nnk (BioDeep_00001871777)
Main id: BioDeep_00000011193
代谢物信息卡片
化学式: C10H13N3O2 (207.10077180000002)
中文名称: 4-甲基亚硝胺基-1-3-吡啶基-1-丁酮
谱图信息:
最多检出来源 Homo sapiens(blood) 31.88%
分子结构信息
SMILES: CN(CCCC(=O)C1=CN=CC=C1)N=O
InChI: InChI=1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3
描述信息
D009676 - Noxae > D002273 - Carcinogens
同义名列表
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:32692
- KEGG: C16453
- PubChem: 47289
- ChEMBL: CHEMBL2311069
- CAS: 64091-50-5
- CAS: 64091-91-4
- PubChem: 47205749
- PDB-CCD: 0QA
- NIKKAJI: J1.123A
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Shu-Chieh Hu, Seonggi Min, Hyun-Ki Kang, Dong-Jin Yang, Mallikarjuna Basavarajappa, Sherry M Lewis, Kelly J Davis, Ralph E Patton, Matthew S Bryant, Estatira Sepehr, Raul Trbojevich, Mason G Pearce, Michelle E Bishop, Wei Ding, Robert H Heflich, MacKean P Maisha, Robert Felton, Susan Chemerynski, Steven B Yee, Melis Coraggio, Hans Rosenfeldt, R Philip Yeager, Paul C Howard, Yunan Tang. 90-day nose-only inhalation toxicity study of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in Sprague-Dawley rats.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2022 Feb; 160(?):112780. doi:
10.1016/j.fct.2021.112780
. [PMID: 34965465] - Zhuo Qu, Lei Zhang, Ruilin Hou, Xueqin Ma, Jianqiang Yu, Wannian Zhang, Chunlin Zhuang. Exposure to a mixture of cigarette smoke carcinogens disturbs gut microbiota and influences metabolic homeostasis in A/J mice.
Chemico-biological interactions.
2021 Aug; 344(?):109496. doi:
10.1016/j.cbi.2021.109496
. [PMID: 33939976] - Laura P Stabile, Vinod Kumar, Autumn Gaither-Davis, Eric H Huang, Frank P Vendetti, Princey Devadassan, Sanja Dacic, Riyue Bao, Richard A Steinman, Timothy F Burns, Christopher J Bakkenist. Syngeneic tobacco carcinogen-induced mouse lung adenocarcinoma model exhibits PD-L1 expression and high tumor mutational burden.
JCI insight.
2021 02; 6(3):. doi:
10.1172/jci.insight.145307
. [PMID: 33351788] - Myung-Bae Park, Tae Sic Lee, Jee Eun Oh, Do Hoon Lee. Does the implementation of smoke-free laws and smoking culture affect exposure to tobacco smoking? Results from 3 hospitality settings in South Korea.
International journal of occupational medicine and environmental health.
2021 Jan; 34(1):53-67. doi:
10.13075/ijomeh.1896.01561
. [PMID: 33324012] - Benjamin W Chaffee, Peyton Jacob, Elizabeth T Couch, Neal L Benowitz. Exposure to a Tobacco-Specific Carcinogen Among Adolescent Smokeless Tobacco Users in Rural California, United States.
Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco.
2020 10; 22(10):1764-1771. doi:
10.1093/ntr/ntz147
. [PMID: 31504879] - Rumasha N T Kankanamage, Abhisek Brata Ghosh, Di Jiang, Karmel Gkika, Tia Keyes, Laura A Achola, Steven Suib, James F Rusling. Metabolites of Tobacco- and E-Cigarette-Related Nitrosamines Can Drive Cu2+-Mediated DNA Oxidation.
Chemical research in toxicology.
2020 08; 33(8):2072-2086. doi:
10.1021/acs.chemrestox.0c00027
. [PMID: 32672941] - Ingrid Elisia, Mariah Hay, Brandon Cho, Michelle Yeung, Sara Kowalski, Jennifer Wong, Vivian Lam, Meegan Larsen, Gerald Krystal. Low carbohydrate diets containing soy protein and fish oil slow the growth of established NNK-induced lung tumors.
