2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline (BioDeep_00000003642)
Secondary id: BioDeep_00001868140
human metabolite Endogenous
代谢物信息卡片
2-Amino-3,8-dimethylimidazo-[4,5-f]quinoxaline (MeIQx)
化学式: C11H11N5 (213.1014406)
中文名称: 2-氨基-3,8-二甲基咪唑并[4,5-f]喹恶啉
谱图信息:
最多检出来源 Viridiplantae(plant) 0.71%
分子结构信息
SMILES: CC1=CN=C2C=CC3=C(C2=N1)N=C(N3C)N
InChI: InChI=1S/C11H11N5/c1-6-5-13-7-3-4-8-10(9(7)14-6)15-11(12)16(8)2/h3-5H,1-2H3,(H2,12,15)
描述信息
2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline is found in animal foods. 2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline is a food-related mutagen isolated from cooked meats (especially grilled/barbecued
Food-related mutagen isolated from cooked meats (especies grilled/barbecued). 2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline is found in animal foods.
CONFIDENCE standard compound; INTERNAL_ID 2292
CONFIDENCE standard compound; INTERNAL_ID 6
D009676 - Noxae > D002273 - Carcinogens
D009676 - Noxae > D009153 - Mutagens
同义名列表
17 个代谢物同义名
2-Amino-3,8-dimethylimidazo-[4,5-f]quinoxaline (MeIQx); 3,8-Dimethyl-3H-imidazo[4,5-F]quinoxalin-2-amine, 9ci; 2-Amino-3,8-dimethyl-3H-imidazo(4,5-F)quinoxaline; 2-Amino-3,8-dimethyl-3H-imidazo[4,5-f]quinoxaline; 3,8-Dimethyl-3H-imidazo(4,5-F)quinoxalin-2-amine; 3,8-Dimethyl-3H-imidazo[4,5-F]quinoxalin-2-amine; 2-amino-3,8-dimethylimidazo[4,5-F ]Quinoxaline; 3,8-dimethylimidazo(4,5-F)Quinoxaline-2-amine; 2-amino-3,8-dimethylimidazo(4,5-F)Quinoxaline; 2-Amino-3,8-dimethylimidazo[4,5-F]quinoxaline; 3,8-dimethylimidazo[4,5-f]quinoxalin-2-amine; 8-Methyl-iqx; 3,8-DiMeIQX; Meiqx CPD; 8-MeIQX; Me-iqx; MeIQx
数据库引用编号
20 个数据库交叉引用编号
- ChEBI: CHEBI:76604
- KEGG: C19255
- PubChem: 62275
- HMDB: HMDB0029864
- Metlin: METLIN72975
- foodb: FDB001093
- chemspider: 56076
- CAS: 1185023-44-2
- CAS: 77500-04-0
- MoNA: UA000604
- MoNA: UA000603
- MoNA: AU229202
- MoNA: AU229201
- MoNA: UA000601
- MoNA: AU229206
- MoNA: AU229204
- MoNA: AU229203
- MoNA: AU229205
- PMhub: MS000010692
- PubChem: 124489927
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)
1 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
- Yong Li, Wei Quan, Junhui Wang, Zhiyong He, Fang Qin, Zhaojun Wang, Maomao Zeng, Jie Chen. Effects of ten vegetable oils on heterocyclic amine profiles in roasted beef patties using UPLC-MS/MS combined with principal component analysis.
Food chemistry.
2021 Jun; 347(?):128996. doi:
10.1016/j.foodchem.2020.128996. [PMID: 33508588] - Maïa Meurillon, Magaly Angénieux, Frédéric Mercier, Patrick Blinet, Laurent Chaloin, Sylvie Chevolleau, Laurent Debrauwer, Erwan Engel. Mitigation of heterocyclic aromatic amines in cooked meat. Part I: Informed selection of antioxidants based on molecular modeling.
Food chemistry.
2020 Nov; 331(?):127264. doi:
10.1016/j.foodchem.2020.127264. [PMID: 32619906] - Dan Song, Renpeng Guo, Haibo Huang, Peixiang Zheng, Hong Huang, Qinqin Oyang, Xiaoyue Xiao, Binran Wang, Jingtong Rong, Rong Liu. 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline Alters Autophagosome Maturation, Cellular Lipidomic Profiles, and Expression of Core Pluripotent Factors.
Journal of agricultural and food chemistry.
2019 Jul; 67(28):7977-7985. doi:
10.1021/acs.jafc.9b01041. [PMID: 30932489] - Falco Beer, Felix Urbat, Charles M A P Franz, Melanie Huch, Sabine E Kulling, Mirko Bunzel, Diana Bunzel. The Human Fecal Microbiota Metabolizes Foodborne Heterocyclic Aromatic Amines by Reuterin Conjugation and Further Transformations.
Molecular nutrition & food research.
