen, H. Ischiropoulos, and J.P. Crow Oxidative chemistry of peroxynitrite Methods Enzymol. 233 1994 229 240 (Pubitemid 24177546)
73. J.P. Eiserich, M. Hristova, C.E. Cross, A.D. Jones, B.A. Freeman, B. Halliwell, and A. van der Vliet Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils Nature 391 1998 393 397 (Pubitemid 28093514)
74. J.P. Gaut, J. Byun, H.D. Tran, W.M. Lauber, J.A. Carroll, R.S. Hotchkiss, A. Belaaouaj, and J.W. Heinecke Myeloperoxidase produces nitrating oxidants in vivo J. Clin. Invest. 109 2002 1311 1319 (Pubitemid 34546895)
75. M.L. Brennan, M.M. Anderson, D.M. Shih, X.D. Qu, X. Wang, A.C. Mehta, L.L. Lim, W. Shi, S.L. Hazen, J.S. Jacob, J.R. Crowley, J.W. Heinecke, and A.J. Lusis Increased atherosclerosis in myeloperoxidase-deficient mice J. Clin. Invest. 107 2001 419 430 (Pubitemid 32167988)
76. T.S. McMillen, J.W. Heinecke, and R.C. LeBoeuf Expression of human myeloperoxidase by macrophages promotes atherosclerosis in mice Circulation 111 2005 2798 2804 (Pubitemid 40791552)
77. G.A. Francis, R.H. Knopp, and J.F. Oram Defective removal of cellular cholesterol and phospholipids by apolipoprotein A-I in Tangier Disease J. Clin. Invest. 96 1995 78 87
78. A.J. Mendez, G.M. Anantharamaiah, J.P. Segrest, and J.F. Oram Synthetic amphipathic helical peptides that mimic apolipoprotein A-I in clearing cellular cholesterol J. Clin. Invest. 94 1994 1698 1705 (Pubitemid 24309896)
79. C.G. Brouillette, G.M. Anantharamaiah, J.A. Engler, and D.W. Borhani Structural models of human apolipoprotein A-I: a critical analysis and review Biochim. Biophys. Acta 1531 2001 4 46 (Pubitemid 32241248)
80. W.S. Davidson, and R.A. Silva Apolipoprotein structural organization in high density lipoproteins: belts, bundles, hinges and hairpins Curr. Opin. Lipidol. 16 2005 295 300 (Pubitemid 40839758)
81. B. Shao, C. Bergt, X. Fu, P. Green, J.C. Voss, M.N. Oda, J.F. Oram, and J.W. Heinecke Tyrosine 192 in apolipoprotein A-I is the major site of nitration and chlorination by myeloperoxidase, but only chlorination markedly impairs ABCA1-dependent cholesterol transport J. Biol. Chem. 280 2005 5983 5993 (Pubitemid 40280082)
82. C. Bergt, X. Fu, N.P. Huq, J. Kao, and J.W. Heinecke Lysine residues direct the chlorination of tyrosines in YXXK motifs of apolipoprotein A-I when hypochlorous acid oxidizes high density lipoprotein J. Biol. Chem. 279 2004 7856 7866 (Pubitemid 38294672)
83. B. Shao, C. Tang, J.W. Heinecke, and J.F. Oram Oxidation of apolipoprotein A-I by myeloperoxidase impairs the initial interactions with ABCA1 required for signaling and cholesterol export J. Lipid Res. 51 2010 1849 1858
84. B. Shao, M.N. Oda, C. Bergt, X. Fu, P.S. Green, N. Brot, J.F. Oram, and J.W. Heinecke Myeloperoxidase impairs ABCA1-dependent cholesterol efflux through methionine oxidation and site-specific tyrosine chlorination of apolipoprotein A-I J. Biol. Chem. 281 2006 9001 9004 (Pubitemid 43864611)
85. C. Bergt, K. Oettl, W. Keller, F. Andreae, H.J. Leis, E. Malle, and W. Sattler Reagent or myeloperoxidase-generated hypochlorite affects discrete regions in lipid-free and lipid-associated human apolipoprotein A-I Biochem. J. 346 Pt 2 2000 345 354 (Pubitemid 30148119)