Carcinogenesis.
2020 08; 41(8):1083-1093. doi:
10.1093/carcin/bgaa028
. [PMID: 32215551] - Yue Sun, Yanhui Han, Mingyue Song, Noppawat Charoensinphon, Jinkai Zheng, Peiju Qiu, Xian Wu, Hang Xiao. Inhibitory effects of nobiletin and its major metabolites on lung tumorigenesis.
Food & function.
2019 Nov; 10(11):7444-7452. doi:
10.1039/c9fo01966a
. [PMID: 31664275] - Yi Wang, Sreekanth Chanickal Narayanapillai, Qi Hu, Naomi Fujioka, Chengguo Xing. Detection and quantification of 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB) from smoker albumin and its potential as a surrogate biomarker of tobacco-specific nitrosamines exposure and bioactivation.
Toxicology letters.
2019 Sep; 311(?):11-16. doi:
10.1016/j.toxlet.2019.04.020
. [PMID: 31026483] - Han-Hsing Tsou, Hsiao-Tung Ko, Chia-Tzu Chen, Tse-Wen Wang, Chien-Hung Lee, Tsung-Yun Liu, Hsiang-Tsui Wang. Betel quid containing safrole enhances metabolic activation of tobacco specific 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK).
Environmental pollution (Barking, Essex : 1987).
2019 Aug; 251(?):13-21. doi:
10.1016/j.envpol.2019.04.080
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Carcinogenesis.
2019 05; 40(3):448-460. doi:
10.1093/carcin/bgz060
. [PMID: 30874285] - Alpana K Gupta, Sonam Tulsyan, Mausumi Bharadwaj, Ravi Mehrotra. Grass roots approach to control levels of carcinogenic nitrosamines, NNN and NNK in smokeless tobacco products.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2019 Feb; 124(?):359-366. doi:
10.1016/j.fct.2018.12.011
. [PMID: 30543893] - Rasika R Hudlikar, Venkatesh Pai, Rajiv Kumar, Rahul A Thorat, Sadhana Kannan, Arvind D Ingle, Girish B Maru, Manoj B Mahimkar. Dose-Related Modulatory Effects of Polymeric Black Tea Polyphenols (PBPs) on Initiation and Promotion Events in B(a)P and NNK-Induced Lung Carcinogenesis.
Nutrition and cancer.
2019; 71(3):508-523. doi:
10.1080/01635581.2019.1578389
. [PMID: 30857437] - Romel Dator, Linda B von Weymarn, Peter W Villalta, Cory J Hooyman, Laura A Maertens, Pramod Upadhyaya, Sharon E Murphy, Silvia Balbo. In Vivo Stable-Isotope Labeling and Mass-Spectrometry-Based Metabolic Profiling of a Potent Tobacco-Specific Carcinogen in Rats.
Analytical chemistry.
2018 10; 90(20):11863-11872. doi:
10.1021/acs.analchem.8b01881
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Chemical research in toxicology.
2018 09; 31(9):836-838. doi:
10.1021/acs.chemrestox.8b00155
. [PMID: 30136842] - Lucie Loukotková, Linda S VonTungeln, Michelle Vanlandingham, Gonçalo Gamboa da Costa. A simple and highly sensitive UPLC-ESI-MS/MS method for the simultaneous quantification of nicotine, cotinine, and the tobacco-specific carcinogens N'-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in serum samples.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2018 Jan; 1072(?):229-234. doi:
10.1016/j.jchromb.2017.11.022
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Cancer prevention research (Philadelphia, Pa.).
2018 01; 11(1):27-37. doi:
10.1158/1940-6207.capr-17-0119
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Cancer prevention research (Philadelphia, Pa.).
2017 Oct; 10(10):588-597. doi:
10.1158/1940-6207.capr-17-0198
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Tobacco control.