2019 05; 63(10):e1801177. doi:
10.1002/mnfr.201801177. [PMID: 30815965] - Michael A Malfatti, Edward A Kuhn, Kenneth W Turteltaub, Selwyn M Vickers, Eric H Jensen, Lori Strayer, Kristin E Anderson. Disposition of the Dietary Mutagen 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline in Healthy and Pancreatic Cancer Compromised Humans.
Chemical research in toxicology.
2016 Mar; 29(3):352-8. doi:
10.1021/acs.chemrestox.5b00495. [PMID: 26918625] - Stephanie C Melkonian, Carrie R Daniel, Yuanqing Ye, Nizar M Tannir, Jose A Karam, Surena F Matin, Christopher G Wood, Xifeng Wu. Gene-environment interaction of genome-wide association study-identified susceptibility loci and meat-cooking mutagens in the etiology of renal cell carcinoma.
Cancer.
2016 Jan; 122(1):108-15. doi:
10.1002/cncr.29543. [PMID: 26551148] - Renato Tavares dos Santos Pereira, Felipe Augusto Dörr, Ernani Pinto, Marina Yazigi Solis, Guilherme Giannini Artioli, Alan Lins Fernandes, Igor Hisashi Murai, Wagner Silva Dantas, Antônio Carlos Seguro, Mirela Aparecida Rodrigues Santinho, Hamilton Roschel, Alain Carpentier, Jacques Remi Poortmans, Bruno Gualano. Can creatine supplementation form carcinogenic heterocyclic amines in humans?.
The Journal of physiology.
2015 Sep; 593(17):3959-71. doi:
10.1113/jp270861. [PMID: 26148133] - Kevin M Cooper, Natcha Jankhaikhot, Geraldine Cuskelly. Optimised extraction of heterocyclic aromatic amines from blood using hollow fibre membrane liquid-phase microextraction and triple quadrupole mass spectrometry.
Journal of chromatography. A.
2014 Sep; 1358(?):20-8. doi:
10.1016/j.chroma.2014.06.061. [PMID: 25037778] - Yan Zhang, Chundi Yu, Jingbo Mei, Shuo Wang. Formation and mitigation of heterocyclic aromatic amines in fried pork.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.
2013; 30(9):1501-7. doi:
10.1080/19440049.2013.809627. [PMID: 23862679] - Liliana Rounds, Cody M Havens, Yelena Feinstein, Mendel Friedman, Sadhana Ravishankar. Plant extracts, spices, and essential oils inactivate Escherichia coli O157:H7 and reduce formation of potentially carcinogenic heterocyclic amines in cooked beef patties.
Journal of agricultural and food chemistry.
2012 Apr; 60(14):3792-9. doi:
10.1021/jf204062p. [PMID: 22397498] - Hitomi Hayashi, Eriko Taniai, Reiko Morita, Masahiro Hayashi, Daichi Nakamura, Atsushi Wakita, Kazuhiko Suzuki, Makoto Shibutani, Kunitoshi Mitsumori. Enhanced liver tumor promotion but not liver initiation activity in rats subjected to combined administration of omeprazole and β-naphthoflavone.
The Journal of toxicological sciences.
2012; 37(5):969-85. doi:
10.2131/jts.37.969. [PMID: 23038005] - Kanithaporn Puangsombat, Wannee Jirapakkul, J Scott Smith. Inhibitory activity of Asian spices on heterocyclic amines formation in cooked beef patties.
Journal of food science.
2011 Oct; 76(8):T174-80. doi:
10.1111/j.1750-3841.2011.02338.x. [PMID: 21913920] - Padma Ambalam, J M Dave, Baboo M Nair, B R M Vyas. In vitro mutagen binding and antimutagenic activity of human Lactobacillus rhamnosus 231.
Anaerobe.
2011 Oct; 17(5):217-22. doi:
10.1016/j.anaerobe.2011.07.001. [PMID: 21777684] - Dan Gu, Melissa M Raymundo, Fred F Kadlubar, Robert J Turesky. Ultraperformance liquid chromatography-tandem mass spectrometry method for biomonitoring cooked meat carcinogens and their metabolites in human urine.
Analytical chemistry.
2011 Feb; 83(3):1093-101. doi:
10.1021/ac102918b. [PMID: 21194225] - Fernando De Andrés, Mohammed Zougagh, Gregorio Castañeda, Angel Ríos. Determination of heterocyclic amines in urine samples by capillary liquid chromatography with evaporated light-scattering detection.
Analytical and bioanalytical chemistry.
2010 May; 397(1):223-231. doi:
10.1007/s00216-009-3370-z. [PMID: 20396988] - Dan Gu, Lynn McNaughton, David Lemaster, Brian G Lake, Nigel J Gooderham, Fred F Kadlubar, Robert J Turesky. A comprehensive approach to the profiling of the cooked meat carcinogens 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, and their metabolites in human urine.
