Paraoxonase 1 attenuates human plaque atherogenicity: Relevance to the enzyme lactonase activity

Advances in Experimental Medicine and Biology

Volumn 660, Issue , 2010, Pages 99-111

  Tavori, Hagai ^a   Vaya, Jacob ^a   Aviram, Michael ^a  

^a NONE

Author keywords

Atherosclerosis; Docking; Lactones; Modeling; Oxidative stress; Paraoxonase; Plaque

Indexed keywords

ARYLDIALKYLPHOSPHATASE 1; GLUCONOLACTONASE; LACTONE;

ARTICLE; ATHEROGENESIS; ATHEROSCLEROTIC PLAQUE; CAROTID ATHEROSCLEROSIS; CHOLESTEROL TRANSPORT; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; LIPID ANALYSIS; LIPID OXIDATION; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; OXIDATIVE STRESS; PATHOPHYSIOLOGY; PRIORITY JOURNAL;

ARYLDIALKYLPHOSPHATASE; ATHEROSCLEROSIS; CAROTID ARTERIES; CATALYTIC DOMAIN; HUMANS; LACTONES; MACROPHAGES; MODELS, BIOLOGICAL; MODELS, CHEMICAL; MODELS, MOLECULAR; OXIDATIVE STRESS; OXYGEN; PLAQUE, ATHEROSCLEROTIC; PROTEIN CONFORMATION;

EID: 78149420429     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-60761-350-3_10     Document Type: Article

References (64)