2016 11; 25(6):619-623. doi:
10.1136/tobaccocontrol-2015-052506
. [PMID: 26635031] - Jiexia Wen, Yan Pang, Tao Zhou, Ximing Qi, Min Zhao, Bin Xuan, Xiangcai Meng, Yunsheng Guo, Qingbin Liu, Huagang Liang, Yang Li, Hui Dong, Yimin Wang. Essential role of Na+/Ca2+ exchanger 1 in smoking-induced growth and migration of esophageal squamous cell carcinoma.
Oncotarget.
2016 Sep; 7(39):63816-63828. doi:
10.18632/oncotarget.11695
. [PMID: 27588478] - Jung Min Song, Arunkumar Anandharaj, Pramod Upadhyaya, Ameya R Kirtane, Jong-Hyuk Kim, Kwon Ho Hong, Jayanth Panyam, Fekadu Kassie. Honokiol suppresses lung tumorigenesis by targeting EGFR and its downstream effectors.
Oncotarget.
2016 Sep; 7(36):57752-57769. doi:
10.18632/oncotarget.10759
. [PMID: 27458163] - Kyeong-Nam Yu, Hyeon-Jeong Kim, Sanghwa Kim, Orkhouselenge Dawaadamdin, Ah-Young Lee, Sung-Ho Hong, Seung-Hee Chang, Seong-Jin Choi, Soon-Mi Shim, Kyuhong Lee, Myung-Haing Cho. Cigarette Smoking Condensate Disrupts Endoplasmic Reticulum-Golgi Network Homeostasis Through GOLPH3 Expression in Normal Lung Epithelial Cells.
Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco.
2016 09; 18(9):1877-1885. doi:
10.1093/ntr/ntw079
. [PMID: 27611309] - Nahid Moghbel, BoMi Ryu, Peter J Cabot, Angela Ratsch, Kathryn J Steadman. In vitro cytotoxicity of Nicotiana gossei leaves, used in the Australian Aboriginal smokeless tobacco known as pituri or mingkulpa.
Toxicology letters.
2016 07; 254(?):45-51. doi:
10.1016/j.toxlet.2016.05.011
. [PMID: 27178269] - Gang Chen, Shaman Luo, Shannon Kozlovich, Philip Lazarus. Association between Glucuronidation Genotypes and Urinary NNAL Metabolic Phenotypes in Smokers.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2016 07; 25(7):1175-1184. doi:
10.1158/1055-9965.epi-15-1245
. [PMID: 27197298] - Naomi Fujioka, Vincent Fritz, Pramod Upadhyaya, Fekadu Kassie, Stephen S Hecht. Research on cruciferous vegetables, indole-3-carbinol, and cancer prevention: A tribute to Lee W. Wattenberg.
Molecular nutrition & food research.
2016 06; 60(6):1228-38. doi:
10.1002/mnfr.201500889
. [PMID: 26840393] - Padmanabhan Srinivasan, Edwin C Thrower, Fred S Gorelick, Hamid M Said. Inhibition of pancreatic acinar mitochondrial thiamin pyrophosphate uptake by the cigarette smoke component 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone.
American journal of physiology. Gastrointestinal and liver physiology.
2016 05; 310(10):G874-83. doi:
10.1152/ajpgi.00461.2015
. [PMID: 26999808] - Jian-Min Yuan, Irina Stepanov, Sharon E Murphy, Renwei Wang, Sharon Allen, Joni Jensen, Lori Strayer, Jennifer Adams-Haduch, Pramod Upadhyaya, Chap Le, Mindy S Kurzer, Heather H Nelson, Mimi C Yu, Dorothy Hatsukami, Stephen S Hecht. Clinical Trial of 2-Phenethyl Isothiocyanate as an Inhibitor of Metabolic Activation of a Tobacco-Specific Lung Carcinogen in Cigarette Smokers.
Cancer prevention research (Philadelphia, Pa.).
2016 05; 9(5):396-405. doi:
10.1158/1940-6207.capr-15-0380
. [PMID: 26951845] - Binnian Wei, Benjamin C Blount, Baoyun Xia, Lanqing Wang. Assessing exposure to tobacco-specific carcinogen NNK using its urinary metabolite NNAL measured in US population: 2011-2012.