86. G.A. Francis, A.J. Mendez, E.L. Bierman, and J.W. Heinecke Oxidative tyrosylation of high density lipoprotein by peroxidase enhances cholesterol removal from cultured fibroblasts and macrophage foam cells Proc. Natl. Acad. Sci. U.S.A. 90 1993 6631 6635 (Pubitemid 23207267)
87. U. Panzenboeck, S. Raitmayer, H. Reicher, H. Lindner, O. Glatter, E. Malle, and W. Sattler Effects of reagent and enzymatically generated hypochlorite on physicochemical and metabolic properties of high density lipoproteins J. Biol. Chem. 272 1997 29711 29720 (Pubitemid 27508065)
88. D.Q. Peng, Z. Wu, G. Brubaker, L. Zheng, M. Settle, E. Gross, M. Kinter, S.L. Hazen, and J.D. Smith Tyrosine modification is not required for myeloperoxidase-induced loss of apolipoprotein A-I functional activities J. Biol. Chem. 280 2005 33775 33784 (Pubitemid 41443096)
89. C.L. Hawkins, D.I. Pattison, and M.J. Davies Hypochlorite-induced oxidation of amino acids, peptides and proteins Amino Acids 25 2003 259 274 (Pubitemid 38041264)
90. U. Panzenbock, and R. Stocker Formation of methionine sulfoxide-containing specific forms of oxidized high-density lipoproteins Biochim. Biophys. Acta 1703 2005 171 181 (Pubitemid 40170440)
91. H. Weissbach, L. Resnick, and N. Brot Methionine sulfoxide reductases: history and cellular role in protecting against oxidative damage Biochim. Biophys. Acta 1703 2005 203 212 (Pubitemid 40170443)
92. B. Shao, and J.W. Heinecke Using tandem mass spectrometry to quantify site-specific chlorination and nitration of proteins: model system studies with high-density lipoprotein oxidized by myeloperoxidase Methods Enzymol. 440 2008 33 63
93. D.Q. Peng, G. Brubaker, Z. Wu, L. Zheng, B. Willard, M. Kinter, S.L. Hazen, and J.D. Smith Apolipoprotein A-I tryptophan substitution leads to resistance to myeloperoxidase-mediated loss of function Arterioscler. Thromb. Vasc. Biol. 28 2008 2063 2070
94. A. Chroni, T. Liu, M.L. Fitzgerald, M.W. Freeman, and V.I. Zannis Cross-linking and lipid efflux properties of apoA-I mutants suggest direct association between apoA-I helices and ABCA1 Biochemistry 43 2004 2126 2139 (Pubitemid 38233274)
95. H.H. Hassan, M. Denis, D.Y. Lee, I. Iatan, D. Nyholt, I. Ruel, L. Krimbou, and J. Genest Identification of an ABCA1-dependent phospholipid-rich plasma membrane apolipoprotein A-I binding site for nascent HDL formation: implications for current models of HDL biogenesis J. Lipid Res. 48 2007 2428 2442 (Pubitemid 350058754)
96. C. Vedhachalam, P.T. Duong, M. Nickel, D. Nguyen, P. Dhanasekaran, H. Saito, G.H. Rothblat, S. Lund-Katz, and M.C. Phillips Mechanism of ATP-binding cassette transporter A1-mediated cellular lipid efflux to apolipoprotein A-I and formation of high density lipoprotein particles J. Biol. Chem. 282 2007 25123 25130 (Pubitemid 47347535)
97. G. Lin, and J.F. Oram Apolipoprotein binding to protruding membrane domains during removal of excess cellular cholesterol Atherosclerosis 149 2000 359 370 (Pubitemid 30145546)