Chemical research in toxicology.
2010 Apr; 23(4):788-801. doi:
10.1021/tx900436m. [PMID: 20192249] - Kanithaporn Puangsombat, J Scott Smith. Inhibition of heterocyclic amine formation in beef patties by ethanolic extracts of rosemary.
Journal of food science.
2010 Mar; 75(2):T40-7. doi:
10.1111/j.1750-3841.2009.01491.x. [PMID: 20492265] - Rosa Busquets, Jan Ake Jönsson, Henrik Frandsen, Lluís Puignou, Maria Teresa Galceran, Kerstin Skog. Hollow fibre-supported liquid membrane extraction and LC-MS/MS detection for the analysis of heterocyclic amines in urine samples.
Molecular nutrition & food research.
2009 Dec; 53(12):1496-504. doi:
10.1002/mnfr.200800577. [PMID: 19810020] - Volker Mai, Quintece M McCrary, Rashmi Sinha, Michael Glei. Associations between dietary habits and body mass index with gut microbiota composition and fecal water genotoxicity: an observational study in African American and Caucasian American volunteers.
Nutrition journal.
2009 Oct; 8(?):49. doi:
10.1186/1475-2891-8-49. [PMID: 19845958] - Erin E Bessette, Angela K Goodenough, Sophie Langouët, Isil Yasa, Ivan D Kozekov, Simon D Spivack, Robert J Turesky. Screening for DNA adducts by data-dependent constant neutral loss-triple stage mass spectrometry with a linear quadrupole ion trap mass spectrometer.
Analytical chemistry.
2009 Jan; 81(2):809-19. doi:
10.1021/ac802096p. [PMID: 19086795] - Junichi Enokizono, Hiroyuki Kusuhara, Atsushi Ose, Alfred H Schinkel, Yuichi Sugiyama. Quantitative investigation of the role of breast cancer resistance protein (Bcrp/Abcg2) in limiting brain and testis penetration of xenobiotic compounds.
Drug metabolism and disposition: the biological fate of chemicals.
2008 Jun; 36(6):995-1002. doi:
10.1124/dmd.107.019257. [PMID: 18322075] - Monika Gibis. Effect of oil marinades with garlic, onion, and lemon juice on the formation of heterocyclic aromatic amines in fried beef patties.
Journal of agricultural and food chemistry.
2007 Dec; 55(25):10240-7. doi:
10.1021/jf071720t. [PMID: 17988088] - Ka-Wing Cheng, Qingli Wu, Zong Ping Zheng, Xiaofang Peng, James E Simon, Feng Chen, Mingfu Wang. Inhibitory effect of fruit extracts on the formation of heterocyclic amines.
Journal of agricultural and food chemistry.
2007 Dec; 55(25):10359-65. doi:
10.1021/jf071820z. [PMID: 18004801] - Robert J Turesky, Jian-Min Yuan, Renwei Wang, Sabrina Peterson, Mimi C Yu. Tobacco smoking and urinary levels of 2-amino-9H-pyrido[2,3-b]indole in men of Shanghai, China.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2007 Aug; 16(8):1554-60. doi:
10.1158/1055-9965.epi-07-0132. [PMID: 17684128] - Eizo Takahashi, Sakae Arimoto, Keinosuke Okamoto, Tomoe Negishi. Enhancement of phase II enzyme activity by purpurin resulting in the suppression of MeIQx-DNA-adduct formation in mice.
Mutation research.
2007 Jan; 626(1-2):128-34. doi:
10.1016/j.mrgentox.2006.09.011. [PMID: 17137831] - Masahiko Kushida, Hideki Wanibuchi, Keiichirou Morimura, Anna Kinoshita, Jin Seok Kang, Rawiwan Puatanachokchai, Min Wei, Yoshihiko Funae, Shoji Fukushima. Dose-dependence of promotion of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline-induced rat hepatocarcinogenesis by ethanol: evidence for a threshold.
Cancer science.
2005 Nov; 96(11):747-57. doi:
10.1111/j.1349-7006.2005.00110.x. [PMID: 16271068] - Ricky D Holland, Theresa Gehring, Jason Taylor, Brian G Lake, Nigel J Gooderham, Robert J Turesky. Formation of a mutagenic heterocyclic aromatic amine from creatinine in urine of meat eaters and vegetarians.
Chemical research in toxicology.
2005 Mar; 18(3):579-90. doi:
10.1021/tx049675w. [PMID: 15777097] - Sakae Arimoto-Kobayashi, Jun Takata, Namiko Nakandakari, Rie Fujioka, Keinosuke Okamoto, Toshimitsu Konuma. Inhibitory effects of heterocyclic amine-induced DNA adduct formation in mouse liver and lungs by beer.