Journal of exposure science & environmental epidemiology.
2016 May; 26(3):249-56. doi:
10.1038/jes.2014.88
. [PMID: 25564369] - Samriddhi Shukla, Sonam Sinha, Sajid Khan, Sudhir Kumar, Kavita Singh, Kalyan Mitra, Rakesh Maurya, Syed Musthapa Meeran. Cucurbitacin B inhibits the stemness and metastatic abilities of NSCLC via downregulation of canonical Wnt/β-catenin signaling axis.
Scientific reports.
2016 Feb; 6(?):21860. doi:
10.1038/srep21860
. [PMID: 26905250] - Stephen S Hecht, Irina Stepanov, Steven G Carmella. Exposure and Metabolic Activation Biomarkers of Carcinogenic Tobacco-Specific Nitrosamines.
Accounts of chemical research.
2016 Jan; 49(1):106-14. doi:
10.1021/acs.accounts.5b00472
. [PMID: 26678241] - Eun Young Park, E Hwa Yun, Min Kyung Lim, Do-Hoon Lee, Wonho Yang, Bo Yoon Jeong, Sang-Hyun Hwang. Consequences of Incomplete Smoke-Free Legislation in the Republic of Korea: Results from Environmental and Biochemical Monitoring: Community Based Study.
Cancer research and treatment.
2016 Jan; 48(1):376-83. doi:
10.4143/crt.2014.269
. [PMID: 25943320] - Neal L Benowitz, Quan Gan, Maciej L Goniewicz, Wei Lu, Jiying Xu, Xinjian Li, Peyton Jacob, Stanton Glantz. Different profiles of carcinogen exposure in Chinese compared with US cigarette smokers.
Tobacco control.
2015 Dec; 24(e4):e258-63. doi:
10.1136/tobaccocontrol-2014-051945
. [PMID: 25535294] - Savithri Weerasooriya, Vijay P Jasti, Arindam Bose, Thomas E Spratt, Ashis K Basu. Roles of translesion synthesis DNA polymerases in the potent mutagenicity of tobacco-specific nitrosamine-derived O2-alkylthymidines in human cells.
DNA repair.
2015 Nov; 35(?):63-70. doi:
10.1016/j.dnarep.2015.09.023
. [PMID: 26460881] - Min-ting Li, Yong-yan Zhu, Li Li, Wen-na Wang, Yong-guan Yin, Quan-hong Zhu. Molecularly imprinted polymers on a silica surface for the adsorption of tobacco-specific nitrosamines in mainstream cigarette smoke.
Journal of separation science.
2015 Jul; 38(14):2551-7. doi:
10.1002/jssc.201500193
. [PMID: 25914259] - Sungshim L Park, Steven G Carmella, Xun Ming, Elizabeth Vielguth, Daniel O Stram, Loic Le Marchand, Stephen S Hecht. Variation in levels of the lung carcinogen NNAL and its glucuronides in the urine of cigarette smokers from five ethnic groups with differing risks for lung cancer.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2015 Mar; 24(3):561-9. doi:
10.1158/1055-9965.epi-14-1054
. [PMID: 25542827] - Valerie Zabala, Ming Tong, Rosa Yu, Teresa Ramirez, Emine B Yalcin, Silvia Balbo, Elizabeth Silbermann, Chetram Deochand, Kavin Nunez, Stephen Hecht, Suzanne M de la Monte. Potential contributions of the tobacco nicotine-derived nitrosamine ketone (NNK) in the pathogenesis of steatohepatitis in a chronic plus binge rat model of alcoholic liver disease.
Alcohol and alcoholism (Oxford, Oxfordshire).
2015 Mar; 50(2):118-31. doi:
10.1093/alcalc/agu083
. [PMID: 25618784] - Gerhard Lang, Aline Vuarnoz. Matrix-bound 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in tobacco: quantification and evidence for an origin from lignin-incorporated alkaloids.
Journal of natural products.
