ArticleChemical research in toxicology2013
Identification of stable benzo[a]pyrene-7,8-dione-DNA adducts in human lung cells.
Article in Chemical research in toxicology, 2013. 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, 36 citations in OpenAlex.
- Detection of the Carcinogen Benzo[Analytical chemistry · 2026Article
- Cigarette smoking enhances the metabolic activation of the polycyclic aromatic hydrocarbon phenanthrene in humans.Carcinogenesis · 2021Article
- Identification and quantification of phenanthrene ortho-quinones in human urine and their association with lipid peroxidation.Environmental pollution (Barking, Essex : 1987) · 2020Article
- Cytochrome bArchives of toxicology · 2018Article
- Formation and Biological Targets of Quinones: Cytotoxic versus Cytoprotective Effects.Chemical research in toxicology · 2017Article
- Genotoxicity ofToxicology research · 2017Article
- Human Microdosing with Carcinogenic Polycyclic Aromatic Hydrocarbons: In Vivo Pharmacokinetics of Dibenzo[def,p]chrysene and Metabolites by UPLC Accelerator Mass Spectrometry.Chemical research in toxicology · 2016Article
- Human Biomonitoring of DNA Adducts by Ion Trap Multistage Mass Spectrometry.Current protocols in nucleic acid chemistry · 2016Article
- Human aldo-keto reductases and the metabolic activation of polycyclic aromatic hydrocarbons.Chemical research in toxicology · 2014Review
- Inhibitory action of benzo[α]pyrene on hepatic lipoprotein receptors in vitro and on liver lipid homeostasis in mice.PloS one · 2014Article
- Interception of benzo[a]pyrene-7,8-dione by UDP glucuronosyltransferases (UGTs) in human lung cells.Chemical research in toxicology · 2013Article
- The Role of Human Aldo-Keto Reductases in the Metabolic Activation and Detoxication of Polycyclic Aromatic Hydrocarbons: Interconversion of PAH Catechols and PAH o-Quinones.Frontiers in pharmacology · 2012Article
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3 authors at 1 institution in 1 country.
Funding
Abstract
Metabolic activation of the proximate carcinogen benzo[a]pyrene-7,8-trans-dihydrodiol (B[a]P-7,8-trans-dihydrodiol) by aldo-keto reductases (AKRs) leads to B[a]P-7,8-dione that is both electrophilic and redox-active. B[a]P-7,8-dione generates reactive oxygen species resulting in oxidative DNA damage in human lung cells. However, information on the formation of stable B[a]P-7,8-dione-DNA adducts in these cells is lacking. We studied stable DNA adduct formation of B[a]P-7,8-dione in human lung adenocarcinoma A549 cells, human bronchoalveolar H358 cells, and immortalized human bronchial epithelial HBEC-KT cells. After treatment with 2 μM B[a]P-7,8-dione, the cellular DNA was extracted from the cell pellets subjected to enzyme hydrolysis and subsequent analysis by LC-MS/MS. Several stable DNA adducts of B[a]P-7,8-dione were only detected in A549 and HBEC-KT cells. In A549 cells, the structures of stable B[a]P-7,8-dione-DNA adducts were identified as hydrated-B[a]P-7,8-dione-N(2)-2'-deoxyguanosine and hydrated-B[a]P-7,8-dione-N1-2'-deoxyguanosine. In HBEC-KT cells, the structures of stable B[a]P-7,8-dione-DNA adducts were identified as hydrated-B[a]P-7,8-dione-2'-deoxyadenosine, hydrated-B[a]P-7,8-dione-N1- or N3-2'-deoxyadenosine, and B[a]P-7,8-dione-N1- or N3-2'-deoxyadenosine. In each case, adduct structures were characterized by MS(n) spectra. Adduct structures were also compared to those synthesized from reactions of B[a]P-7,8-dione with either deoxyribonucleosides or salmon testis DNA in vitro but were found to be different.
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