7H-Dibenzo[c,g]carbazole: Metabolic pathways and toxicity.

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ID: 102982
2020
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Abstract
7H-Dibenzo[c,g]carbazole (DBC), a local and systemic carcinogen in animal studies, is a common environmental pollutant. It generally co-occurs in a variety of organic complex mixtures derived from incomplete combustion of organic matter. Despite high lipophilicity, DBC is more water-soluble and faster metabolized than the homocyclic aromatics. Moreover, greater polarity, high bioaccumulation potential, and persistence in the environment may imply DBC's higher biological significance and impact on human health, even at lower concentrations. The biotransformation pathways of DBC are incompletely known and the ultimate carcinogenic metabolite(s) are not clearly identified as yet. Structure-biological studies suggest two ways of activation: at the ring carbon atoms and at the pyrrole nitrogen. It is supposed that the particular pathway of biotransformation might be connected with the tissue/organ specificity of DBC. Cytochrome P450 (CYP) family of enzymes plays a pivotal role in the metabolism of DBC; though, the one-electron activation and the aldo-keto reductase-catalyzed oxidation are also involved in metabolic activation. Additionally, DBC can be photoactivated even at physiologically relevant doses of UVA light due to the extended aromatic ring system resulting in strong genotoxicity and oxidative stress. The goal of this review is to summarize current knowledge on mechanisms of DBC activation and possible implications for toxicity, genotoxicity, and carcinogenicity.
Reference Key
gabelova20207hdibenzocgcarbazolechemicobiological Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Gabelova, Alena;
Journal Chemico-biological interactions
Year 2020
DOI
S0009-2797(19)32079-4
URL
Keywords
genotoxicity 7h-dibenzo[c,g]carbazole cytochrome p450 enzymes dna-adducts gene mutations photoactivation

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