Journal of agricultural and food chemistry.
2005 Feb; 53(3):812-5. doi:
10.1021/jf049208k. [PMID: 15686438] - Ricky D Holland, Jason Taylor, Laura Schoenbachler, Richard C Jones, James P Freeman, Dwight W Miller, Brian G Lake, Nigel J Gooderham, Robert J Turesky. Rapid biomonitoring of heterocyclic aromatic amines in human urine by tandem solvent solid phase extraction liquid chromatography electrospray ionization mass spectrometry.
Chemical research in toxicology.
2004 Aug; 17(8):1121-36. doi:
10.1021/tx049910a. [PMID: 15310244] - Christian Malaveille, Laura Fiorini, Monica Bianchini, Laura Davico, Sabrina Bertinetti, Giovanni Allegro, Agnès Hautefeuille, Carlotta Sacerdote, Paolo Vineis. Randomized controlled trial of dietary intervention: association between level of urinary phenolics and anti-mutagenicity.
Mutation research.
2004 Jul; 561(1-2):83-90. doi:
10.1016/j.mrgentox.2004.03.007. [PMID: 15238233] - Antony Boyce, Johannes Doehmer, Nigel J Gooderham. Phytoalexin resveratrol attenuates the mutagenicity of the heterocyclic amines 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2004 Mar; 802(1):217-23. doi:
10.1016/j.jchromb.2003.10.057. [PMID: 15036014] - Chi-Chen Hong, Bing-Kou Tang, Venketeshwer Rao, Sanjiv Agarwal, Lisa Martin, David Tritchler, Martin Yaffe, Norman F Boyd. Cytochrome P450 1A2 (CYP1A2) activity, mammographic density, and oxidative stress: a cross-sectional study.
Breast cancer research : BCR.
2004; 6(4):R338-51. doi:
10.1186/bcr797. [PMID: 15217501] - Markus Zsivkovits, Kassie Fekadu, Gerhard Sontag, Ursula Nabinger, Wolfgang W Huber, Michael Kundi, Asima Chakraborty, Helmuth Foissy, Siegfried Knasmüller. Prevention of heterocyclic amine-induced DNA damage in colon and liver of rats by different lactobacillus strains.
Carcinogenesis.
2003 Dec; 24(12):1913-8. doi:
10.1093/carcin/bgg167. [PMID: 12970070] - Ken-ichi Masumura, Yukari Totsuka, Keiji Wakabayashi, Takehiko Nohmi. Potent genotoxicity of aminophenylnorharman, formed from non-mutagenic norharman and aniline, in the liver of gpt delta transgenic mouse.
Carcinogenesis.
2003 Dec; 24(12):1985-93. doi:
10.1093/carcin/bgg170. [PMID: 12970073] - J Alexander, R Reistad, S Hegstad, H Frandsen, K Ingebrigtsen, J E Paulsen, G Becher. Biomarkers of exposure to heterocyclic amines: approaches to improve the exposure assessment.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2002 Aug; 40(8):1131-7. doi:
10.1016/s0278-6915(02)00053-4. [PMID: 12067575] - Yaowarate Intiyot, Takemi Kinouchi, Keiko Kataoka, Hideki Arimochi, Tomomi Kuwahara, Usanee Vinitketkumnuen, Yoshinari Ohnishi. Antimutagenicity of Murdannia loriformis in the Salmonella mutation assay and its inhibitory effects on azoxymethane-induced DNA methylation and aberrant crypt focus formation in male F344 rats.
The journal of medical investigation : JMI.
2002 Feb; 49(1-2):25-34. doi:
". [PMID: 11901756] - S Murray, B G Lake, S Gray, A J Edwards, C Springall, E A Bowey, G Williamson, A R Boobis, N J Gooderham. Effect of cruciferous vegetable consumption on heterocyclic aromatic amine metabolism in man.
Carcinogenesis.
2001 Sep; 22(9):1413-20. doi:
10.1093/carcin/22.9.1413. [PMID: 11532863] - S M Monti, A Ritieni, R Sacchi, K Skog, E Borgen, V Fogliano. Characterization of phenolic compounds in virgin olive oil and their effect on the formation of carcinogenic/mutagenic heterocyclic amines in a model system.
Journal of agricultural and food chemistry.
2001 Aug; 49(8):3969-75. doi:
10.1021/jf010240d. [PMID: 11513697] - S Langouët, D H Welti, N Kerriguy, L B Fay, T Huynh-Ba, J Markovic, F P Guengerich, A Guillouzo, R J Turesky. Metabolism of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in human hepatocytes: 2-amino-3-methylimidazo[4,5-f]quinoxaline-8-carboxylic acid is a major detoxification pathway catalyzed by cytochrome P450 1A2.
Chemical research in toxicology.
