Chromatographic and spectrophotometric characterization of adducts formed during the reaction of trans,trans-muconaldehyde with sup 14 C-deoxyguanosine 5 prime -phosphate

Journal Article · Sat Jul 01 04:00:00 EDT 1989 · Environmental Health Perspectives; (USA)

DOI:https://doi.org/10.2307/3430782· OSTI ID:7195030

Latriano, L; Jeffrey, A M ^[1]; Witz, G; Goldstein, B D ^[2]

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1. Columbia Univ., New York, NY (USA)
2. Robert Woods Johnson Medical School, Piscataway, NJ (USA)

Mice liver microsomes oxidatively open the benzene ring to form trans,trans-muconaldehyde, a hematotoxic unsaturated aldehyde. In the present studies, 4.5 {mu}mole trans,trans-muconaldehyde was reacted with {sup 14}C-2{prime}deoxyguanosine 5{prime}-phosphate in phosphate buffer. Products were separated by high performance liquid chromatography (HPLC). Absorbance was monitored using a diode array detector, and aliquots of the HPLC eluant were collected for UV spectrophotometric analysis and scintillation counting. Under these conditions, deoxyguanosine 5{prime}-phosphate eluted at 12.5 min and muconaldehyde at 22.0 min. The HPLC and radioactivity profiles of the muconaldehyde/deoxyguanosine reaction mixture indicated the presence of multiple adducts. Three adducts were detected eluting at 36, 39, and 42 min, which represented approximately 2.5, 2.5, and 1% of the radioactivity, respectively. These adducts had similar UV spectra with absorption maxima between 334 and 347 nm. Another product of the reaction mixture, eluting at 19.0 min and accounting for 10% of the radioactivity, was also observed. This compound had absorption maxima at 348 and 372 nm. These results suggest that trans,trans-muconaldehyde can react with deoxyguanosine monophosphate in vitro under physiological conditions to form stable adducts. Studies are being conducted to determine the structure of these adducts and whether these adducts are formed by the reaction of DNA with muconaldehyde or metabolically activated benzene.

• OSTI ID: 7195030
• Journal Information: Environmental Health Perspectives; (USA), Journal Name: Environmental Health Perspectives; (USA) Vol. 82; ISSN 0091-6765; ISSN EVHPA
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
560300 -- Chemicals Metabolism & Toxicology
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ADDUCTS
ALDEHYDES
ANIMALS
AROMATICS
AZAARENES
BENZENE
BIOLOGICAL EFFECTS
BODY
CARBON 14 COMPOUNDS
CHROMATOGRAPHY
COUNTING TECHNIQUES
DIGESTIVE SYSTEM
DNA ADDUCTS
GLANDS
GUANOSINE
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
LABELLED COMPOUNDS
LIQUID COLUMN CHROMATOGRAPHY
LIVER
MAMMALS
METABOLISM
MICE
NUCLEOSIDES
NUCLEOTIDES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANS
PURINES
RADIOASSAY
REACTION INTERMEDIATES
RIBOSIDES
RODENTS
SCINTILLATION COUNTING
SEPARATION PROCESSES
SPECTRA
SPECTROPHOTOMETRY
ULTRAVIOLET SPECTRA
VERTEBRATES