ArticleChemical research in toxicology2007
Covalent modification of microsomal lipids by thiobenzamide metabolites in vivo.
Article in Chemical research in toxicology, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 31 citations in OpenAlex.
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- Pregnane X receptor activation potentiates ritonavir hepatotoxicity.The Journal of clinical investigation · 2019Article
- Flavin-containing monooxygenase S-oxygenation of a series of thioureas and thiones.Toxicology and applied pharmacology · 2014Article
- Protein targets of thioacetamide metabolites in rat hepatocytes.Chemical research in toxicology · 2013Article
- Metabolism and toxicity of thioacetamide and thioacetamide S-oxide in rat hepatocytes.Chemical research in toxicology · 2012Article
- Covalent modification of lipids and proteins in rat hepatocytes and in vitro by thioacetamide metabolites.Chemical research in toxicology · 2012Article
- Identification of protein targets of reactive metabolites of tienilic acid in human hepatocytes.Chemical research in toxicology · 2012Article
- Metabolomic screening and identification of the bioactivation pathways of ritonavir.Chemical research in toxicology · 2011Article
- Synthesis of carbon-14, carbon-13 and deuterium labeled forms of thioacetamide and thioacetamideJournal of labelled compounds & radiopharmaceuticals · 2011Article
- CYP3A-mediated generation of aldehyde and hydrazine in atazanavir metabolism.Drug metabolism and disposition: the biological fate of chemicals · 2011Article
- Bioinformatic analysis of xenobiotic reactive metabolite target proteins and their interacting partners.BMC chemical biology · 2009Article
- Protein targets of reactive metabolites of thiobenzamide in rat liver in vivo.Chemical research in toxicology · 2008Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
Thiobenzamide (TB) is hepatotoxic in rats causing centrolobular necrosis, steatosis, cholestasis, and hyperbilirubinemia. It serves as a model compound for a number of thiocarbonyl compounds that undergo oxidative bioactivation to chemically reactive metabolites. The hepatotoxicity of TB is strongly dependent on the electronic character of substituents in the meta- and para-positions, with Hammett rho values ranging from -4 to -2. On the other hand, ortho substituents that hinder nucleophilic addition to the benzylic carbon of S-oxidized TB metabolites abrogate the toxicity and protein covalent binding of TB. This strong linkage between the chemistry of TB and its metabolites and their toxicity suggests that this model is a good one for probing the overall mechanism of chemically induced biological responses. While investigating the protein covalent binding of TB metabolites, we noticed an unusually large amount of radioactivity associated with the lipid fraction of rat liver microsomes. Thin-layer chromatography showed that most of the radioactivity was contained in a single spot more polar than the neutral lipids but less polar than the phospholipid fractions. Mass spectral analyses aided by the use of synthetic standards identified the material as N-benzimidoyl derivatives of typical microsomal phosphatidylethanolamine (PE) lipids. Quantitative analysis indicated that up to 25% of total microsomal PE became modified within 5 h after a hepatotoxic dose of TB. Further studies will be required to determine the contribution of lipid modification to the hepatotoxicity of TB.
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