98. C. Vedhachalam, A.B. Ghering, W.S. Davidson, S. Lund-Katz, G.H. Rothblat, and M.C. Phillips ABCA1-induced cell surface binding sites for ApoA-I Arterioscler. Thromb. Vasc. Biol. 27 2007 1603 1609 (Pubitemid 46986116)
99. C. Tang, A.M. Vaughan, G.M. Anantharamaiah, and J.F. Oram Janus kinase 2 modulates the lipid-removing but not protein-stabilizing interactions of amphipathic helices with ABCA1 J. Lipid Res. 47 2006 107 114 (Pubitemid 43107454)
100. J.F. Oram, R.M. Lawn, M.R. Garvin, and D.P. Wade ABCA1 is the cAMP-inducible apolipoprotein receptor that mediates cholesterol secretion from macrophages J. Biol. Chem. 275 2000 34508 34511
101. Y. Wang, and J.F. Oram Unsaturated fatty acids inhibit cholesterol efflux from macrophages by increasing degradation of ATP-binding cassette transporter A1 J. Biol. Chem. 277 2002 5692 5697 (Pubitemid 34968625)
102. U. Panzenbock, L. Kritharides, M. Raftery, K.A. Rye, and R. Stocker Oxidation of methionine residues to methionine sulfoxides does not decrease potential antiatherogenic properties of apolipoprotein A-I J. Biol. Chem. 275 2000 19536 19544 (Pubitemid 30441546)
103. L. Zheng, M. Settle, G. Brubaker, D. Schmitt, S.L. Hazen, J.D. Smith, and M. Kinter Localization of nitration and chlorination sites on apolipoprotein A-I catalyzed by myeloperoxidase in human atheroma and associated oxidative impairment in ABCA1-dependent cholesterol efflux from macrophages J. Biol. Chem. 280 2005 38 47 (Pubitemid 40164962)
104. J.W. Baynes, and S.R. Thorpe Role of oxidative stress in diabetic complications: a new perspective on an old paradigm Diabetes 48 1999 1 9 (Pubitemid 29019345)
105. N. Shaklai, R.L. Garlick, and H.F. Bunn Nonenzymatic glycosylation of human serum albumin alters its conformation and function J. Biol. Chem. 259 1984 3812 3817 (Pubitemid 14170093)
106. H. Esterbauer, R.J. Schaur, and H. Zollner Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes Free Radic. Biol. Med. 11 1991 81 128 (Pubitemid 121003917)
107. M.E. Rosenfeld, W. Palinski, S. Yla-Herttuala, S. Butler, and J.L. Witztum Distribution of oxidation specific lipid-protein adducts and apolipoprotein B in atherosclerotic lesions of varying severity from WHHL rabbits Arteriosclerosis 10 1990 336 349 (Pubitemid 20178662)
108. E.R. Stadtman, and R.L. Levine Free radical-mediated oxidation of free amino acids and amino acid residues in proteins Amino Acids 25 2003 207 218 (Pubitemid 38043943)
109. M. Brownlee, A. Cerami, and H. Vlassara Advanced glycosylation end products in tissue and the biochemical basis of diabetic complications N. Engl. J. Med. 318 1988 1315 1321
110. M. Passarelli, C. Tang, T.O. McDonald, K.D. O'Brien, R.G. Gerrity, J.W. Heinecke, and J.F. Oram Advanced glycation end product precursors impair ABCA1-dependent cholesterol removal from cells Diabetes 54 2005 2198 2205 (Pubitemid 40911284)
111. V.W. Bowry, K.K. Stanley, and R. Stocker High density lipoprotein is the major carrier of lipid hydroperoxides in human blood plasma from fasting donors Proc. Natl. Acad. Sci. U.S.A. 89 1992 10316 10320