2015 Jan; 78(1):85-92. doi:
10.1021/np500725a
. [PMID: 25537002] - Silvia Balbo, Charles S Johnson, Ramesh C Kovi, Sandra A James-Yi, M Gerard O'Sullivan, Mingyao Wang, Chap T Le, Samir S Khariwala, Pramod Upadhyaya, Stephen S Hecht. Carcinogenicity and DNA adduct formation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and enantiomers of its metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in F-344 rats.
Carcinogenesis.
2014 Dec; 35(12):2798-806. doi:
10.1093/carcin/bgu204
. [PMID: 25269804] - Meng Jing, Yaohua Wang, Pramod Upadhyaya, Vipin Jain, Jian-Min Yuan, Dorothy K Hatsukami, Stephen S Hecht, Irina Stepanov. Liquid chromatography-electrospray ionization-tandem mass spectrometry quantitation of urinary [pyridine-D4]4-hydroxy-4-(3-pyridyl)butanoic acid, a biomarker of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolic activation in smokers.
Chemical research in toxicology.
2014 Sep; 27(9):1547-55. doi:
10.1021/tx5001915
. [PMID: 25098652] - Takahito Nishiyama, Nahoko Hayashi, Naoki Kakurai, Hiromi Yanagita, Ai Kuriyama, Chika Miyamoto, Yumi Ishihara, Kenichiro Ogura, Tomokazu Ohnuma, Akira Hiratsuka. Formation and stability of 4-(hydroxymethylnitrosamino)-1-(3-pyridyl)-1-butanone glucuronide, a stable form of reactive intermediate produced from 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, in mice.
The Journal of toxicological sciences.
2014 Aug; 39(4):515-21. doi:
10.2131/jts.39.515
. [PMID: 25056776] - Nada O F Kassem, Reem M Daffa, Sandy Liles, Sheila R Jackson, Noura O Kassem, Maram A Younis, Setoo Mehta, Menglan Chen, Peyton Jacob, Steve G Carmella, Dale A Chatfield, Neal L Benowitz, Georg E Matt, Stephen S Hecht, Melbourne F Hovell. Children's exposure to secondhand and thirdhand smoke carcinogens and toxicants in homes of hookah smokers.
Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco.
2014 Jul; 16(7):961-75. doi:
10.1093/ntr/ntu016
. [PMID: 24590387] - Irina Stepanov, Erin Sebero, Renwei Wang, Yu-Tang Gao, Stephen S Hecht, Jian-Min Yuan. Tobacco-specific N-nitrosamine exposures and cancer risk in the Shanghai Cohort Study: remarkable coherence with rat tumor sites.
International journal of cancer.
2014 May; 134(10):2278-83. doi:
10.1002/ijc.28575
. [PMID: 24243522] - Takahito Nishiyama, Kenichiro Ogura, Tomokazu Ohnuma, Akira Hiratsuka. Tissue distributions of 4-(hydroxymethylnitrosamino)-1-(3-pyridyl)-1-butanone glucuronide, a stable form of reactive intermediate produced from 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, in the rat.
The Journal of toxicological sciences.
2014 Apr; 39(2):263-7. doi:
10.2131/jts.39.263
. [PMID: 24646707] - Chiung-Wen Hu, Yu-Wen Hsu, Jian-Lian Chen, Lai-Man Tam, Mu-Rong Chao. Direct analysis of tobacco-specific nitrosamine NNK and its metabolite NNAL in human urine by LC-MS/MS: evidence of linkage to methylated DNA lesions.
Archives of toxicology.
2014 Feb; 88(2):291-9. doi:
10.1007/s00204-013-1137-y
. [PMID: 24057573] - Jian-Min Yuan, Lesley M Butler, Irina Stepanov, Stephen S Hecht. Urinary tobacco smoke-constituent biomarkers for assessing risk of lung cancer.
Cancer research.
2014 Jan; 74(2):401-11. doi:
10.1158/0008-5472.can-13-3178
. [PMID: 24408916] - Hong Zhou, Jayson X Chen, Chung S Yang, Mary Qu Yang, Youping Deng, Hong Wang. Gene regulation mediated by microRNAs in response to green tea polyphenol EGCG in mouse lung cancer.
