Stereospecific metabolism of the tobacco-specific nitrosamine, NNAL

S Kozlovich, G Chen, P Lazarus - Chemical research in toxicology, 2015 - ACS Publications
Among the most potent carcinogens in tobacco are the tobacco-specific nitrosamines
(TSNAs), with 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) being the most potent …

Prominent stereoselectivity of NNAL glucuronidation in upper aerodigestive tract tissues

S Kozlovich, G Chen, CJW Watson… - Chemical research in …, 2019 - ACS Publications
Tobacco specific nitrosamines (TSNAs) are among the most potent carcinogens found in
cigarettes and smokeless tobacco products. Decreases in TSNA detoxification, particularly 4 …

Stereoselective metabolism and tissue retention in rats of the individual enantiomers of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL), metabolites of the …

CL Zimmerman, Z Wu, P Upadhyaya… - …, 2004 - academic.oup.com
(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is reduced to its main metabolite, 4-
(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in a reaction that is both stereoselective …

Absolute configuration of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol formed metabolically from 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone.

SS Hecht, TE Spratt, N Trushin - Carcinogenesis, 1997 - academic.oup.com
(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) is an important metabolite of the tobacco-
specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Using the chiral …

Enantiomeric composition of N′-nitrosonornicotine and N′-nitrosoanatabine in tobacco

SG Carmella, EJ McIntee, M Chen, SS Hecht - Carcinogenesis, 2000 - academic.oup.com
The tobacco-specific nitrosamines N′-nitrosonornicotine (NNN) and N′-nitrosoanatabine
(NAT) are found in substantial quantities in unburned tobacco. Although this has been …

Association between glucuronidation genotypes and urinary NNAL metabolic phenotypes in smokers

G Chen, S Luo, S Kozlovich, P Lazarus - Cancer epidemiology, biomarkers & …, 2016 - AACR
Background: The most abundant and potent carcinogenic tobacco-specific nitrosamine in
tobacco and tobacco smoke is 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). In …

Stereochemistry of metabolites of a tobacco-specific lung carcinogen in smokers' urine

SG Carmella, M Ye, P Upadhyaya, SS Hecht - Cancer research, 1999 - AACR
(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a tobacco-specific lung carcinogen, is
believed to be important as a causative agent for lung cancer in smokers. NNK is extensively …

Identification of a prevalent functional missense polymorphism in the UGT2B10 gene and its association with UGT2B10 inactivation against tobacco-specific …

G Chen, RW Dellinger, CJ Gallagher… - Pharmacogenetics …, 2008 - journals.lww.com
Objective To study the potential association between UDP-glucuronosyltransferase (UGT)
2B10 genotypes and [4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol] NNAL-N …

Metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in the patas monkey: pharmacokinetics and characterization of …

SS Hecht, N Trushin, CA Reid-Quinn, ES Burak… - …, 1993 - academic.oup.com
The metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-
butanone (NNK) was examined in the patas monkey, in order to provide further information …

Formation and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol enantiomers in vitro in mouse, rat and human tissues

P Upadhyaya, SG Carmella, FP Guengerich… - …, 2000 - academic.oup.com
(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) is a major metabolite of the tobacco-
specific lung carcino-gen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). NNAL has …