The Repair of the Tobacco Specific Nitrosamine Derived Adduct O6-[4-Oxo-4-(3-pyridyl)butyl]guanine by O6-Alkylguanine-DNA Alkyltransferase Variants

RS Mijal, NM Thomson, NL Fleischer… - Chemical research in …, 2004 - ACS Publications
The tobacco specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a
potent pulmonary carcinogen, both methylates and pyridyloxobutylates DNA. Both reaction …

Stereospecific deuterium substitution attenuates the tumorigenicity and metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone …

JR Jalas, EJ McIntee, PMJ Kenney… - Chemical research in …, 2003 - ACS Publications
Stereochemical determinants of the tumorigenicity and metabolism of the tobacco-specific
nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) were investigated using …

Bis (hydroxyphenylethyl) deoxyguanosine adducts identified by phosphorus-32-postlabeling and four-sector tandem mass spectrometry: Unanticipated adducts …

S Kaur, K Pongracz, WJ Bodell… - Chemical research in …, 1993 - ACS Publications
Calf thymus DNA was incubated with [8-14C] styrene oxide in vitro, and six covalent
xenobiotic-DNA adducts were detected using the [32P]-postlabeling procedure. Adducts 1-3 …

Mass spectrometric quantitation of apurinic/apyrimidinic sites in tissue DNA of rats exposed to tobacco-specific nitrosamines and in lung and leukocyte DNA of …

J Guo, H Chen, P Upadhyaya, Y Zhao… - Chemical research in …, 2020 - ACS Publications
Metabolic activation of the carcinogenic tobacco-specific nitrosamines 4-(methylnitrosamino)-
1-(3-pyridyl)-1-butanone (NNK) and N′-nitrosonornicotine (NNN) results in formation of …

Mass spectrometric analysis of tobacco-specific nitrosamine-DNA adducts in smokers and nonsmokers

PG Foiles, SA Akerkar, SG Carmella… - Chemical research in …, 1991 - ACS Publications
9) for smokers and 0.9±2.3 (= 8) for nonsmokers. Mean adduct levels in tracheobronchus
were 16±18 (= 4) for smokers and 0.9±1.7 (= 4) for nonsmokers. These are the first …

Human CYP2A6 activation of 4-(methylnitrosamino)-l-(3-pyridyl)-1-butanone (NNK): mutational specificity in the gpt gene of AS52 cells

HF Tiano, RL Wang, M Hosokawa, C Crespi… - …, 1994 - academic.oup.com
Abstract The tobacco-specific nitrosamine 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone
(NNK) is a potential human carcinogen that is known to be metabolized to DNA-reactive …

Detection and characterization of two major ethylated deoxyguanosine adducts by high performance liquid chromatography, electrospray mass spectrometry, and 32P …

R Singh, GMA Sweetman, PB Farmer… - Chemical research in …, 1997 - ACS Publications
Postlabeling can be one of the most sensitive methods for the measurement of DNA
adducts. However, for the determination of alkylated adducts, essential requirements are …

Oxidative DNA damage in tissues of pregnant female mice and fetuses caused by the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone …

MA Sipowicz, S Amin, D Desai, KS Kasprzak… - Cancer letters, 1997 - Elsevier
The tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK),
induces the promutagenic oxidative-damage DNA lesion, 8-oxo-2′-deoxyguanosine (8-oxo …

Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human placental microsomes

NR Collazo, LG Sultatos - Biochemical pharmacology, 1995 - Elsevier
The tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) can
be activated metabolically by cytochrome (s) P450 to DNA-damaging agents that result in …

Biomarkers for human uptake and metabolic activation of tobacco-specific nitrosamines

SS Hecht, SG Carmella, PG Foiles, SE Murphy - Cancer research, 1994 - AACR
Tobacco-specific nitrosamines are a group of carcinogens formed from nicotine and related
tobacco alkaloids. Two of these compounds, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone …