Molecular mechanisms of DNA damage initiated by. alpha. ,. beta. -unsaturated carbonyl compounds as criteria for genotoxicity and mutagenicity

Journal Article · Wed Aug 01 00:00:00 EDT 1990 · Environmental Health Perspectives; (USA)

DOI:https://doi.org/10.1289/ehp.908899· OSTI ID:5839611

Eder, E; Hoffman, C; Bastian, H; Deininger, C; Scheckenbach, S ^[1]

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1. Univ. Wuerzburg (West Germany)

{alpha},{beta}-Unsaturated carbonyl compounds are important not only from a theoretical but also a practical standpoint. These ubiquitous compounds can interact with DNA through various mechanisms. The predominant interaction is the formation of cyclic 1,N{sup 2}-deoxyguanosine adducts; 7,8-cyclic guanine adducts are also found. The authors have synthesized and characterized the stereoisomers of adducts formed by about 20 {alpha},{beta}-unsaturated carbonyl compounds. The different types of adducts and the mutagenic and genotoxic response can be explained by the molecular structures of the agents. Metabolic epoxidation of the double bond and other metabolic activation, e.g., activation of the nitrogroups via nitroreductases, were also found to contribute to genotoxic and mutagenic activities. The results have further elucidated the genotoxic mechanisms of these compounds; however, additional investigations are required for a complete understanding of the genotoxic activity of this class of compounds.

• OSTI ID: 5839611
• Journal Information: Environmental Health Perspectives; (USA), Journal Name: Environmental Health Perspectives; (USA) Vol. 88; ISSN 0091-6765; ISSN EVHPA
• Country of Publication: United States
• Language: English

Related Subjects

550601 -- Medicine-- Unsealed Radionuclides in Diagnostics
560300* -- Chemicals Metabolism & Toxicology
62 RADIOLOGY AND NUCLEAR MEDICINE
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ADDUCTS
AROMATICS
AZAARENES
BACTERIA
BARYONS
BIOLOGICAL EFFECTS
CARBONYLS
DNA ADDUCTS
ELEMENTARY PARTICLES
EMISSION SPECTRA
FERMIONS
GENETIC EFFECTS
GUANOSINE
HADRONS
HETEROCYCLIC COMPOUNDS
MAGNETIC RESONANCE
MICROORGANISMS
MOLECULAR BIOLOGY
MUTAGENESIS
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
NUCLEONS
NUCLEOSIDES
NUCLEOTIDES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PROTONS
PURINES
RESONANCE
RIBOSIDES
SALMONELLA
SALMONELLA TYPHIMURIUM
SPECTRA