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Synergistic Effect between Human Papillomavirus 18 and 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone on Malignant Transformation of Immortalized SHEE Cells.
Chem Res Toxicol
February 2020
Beijing Key Laboratory of Environmental and Viral Oncology, College of Life Sciences and Bioengineering , Beijing University of Technology, Beijing 100124 , China.
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is an important tobacco-specific nitrosamine (TSNA) that induces malignant tumors in rodents. High-risk human papillomavirus (hr-HPV) infection is an important cause of several human cancers. Epidemiological evidence has shown that HPV cooperatively induces carcinogenesis with tobacco smoke.
View Article and Find Full Text PDFFormation, repair, and genotoxic properties of bulky DNA adducts formed from tobacco-specific nitrosamines.
J Nucleic Acids
September 2010
Division of Environmental Health Sciences, Masonic Cancer Center, Mayo Mail Code 806, 420 Delaware St SE, Minneapolis, MN 55455, USA.
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and N'-nitrosonornicotine (NNN) are tobacco-specific nitrosamines present in tobacco products and smoke. Both compounds are carcinogenic in laboratory animals, generating tumors at sites comparable to those observed in smokers. These Group 1 human carcinogens are metabolized to reactive intermediates that alkylate DNA.
View Article and Find Full Text PDFThe influence of repair pathways on the cytotoxicity and mutagenicity induced by the pyridyloxobutylation pathway of tobacco-specific nitrosamines.
Chem Res Toxicol
August 2009
Division of Environmental Health Sciences and Masonic Cancer Center, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Article Synopsis
- Tobacco-specific nitrosamines like 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone are known carcinogens that form DNA adducts capable of mutating genetic material.
- Research shows that these DNA adducts, particularly O(6)-pobdG, are linked to mutations, with NNKOAc causing higher cytotoxicity and mutations in cell lines lacking DNA repair mechanisms like AGT, BER, and NER.
- The study concludes that while certain repair pathways can fix specific lesions, they do not protect against the overall mutagenic effects of these tobacco-derived agents, particularly focusing on point mutations.
Quantitation of pyridyloxobutyl DNA adducts in nasal and oral mucosa of rats treated chronically with enantiomers of N'-nitrosonornicotine.
Chem Res Toxicol
May 2009
Department of Medicinal Chemistry and Masonic Cancer Center, University of Minnesota, MMC 806, 420 Delaware Street SE, Minneapolis, Minnesota 55455, USA.
N'-Nitrosonornicotine (NNN) is one of the most important strong carcinogens in tobacco products and is believed to play a significant role in the induction of esophageal cancer in smokers and oral cavity cancer in snuff dippers. NNN is metabolically activated through cytochrome P450-catalyzed alpha-hydroxylation. 2'-Hydroxylation produces a reactive intermediate 4-(3-pyridyl)-4-oxobutanediazohydroxide (7), which alkylates DNA to form pyridyloxobutyl (POB)-DNA adducts.
View Article and Find Full Text PDF4-Hydroxy-1-(3-pyridyl)-1-butanone-releasing DNA adducts in lung, lower esophagus and cardia of sudden death victims.
Toxicology
March 2008
Walther Straub Institute, Department of Toxicology, Ludwig-Maximilians University, Nussbaumstrasse 26, D-80336 Munich, Germany.
4-Hydroxy-l-(3-pyridyl)-l-butanone (HPB)-releasing adducts are formed by metabolic activation of N'-nitrosonornicotine and 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone and have been proposed as specific biomarkers for exposure to tobacco smoke. However, in several studies hemoglobin adducts releasing HPB were on average less than threefold higher in smokers compared to nonsmokers. Using an improved analytical method we have recently found a sevenfold difference in DNA adduct levels in the lung from smoking and nonsmoking lung cancer patients.
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