Prostaglandin H synthase catalyzed oxidation of hydroquinone to a sulfhydryl-binding and DNA-damaging metabolite

Journal Article · · Chemical Research in Toxicology; (USA)

DOI:https://doi.org/10.1021/tx00016a010· OSTI ID:6320014

Schlosser, M J; Shurina, R D; Kalf, G F ^[1]

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1. Jefferson Medical College of Thomas Jefferson Univ., Philadelphia, PA (USA)

Hydroquinone, a metabolite that accumulates in bone marrow following benzene exposure, was oxidized by prostaglandin H synthase (PHS) to 1,4-benzoquinone, which was measured by HPLC with reductive electrochemistry. Hydroquinone metabolism in the presence of cysteine generated a thiol adduct, which was identified as the monosubstituted cysteine conjugate of hydroquinone by HPLC with oxidative electrochemical and radiochemical detection. The time-dependent formation of both 1,4-benzoquinone and the monocysteine-hydroquinone conjugate was monitored spectrophotometrically at 250 and 305 nm, respectively. Because prostaglandin synthesis is elevated in bone marrow following benzene exposure and inhibitors of PHS cyclooxygenase prevent benzene-induced myelotoxicity, the activation of hydroquinone by PHS represents a possible mechanism for benzene's effects.

• OSTI ID: 6320014
• Journal Information: Chemical Research in Toxicology; (USA), Journal Name: Chemical Research in Toxicology; (USA) Vol. 3:4; ISSN CRTOE; ISSN 0893-228X
• Country of Publication: United States
• Language: English

Related Subjects

560300* -- Chemicals Metabolism & Toxicology
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AROMATICS
BENZENE
CHEMICAL ANALYSIS
CHEMICAL REACTIONS
CHEMISTRY
CHROMATOGRAPHY
DNA
ELECTROCHEMISTRY
HYDROCARBONS
LIQUID COLUMN CHROMATOGRAPHY
METABOLITES
NUCLEIC ACIDS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXIDATION
PROSTAGLANDINS
QUANTITATIVE CHEMICAL ANALYSIS
QUINONES
RADIOCHEMICAL ANALYSIS
SEPARATION PROCESSES