2001 Feb; 14(2):211-21. doi:
10.1021/tx000176e. [PMID: 11258970] - W G Stillwell, R J Turesky, R Sinha, S R Tannenbaum. N-oxidative metabolism of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in humans: excretion of the N2-glucuronide conjugate of 2-hydroxyamino-MeIQx in urine.
Cancer research.
1999 Oct; 59(20):5154-9. doi:
. [PMID: 10537291] - W G Stillwell, R J Turesky, R Sinha, P L Skipper, S R Tannenbaum. Biomonitoring of heterocyclic aromatic amine metabolites in human urine.
Cancer letters.
1999 Sep; 143(2):145-8. doi:
10.1016/s0304-3835(99)00144-5. [PMID: 10503894] - M Hirose, S Takahashi, K Ogawa, M Futakuchi, T Shirai. Phenolics: blocking agents for heterocyclic amine-induced carcinogenesis.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
1999 Sep; 37(9-10):985-92. doi:
10.1016/s0278-6915(99)00092-7. [PMID: 10541455] - R C Garner, T J Lightfoot, B C Cupid, D Russell, J M Coxhead, W Kutschera, A Priller, W Rom, P Steier, D J Alexander, S H Leveson, K H Dingley, R J Mauthe, K W Turteltaub. Comparative biotransformation studies of MeIQx and PhIP in animal models and humans.
Cancer letters.
1999 Sep; 143(2):161-5. doi:
10.1016/s0304-3835(99)00118-4. [PMID: 10503897] - K Ogawa, H Tsuda, T Shirai, T Ogiso, K Wakabayashi, D W Dalgard, U P Thorgeirsson, S S Thorgeirsson, R H Adamson, T Sugimura. Lack of carcinogenicity of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in cynomolgus monkeys.
Japanese journal of cancer research : Gann.
1999 Jun; 90(6):622-8. doi:
10.1111/j.1349-7006.1999.tb00792.x. [PMID: 10429653] - L C Kidd, W G Stillwell, M C Yu, J S Wishnok, P L Skipper, R K Ross, B E Henderson, S R Tannenbaum. Urinary excretion of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in White, African-American, and Asian-American men in Los Angeles County.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
1999 May; 8(5):439-45. doi:
NULL. [PMID: 10350440] - K H Dingley, S P Freeman, D O Nelson, R C Garner, K W Turteltaub. Covalent binding of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline to albumin and hemoglobin at environmentally relevant doses. Comparison of human subjects and F344 rats.
Drug metabolism and disposition: the biological fate of chemicals.
1998 Aug; 26(8):825-8. doi:
. [PMID: 9698300] - R J Turesky, R C Garner, D H Welti, J Richoz, S H Leveson, K H Dingley, K W Turteltaub, L B Fay. Metabolism of the food-borne mutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in humans.
Chemical research in toxicology.
1998 Mar; 11(3):217-25. doi:
10.1021/tx9701891. [PMID: 9544620] - Y F Sasaki, A Saga, M Akasaka, E Nishidate, M Watanabe-Akanuma, T Ohta, N Matsusaka, S Tsuda. In vivo genotoxicity of heterocyclic amines detected by a modified alkaline single cell gel electrophoresis assay in a multiple organ study in the mouse.
Mutation research.
1997 Dec; 395(1):57-73. doi:
10.1016/s1383-5718(97)00142-3. [PMID: 9465914] - R Reistad, O J Rossland, K J Latva-Kala, T Rasmussen, R Vikse, G Becher, J Alexander. Heterocyclic aromatic amines in human urine following a fried meat meal.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
1997 Oct; 35(10-11):945-55. doi:
10.1016/s0278-6915(97)00112-9. [PMID: 9463528] - T Sakuma, T Igarashi, M Hieda, S Ohgiya, M Isogai, S Ninomiya, R Nagata, N Nemoto, T Kamataki. Marmoset CYP1A2: primary structure and constitutive expression in livers.
Carcinogenesis.
1997 Oct; 18(10):1985-91. doi:
10.1093/carcin/18.10.1985. [PMID: 9364010] - W G Stillwell, L C Kidd, J S Wishnok, S R Tannenbaum, R Sinha. Urinary excretion of unmetabolized and phase II conjugates of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in humans: relationship to cytochrome P4501A2 and N-acetyltransferase activity.
Cancer research.
1997 Aug; 57(16):3457-64. doi:
NULL. [PMID: 9270013] - M Nagao, K Wakabayashi, T Ushijima, M Toyota, Y Totsuka, T Sugimura. Human exposure to carcinogenic heterocyclic amines and their mutational fingerprints in experimental animals.
Environmental health perspectives.
1996 May; 104 Suppl 3(?):497-501. doi:
10.1289/ehp.96104s3497. [PMID: 8781372] - Y Totsuka, K Fukutome, M Takahashi, S Takahashi, A Tada, T Sugimura, K Wakabayashi. Presence of N2-(deoxyguanosin-8-yl)-2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (dG-C8-MeIQx) in human tissues.
