The oxidative stress metabolite 4-hydroxynonenal promotes Alzheimer protofibril formation

Biochemistry

Volumn 46, Issue 6, 2007, Pages 1503-1510

  Siegel, Sarah J ^a   Bieschke, Jan ^a,b   Powers, Evan T ^a   Kelly, Jeffery W ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b MAX DELBRÜCK CENTER FOR MOLECULAR MEDICINE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; LIPIDS; OLIGOMERS; OXIDATION; PATIENT MONITORING;

ALZHEIMER'S DISEASE (AD); OXIDATIVE STRESS; PEROXIDATION; PROTOFIBRIL; SCHIFF BASE;

METABOLITES;

4 HYDROXYNONENAL; AMYLOID BETA PROTEIN;

ALZHEIMER DISEASE; ARTICLE; CONTROLLED STUDY; COVALENT BOND; DISEASE ASSOCIATION; LIPID PEROXIDATION; METABOLITE; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN AGGREGATION; PROTEIN ASSEMBLY; PROTEIN CONFORMATION; PROTEIN INDUCTION; PROTEIN MODIFICATION; PROTEIN PROTEIN INTERACTION;

ALDEHYDES; ALZHEIMER DISEASE; AMYLOID BETA-PROTEIN; CHROMATOGRAPHY, GEL; HUMANS; OXIDATIVE STRESS; PEPTIDE FRAGMENTS; PROTEIN CONFORMATION; PROTEIN STRUCTURE, QUATERNARY; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 33846949357     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi061853s     Document Type: Article

References (38)