1. Ahmed, Z. ; Ravandi, A. ; Maguire, G. F. ; Emili, A. ; Draganov, D. ; La Du, B. N. ; Kuksis, A. ; Connelly, P. W. Multiple substrates for paraoxonase-1 during oxidation of phosphatidylcholine by peroxynitrite. Biochem Biophys Res Commun 290:391-396; 2002. (Pubitemid 34694511)
2. Ahmed, Z. ; Ravandi, A. ; Maguire, G. F. ; Emili, A. ; Draganov, D. ; La Du, B. N. ; Kuksis, A. ; Connelly, P. W. Apolipoprotein A-I promotes the formation of phosphatidylcholine core aldehydes that are hydrolyzed by paraoxonase (PON-1) during high density lipoprotein oxidation with a peroxynitrite donor. J Biol Chem 276:24473-24481; 2001.
3. Aviram, M. Review of human studies on oxidative damage and antioxidant protection related to cardiovascular diseases. Free Radic Res 33 (Suppl):S85-S97; 2000. (Pubitemid 32055068)
4. Aviram, M. ; Hardak, E. ; Vaya, J. ; Mahmood, S. ; Milo, S. ; Hoffman, A. ; Billicke, S. ; Draganov, D. ; Rosenblat, M. Human serum paraoxonases (PON1) Q and R selectively decrease lipid peroxides in human coronary and carotid atherosclerotic lesions: PON1 esterase and peroxidase-like activities. Circulation 101:2510-2517; 2000. (Pubitemid 30366256)
5. Aviram, M. ; Kaplan, M. ; Rosenblat, M. ; Fuhrman, B. Dietary antioxidants and paraoxonases against LDL oxidation and atherosclerosis development. Handb Exp Pharmacol 170: 263-300; 2005.
6. Aviram, M. ; Maor, I. ; Keidar, S. ; Hayek, T. ; Oiknine, J. ; Bar-El, Y. ; Adler, Z. ; Kertzman, V. ; Milo, S. Lesioned low density lipoprotein in atherosclerotic apolipoprotein E-deficient transgenic mice and in humans is oxidized and aggregated. Biochem Biophys Res Commun 216: 501-513; 1995.
7. Aviram, M. ; Rosenblat, M. ; Bisgaier, C. L. ; Newton, R. S. ; Primo-Parmo, S. L. ; La Du, B. N. Paraoxonase inhibits high-density lipoprotein oxidation and preserves its functions. A possible peroxidative role for paraoxonase. J Clin Invest 101:1581-1590; 1998. (Pubitemid 28198486)
8. Billecke, S. ; Draganov, D. ; Counsell, R. ; Stetson, P. ; Watson, C. ; Hsu, C. ; La Du, B. N. Human serum paraoxonase (PON1) isozymes Q and R hydrolyze lactones and cyclic carbonate esters. Drug Metab Dispos 28:1335-1342; 2000.
9. Bonete, M. J. ; Perez-Pomares, F. ; Ferrer, J. ; Camacho, M. L. NAD-glutamate dehydrogenase from Halobacterium halobium: inhibition and activation by TCA intermediates and amino acids. Biochim Biophys Acta 1289:14-24; 1996. (Pubitemid 26076603)
10. Costa, L. G. ; Vitalone, A. ; Cole, T. B. ; Furlong, C. E. Modulation of paraoxonase (PON1) activity. Biochem Pharmacol 69:541-550; 2005.
11. Deakin, S. P. ; James, R. W. Genetic and environmental factors modulating serum concentrations and activities of the antioxidant enzyme paraoxonase-1. Clin Sci (Lond) 107:435-447; 2004. (Pubitemid 39506735)
12. Draganov, D. I. ; La Du, B. N. Pharmacogenetics of paraoxonases: a brief review. Naunyn Schmiedebergs Arch Pharmacol 369:78-88; 2004. (Pubitemid 38161225)
13. Draganov, D. I. ; Teiber, J. F. ; Speelman, A. ; Osawa, Y. ; Sunahara, R. ; La Du, B. N. Human paraoxonases (PON1, PON2, and PON3) are lactonases with overlapping and distinct substrate specificities. J Lipid Res 46:1239-1247; 2005. (Pubitemid 43109838)
14. Efrat, M. ; Aviram, M. Macrophage paraoxonase 1 (PON1) binding sites. Biochem Biophys Res Commun 376:105-110; 2008.
15. Efrat, M. ; Rosenblat, M. ; Mahmood, S. ; Vaya, J. ; Aviram, M. Di-oleoyl phosphatidylcholine (PC- 18:1) stimulates paraoxonase 1 (PON1) enzymatic and biological activities: In vitro and in vivo studies. Atherosclerosis 202:461-469; 2008.
