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Cited by 9Free Radicals and AntioxidantsRedox biology and oxidative stressElectron Spin Resonance Studies

Intra and intermolecular charge effects on the reaction of the superoxide radical anion with semi-oxidized tryptophan in peptides and N-acetyl tryptophan

Santus, R., Patterson, L.K., Bazin, M., Mazière, J.C., Morlière, P.·1998·Free Radical Research
DOI 10.1080/10715769800300451
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Abstract

The reaction of the superoxide radical anion (O2-*), with the semi-oxidized tryptophan neutral radical (Trp*) generated from tryptophan (Trp) by pulse radiolysis has been observed in a variety of functionalized Trp derivatives including peptides. It is found that the reaction proceeds 4-5 times faster in positively charged peptides, such as Lys-Trp-Lys, Lys-Gly-Trp-Lys and Lys-Gly-Trp-Lys-O-tert-butyl, than in solutions of the negatively charged N-acetyl tryptophan (NAT). However, the reactivity of O2-* with the Trp* radical is totally inhibited upon binding of these peptides to micelles of negatively charged SDS and is reduced upon binding to native DNA. By contrast, no change in reactivity is observed in a medium containing CTAB, where the peptides cannot bind to the positively charged micelles. On the other hand, the reactivity of the Trp* radical formed from NAT with O2-* is reduced to half that of the free Trp* in buffer but is markedly increased in CTAB micelles. The models studied here incorporate elements of the complex environment in which Trp* and O2-* may be concomitantly formed in biological system and demonstrate the magnitude of the influence such elements may have on the kinetics of reactions involving these two species.

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  • Trp• reacts very rapidly with O2•− with second-order rate constants k in the range 0.7-2.2 × 10^9 M−1 s−1, mainly giving hydroperoxides in almost quantitative yields.

    “Trp• reacts very rapidly with O2•− with second order rate constants, k, in the range 0.7–2.2 × 109 M−1 s−1, the main initial products being hydroperoxides, in almost quantitative yields [145,146,147,148,149,150,151], Figure 56.”

    From Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity (2023) · cites this paper as [150]

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Authors
Santus, R., Patterson, L. K., Bazin, M., Mazière, J. C., & Morlière, P.
Affiliations
  • Inserm (FR)
  • University of Notre Dame (US)
ORCID
Venue
Free Radical Research
Publisher
Informa UK Limited
Published
1998-01
Volume
29
Issue
5
Pages
409-419
ISSN
  • 1029-2470 (ISSN-L)
  • 1071-5762
DOI
10.1080/10715769800300451
OpenAlex
W2011190304
Cited by
9
References
32
Citations by year
2025: 1 · 2023: 1 · 2020: 1 · 2018: 2
FWCI
0.60
Type
journal article
Language
en
Open access
closed
Locations
  • Free Radical Research (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Biophysics › Electron Spin Resonance Studies
Keywords
superoxide, tryptophan radical, intramolecular charge transfer, intermolecular charge transfer, reaction kinetics, sodium dodecyl sulfate micelles, CTAB micelles, DNA binding, pulse radiolysis
MeSH terms
Cetrimonium, Amino Acid Sequence, Anions, Cetrimonium Compounds, DNA, Electrochemistry, Micelles, Oxidation-Reduction, Peptides, Pulse Radiolysis, Sodium Dodecyl Sulfate, Superoxides, Tryptophan

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