Quenching of singlet molecular oxygen by carnosine and related antioxidants. Monitoring 1270‐nm phosphorescence in aqueous media
Open accessAbstract
In order to elucidate the biochemical roles of imidazol‐containing dipeptides, we have studied quenching of singlet molecular oxygen (1O2) by carnosine (β‐alanyl‐L‐histidine), its structural components (L‐histidine, imidazole, and β‐alanine), and related natural free‐radical scavengers ‐ L‐anserine (β‐alanyl‐l‐methyl‐histidine), ergothioneine (2‐thiol‐ L‐histidine‐betaine), and taurine (2‐aminoethanesulfonic acid) in aqueous (D2O, pD 7) solutions by using monitoring of 1O2‐phosphorescence (1270‐nm). The rate constants of 1O2 quenching (Kq) by carnosine, anserine, and ergothioneine were shown to be similar [(3±1)×107 M‐1s‐1]. Their values resembled those of free L‐histidine [Kq=(4±1)×107 M‐1s‐1] and imidazole [Kq=(2±1)×107 M‐1s‐1]. Non‐aromatic amino acids ‐ taurine and β‐alanine ‐ showed very low quenching activities (Kq<3×103 M‐1c‐1). The Kq values did not correlate with the literature data on abilities of the tested compounds to stimulate muscle working capacities and inhibit myeloperoxidase‐catalyzed oxygenation. Thus, the dipeptides can be used as potent water‐soluble protectors against 102 attack whereas their natural biochemical functions are most probably determined by the processes of different nature.
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ERG can react with and detoxify, or prevent the formation of, hydroxyl radicals, singlet oxygen, ozone, superoxide, peroxide, hypochlorite and peroxynitrite.
“Although the literature is somewhat scattered and heterogeneous, it seems clear that as well as hydroxyl radicals(228–232), ERG can also react with and detoxify, or prevent the formation of, singlet oxygen(233–242), ozone(243), superoxide(231,241,244–246), peroxide(32,124,247,248), hypochlorite(32,232,249) and peroxynitrite(224,231,250,251).”
From The biology of ergothioneine, an antioxidant nutraceutical (2020) · cites this paper as [237]
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- Authors
- Egorov, S. Y., Kurella, E. G., Boldyrev, A. A., & Krasnovsky, A. A.
- Affiliations
- Russian Academy of Sciences (RU)
- Venue
- IUBMB Life
- Publisher
- Wiley
- Published
- 1997-04
- Volume
- 41
- Issue
- 4
- Pages
- 687-694
- ISSN
- 1521-6543 (ISSN-L)
- 1521-6551
- OpenAlex
- W2070917995
- Cited by
- 34
- References
- 2
- Citations by year
- 2025: 1 · 2024: 1 · 2023: 3 · 2022: 4 · 2021: 2 · 2020: 2 · 2019: 1 · 2018: 2 · 2015: 1 · 2014: 1 · 2013: 3 · 2012: 1
- FWCI
- 0.60
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- IUBMB Life (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Medicine › Physiology › Biochemical effects in animals
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Health Sciences › Medicine › Biochemistry › Phytochemicals and Antioxidant Activities
- Keywords
- singlet oxygen, singlet oxygen quenching, carnosine, histidine, imidazole, beta-alanine, ergothioneine, taurine, antioxidants, quenching rate constants, radical scavengers, myeloperoxidase inhibition
- MeSH terms
- Amino Acids, Anserine, Antioxidants, Carnosine, Ergothioneine, Imidazoles, Lasers, Luminescent Measurements, Oxygen, Spectrum Analysis, Free Radical Scavengers, Singlet Oxygen
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