Carcinogenesis.
1996 May; 17(5):1029-34. doi:
10.1093/carcin/17.5.1029. [PMID: 8640908] - D S Davies, N J Gooderham, S Murray, A Lynch, R de la Torre, J Segura, A R Boobis. Chemical methods for assessing systemic exposure to dietary heterocyclic amines in man.
Archives of toxicology. Supplement. = Archiv fur Toxikologie. Supplement.
1996; 18(?):251-8. doi:
10.1007/978-3-642-61105-6_25. [PMID: 8678801] - R Sinha, N Rothman, S D Mark, S Murray, E D Brown, O A Levander, D S Davies, N P Lang, F F Kadlubar, R N Hoover. Lower levels of urinary 2-amino-3,8-dimethylimidazo[4,5-f]-quinoxaline (MeIQx) in humans with higher CYP1A2 activity.
Carcinogenesis.
1995 Nov; 16(11):2859-61. doi:
10.1093/carcin/16.11.2859. [PMID: 7586210] - R Vikse, K Ingebrigtsen, L Klungsøyr, J Alexander. Effects of enzyme induction on the distribution of the food carcinogen 2-amino-3,8-dimethyl-imidazo[4,5-ss]-quinoxaline (MeIQx) in Ah-receptor- responsive- and Ah-receptor-non-responsive mice.
Pharmacology & toxicology.
1995 Jul; 77(1):57-64. doi:
10.1111/j.1600-0773.1995.tb01914.x. [PMID: 8532613] - E G Snyderwine, D H Welti, C D Davis, L B Fay, R J Turesky. Metabolism of the food-derived carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in nonhuman primates.
Carcinogenesis.
1995 Jun; 16(6):1377-84. doi:
10.1093/carcin/16.6.1377. [PMID: 7788858] - R J Turesky, L B Fay, D H Welti. Metabolism of heterocyclic aromatic amines and strategies of human biomonitoring.
Princess Takamatsu symposia.
1995; 23(?):59-68. doi:
NULL. [PMID: 8844796] - E G Snyderwine, R J Turesky, M H Buonarati, K W Turteltaub, R H Adamson. Metabolic processing and disposition of 2-amino-3-methylimidazo[4,5-f] quinoline (IQ), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in nonhuman primates.
Princess Takamatsu symposia.
1995; 23(?):69-77. doi:
. [PMID: 8844797] - S R Tannenbaum, W G Stillwell, H Ji, P L Skipper, M C Yu, R K Ross, B E Henderson, R J Turesky, G A Gross. MeIQx (2-amino-3,8-dimethylimidazo [4,5-f]quinoxaline): metabolism in humans and urinary metabolites in human populations.
Princess Takamatsu symposia.
1995; 23(?):197-206. doi:
NULL. [PMID: 8844811] - S Grivas. Synthetic routes to the food carcinogen 2 amino-3,8-dimethylimidazo[4,5-f]quinoxaline (8-MeIQx) and related compounds.
Princess Takamatsu symposia.
1995; 23(?):1-8. doi:
". [PMID: 8844790] - M G Knize, F A Dolbeare, P L Cunningham, J S Felton. Mutagenic activity and heterocyclic amine content of the human diet.
Princess Takamatsu symposia.
1995; 23(?):30-8. doi:
NULL. [PMID: 8844793] - S S Thorgeirsson, C D Davis, H A Schut, R H Adamson, E G Snyderwine. Possible relationship between tissue distribution of DNA adducts and genotoxicity of food-derived heterocyclic amines.
Princess Takamatsu symposia.
1995; 23(?):85-92. doi:
NULL. [PMID: 8844799] - H Ji, M C Yu, W G Stillwell, P L Skipper, R K Ross, B E Henderson, S R Tannenbaum. Urinary excretion of 2-amino-3,8-dimethylimidazo-[4,5-f]quinoxaline in white, black, and Asian men in Los Angeles County.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
1994 Jul; 3(5):407-11. doi:
. [PMID: 7920208] - W G Stillwell, R J Turesky, G A Gross, P L Skipper, S R Tannenbaum. Human urinary excretion of sulfamate and glucuronide conjugates of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MelQx).
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
1994 Jul; 3(5):399-405. doi:
. [PMID: 7920207] - A R Boobis, A M Lynch, S Murray, R de la Torre, A Solans, M Farré, J Segura, N J Gooderham, D S Davies. CYP1A2-catalyzed conversion of dietary heterocyclic amines to their proximate carcinogens is their major route of metabolism in humans.
Cancer research.
1994 Jan; 54(1):89-94. doi:
. [PMID: 8261468] - A Ghoshal, E G Snyderwine. Excretion of food-derived heterocyclic amine carcinogens into breast milk of lactating rats and formation of DNA adducts in the newborn.
