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Book: Tobacco and Cancer

Dorothy K Hatsukami / Stephen S Hecht

The Science and the Story

2022

Keywords	Tobacco Carcinogenesis ; Tobacco Use History
Language	English
Size	450 p.
Publisher	WSPC
Document type	Book
Note	PDA Manuell_15
Format	157 x 235 x 29
ISBN	9789811239526 ; 9811239525
Database	PDA

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Article ; Online: Metabolic Activation and DNA Interactions of Carcinogenic N -Nitrosamines to Which Humans Are Commonly Exposed

Yupeng Li / Stephen S. Hecht

International Journal of Molecular Sciences, Vol 23, Iss 4559, p

2022 Volume 4559

Abstract: Carcinogenic N -nitrosamine contamination in certain drugs has recently caused great concern and the attention of regulatory agencies. These carcinogens—widely detectable in relatively low levels in food, water, cosmetics, and drugs—are well-established ... ...

Abstract	Carcinogenic N -nitrosamine contamination in certain drugs has recently caused great concern and the attention of regulatory agencies. These carcinogens—widely detectable in relatively low levels in food, water, cosmetics, and drugs—are well-established and powerful animal carcinogens. The electrophiles resulting from the cytochrome P450-mediated metabolism of N -nitrosamines can readily react with DNA and form covalent addition products (DNA adducts) that play a central role in carcinogenesis if not repaired. In this review, we aim to provide a comprehensive and updated review of progress on the metabolic activation and DNA interactions of 10 carcinogenic N -nitrosamines to which humans are commonly exposed. Certain DNA adducts such as O 6 -methylguanine with established miscoding properties play central roles in the cancer induction process, whereas others have been linked to the high incidence of certain types of cancers. We hope the data summarized here will help researchers gain a better understanding of the bioactivation and DNA interactions of these 10 carcinogenic N -nitrosamines and facilitate further research on their toxicologic and carcinogenic properties.
Keywords	N -nitrosamines ; metabolism ; DNA adducts ; NDMA ; P450s ; Biology (General) ; QH301-705.5 ; Chemistry ; QD1-999
Subject code	612
Language	English
Publishing date	2022-04-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Metabolism and DNA Adduct Formation of Tobacco-Specific N -Nitrosamines

Yupeng Li / Stephen S. Hecht

International Journal of Molecular Sciences, Vol 23, Iss 5109, p

2022 Volume 5109

Abstract: 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 products or in environments contaminated by tobacco smoke. They have been ... ...

Abstract	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 products or in environments contaminated by tobacco smoke. They have been classified as “carcinogenic to humans” by the International Agency for Research on Cancer. In 1998, we published a review of the biochemistry, biology and carcinogenicity of tobacco-specific nitrosamines. Over the past 20 years, considerable progress has been made in our understanding of the mechanisms of metabolism and DNA adduct formation by these two important carcinogens, along with progress on their carcinogenicity and mutagenicity. In this review, we aim to provide an update on the carcinogenicity and mechanisms of the metabolism and DNA interactions of NNK and NNN.
Keywords	metabolism ; DNA adducts ; tobacco-specific N -nitrosamines ; NNK ; NNN ; Biology (General) ; QH301-705.5 ; Chemistry ; QD1-999
Subject code	580
Language	English
Publishing date	2022-05-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Characterization and quantitation of busulfan DNA adducts in the blood of patients receiving busulfan therapy

Valeria Guidolin / Yupeng Li / Foster C. Jacobs / Margaret L. MacMillan / Peter W. Villalta / Stephen S. Hecht / Silvia Balbo

Molecular Therapy: Oncolytics, Vol 28, Iss , Pp 197-

2023 Volume 210

Abstract: DNA alkylating drugs have been used as cancer chemotherapy with variable outcomes. The establishment of predictive biomarkers to identify patients who will effectively respond to treatment would allow for the development of personalized therapies. As the ...