112. M.E. Szapacs, H.Y. Kim, N.A. Porter, and D.C. Liebler Identification of proteins adducted by lipid peroxidation products in plasma and modifications of apolipoprotein A1 with a novel biotinylated phospholipid probe J. Proteome Res. 7 2008 4237 4246
113. M.R. McCall, J.Y. Tang, J.K. Bielicki, and T.M. Forte Inhibition of lecithin-cholesterol acyltransferase and modification of HDL apolipoproteins by aldehydes Arterioscler. Thromb. Vasc. Biol. 15 1995 1599 1606
114. E. Nobecourt, M.J. Davies, B.E. Brown, L.K. Curtiss, D.J. Bonnet, F. Charlton, A.S. Januszewski, A.J. Jenkins, P.J. Barter, and K.A. Rye The impact of glycation on apolipoprotein A-I structure and its ability to activate lecithin:cholesterol acyltransferase Diabetologia 50 2007 643 653 (Pubitemid 46215509)
115. G. Witz Biological interactions of alpha, beta-unsaturated aldehydes Free Radic. Biol. Med. 7 1989 333 349 (Pubitemid 19234180)
116. M.M. Anderson, S.L. Hazen, F.F. Hsu, and J.W. Heinecke Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to convert hydroxy-amino acids into glycolaldehyde, 2-hydroxypropanal, and acrolein. A mechanism for the generation of highly reactive alpha-hydroxy and alpha,beta-unsaturated aldehydes by phagocytes at sites of inflammation. J. Clin. Invest. 99 1997 424 432 (Pubitemid 27414799)
117. K. Uchida Current status of acrolein as a lipid peroxidation product Trends Cardiovasc. Med. 9 1999 109 113 (Pubitemid 30001888)
118. K. Uchida, M. Kanematsu, K. Sakai, T. Matsuda, N. Hattori, Y. Mizuno, D. Suzuki, T. Miyata, N. Noguchi, E. Niki, and T. Osawa Protein-bound acrolein: potential markers for oxidative stress Proc. Natl. Acad. Sci. U.S.A. 95 1998 4882 4887 (Pubitemid 28208519)
119. J.W. Heinecke Mechanisms of oxidative damage by myeloperoxidase in atherosclerosis and other inflammatory disorders J. Lab. Clin. Med. 133 1999 321 325 (Pubitemid 29373028)
120. B. Shao, X. Fu, T.O. McDonald, P.S. Green, K. Uchida, K.D. O'Brien, J.F. Oram, and J.W. Heinecke Acrolein impairs ATP binding cassette transporter A1-dependent cholesterol export from cells through site-specific modification of apolipoprotein A-I J. Biol. Chem. 280 2005 36386 36396 (Pubitemid 41633913)
121. A. Furuhata, T. Ishii, S. Kumazawa, T. Yamada, T. Nakayama, and K. Uchida N(epsilon)-(3-methylpyridinium)lysine, a major antigenic adduct generated in acrolein-modified protein J. Biol. Chem. 278 2003 48658 48665 (Pubitemid 41079505)
122. K. Uchida, M. Kanematsu, Y. Morimitsu, T. Osawa, N. Noguchi, and E. Niki Acrolein is a product of lipid peroxidation reaction. Formation of free acrolein and its conjugate with lysine residues in oxidized low density lipoproteins J. Biol. Chem. 273 1998 16058 16066 (Pubitemid 28311374)
123. T. Richter, G. Munch, H.J. Luth, T. Arendt, R. Kientsch-Engel, P. Stahl, D. Fengler, and B. Kuhla Immunochemical crossreactivity of antibodies specific for "advanced glycation endproducts" with "advanced lipoxidation endproducts" Neurobiol. Aging 26 2005 465 474 (Pubitemid 40093930)