16. Fuhrman, B. ; Judith, O. ; Keidar, S. ; Ben-Yaish, L. ; Kaplan, M. ; Aviram, M. Increased uptake of LDL by oxidized macrophages is the result of an initial enhanced LDL receptor activity and of a further progressive oxidation of LDL. Free Radic Biol Med 23:34-46; 1997. (Pubitemid 27217006)
17. Fuhrman, B. ; Oiknine, J. ; Aviram, M. Iron induces lipid peroxidation in cultured macrophages, increases their ability to oxidatively modify LDL, and affects their secretory properties. Atherosclerosis 111:65-78; 1994. (Pubitemid 24330618)
18. Fuhrman, B. ; Shiner, M. ; Volkova, N. ; Aviram, M. Cell-induced copper ion-mediated low density lipoprotein oxidation increases during in vivo monocyte-to-macrophage differentiation. Free Radic Biol Med 37:259-271; 2004. (Pubitemid 38760262)
19. Gaidukov, L.;Rosenblat, M. ; Aviram, M. ; Tawfik, D. S. The 192R/Q polymorphs of serum paraoxonase PON1 differ in HDL binding, lipolactonase stimulation, and cholesterol efflux. J Lipid Res 47:2492-2502; 2006. (Pubitemid 44936111)
20. Gaidukov, L. ; Tawfik, D. S. The development of human sera tests for HDL-bound serum PON1 and its lipolactonase activity. J Lipid Res 48:1637-1646; 2007. (Pubitemid 47312025)
21. Glass, C. K. ; Witztum, J. L. Atherosclerosis. the road ahead. Cell 104:503-516; 2001.
22. Goodsell, D. S. ; Morris, G. M. ; Olson, A. J. Automated docking of flexible ligands: applications of AutoDock. J Mol Recognit 9:1-5; 1996. (Pubitemid 126565462)
23. Guardiola, F. ; Codony, R. ; Addis, P. B. ; Rafecas, M. ; Boatella, J. Biological effects of oxysterols: current status. Food Chem Toxicol 34:193-211; 1996. (Pubitemid 26076847)
24. Harel, M. ; Aharoni, A. ; Gaidukov, L. ; Brumshtein, B. ; Khersonsky, O. ; Meged, R. ; Dvir, H. ; Ravelli, R. B. ; McCarthy, A. ; Toker, L. ; Silman, I. ; Sussman, J. L. ; Tawfik, D. S. Structure and evolution of the serum paraoxonase family of detoxifying and anti-atherosclerotic enzymes. Nat Struct Mol Biol 11:412-419; 2004. (Pubitemid 38568944)
25. Ibanez, B. ; Vilahur, G. ; Badimon, J. J. Plaque progression and regression in atherothrombosis. J Thromb Haemost 5(Suppl 1):292-299; 2007. (Pubitemid 46958845)
26. Jakubowski, H. ; Zhang, L. ; Bardeguez, A. ; Aviv, A. Homocysteine thiolactone and protein homocysteinylation in human endothelial cells: implications for atherosclerosis. Circ Res 87: 45-51; 2000. (Pubitemid 30456934)
27. Khan-Merchant, N. ; Penumetcha, M. ; Meilhac, O. ; Parthasarathy, S. Oxidized fatty acids promote atherosclerosis only in the presence of dietary cholesterol in low-density lipoprotein receptor knockout mice. J Nutr 132:3256-3262; 2002. (Pubitemid 35304230)
28. Khatib, S. ; Musa, R. ; Vaya, J. An exogenous marker: a novel approach for the characterization of oxidative stress. Bioorg Med Chem 15:3661-3666; 2007. (Pubitemid 46635149)
29. Khatib, S. ; Nerya, O. ; Musa, R. ; Tamir, S. ; Peter, T. ; Vaya, J. Enhanced substituted resorcinol hydrophobicity augments tyrosinase inhibition potency. J Med Chem 50:2676-2681; 2007. (Pubitemid 46896075)
30. Khersonsky, O. ; Tawfik, D. S. Structure-reactivity studies of serum paraoxonase PON1 suggest that its native activity is lactonase. Biochemistry 44:6371-6382; 2005. (Pubitemid 40570731)
31. Khersonsky, O. ; Tawfik, D. S. The histidine 115-histidine 134 dyad mediates the lactonase activity of mammalian serum paraoxonases. J Biol Chem 281:7649-7656; 2006. (Pubitemid 43847535)