Abstract	DNA alkylating drugs have been used as cancer chemotherapy with variable outcomes. The establishment of predictive biomarkers to identify patients who will effectively respond to treatment would allow for the development of personalized therapies. As the degree of interaction of alkylating drug with DNA plays a key role in their mechanism of action, our hypothesis is that the measurement of the DNA adducts formed by alkylating drugs could be used to inform patient stratification. Beginning with busulfan, we took advantage of our DNA adductomic approach to characterize DNA adducts formed by reacting busulfan with calf-thymus DNA. Samples collected from six patients undergoing busulfan-based chemotherapy prior to allogeneic hematopoietic cell transplantation were analyzed for the presence of busulfan-derived DNA adducts. Among the 15 adducts detected in vitro, 12 were observed in the patient blood confirming the presence of a large profile of DNA adducts in vivo. Two of the detected adducts were structurally confirmed by comparison with synthetic standards and quantified in patients. These data confirm our ability to comprehensively characterize busulfan-derived DNA damage and set the stage for the development of methods to support personalized chemotherapy.
Keywords	precision medicine ; DNA adduct ; biomarker ; busulfan ; mass spectrometry ; alkylating agents ; Neoplasms. Tumors. Oncology. Including cancer and carcinogens ; RC254-282
Subject code	612 ; 610
Language	English
Publishing date	2023-03-01T00:00:00Z
Publisher	Elsevier
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: Analysis of N′-nitrosonornicotine enantiomers in human urine by chiral stationary phase liquid chromatography–nanoelectrospray ionization–high resolution tandem mass spectrometry

Yang, Jing / Stephen S. Hecht / Steven G. Carmella

Journal of chromatography. 2017 Feb. 15, v. 1044-1045

2017

Abstract: We have developed a chiral stationary phase liquid chromatography-nanoelectrospray ionization-high resolution tandem mass spectrometry (LC–NSI–HRMS/MS) method to investigate the enantiomeric composition of low parts per trillion amounts of the carcinogen ...

Abstract	We have developed a chiral stationary phase liquid chromatography-nanoelectrospray ionization-high resolution tandem mass spectrometry (LC–NSI–HRMS/MS) method to investigate the enantiomeric composition of low parts per trillion amounts of the carcinogen N'-nitrosonornicotine (NNN) in the urine of cigarette smokers and smokeless tobacco users. (S)-NNN is the major enantiomer in tobacco and is more carcinogenic than (R)-NNN in rats, but no data are available on the enantiomeric composition of NNN in humans. The method used [13C6]NNN as an internal standard and [pyridine-D4]nornicotine to monitor possible artifactual formation of NNN, which was found to be less than 2% of the quantified NNN. The enantiomeric composition of NNN (20.5±27.1fmol/mL urine) in 20 cigarette smokers was 67±5% (S)-NNN while that in 10 smokeless tobacco users (67.1±56.7 fmol/mL urine) was 56±3% (S)-NNN. These results demonstrate that the highly carcinogenic (S)-NNN is the major enantiomer in human urine, and that the enantiomeric composition of NNN in human urine is remarkably similar to that in cigarette smoke and smokeless tobacco. This is the first study to combine chiral stationary phase separations with nanoelectrospray ionization and high resolution tandem mass spectrometry to quantify trace levels of enantiomeric metabolites in human urine.
Keywords	carcinogens ; chromatography ; cigarettes ; enantiomers ; humans ; ionization ; metabolites ; nornicotine ; rats ; separation ; smokeless tobacco ; tandem mass spectrometry ; urine
Language	English
Dates of publication	2017-0215
Size	p. 127-131.
Publishing place	Elsevier B.V.
Document type	Article
ISSN	1570-0232
DOI	10.1016/j.jchromb.2017.01.008
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Identification of 4‑(3-Pyridyl)-4-oxobutyl-2′-deoxycytidine Adducts Formed in the Reaction of DNA with 4‑(Acetoxymethylnitrosamino)-1-(3-pyridyl)-1-butanone

Anna K. Michel / Adam T. Zarth / Pramod Upadhyaya / Stephen S. Hecht

ACS Omega, Vol 2, Iss 3, Pp 1180-

A Chemically Activated Form of Tobacco-Specific Carcinogens

2017 Volume 1190

Keywords	Chemistry ; QD1-999
Language	English
Publishing date	2017-03-01T00:00:00Z
Publisher	American Chemical Society
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Association of CYP2A6 activity with lung cancer incidence in smokers

Sungshim L Park / Sharon E Murphy / Lynne R Wilkens / Daniel O Stram / Stephen S Hecht / Loïc Le Marchand

PLoS ONE, Vol 12, Iss 5, p e

The multiethnic cohort study.

2017 Volume 0178435

Abstract: While smoking is the primary cause of lung cancer, only 11-24% of smokers develop the malignancy over their lifetime. The primary addictive agent in tobacco smoke is nicotine and variation in nicotine metabolism may influence the smoking levels of an ... ...

