» Articles » PMID: 3026319

Aromatic Hydroxylation As a Potential Measure of Hydroxyl-radical Formation in Vivo. Identification of Hydroxylated Derivatives of Salicylate in Human Body Fluids

Overview
Journal Biochem J
Specialty Biochemistry
Date 1986 Jul 15
PMID 3026319
Citations 47
Authors
Affiliations
Soon will be listed here.
Abstract

Attack by .OH radicals, generated by a Fenton system, upon salicylate produces 2,3-dihydroxybenzoate and 2,5-dihydroxybenzoate as major products and catechol as a minor product. H.p.l.c. separation combined with electrochemical detection was used to identify and quantify 2,3-dihydroxybenzoate and 2,5-dihydroxybenzoate in human plasma and synovial fluid. We propose that conversion of salicylate into 2,3-dihydroxybenzoate, or of other aromatic compounds into specific hydroxylated products, may be a useful assay for .OH formation in the human body.

Citing Articles

New Insights into Aspirin's Anticancer Activity: The Predominant Role of Its Iron-Chelating Antioxidant Metabolites.

Kontoghiorghes G Antioxidants (Basel). 2025; 14(1).

PMID: 39857363 PMC: 11763074. DOI: 10.3390/antiox14010029.


The Puzzle of Aspirin and Iron Deficiency: The Vital Missing Link of the Iron-Chelating Metabolites.

Kontoghiorghes G Int J Mol Sci. 2024; 25(10).

PMID: 38791185 PMC: 11121054. DOI: 10.3390/ijms25105150.


Molecular mechanism of the metal-independent production of hydroxyl radicals by thiourea dioxide and HO.

Mao L, Quan Z, Liu Z, Huang C, Wang Z, Tang T Proc Natl Acad Sci U S A. 2024; 121(14):e2302967120.

PMID: 38547063 PMC: 10998598. DOI: 10.1073/pnas.2302967120.


Primary Processes of Free Radical Formation in Pharmaceutical Formulations of Therapeutic Proteins.

Schoneich C Biomolecules. 2023; 13(7).

PMID: 37509177 PMC: 10376966. DOI: 10.3390/biom13071142.


Structural Features of Small Molecule Antioxidants and Strategic Modifications to Improve Potential Bioactivity.

Charlton N, Mastyugin M, Torok B, Torok M Molecules. 2023; 28(3).

PMID: 36770724 PMC: 9920158. DOI: 10.3390/molecules28031057.


References
1.
Floyd R, Watson J, Wong P . Sensitive assay of hydroxyl free radical formation utilizing high pressure liquid chromatography with electrochemical detection of phenol and salicylate hydroxylation products. J Biochem Biophys Methods. 1984; 10(3-4):221-35. DOI: 10.1016/0165-022x(84)90042-3. View

2.
DiGuiseppi J, Fridovich I . The toxicology of molecular oxygen. Crit Rev Toxicol. 1984; 12(4):315-42. DOI: 10.3109/10408448409044213. View

3.
Cleland L, Lowthian P, Imhoff D, Bochner F, Betts W, OCallaghan J . Plasma and synovial fluid gentisate in patients receiving salicylate therapy. J Rheumatol. 1985; 12(1):136-9. View

4.
Lawrence G, Cohen G . In vivo production of ethylene from 2-keto-4-methylthiobutyrate in mice. Biochem Pharmacol. 1985; 34(18):3231-6. DOI: 10.1016/0006-2952(85)90339-9. View

5.
Moorhouse C, Halliwell B, Grootveld M, Gutteridge J . Cobalt(II) ion as a promoter of hydroxyl radical and possible 'crypto-hydroxyl' radical formation under physiological conditions. Differential effects of hydroxyl radical scavengers. Biochim Biophys Acta. 1985; 843(3):261-8. DOI: 10.1016/0304-4165(85)90147-3. View