32. Kriska, T. ; Marathe, G. K. ; Schmidt, J. C. ; McIntyre, T. M. ; Girotti, A. W. Phospholipase action of platelet-activating factor acetylhydrolase, but not paraoxonase-1, on long fatty acyl chain phospholipid hydroperoxides. J Biol Chem 282: 100-108; 2007. (Pubitemid 47076629)
33. La Du, B. N. Genetic Factors Influencing the Metabolism of Foreign Compounds. New York: (international encyclopedia of pharmacology and therapeutics), Pergamon Press; 1992.
34. La Du, B. N. ; Aviram, M. ; Billecke, S. ; Navab, M. ; Primo-Parmo, S. ; Sorenson, R. C. ; Standiford, T. J. On the physiological role(s) of the paraoxonases. Chem Biol Interact 119-120: 379-388; 1999. (Pubitemid 29278574)
35. Lusis, A. J. Atherosclerosis. Nature 407:233-241; 2000.
36. Lyons, M. A. ; Brown, A. J. 7-Ketocholesterol. Int J Biochem Cell Biol 31:369-375; 1999. (Pubitemid 29112897)
37. Mackness, B. ; Hunt, R. ; Durrington, P. N. ; Mackness, M. I. Increased immunolocalization of paraoxonase, clusterin, and apolipoprotein A-I in the human artery wall with the progression of atherosclerosis. Arterioscler Thromb Vasc Biol 17:1233-1238; 1997. (Pubitemid 27329844)
38. Mackness, B. ; Quarck, R. ; Verreth, W. ; Mackness, M. ; Holvoet, P. Human paraoxonase-1 overexpression inhibits atherosclerosis in a mouse model of metabolic syndrome. Arterioscler Thromb Vasc Biol 26:1545-1550; 2006. (Pubitemid 44288981)
39. Marathe, G. K. ; Zimmerman, G. A. ; McIntyre, T. M. Platelet-activating factor acetylhydrolase, and not paraoxonase-1, is the oxidized phospholipid hydrolase of high density lipoprotein particles. J Biol Chem 278:3937-3947; 2003. (Pubitemid 36801125)
40. March, J. Advanced Organic Chemistry. NewYork: Wiley-Interscience; 1985.
41. Murphy, R. C. ; Johnson, K. M. Cholesterol, reactive oxygen species, and the formation of biologically active mediators. J Biol Chem 283:15521-15525; 2008.
42. Navab, M. ; Berliner, J. A. ; Watson, A. D. ; Hama, S. Y. ; Territo, M. C. ; Lusis, A. J. ; Shih, D. M. ; Van Lenten, B. J. ; Frank, J. S. ; Demer, L. L. ; Edwards, P. A. ; Fogelman, A. M. The Yin and Yang of oxidation in the development of the fatty streak. A review based on the 1994 George Lyman Duff Memorial Lecture. Arterioscler Thromb Vasc Biol 16:831-842; 1996. (Pubitemid 26234980)
43. Paravicini, T. M. ; Touyz, R. M. NADPH oxidases, reactive oxygen species, and hypertension: clinical implications and therapeutic possibilities. Diabetes Care 31 (Suppl 2): S170-S180; 2008.
44. Parthasarathy, S. ; Litvinov, D. ; Selvarajan, K. ; Garelnabi, M. Lipid peroxidation and decomposition-conflicting roles in plaque vulnerability and stability. Biochim Biophys Acta 1781:221-231; 2008.
45. Rosenblat, M. ; Gaidukov, L. ; Khersonsky, O. ; Vaya, J. ; Oren, R. ; Tawfik, D. S. ; Aviram, M. The catalytic histidine dyad of high density lipoprotein-associated serum paraoxonase-1 (PON1) is essential for PON1-mediated inhibition of low density lipoprotein oxidation and stimulation of macrophage cholesterol efflux. J Biol Chem 281:7657-7665; 2006. (Pubitemid 43847536)
46. Rosenblat, M. ; Vaya, J. ; Shih, D. ; Aviram, M. Paraoxonase 1 (PON1) enhances HDL-mediated macrophage cholesterol efflux via the ABCA1 transporter in association with increased HDL binding to the cells: a possible role for lysophosphatidylcholine. Atherosclerosis 179: 69-77; 2005. (Pubitemid 40249787)
47. Rozenberg, O. ; Rosenblat, M. ; Coleman, R. ; Shih, D. M. ; Aviram, M. Paraoxonase (PON1) deficiency is associated with increased macrophage oxidative stress: studies in PON1-knockout mice. Free Radic Biol Med 34:774-784; 2003. (Pubitemid 36288542)