1. Tanzi, R. E., and Bertram, L. (2005) Twenty years of the Alzheimer's disease amyloid hypothesis: a genetic perspective, Cell 120, 545-555.
2. Hardy, J., and Selkoe, D. J. (2002) The amyloid hypothesis of Alzheimer's disease: progress and problems on the road to therapeutics, Science 297, 353-356.
3. Berg, L., McKeel, D. W., Jr., Miller, J. P., Storandt, M., Rubin, E. H., Morris, J. C., Baty, J., Coats, M., Norton, J., Goate, A. M., Price, J. L., Gearing, M., Mirra, S. S., and Saunders, A. M. (1998) Clinicopathologic studies in cognitively healthy aging and Alzheimer's disease: relation of histologic markers to dementia severity, age, sex, and apolipoprotein E genotype, Arch. Neurol. 55, 326-335.
4. Caughey, B., and Lansbury, P. T. (2003) Protofibrils, pores, fibrils, and neurodegeneration: separating the responsible protein aggregates from the innocent bystanders, Annu. Rev. Neurosci. 26, 267-298.
5. Cohen, E., Bieschke, J., Perciavalle, R. M., Kelly, J. W., and Dillin, A. (2006) Opposing activities protect against age onset proteotoxicity, Science 313, 1604-1610.
6. Lue, L. F., Kuo, Y. M., Roher, A. E., Brachova, L., Shen, Y., Sue, L., Beach, T., Kurth, J. H., Rydel, R. E., and Rogers, J. (1999) Soluble amyloid beta peptide concentration as a predictor of synaptic change in Alzheimer's disease, Am. J. Pathol. 155, 853-862.
7. McLean, C. A., Cherny, R. A., Fraser, F. W., Fuller, S. J., Smith, M. J., Beyreuther, K., Bush, A. I., and Masters, C. L. (1999) Soluble pool of Abeta amyloid as a determinant of severity of neurodegeneration in Alzheimer's disease, Ann. Neurol. 46, 860-866.
8. Dahlgren, K. N., Manelli, A. M., Stine, W. B., Jr., Baker, L. K., Krafft, G. A., and LaDu, M. J. (2002) Oligomeric and fibrillar species of amyloid-beta peptides differentially affect neuronal viability, J. Biol. Chem. 277, 32046-32053.
9. Lambert, M. P., Barlow, A. K., Chromy, B. A., Edwards, C., Freed, R., Liosatos, M., Morgan, T. E., Rozovsky, I., Trommer, B., Viola, K. L., Wals, P., Zhang, C., Finch, C. E., Krafft, G. A., and Klein, W. L. (1998) Diffusible, nonfibrillar ligands derived from Abeta1-42 are potent central nervous system neurotoxins, Proc. Natl. Acad. Sci. U.S.A. 95, 6448-6453.
10. Walsh, D. M., Klyubin, I., Fadeeva, J. V., Cullen, W. K., Anwyl, R., Wolfe, M. S., Rowan, M. J., and Selkoe, D. J. (2002) Naturally secreted oligomers of amyloid beta protein potently inhibit hippocampal long-term potentiation in vivo, Nature 416, 535-539.
11. Hartley, D. M., Walsh, D. M., Ye, C. P., Diehl, T., Vasquez, S., Vassilev, P. M., Teplow, D. B., and Selkoe, D. J. (1999) Protofibrillar intermediates of amyloid beta-protein induce acute electrophysiological changes and progressive neurotoxicity in cortical neurons, J. Neurosci. 19, 8876-8884.
12. Lesne, S., Koh, M. T., Kotilinek, L., Kayed, R., Glabe, C. G., Yang, A., Gallagher, M., and Ashe, K. H. (2006) A specific amyloid-beta protein assembly in the brain impairs memory, Nature 440, 352-357.
13. Baglioni, S., Casamenti, F., Bucciantini, M., Luheshi, L. M., Taddei, N., Chili, F., Dobson, C. M., and Stefani, M. (2006) Prefibrillar amyloid aggregates could be generic toxins in higher organisms, J. Neurosci. 26, 8160-8167.
14. Wentworth, P., Jr., 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. (2003) Evidence for ozone formation in human atherosclerotic arteries, Science 302, 1053-1056.
15. Bieschke, J., Zhang, Q., Powers, E. T., Lerner, R. A., and Kelly, J. W. (2005) Oxidative metabolites accelerate Alzheimer's amyloidogenesis by a two-step mechanism, eliminating the requirement for nucleation, Biochemistry 44, 4977-4983.
16. Zhang, Q., Powers, E. T., Nieva, J., Huff, M. E., Dendle, M. A., Bieschke, J., Glabe, C. G., Eschenmoser, A., Wentworth, P., Jr., Lerner, R. A., and Kelly, J. W. (2004) Metabolite-initiated protein misfolding may trigger Alzheimer's disease, Proc. Natl. Acad. Sci. U.S.A. 101, 4752-4757.
17. Bosco, D. A., Fowler, D. M., Zhang, Q., Nieva, J., Powers, E. T., Wentworth, P., Jr., Lerner, R. A., and Kelly, J. W. (2006) Elevated levels of oxidized cholesterol metabolites in Lewy body disease brains accelerate alpha-synuclein fibrilization, Nat. Chem. Biol. 2, 249-253.
