Metabolism and DNA Adduct Formation of Tobacco-Specific N-Nitrosamines

Y Li, SS Hecht - International journal of molecular sciences, 2022 - mdpi.com
The tobacco-specific N-nitrosamines 4-(N-nitrosomethylamino)-1-(3-pyridyl)-1-butanone
(NNK) and N′-nitrosonornicotine (NNN) always occur together and exclusively in tobacco …

Recent studies on mechanisms of bioactivation and detoxification of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a tobacco-specific lung carcinogen

SS Hecht - Tobacco-Specific N-Nitrosamines Recent …, 2017 - api.taylorfrancis.com
This article reviews recent advances in the biochemistry and molecular biology of 4-
(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a tobacco-specific pulmonary car …

Identification of formaldehyde-induced DNA–RNA cross-links in the A/J mouse lung tumorigenesis model

RP Dator, KJ Murray, MW Luedtke… - Chemical research in …, 2022 - ACS Publications
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is a potent lung carcinogen present in
tobacco products, and exposure to it is likely one of the factors contributing to the …

Microsomal metabolism of delavirdine: evidence for mechanism-based inactivation of human cytochrome P450 3A

RL Voorman, SM Maio, NA Payne, Z Zhao… - … of Pharmacology and …, 1998 - ASPET
Administration of delavirdine, an HIV-1 reverse transcriptase inhibitor, to rats or monkeys
resulted in apparent loss of hepatic microsomal CYP3A and delavirdine desalkylation …

Extensive metabolic activation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers

I Stepanov, P Upadhyaya, SG Carmella, R Feuer… - … Biomarkers & Prevention, 2008 - AACR
(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is a potent lung carcinogen present in
both unburned tobacco and cigarette smoke. The sum of 4-(methylnitrosamino)-1-(3-pyridyl) …

[PDF][PDF] IARC monographs on the evaluation of carcinogenic risks to humans

F Lyon - … organization, International agency for research on …, 2014 - monographs.iarc.who.int
An IARC Advisory Group to Recommend Priorities for IARC Monographs during 2015–2019
met in Lyon, France, on 7–9 April 2014. Before the meeting, IARC solicited nominations of …

Synthesis of tobacco-specific N-nitrosamines and their metabolites and results of related bioassays

S Amin, D Desai, SS Hecht… - Tobacco-Specific N …, 2017 - api.taylorfrancis.com
Tobacco-specific A-nitrosamines (TSNA) are the most abundant, strong carcino gens in
tobacco smoke. Seven TSNA have been identified in tobacco products: N'-nitrosonornicotine …

Stereoselective Metabolism of Nicotine and Tobacco-Specific N-Nitrosamines to 4-Hydroxy-4-(3-pyridyl)butanoic Acid in Rats

N Trushin, SS Hecht - Chemical research in toxicology, 1999 - ACS Publications
The carcinogenic tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-
butanone (NNK) and N '-nitrosonornicotine (NNN) are believed to play a role in cancers …

Nitrosamines derived from nicotine and

SS Hecht, AR Tricker - … of nicotine and related compounds and …, 1999 - books.google.com
Model studies have shown that the reaction of nicotine with nitrous acid in aqueous solution
at pH 3.4 and 20 C yields three nitrosation products; 4-(methylnitrosamino)-4-(3-pyridyl) …

Disposition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in bile duct-cannulated rats …

Z Wu, P Upadhyaya, SG Carmella, SS Hecht… - …, 2002 - academic.oup.com
(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) is a chiral compound, and the primary
metabolite of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a major carcinogen in …