48. Rozenberg, O. ; Shih, D. M. ; Aviram, M. Human serum paraoxonase 1 decreases macrophage cholesterol biosynthesis: possible role for its phospholipase-A2-like activity and lysophosphatidylcholine formation. Arterioscler Thromb Vasc Biol 23:461-467; 2003. (Pubitemid 36337223)
49. Santanam, N. ; Parthasarathy, S. Aspirin is a substrate for paraoxonase-like activity: implications in atherosclerosis. Atherosclerosis 191:272-275; 2007. (Pubitemid 46415635)
50. Sheng, G. D. M. a. X. C. Yields of excited carbonyl species from alkoxy1 and from alkylperoxyl radical dismutations. J Am Chem Soc 113:8976-8977; 1991.
51. Shih, D. M. ; Welch, C. ; Lusis, A. J. New insights into atherosclerosis from studies with mouse models. Mol Med Today 1:364-372; 1995.
52. Skoczynska, A. The role of lipids in atherogenesis. Postepy Hig Med Dosw (Online) 59: 346-357; 2005.
53. Stadler, N. ; Stanley, N. ; Heeneman, S. ; Vacata, V. ; Daemen, M. J. ; Bannon, P. G. ;Waltenberger, J. ; Davies, M. J. Accumulation of zinc in human atherosclerotic lesions correlates with calcium levels but does not protect against protein oxidation. Arterioscler Thromb Vasc Biol 28:1024-1030; 2008. (Pubitemid 351544123)
54. Stocker, R. ; Keaney, J. F. , Jr. Role of oxidative modifications in atherosclerosis. Physiol Rev 84:1381-1478; 2004.
55. Szuchman, A. ; Aviram, M. ; Musa, R. ; Khatib, S. ; Vaya, J. Characterization of oxidative stress in blood from diabetic vs. hypercholesterolaemic patients, using a novel synthesized marker. Biomarkers 13:119-131; 2008.
56. Szuchman, A. ; Aviram, M. ; Soliman, K. ; Tamir, S. ; Vaya, J. Exogenous N-linoleoyl tyrosine marker as a tool for the characterization of cellular oxidative stress in macrophages. Free Radic Res 40:41-52; 2006. (Pubitemid 43023784)
57. Tavori, H. ; Aviram, M. ; Khatib, S. ; Musa, R. ; Nitecki, S. ; Hofman, A. ; Vaya, J. Human carotid atherosclerotic plaque increases oxidative stress of macrophages and LDL, whereas paraoxonase 1 (PON1) decreases such atherogenic effects. Free Radic Biol Med 46:607-15;2009.
58. Tavori, H. ; Khatib, S. ; Aviram, M. ; Vaya, J. Characterization of the PON1 active site using modeling simulation, in relation to PON1 lactonase activity. Bioorg Med Chem 16: 7504-7509; 2008.
59. Teiber, J. F. ; Draganov, D. I. ; La Du, B. N. Lactonase and lactonizing activities of human serum paraoxonase (PON1) and rabbit serum PON3. Biochem Pharmacol 66:887-896; 2003. (Pubitemid 37083585)
60. Vaya, J. ; Aviram, M. ; Mahmood, S. ; Hayek, T. ; Grenadir, E. ; Hoffman, A. ; Milo, S. Selective distribution of oxysterols in atherosclerotic lesions and human plasma lipoproteins. Free Radic Res 34:485-497; 2001. (Pubitemid 32492688)
61. Vejux, A. ;Malvitte, L. ; Lizard, G. Side effects of oxysterols: cytotoxicity, oxidation, inflammation, and phospholipidosis. Braz J Med Biol Res 41:545-556; 2008.
62. Wamil, M. ; Andrew, R. ; Chapman, K. E. ; Street, J. ; Morton, N. M. ; Seckl, J. R. 7-Oxysterols modulate glucocorticoid activity in adipocytes through competition for 11{beta}-hydroxysteroid dehydrogense type 11. Endocrinology 149(12):5907-5908; 2008.
63. Watson, A. D. ; Berliner, J. A. ; Hama, S. Y. ; La Du, B. N. ; Faull, K. F. ; Fogelman, A. M. ; Navab, M. Protective effect of high density lipoprotein associated paraoxonase. Inhibition of the biological activity of minimally oxidized low density lipoprotein. J Clin Invest 96:2882-2891; 1995.
64. Williams, K. J. ; Feig, J. E. ; Fisher, E. A. Rapid regression of atherosclerosis: insights from the clinical and experimental literature. Nat Clin Pract Cardiovasc Med 5:91-102; 2008. (Pubitemid 351168064)