124. A. Chroni, T. Liu, I. Gorshkova, H.Y. Kan, Y. Uehara, A. Von Eckardstein, and V.I. Zannis The central helices of ApoA-I can promote ATP-binding cassette transporter A1 (ABCA1)-mediated lipid efflux. Amino acid residues 220-231 of the wild-type ApoA-I are required for lipid efflux in vitro and high density lipoprotein formation in vivo J. Biol. Chem. 278 2003 6719 6730 (Pubitemid 36800659)
125. S.E. Panagotopulos, S.R. Witting, E.M. Horace, D.Y. Hui, J.N. Maiorano, and W.S. Davidson The role of apolipoprotein A-I helix 10 in apolipoprotein-mediated cholesterol efflux via the ATP-binding cassette transporter ABCA1 J. Biol. Chem. 277 2002 39477 39484 (Pubitemid 35190924)
126. P. Natarajan, T.M. Forte, B. Chu, M.C. Phillips, J.F. Oram, and J.K. Bielicki Identification of an apolipoprotein A-I structural element that mediates cellular cholesterol efflux and stabilizes ATP binding cassette transporter A1 J. Biol. Chem. 279 2004 24044 24052 (Pubitemid 38725263)
127. M.L. Savenkova, D.M. Mueller, and J.W. Heinecke Tyrosyl radical generated by myeloperoxidase is a physiological catalyst for the initiation of lipid peroxidation in low density lipoprotein J. Biol. Chem. 269 1994 20394 20400 (Pubitemid 24260440)
128. B. Shao, S. Pennathur, I. Pagani, M.N. Oda, J.L. Witztum, J.F. Oram, and J.W. Heinecke Modifying apolipoprotein A-I by malondialdehyde, but not by an array of other reactive carbonyls, blocks cholesterol efflux by the ABCA1 pathway J. Biol. Chem. 285 2010 18473 18484
129. T. Ishii, S. Kumazawa, T. Sakurai, T. Nakayama, and K. Uchida Mass spectroscopic characterization of protein modification by malondialdehyde Chem. Res. Toxicol. 19 2006 122 129 (Pubitemid 43185470)
130. J.R. Requena, M.X. Fu, M.U. Ahmed, A.J. Jenkins, T.J. Lyons, J.W. Baynes, and S.R. Thorpe Quantification of malondialdehyde and 4-hydroxynonenal adducts to lysine residues in native and oxidized human low-density lipoprotein Biochem.
131. J.W. Burgess, P.G. Frank, V. Franklin, P. Liang, D.C. McManus, M. Desforges, E. Rassart, and Y.L. Marcel Deletion of the C-terminal domain of apolipoprotein A-I impairs cell surface binding and lipid efflux in macrophage Biochemistry 38 1999 14524 14533
132. C. Vedhachalam, L. Liu, M. Nickel, P. Dhanasekaran, G.M. Anantharamaiah, S. Lund-Katz, G.H. Rothblat, and M.C. Phillips Influence of ApoA-I structure on the ABCA1-mediated efflux of cellular lipids J. Biol. Chem. 279 2004 49931 49939 (Pubitemid 39577801)
133. D.A. Slatter, C.H. Bolton, and A.J. Bailey The importance of lipid-derived malondialdehyde in diabetes mellitus Diabetologia 43 2000 550 557 (Pubitemid 30322071)
134. W. Palinski, S. Yla-Herttuala, M.E. Rosenfeld, S.W. Butler, S.A. Socher, S. Parthasarathy, L.K. Curtiss, and J.L. Witztum Antisera and monoclonal antibodies specific for epitopes generated during oxidative modification of low density lipoprotein Arteriosclerosis 10 1990 325 335 (Pubitemid 20178661)
135. R.J. Schaur Basic aspects of the biochemical reactivity of 4-hydroxynonenal Mol. Aspects Med. 24 2003 149 159 (Pubitemid 36945015)
136. K. Uchida, and E.R. Stadtman Modification of histidine residues in proteins by reaction with 4-hydroxynonenal Proc. Natl. Acad. Sci. U.S.A. 89 1992 4544 4548