Reductive modification of a methionine residue in the amyloid-β peptide

Angewandte Chemie - International Edition

Volumn 45, Issue 16, 2006, Pages 2595-2598

  Kadlcik, Vojtech ^b   Sicard Roselli, Cécile ^b   Houée Levin, Chantal ^b   Kodicek, Milan ^c   Ferreri, Carla ^a   Chatgilialoglu, Chryssostomos ^a  

^a CNR   (Italy)

^b UNIVERSITÉ PARIS SUD   (France)

^c INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Lipids; Methionine; Peptides; Radicals; Radiolysis

Indexed keywords

METHIONINE; PEPTIDE-LIPOSOME MODEL; PEPTIDES; RADICALS;

CHEMICAL MODIFICATION; HYDROGEN; IRRADIATION; LIPIDS; PROTEINS; RADIOLYSIS; REDUCTION; SOLUTIONS;

NITROGEN COMPOUNDS;

AMYLOID BETA PROTEIN; FREE RADICAL; METHIONINE; PEPTIDE FRAGMENT; PHOSPHOLIPID;

ARTICLE; CATALYSIS; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; MASS SPECTROMETRY; OXIDATION REDUCTION REACTION;

AMYLOID BETA-PEPTIDES; AMYLOID BETA-PROTEIN; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FREE RADICALS; ISOMERISM; METHIONINE; OXIDATION-REDUCTION; PEPTIDE FRAGMENTS; PHOSPHOLIPIDS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 33746306230     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503942     Document Type: Article

References (28)

1. D. J. Selkoe, Physiol. Rev. 2001, 81, 741-766.
2. S. M. Yatin, S. Varadarajian, C. D. Link, D. A. Butterfield, Neurobiol. Aging 1999, 20, 325-330.
3. J. Kanski, M. Aksenova, C. Schöneich, D. A. Butterfield, Free Radical Biol. Med. 2002, 32, 1205-1211.
4. B. L. Miller, K. Kuczera, C. Schöneich, J. Am. Chem. Soc. 1998, 120, 3345-3356.
5. C. Schöneich, D. Pogocki, G. L. Hug, K. Bobrowski, J. Am. Chem. Soc. 2003, 125, 13 700-13 713.
6. B. Lipinski, Br. J. Nutr. 2002, 87, 93-94.
7. a) R. Shapira, G. Stein, Science 1968, 162, 1489-1491;
8. b) L. K. Mee, S. J. Adelstein, G. Stein, Radiat. Res. 1972, 52, 588-602;
9. c) N. N. Lichtin, J. Ogdan, G. Stein, Radiat. Res. 1973, 55, 69-80;
10. d) L. K. Mee, S. J. Adelstein, Radiat. Res. 1974, 60, 422-431;
11. e) N. N. Lichtin, A. Shafferman, Radiat. Res. 1974, 60, 432-440;
12. f) L. K. Mee, S. J. Adelstein, C. M. Steihart, N. N. Lichtin, Radiat. Res. 1977, 71, 493-504.
13. C. Ferreri, I. Manco, M. R. Faraone-Mennella, A. Torreggiani, M. Tamba, C. Chatgilialoglu, ChemBioChem 2004, 5, 1710-1712.
14. H. Houlden, R. Crook, R. J. Dolan, J. McLaughlin, T. Revesz, J. Hardy, Neurosci. Lett. 2001, 313, 93-95.
15. a) C. Chatgilialoglu, C. Ferreri, Acc. Chem. Res. 2005, 38, 441-448;
16. b) C. Ferreri, C. Chatgilialoglu, ChemBioChem 2005, 6, 1722-1734.
17. a) C. Chatgilialoglu, C. Ferreri, M. Ballestri, Q. G. Mulazzani, L. Landi, J. Am. Chem. Soc. 2000, 122, 4593-4601;
18. b) C. Ferreri, C. Costantino, L. Perrotta, L. Landi, Q. G. Mulazzani, C. Chatgilialoglu, J. Am. Chem. Soc. 2001, 123, 4459-4468;
19. c) C. Ferreri, A. Samadi, F. Sassatelli, L. Landi, C. Chatgilialoglu, J. Am. Chem. Soc. 2004, 126, 1063-1072.
20. M. Bokvist, F. Lindström, A. Watts, G. Gröbner, J. Mol. Biol. 2004, 335, 1039-1049.
21. J. F. K. Kramer, V. Fellner, M. E. R. Dugan, F. D. Sauer, M. M. Mossoba, M. P. Yurawecz, Lipids 1997, 32, 1219-1228.
22. a) G. V. Buxton, C. L. Greenstock, W. P. Helman, A. B. Ross, J. Phys. Chem. Ref. Data 1988, 17, 513-886;
23. b) A. B. Ross, W. G. Mallard, W. P. Helman, G. V. Buxton, R. E. Huie, P. Neta, NDRL-NIST Solution Kinetic Database - Version 3, Notre Dame Radiation Laboratory, Notre Dame, IN, and NIST Standard Reference Data, Gaithersburg, MD, 1998.
24. 2O under our conditions, even at the highest concentration of Aβ used.
25. . radicals or one-electron oxidants react with Aβ. See: V. Kadlcik, C. Sicard-Roselli, T. A. Mattioli, M. Kodicek, C. Houée-Levin, Free Radical Biol. Med. 2004, 37, 881-891.
26. The presence of a 4344.2-Da peak is not surprising, because this peak is also present and is even more intense in fractions with both shorter and longer elution times. It is probable that a mixture of 4344.2-Da products, corresponding to hydroxylation isomers, forms a background in this elution range.
27. S. Li, R. W. Roberts, Chem. Biol. 2003, 10, 233-239.
28. S. Kim, T.-J. Jeon, A. Oberai, D. Yang, J. J. Schmidt, J. U. Bowie, Proc. Natl. Acad. Sci. USA 2005, 102, 14 278-14 283.