SCAVENGING OF SINGLET MOLECULAR OXYGEN BY IMIDAZOLE COMPOUNDS: HIGH and SUSTAINED ACTIVITIES OF CARBOXY TERMINAL HISTIDINE DIPEPTIDES and EXCEPTIONAL ACTIVITY OF IMIDAZOLE‐4‐ACETIC ACID
Abstract
Abstract— Singlet molecular oxygen was generated by illumination of phenosafranin in phosphate buffer at pH 7.5. Relative efficiencies of various imidazole compounds to form endoperoxides were assayed by following at 25°C the rate of light‐ and imidazole‐dependent bleaching of N,N‐dimethyl‐4‐nitrosoaniline. Of over 30 imidazole compounds tested, imidazole‐4‐acetic acid, a major catabolite of histamine in mammals, exhibited the highest activity. l‐Carnosine (β‐alanyl‐l‐histidine), a natural dipeptide prevalent in striated muscle of mammals, possessed several properties important for a physiologically significant scavenger of singlet oxygen. On a molar basis, this readily water‐soluble C‐terminal histidine dipeptide reacted with singlet oxygen two‐to four‐fold faster than free L‐histidine and approximately two‐fold faster than the N‐terminal l‐histidine dipeptides tested. Furthermore scavenging ability of L‐carnosine did not appreciably increase or decrease with time of reaction, in contrast to behaviors exhibited by a number of other imidazole compounds that included some other C‐terminal L‐histidine dipeptides. The fungal metabolite, ergothioneine, blocked singlet oxygen generation by illuminated phenosafranin.
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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 [235]
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The biology of ergothioneine, an antioxidant nutraceutical
Borodina, I., Kenny, L. C., McCarthy, C. M., Paramasivan, K., Pretorius, E., Roberts, T. J., van der Hoek, S. A., & Kell, D. B. (2020) · Nutrition Research Reviews · doi:10.1017/s0954422419000301 · Cited by 296 · see citing works
The antioxidant action of ergothioneine
Akanmu, D., Cecchini, R., Aruoma, O. I., & Halliwell, B. (1991) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(91)90158-f · Cited by 251 · see citing works
Protection of proteins from oxidative stress: a new illusion or a novel strategy?
BOLDYREV, A. A. (2005) · Annals of the New York Academy of Sciences · doi:10.1196/annals.1356.013 · Cited by 49 · see citing works
- Authors
- Hartman, P. E., Hartman, Z., & Ault, K. T.
- Affiliations
- Johns Hopkins University (US)
- Corresponding author
- Hartman, Philip E.
- Venue
- Photochemistry and Photobiology
- Publisher
- Wiley
- Published
- 1990-01
- Volume
- 51
- Issue
- 1
- Pages
- 59-66
- ISSN
- 0031-8655 (ISSN-L)
- 1751-1097
- OpenAlex
- W2075027811
- Cited by
- 121
- References
- 0
- Citations by year
- 2026: 5 · 2024: 2 · 2023: 4 · 2022: 7 · 2021: 6 · 2020: 5 · 2019: 7 · 2018: 5 · 2017: 1 · 2016: 1 · 2015: 2 · 2014: 5 · 2013: 3 · 2012: 2
- FWCI
- 2.86
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Photochemistry and Photobiology (publishedVersion)
- PubMed (publishedVersion)
- Funders
- U.S. Public Health Service (S07 07041)
- Topics
- Health Sciences › Medicine › Physiology › Biochemical effects in animals
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Keywords
- singlet oxygen, singlet oxygen scavenging, imidazole derivatives, imidazole-4-acetic acid, L-carnosine, histidine dipeptides, endoperoxide formation, phenosafranin, ergothioneine
- MeSH terms
- Carnosine, Dipeptides, Histamine, Histidine, Imidazoles, Kinetics, Oxygen, Phenazines, Photochemistry, Rose Bengal, Solubility, Singlet Oxygen
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