Abstract	While smoking is the primary cause of lung cancer, only 11-24% of smokers develop the malignancy over their lifetime. The primary addictive agent in tobacco smoke is nicotine and variation in nicotine metabolism may influence the smoking levels of an individual. Therefore, inter-individual variation in lung cancer risk among smokers may be due in part to differences in the activity of enzymes involved in nicotine metabolism. In most smokers, cytochrome P450 2A6 (CYP2A6)-catalyzed C-oxidation accounts for >75% of nicotine metabolism, and the activity of this enzyme has been shown to correlate with the amount of nicotine and carcinogens drawn from cigarettes. We prospectively evaluated the association of urinary biomarkers of nicotine uptake (total nicotine equivalents [TNE]) and CYP2A6 activity (ratio of urinary total trans-3'-hydroxycotinine to cotinine) with lung cancer risk among 2,309 Multiethnic Cohort Study participants who were current smokers at time of urine collection; 92 cases were diagnosed during a mean follow-up of 9.5 years. We found that higher CYP2A6 activity and TNE was associated with increased lung cancer risk after adjusting for age, sex, race/ethnicity, body mass index, smoking duration, and urinary creatinine (p's = 0.002). The association for CYP2A6 activity remained even after adjusting for self-reported cigarettes per day (CPD) (Hazard Ratio [HR] per unit increase in log-CYP2A6 activity = 1.52; p = 0.005) and after adjusting for TNE (HR = 1.46; p = 0.01). In contrast, the association between TNE and lung cancer risk was of borderline statistical significance when adjusted for CPD (HR = 1.53; p = 0.06) and not statistically significant when further adjusted for CYP2A6 activity (HR = 1.30; p = 0.22). These findings suggest that CYP2A6 activity provides information on lung cancer risk that is not captured by smoking history or a (short-term) biomarker of dose. CYP2A6 activity should be further studied as a risk biomarker for smoking-related lung cancer.
Keywords	Medicine ; R ; Science ; Q
Subject code	610
Language	English
Publishing date	2017-01-01T00:00:00Z
Publisher	Public Library of Science (PLoS)
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: Combined analysis of Nâ²-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in the urine of cigarette smokers and e-cigarette users

Kotandeniya, Delshanee / Makenzie E. Pillsbury / Stephen S. Hecht / Steven G. Carmella

Journal of Chromatography B. 2015 Dec. 15, v. 1007

2015

Abstract: A liquid chromatographyâelectrospray ionizationâtandem mass spectrometry (HPLCâESI+âMS/MS) method for the analysis of the tobacco-specific carcinogens Nâ²-nitrosonornicotine (NNN) and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) and ... ...

Abstract	A liquid chromatographyâelectrospray ionizationâtandem mass spectrometry (HPLCâESI+âMS/MS) method for the analysis of the tobacco-specific carcinogens Nâ²-nitrosonornicotine (NNN) and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) and their glucuronides (total NNN and total NNAL) in human urine was developed. The method has excellent accuracy and intra-day and inter-day precision, and limits of quantitation of 0.015 and 0.075pmol/mL urine, respectively, for total NNN and total NNAL. A unique aspect of this method is internal assessment of possible artifactual formation of NNN by inclusion of the monitor amine [pyridine-D4]nornicotine. We found that artifactual formation of NNN comprised only 2.5% of the measured amounts of total NNN in urine of cigarette smokers, under our conditions using ammonium sulfamate as an inhibitor of nitrosation. The method was applied to urine samples from cigarette smokers and e-cigarette users. Levels of total NNN and total NNAL in the urine of cigarette smokers averaged 0.060Â±0.035pmol/mL and 2.41Â±1.41pmol/mL urine, (N=38), respectively, which were both significantly greater than in the urine of 27 e-cigarette users.
Keywords	carcinogens ; chromatography ; humans ; nornicotine ; tandem mass spectrometry ; urine
Language	English
Dates of publication	2015-1215
Size	p. 121-126.
Publishing place	Elsevier B.V.
Document type	Article
ISSN	1570-0232
DOI	10.1016/j.jchromb.2015.10.012
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Effects of cessation of cigarette smoking on eicosanoid biomarkers of inflammation and oxidative damage.