Carcinogenesis.
1993 Nov; 14(11):2199-203. doi:
10.1093/carcin/14.11.2199. [PMID: 8242844] - C D Davis, H A Schut, E G Snyderwine. Enzymatic phase II activation of the N-hydroxylamines of IQ, MeIQx and PhIP by various organs of monkeys and rats.
Carcinogenesis.
1993 Oct; 14(10):2091-6. doi:
10.1093/carcin/14.10.2091. [PMID: 8222059] - M Vanderlaan, M Hwang, T Djanegara. Immunoaffinity purification of dietary heterocyclic amine carcinogens.
Environmental health perspectives.
1993 Mar; 99(?):285-7. doi:
10.1289/ehp.9399285. [PMID: 8319645] - K Wakabayashi, H Ushiyama, M Takahashi, H Nukaya, S B Kim, M Hirose, M Ochiai, T Sugimura, M Nagao. Exposure to heterocyclic amines.
Environmental health perspectives.
1993 Mar; 99(?):129-34. doi:
10.1289/ehp.9399129. [PMID: 8319610] - R J Turesky, W G Stillwell, P L Skipper, S R Tannenbaum. Metabolism of the food-borne carcinogens 2-amino-3-methylimidazo-[4,5-f]quinoline and 2-amino-3,8- dimethylimidazo[4,5-f]-quinoxaline in the rat as a model for human biomonitoring.
Environmental health perspectives.
1993 Mar; 99(?):123-8. doi:
10.1289/ehp.9399123. [PMID: 8319609] - A M Lynch, S Murray, K Zhao, N J Gooderham, A R Boobis, D S Davies. Molecular dosimetry of the food-borne carcinogen MeIQx using adducts of serum albumin.
Carcinogenesis.
1993 Feb; 14(2):191-4. doi:
10.1093/carcin/14.2.191. [PMID: 8435859] - C D Davis, H A Schut, R H Adamson, U P Thorgeirsson, S S Thorgeirsson, E G Snyderwine. Mutagenic activation of IQ, PhIP and MeIQx by hepatic microsomes from rat, monkey and man: low mutagenic activation of MeIQx in cynomolgus monkeys in vitro reflects low DNA adduct levels in vivo.
Carcinogenesis.
1993 Jan; 14(1):61-5. doi:
10.1093/carcin/14.1.61. [PMID: 8425272] - A M Lynch, M G Knize, A R Boobis, N J Gooderham, D S Davies, S Murray. Intra- and interindividual variability in systemic exposure in humans to 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline and 2-amino-1-methyl- 6-phenylimidazo[4,5-b]pyridine, carcinogens present in cooked beef.
Cancer research.
1992 Nov; 52(22):6216-23. doi:
NULL. [PMID: 1423264] - K Tjøtta, K Ingebrigtsen, T Aune. Tissue distribution of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in two strains of male rats.
Carcinogenesis.
1992 May; 13(5):779-82. doi:
10.1093/carcin/13.5.779. [PMID: 1586989] - E G Snyderwine, H A Schut, R H Adamson, U P Thorgeirsson, S S Thorgeirsson. Metabolic activation and genotoxicity of heterocyclic arylamines.
Cancer research.
1992 Apr; 52(7 Suppl):2099s-2102s. doi:
NULL. [PMID: 1544147] - H Wallin, J A Holme, J Alexander. Covalent binding of food carcinogens MeIQx, MeIQ and IQ to DNA and protein in microsomal incubations and isolated rat hepatocytes.
Pharmacology & toxicology.
1992 Mar; 70(3):220-5. doi:
10.1111/j.1600-0773.1992.tb00460.x. [PMID: 1579548] - P Sjödin, M Nyman, L L Nielsen, H Wallin, M Jägerstad. Effect of dietary fiber on the disposition and excretion of a food carcinogen (2-14C-labeled MeIQx) in rats.
Nutrition and cancer.
1992; 17(2):139-51. doi:
10.1080/01635589209514181. [PMID: 1316601] - R J Turesky, J Markovic, I Bracco-Hammer, L B Fay. The effect of dose and cytochrome P450 induction on the metabolism and disposition of the food-borne carcinogen 2-amino-3,8-dimethylimidazo[4,5-f] quinoxaline (MeIQx) in the rat.
Carcinogenesis.
1991 Oct; 12(10):1847-55. doi:
10.1093/carcin/12.10.1847. [PMID: 1934266] - N J Gooderham, A Soames, J C Rice, A R Boobis, D S Davies. Distribution and elimination of [2-14C]amino-3,8-dimethylimidazo [4, 5-f] quinoxaline in mice. Analysis by whole animal autoradiography.
Human & experimental toxicology.