BMC genomics.
2014; 15 Suppl 11(?):S3. doi:
10.1186/1471-2164-15-s11-s3
. [PMID: 25559244] - Fumiko Ninomiya, Masanao Yokohira, Sosuke Kishi, Yuko Nakano, Keiko Yamakawa, Tatsushi Inoue, Toshiya Kuno, Katsumi Imaida. Gender-dependent effects of gonadectomy on lung carcinogenesis by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in female and male A/J mice.
Oncology reports.
2013 Dec; 30(6):2632-8. doi:
10.3892/or.2013.2759
. [PMID: 24085151] - Jagan M R Patlolla, Li Qian, Laura Biddick, Yuting Zhang, Dhimant Desai, Shantu Amin, Stan Lightfoot, Chinthalapally V Rao. β-Escin inhibits NNK-induced lung adenocarcinoma and ALDH1A1 and RhoA/Rock expression in A/J mice and growth of H460 human lung cancer cells.
Cancer prevention research (Philadelphia, Pa.).
2013 Oct; 6(10):1140-9. doi:
10.1158/1940-6207.capr-13-0216
. [PMID: 23963803] - Brendan J Quinn, Matthew Dallos, Hiroshi Kitagawa, Ajaikumar B Kunnumakkara, Regan M Memmott, M Christine Hollander, Joell J Gills, Phillip A Dennis. Inhibition of lung tumorigenesis by metformin is associated with decreased plasma IGF-I and diminished receptor tyrosine kinase signaling.
Cancer prevention research (Philadelphia, Pa.).
2013 Aug; 6(8):801-10. doi:
10.1158/1940-6207.capr-13-0058-t
. [PMID: 23771523] - Shilpa Bhatnagar, Naveen Chaudhary, Deepshikha Pande Katare, S K Jain. A non-surgical method for induction of lung cancer in Wistar rats using a combination of NNK and high dietary fats.
Protoplasma.
2013 Aug; 250(4):919-29. doi:
10.1007/s00709-012-0478-3
. [PMID: 23315092] - Jianjun Wu, Ti Yang, Xun Li, Qiaoyuan Yang, Rong Liu, Jinkun Huang, Yuanqi Li, Chengfeng Yang, Yiguo Jiang. Alteration of serum miR-206 and miR-133b is associated with lung carcinogenesis induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone.
Toxicology and applied pharmacology.
2013 Mar; 267(3):238-46. doi:
10.1016/j.taap.2013.01.002
. [PMID: 23337359] - Irina Stepanov, John Muzic, Chap T Le, Erin Sebero, Peter Villalta, Bin Ma, Joni Jensen, Dorothy Hatsukami, Stephen S Hecht. Analysis of 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB)-releasing DNA adducts in human exfoliated oral mucosa cells by liquid chromatography-electrospray ionization-tandem mass spectrometry.
Chemical research in toxicology.
2013 Jan; 26(1):37-45. doi:
10.1021/tx300282k
. [PMID: 23252610] - Chi-Jung Chung, Yeong-Shiau Pu, Horng-Sheng Shiue, Hui-Ling Lee, Pinpin Lin, Hsiu-Yuan Yang, Chien-Tien Su, Yu-Mei Hsueh. 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism-related enzymes gene polymorphisms, NNK metabolites levels and urothelial carcinoma.
Toxicology letters.
2013 Jan; 216(1):16-22. doi:
10.1016/j.toxlet.2012.11.002
. [PMID: 23142425] - Chia-Chang Wu, Chien-Tien Su, Hui-Ling Lee, Chi-Jung Chung, Chao-Yuan Huang, Yeong-Shiau Pu, Pinpin Lin, Yu-Mei Hsueh. Joint effect of arsenic methylation profile and NNK metabolites on urothelial carcinoma.
The Journal of urology.
2012 Nov; 188(5):1701-5. doi:
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