Joseph P McElroy / Steven G Carmella / Alisa K Heskin / Mei Kuen Tang / Sharon E Murphy / Sarah A Reisinger / Joni A Jensen / Dorothy K Hatsukami / Stephen S Hecht / Peter G Shields

PLoS ONE, Vol 14, Iss 6, p e

2019 Volume 0218386

Abstract: The urinary metabolites "prostaglandin E2 metabolite" (PGE-M) and (Z)-7-[1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid (8-iso-PGF2α) are biomarkers of inflammation and oxidative damage, respectively, and are ... ...

Abstract	The urinary metabolites "prostaglandin E2 metabolite" (PGE-M) and (Z)-7-[1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid (8-iso-PGF2α) are biomarkers of inflammation and oxidative damage, respectively, and are elevated in cigarette smokers. Relatively little is known about the effects of smoking cessation on these biomarkers. To investigate this, current cigarette smokers interested in quitting were recruited and invited to participate in a smoking cessation study where varenicline (Chantix) and brief supportive behavioral counseling were offered at each visit after baseline. Subjects returned to the clinic during the 12 week treatment phase for 9 visits post cessation on days 3, 7, 14, 21, 28, 42, 56, 70 and 84. Urine samples were collected at each visit and analyzed by liquid chromatography-tandem mass spectrometry for PGE-M, 8-iso-PGF2α, and cotinine. Cotinine values demonstrated that 15 of 38 subjects quit smoking for the entire 84 day period. Significant decreases in mean levels of PGE-M and 8-iso-PGF2α per milligram creatinine were observed in these subjects, by 44% (p = 0.0014) and 27% (p<0.001), respectively. The results of this study demonstrate that cessation of smoking for 84 days results in modest but significant declines in urinary PGE-M and 8-iso-PGF2α indicating reductions in systemic inflammation and oxidative damage. Given that levels were only modestly decreased, these markers are not specific to tobacco-smoke exposure. The modest declines in these biomarkers should be considered when planning studies with ex-smokers. There is a "hangover" from smoking that lasts at least 3 months.
Keywords	Medicine ; R ; Science ; Q
Language	English
Publishing date	2019-01-01T00:00:00Z
Publisher	Public Library of Science (PLoS)
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: Effect of cigarette smoking on urinary 2-hydroxypropylmercapturic acid, a metabolite of propylene oxide

Zarth, Adam T / Chap T. Le / Stephen S. Hecht / Steven G. Carmella

Journal of Chromatography B. 2014 Mar. 15, v. 953-954

2014

Abstract: 2-Hydroxypropylmercapturic acid (2-HPMA) is a urinary biomarker of exposure to propylene oxide, a mutagen and carcinogen to which humans are exposed through inhalation of cigarette smoke as well as in certain environmental and occupational settings. 2- ... ...

Abstract	2-Hydroxypropylmercapturic acid (2-HPMA) is a urinary biomarker of exposure to propylene oxide, a mutagen and carcinogen to which humans are exposed through inhalation of cigarette smoke as well as in certain environmental and occupational settings. 2-HPMA is the final product of a detoxification pathway in which propylene oxide is conjugated with glutathione, and the resulting conjugate is further metabolized and excreted. We have developed and validated a liquid chromatography-atmospheric pressure chemical ionizationâtandem mass spectrometric (LC-APCIâMS/MS) method for the rapid quantitation of 2-HPMA in human urine. The method was applied to an analysis of urine samples from 40 smokers and 40 nonsmokers as well as from a group of 15 subjects who quit smoking. The results demonstrate that smokers have significantly (P<0.001) higher levels of urinary 2-HPMA (median=480pmol/mg creatinine) than do nonsmokers (208pmol/mg). Similarly, subjects who quit smoking for four weeks exhibited a significant (P<0.001) 52% median decrease in urinary 2-HPMA upon cessation. Approximately 5% of all urine samples had unusually high levels of 2-HPMA (>10 times higher than the median), apparently unrelated to tobacco smoke exposure or available demographic data. The method presented here can be used to rapidly quantify an individual's exposure to propylene oxide via tobacco smoke or other sources.
Keywords	biomarkers ; breathing ; carcinogens ; chromatography ; creatinine ; glutathione ; humans ; mass spectrometry ; metabolites ; mutagenicity ; propylene oxide ; rapid methods ; smoking (habit) ; urinalysis ; urine
Language	English
Dates of publication	2014-0315
Size	p. 126-131.
Publishing place	Elsevier B.V.
Document type	Article
ISSN	1570-0232
DOI	10.1016/j.jchromb.2014.02.001
Database	NAL-Catalogue (AGRICOLA)

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