1991 Sep; 10(5):337-45. doi:
10.1177/096032719101000507. [PMID: 1683547] - H Ushiyama, K Wakabayashi, M Hirose, H Itoh, T Sugimura, M Nagao. Presence of carcinogenic heterocyclic amines in urine of healthy volunteers eating normal diet, but not of inpatients receiving parenteral alimentation.
Carcinogenesis.
1991 Aug; 12(8):1417-22. doi:
10.1093/carcin/12.8.1417. [PMID: 1907222] - N Loprieno, G Boncristiani, G Loprieno. An experimental approach to identifying the genotoxic risk from cooked meat mutagens.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
1991 Jun; 29(6):377-86. doi:
10.1016/0278-6915(91)90077-k. [PMID: 1874465] - N Loprieno, G Boncristiani, G Loprieno. An experimental approach to identifying the genotoxic risk by cooked meat mutagens.
Advances in experimental medicine and biology.
1991; 289(?):115-31. doi:
10.1007/978-1-4899-2626-5_9. [PMID: 1897387] - M Kleman, E Overvik, G Mason, J A Gustafsson. Effects of the food mutagens MeIQx and PhIP on the expression of cytochrome P450IA proteins in various tissues of male and female rats.
Carcinogenesis.
1990 Dec; 11(12):2185-9. doi:
10.1093/carcin/11.12.2185. [PMID: 1702369] - R H Adamson, E G Snyderwine, U P Thorgeirsson, H A Schut, R J Turesky, S S Thorgeirsson, S Takayama, T Sugimura. Metabolic processing and carcinogenicity of heterocyclic amines in nonhuman primates.
Princess Takamatsu symposia.
1990; 21(?):289-301. doi:
NULL. [PMID: 2134682] - P Sjödin, H Wallin, J Alexander, M Jägerstad. Disposition and metabolism of the food mutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in rats.
Carcinogenesis.
1989 Jul; 10(7):1269-75. doi:
10.1093/carcin/10.7.1269. [PMID: 2661045] - S Murray, N J Gooderham, A R Boobis, D S Davies. Detection and measurement of MeIQx in human urine after ingestion of a cooked meat meal.
Carcinogenesis.
1989 Apr; 10(4):763-5. doi:
10.1093/carcin/10.4.763. [PMID: 2702724] - H Yanagisawa, O Wada. Significant increase of IQ-type heterocyclic amines, dietary carcinogens in the plasma of patients with uremia just before induction of hemodialysis treatment.
Nephron.
1989; 52(1):6-10. doi:
10.1159/000185574. [PMID: 2710268] - A J Alldrick, I R Rowland. Distribution of radiolabelled [2-14C]IQ and MeIQx in the mouse.
Toxicology letters.
1988 Nov; 44(1-2):183-90. doi:
10.1016/0378-4274(88)90145-2. [PMID: 3188077] - R J Turesky, H U Aeschbacher, H P Würzner, P L Skipper, S R Tannenbaum. Major routes of metabolism of the food-borne carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in the rat.
Carcinogenesis.
1988 Jun; 9(6):1043-8. doi:
10.1093/carcin/9.6.1043. [PMID: 3370749] - R J Turesky, H U Aeschbacher, A Malnoë, H P Würzner. Metabolism of the food-borne mutagen/carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in the rat: assessment of biliary metabolites for genotoxicity.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
1988 Feb; 26(2):105-10. doi:
10.1016/0278-6915(88)90106-8. [PMID: 3366409] - N J Gooderham, D Watson, J C Rice, S Murray, G W Taylor, D S Davies. Metabolism of the mutagen MeIQx in vivo: metabolite screening by liquid chromatography-thermospray mass spectrometry.
Biochemical and biophysical research communications.
1987 Nov; 148(3):1377-82. doi:
10.1016/s0006-291x(87)80284-x. [PMID: 3689400] - H Hayatsu, H Kasai, S Yokoyama, T Miyazawa, Z Yamaizumi, S Sato, S Nishimura, S Arimoto, T Hayatsu, Y Ohara. Mutagenic metabolites in urine and feces of rats fed with 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, a carcinogenic mutagen present in cooked meat.
Cancer research.
1987 Feb; 47(3):791-4. doi:
NULL. [PMID: 3542193] - H Yanagisawa, S Manabe, Y Kitagawa, S Ishikawa, K Nakajima, O Wada. Presence of 2-amino-3,8-dimethylimidazo [4,5-f]quinoxaline (MeIQx) in dialysate from patients with uremia.
Biochemical and biophysical research communications.
1986 Aug; 138(3):1084-9. doi:
10.1016/s0006-291x(86)80393-x. [PMID: 3753488] - R R Bailey. The kidney and antihypertensive therapy.
Drugs.
1976; 11 SUPPL 1(?):70-7. doi:
10.2165/00003495-197600111-00019. [PMID: 6253]