Formation of cholesterol ozonolysis products through an ozone-free mechanism mediated by the myeloperoxidase-H2O2-chloride system

Biochemical and Biophysical Research Communications

Volumn 383, Issue 2, 2009, Pages 222-227

  Tomono, Susumu ^a   Miyoshi, Noriyuki ^a   Sato, Kazuaki ^b   Ohba, Yoshihiro ^b   Ohshima, Hiroshi ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b YAMAGATA UNIVERSITY   (Japan)

Author keywords

Atheronal; Cholesterol; Hypochlorous acid; Myeloperoxidase; Ozone; Singlet oxygen

Indexed keywords

3BETA HYDROXY 5 BETA HYDROXY B NORCHOLESTANE 6 BETA CARBOXALDEHYDE; BENZOIC ACID DERIVATIVE; BETA CAROTENE; BETA HYDROXY 5 OXO 5,6-SECOCHOLESTAN 6 AL; CHLORIDE; CHOLESTANOL; CHOLESTEROL; HYDROGEN PEROXIDE; HYPOCHLOROUS ACID; IMMUNOGLOBULIN G; METHIONINE; MYELOPEROXIDASE; OXYGEN; OZONE; REACTIVE OXYGEN METABOLITE; SODIUM AZIDE; UNCLASSIFIED DRUG; VINYLBENZOIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; OXIDATION KINETICS; OZONOLYSIS; PH MEASUREMENT; PRIORITY JOURNAL; REDUCTION KINETICS; SYNTHESIS;

CHOLESTEROL; HUMANS; HYDROGEN PEROXIDE; OZONE; PEROXIDASE;

EID: 67349288542     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2009.03.155     Document Type: Article

References (20)

1. Klebanoff S.J. Myeloperoxidase: friend and foe. J. Leukoc. Biol. 77 (2005) 598-625
2. Wentworth Jr. P., McDunn J.E., Wentworth A.D., Takeuchi C., Nieva J., Jones T., Bautista C., Ruedi J.M., Gutierrez A., Janda K.D., Babior B.M., Eschenmoser A., and Lerner R.A. Evidence for antibody-catalyzed ozone formation in bacterial killing and inflammation. Science 298 (2002) 2195-2199
3. Wentworth Jr. P., Nieva J., Takeuchi C., Galve R., Wentworth A.D., Dilley R.B., DeLaria G.A., Saven A., Babior B.M., Janda K.D., Eschenmoser A., and Lerner R.A. Evidence for ozone formation in human atherosclerotic arteries. Science 302 (2003) 1053-1056
4. Zhang Q., Powers E.T., Nieva J., Huff M.E., Dendle M.A., Bieschke J., Glabe C.G., Eschenmoser A., Wentworth Jr. P., Lerner R.A., and Kelly J.W. Metabolite-initiated protein misfolding may trigger Alzheimer's disease. Proc. Natl. Acad. Sci. USA 101 (2004) 4752-4757
5. Bosco D.A., Fowler D.M., Zhang Q., Nieva J., Powers E.T., Wentworth Jr. P., Lerner R.A., and Kelly J.W. Elevated levels of oxidized cholesterol metabolites in Lewy body disease brains accelerate alpha-synuclein fibrilization. Nat. Chem. Biol. 2 (2006) 249-253
6. Gumulka J., and Smith L.L. Ozonization of cholesterol. J. Am. Chem. Soc. 105 (1983) 1972-1979
7. Jaworski K., and Smith L.L. Ozonization of cholesterol in nonparticipating solvents. J. Org. Chem. 53 (1988) 545-554
8. Paryzek Z., Martynow J., and Swoboda W. The reaction of cholesterol with ozone and alcohols: a revised mechanism and structure of the principle structure. J. Chem. Soc. Perkin Trans. 1 (1990) 1222-1223
9. Babior B.M., Takeuchi C., Ruedi J., Gutierrez A., and Wentworth Jr. P. Investigating antibody-catalyzed ozone generation by human neutrophils. Proc. Natl. Acad. Sci. USA 100 (2003) 3031-3034
10. Nieva J., and Wentworth Jr. P. The antibody-catalyzed water oxidation pathway-a new chemical arm to immune defense?. Trends Biochem. Sci. 29 (2004) 274-278
11. Kettle A.J., Clark B.M., and Winterbourn C.C. Superoxide converts indigo to isatin sulfonic acid: implications for the hypothesis that neutrophils produce ozone. J. Biol. Chem. 279 (2004) 18521-18525
12. Brinkhorst J., Nara S.J., and Pratt D.A. Hock cleavage of cholesterol 5alpha-hydroperoxide: an ozone-free pathway to the cholesterol ozonolysis products identified in arterial plaque and brain tissue. J. Am. Chem. Soc. 130 (2008) 12224-12225
13. Khan A.U., and Kasha M. Singlet molecular oxygen evolution upon simple acidification of aqueous hypochlorite: application to studies on the deleterious health effects of chlorinated drinking water. Proc. Natl. Acad. Sci. USA 91 (1994) 12362-12364
14. Aubry J.M., Cazin B., and Duprat F. Chemical sources of singlet oxygen. 3. Peroxidation of water-soluble singlet oxygen carriers with the hydrogen peroxide-molybdate system. J. Org. Chem. 54 (1989) 726-728
15. Wang K., Bermudez E., and Pryor W.A. The ozonation of cholesterol: separation and identification of 2,4-dinitrophenylhydrazine derivatization products of 3 beta-hydroxy-5-oxo-5,6-secocholestan-6-al. Steroids 58 (1993) 225-229
16. Sies H., and Stahl W. Vitamins E and C, beta-carotene, and other carotenoids as antioxidants. Am. J. Clin. Nutr. 62 (1995) 1315S-1321S
17. Hazen S.L., Hsu F.F., Mueller D.M., Crowley J.R., and Heinecke J.W. Human neutrophils employ chlorine gas as an oxidant during phagocytosis. J. Clin. Invest. 98 (1996) 1283-1289
18. Sathishkumar K., Haque M., Perumal T.E., Francis J., and Uppu R.M. A major ozonation product of cholesterol, 3beta-hydroxy-5-oxo-5,6-secocholestan-6-al, induces apoptosis in H9c2 cardiomyoblasts. FEBS Lett. 579 (2005) 6444-6450
19. Sathishkumar K., Murthy S.N., and Uppu R.M. Cytotoxic effects of oxysterols produced during ozonolysis of cholesterol in murine GT1-7 hypothalamic neurons. Free Radic. Res. 41 (2007) 82-88
20. Scheinost J.C., Wang H., Boldt G.E., Offer J., and Wentworth Jr. P. Cholesterol seco-sterol-induced aggregation of methylated amyloid-beta peptides-insights into aldehyde-initiated fibrillization of amyloid-beta. Angew. Chem. Int. Ed. Engl. 47 (2008) 3919-3922