18. Esterbauer, H., Schaur, R. J., and Zollner, H. (1991) Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes, Free Radical Biol. Med. 11, 81-128.
19. Ji, C., Amamath, V., Pietenpol, J. A., and Marnett, L. J. (2001) 4-hydroxynonenal induces apoptosis via caspase-3 activation and cytochrome c release, Chem. Res. Toxicol. 14, 1090-1096.
20. Pryor, W. A., and Porter, N. A. (1990) Suggested mechanisms for the production of 4-hydroxy-2-nonenal from the autoxidation of polyunsaturated fatty acids, Free Radical Biol. Med. 8, 541-543.
21. Uchida, K., and Stadtman, E. R. (1992) Modification of histidine residues in proteins by reaction with 4-hydroxynonenal, Proc. Natl. Acad. Sci. U.S.A. 89, 4544-4548.
22. Nadkami, D. V., and Sayre, L. M. (1995) Structural definition of early lysine and histidine adduction chemistry of 4-hydroxynonenal, Chem. Res. Toxicol. 8, 284-291.
23. Carini, M., Aldini, G., and Facino, R. M. (2004) Mass spectrometry for detection of 4-hydroxy-trans-2-nonenal (HNE) adducts with peptides and proteins, Mass Spectrom. Rev. 23, 281-305.
24. Szapacs, M. E., Riggins, J. N., Zimmerman, L. J., and Liebler, D. C. (2006) Covalent adduction of human serum albumin by 4-hydroxy-2-nonenal: kinetic analysis of competing alkylation reactions, Biochemistry 45, 10521-10528.
25. Zarkovic, K. (2003) 4-hydroxynonenal and neurodegenerative diseases, Mol. Aspects Med. 24, 293-303.
26. Sayre, L. M., Zelasko, D. A., Harris, P. L., Perry, G., Salomon, R. G., and Smith, M. A. (1997) 4-Hydroxynonenal-derived advanced lipid peroxidation end products are increased in Alzheimer's disease, J. Neurochem. 68, 2092-2097.
27. Markesbery, W. R., and Lovell, M. A. (1998) Four-hydroxynonenal, a product of lipid peroxidation, is increased in the brain in Alzheimer's disease, Neurobiol. Aging 19, 33-36.
28. McGrath, L. T., McGleenon, B. M., Brennan, S., McColl, D., Mc, I. S., and Passmore, A. P. (2001) Increased oxidative stress in Alzheimer's disease as assessed with 4-hydroxynonenal but not malondialdehyde, QJM: Monthly Journal of the Association of Physicians 94, 485-490.
29. Dianzani, M. U. (2003) 4-hydroxynonenal from pathology to physiology, Mol. Aspects Med. 24, 263-272.
30. Mehta, P. D., Pirttila, T., Patrick, B. A., Barshatzky, M., and Mehta, S. P. (2001) Amyloid beta protein 1-40 and 1-42 levels in matched cerebrospinal fluid and plasma from patients with Alzheimer disease, Neurosci. Lett. 304, 102-106.
31. Seubert, P., Vigo-Pelfrey, C., Esch, F., Lee, M., Dovey, H., Davis, D., Sinha, S., Schlossmacher, M., Whaley, J., Swindlehurst, C., McCormack, R., Wolfert, R., Selkoe, D., Lieberburg, I., and Schenk, D. (1992) Isolation and quantification of soluble Alzheimer's beta-peptide from biological fluids, Nature 359, 325-327.
32. Ando, Y., Brannstrom, T., Uchida, K., Nyhlin, N., Nasman, B., Suhr, O., Yamashita, T., Olsson, T., El Salhy, M., Uchino, M., and Ando, M. (1998) Histochemical detection of 4-hydroxynonenal protein in Alzheimer amyloid, J. Neurol. Sci. 156, 172-176.
33. Magni, F., Galbusera, C., Tremolada, L., Ferrarese, C., and Kienle, M. G. (2002) Characterisation of adducts of the lipid peroxidation product 4-hydroxy-2-nonenal and amyloid beta-peptides by liquid chromatography/ electrospray ionisation mass spectrometry, Rapid Commun. Mass Spectrom. 16, 1485-1493.
34. LeVine, H., III. (1993) Thioflavine T interaction with synthetic Alzheimer's disease beta-amyloid peptides: detection of amyloid aggregation in solution, Protein Sci. 2, 404-410.
35. Walsh, D. M., Lomakin, A., Benedek, G. B., Condron, M. M., and Teplow, D. B. (1997) Amyloid beta-protein fibrillogenesis. Detection of a protofibrillar intermediate, J. Biol. Chem. 272, 22364-22372.
36. Selkoe, D. J. (2001) Alzheimer's disease: genes, proteins, and therapy, Physiol. Rev. 81, 741-766.
37. Butterfield, D. A. (2002) Amyloid beta-peptide (1-42)-induced oxidative stress and neurotoxicity: implications for neurodegeneration in Alzheimer's disease brain. A review, Free Radical Res. 36, 1307-1313.
38. Behl, C. (2005) Oxidative stress in Alzheimer's disease: implications for prevention and therapy, Subcell. Biochem. 38, 65-78.