The DOI matches its Crossref record; 5 of the 5 references it cites were found in a registry or an index.
Free Radical Reactions of Methionine in Peptides: Mechanisms Relevant to β-Amyloid Oxidation and Alzheimer's Disease
Abstract
The pathogenesis of Alzheimer's disease is strongly associated with the formation and deposition of beta-amyloid peptide (beta AP) in the brain. This peptide contains a methionine (Met) residue in the C-terminal domain, which is important for its neurotoxicity and its propensity to reduce transition metals and to form reactive oxygen species. Theoretical studies have proposed the formation of beta AP Met radical cations as intermediates, but no experimental evidence with regard to formation and reactivity of these species in beta AP is available, largely due to the insolubility of the peptide. To define the potential reactions of Met radical cations in beta AP, we have performed time-resolved UV spectroscopic and conductivity studies with small model peptides, which show for the first time that (i) Met radical cations in peptides can be stabilized through bond formation with either the oxygen or the nitrogen atoms of adjacent peptide bonds; (ii) the formation of sulfur-oxygen bonds is kinetically preferred, but on longer time scales, sulfur-oxygen bonds convert into sulfur-nitrogen bonds in a pH-dependent manner; and (iii) ultimately, sulfur-nitrogen bonded radicals may transform intramolecularly into carbon-centered radicals located on the (alpha)C moiety of the peptide backbone.
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Cites
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Isolation and quantification of soluble Alzheimer's β-peptide from biological fluids
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Hensley, K., Carney, J. M., Mattson, M. P., Aksenova, M., Harris, M., Wu, J. F., Floyd, R. A., & Butterfield, D. A. (1994) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.91.8.3270 · Cited by 1,086
Atwood, C. S., Moir, R. D., Huang, X., Scarpa, R. C., Bacarra, N. M. E., Romano, D. M., Hartshorn, M. A., Tanzi, R. E., & Bush, A. I. (1998) · Journal of Biological Chemistry · doi:10.1074/jbc.273.21.12817 · Cited by 1,009
Different Mechanisms of Oxidative Stress and Neurotoxicity for Alzheimer‘s Aβ(1−42) and Aβ(25−35)
Varadarajan, S., Kanski, J., Aksenova, M., Lauderback, C., & Butterfield, D. A. (2001) · Journal of the American Chemical Society · doi:10.1021/ja010452r · Cited by 346
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Oxidative stress and the amyloid beta peptide in Alzheimer’s disease
Cheignon, C., Tomas, M., Bonnefont-Rousselot, D., Faller, P., Hureau, C., & Collin, F. (2018) · Redox Biology · doi:10.1016/j.redox.2017.10.014 · Cited by 2,185
Gaggelli, E., Kozlowski, H., Valensin, D., & Valensin, G. (2006) · Chemical Reviews · doi:10.1021/cr040410w · Cited by 1,729
The oxidative environment and protein damage
Davies, M. J. (2005) · Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics · doi:10.1016/j.bbapap.2004.08.007 · Cited by 1,392
Protein oxidation and peroxidation
Davies, M. J. (2016) · Biochemical Journal · doi:10.1042/bj20151227 · Cited by 952
Oxidative Stress and Neurotoxicity
Sayre, L. M., Perry, G., & Smith, M. A. (2008) · Chemical Research in Toxicology · doi:10.1021/tx700210j · Cited by 867
Metadata
- Authors
- Schöneich, C., Pogocki, D., Hug, G. L., & Bobrowski, K.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-10-18
- Volume
- 125
- Issue
- 45
- Pages
- 13700-13713
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2006126892
- Cited by
- 198
- References
- 5
- FWCI
- 6.88
- Type
- journal article
- Language
- en
- Open access
- closed
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