Home Amines 77500-04-0
77500-04-0,MFCD00210329
Catalog No.:AA008OVR

77500-04-0 | 3,8-Dimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine

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5mg
≥95%
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$108.00   $75.00
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10mg
≥95%
in stock  
$193.00   $135.00
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25mg
≥95%
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA008OVR
Chemical Name:
3,8-Dimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine
CAS Number:
77500-04-0
Molecular Formula:
C11H11N5
Molecular Weight:
213.2385
MDL Number:
MFCD00210329
SMILES:
Cc1cnc2c(n1)c1nc(n(c1cc2)C)N
Properties
Computed Properties
 
Complexity:
271  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
XLogP3:
1  

Downstream Synthesis Route

[1]Grivas,Spiros;Tian,Wei;Ronne,Erik;Lindstroem,Stefan;Olsson,Kjell[ActaChemicaScandinavica,1993,vol.47,#5,p.521-528]

Literature

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Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20161101

Title: Long interspersed element-1 is differentially regulated by food-borne carcinogens via the aryl hydrocarbon receptor.

Journal: Oncogene 20131010

Title: DNA adducts of the tobacco carcinogens 2-amino-9H-pyrido[2,3-b]indole and 4-aminobiphenyl are formed at environmental exposure levels and persist in human hepatocytes.

Journal: Chemical research in toxicology 20130916

Title: Genotoxicity and induction of DNA damage responsive genes by food-borne heterocyclic aromatic amines in human hepatoma HepG2 cells.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20130901

Title: Flumequine enhances the in vivo mutagenicity of MeIQx in the mouse liver.

Journal: Archives of toxicology 20130801

Title: Lack of Hepatocarcinogenicity of Combinations of Low Doses of 2-amino-3, 8-dimethylimidazo[4,5- f ]quinoxaline and Diethylnitrosamine in Rats: Indication for the Existence of a Threshold for Genotoxic Carcinogens.

Journal: Journal of toxicologic pathology 20120901

Title: Response surface optimization of effects of some processing variables on carcinogenic/mutagenic heterocyclic aromatic amine (HAA) content in cooked patties.

Journal: Meat science 20120701

Title: Meat-related mutagen exposure, xenobiotic metabolizing gene polymorphisms and the risk of advanced colorectal adenoma and cancer.

Journal: Carcinogenesis 20120701

Title: Plant extracts, spices, and essential oils inactivate Escherichia coli O157:H7 and reduce formation of potentially carcinogenic heterocyclic amines in cooked beef patties.

Journal: Journal of agricultural and food chemistry 20120411

Title: Occurrence of heterocyclic amines in cooked meat products.

Journal: Meat science 20120301

Title: Protective effects of xanthohumol against the genotoxicity of heterocyclic aromatic amines MeIQx and PhIP in bacteria and in human hepatoma (HepG2) cells.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120301

Title: Cytochrome P450-mediated metabolism and DNA binding of 2-amino-1,7-dimethylimidazo[4,5-g]quinoxaline and its carcinogenic isomer 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in mice.

Journal: Chemical research in toxicology 20120220

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Title: Pancreatic cancer risk: associations with meat-derived carcinogen intake in the Prostate, Lung, Colorectal, and Ovarian Cancer Screening Trial (PLCO) cohort.

Journal: Molecular carcinogenesis 20120101

Title: Heterocyclic aromatic amine [HCA] intake and prostate cancer risk: effect modification by genetic variants.

Journal: Nutrition and cancer 20120101

Title: Formation of heterocyclic amines during cooking of duck meat.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20120101

Title: Enhanced liver tumor promotion but not liver initiation activity in rats subjected to combined administration of omeprazole and β-naphthoflavone.

Journal: The Journal of toxicological sciences 20120101

Title: Well-done meat intake and meat-derived mutagen exposures in relation to breast cancer risk: the Nashville Breast Health Study.

Journal: Breast cancer research and treatment 20111001

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Journal: Anaerobe 20111001

Title: Inhibitory activity of Asian spices on heterocyclic amines formation in cooked beef patties.

Journal: Journal of food science 20111001

Title: Anti-genotoxic activity of Vitis coignetiae Pulliat towards heterocyclic amines and isolation and identification of caftaric acid as an antimutagenic component from the juice.

Journal: Mutation research 20110816

Title: [Simultaneous determination of 9 heterocyclic aromatic amine in poultry products by solid-phase extraction-high performance liquid chromatography].

Journal: Se pu = Chinese journal of chromatography 20110801

Title: Meat consumption and risk of esophageal and gastric cancer in a large prospective study.

Journal: The American journal of gastroenterology 20110301

Title: Ultraperformance liquid chromatography-tandem mass spectrometry method for biomonitoring cooked meat carcinogens and their metabolites in human urine.

Journal: Analytical chemistry 20110201

Title: No effect of meat, meat cooking preferences, meat mutagens or heme iron on lung cancer risk in the prostate, lung, colorectal and ovarian cancer screening trial.

Journal: International journal of cancer 20110115

Title: Effects of (+)-catechin and (-)-epicatechin on heterocyclic amines-induced oxidative DNA damage.

Journal: Journal of applied toxicology : JAT 20110101

Title: Intake of heterocyclic aromatic amines and the risk of prostate cancer in the EPIC-Heidelberg cohort.

Journal: Cancer causes & control : CCC 20110101

Title: New short term prediction method for chemical carcinogenicity by hepatic transcript profiling following 28-day toxicity tests in rats.

Journal: Cancer informatics 20110101

Title: Impact of meat consumption, preparation, and mutagens on aggressive prostate cancer.

Journal: PloS one 20110101

Title: Preferential induction of the AhR gene battery in HepaRG cells after a single or repeated exposure to heterocyclic aromatic amines.

Journal: Toxicology and applied pharmacology 20101115

Title: Capillary liquid chromatography with diode array and mass spectrometry detection for heterocyclic aromatic amine determination in ready-to-eat food treated with electron-beam irradiation.

Journal: Journal of chromatography. A 20101022

Title: Enhancing effects of carbon tetrachloride on in vivo mutagenicity in the liver of mice fed 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx).

Journal: The Journal of toxicological sciences 20101001

Title: Effects of co-treatment of dextran sulfate sodium and MeIQx on genotoxicity and possible carcinogenicity in the colon of p53-deficient mice.

Journal: The Journal of toxicological sciences 20101001

Title: Association of meat and fat intake with liver disease and hepatocellular carcinoma in the NIH-AARP cohort.

Journal: Journal of the National Cancer Institute 20100908

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Journal: Toxins 20100901

Title: Dietary exposure to heterocyclic amines in high-temperature cooked meat and fish in Malaysia.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20100801

Title: Differential toxicity of heterocyclic aromatic amines and their mixture in metabolically competent HepaRG cells.

Journal: Toxicology and applied pharmacology 20100601

Title: 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx)-induced hepatocarcinogenesis is not enhanced by CYP1A inducers, alpha- and beta-naphthoflavone: relationship to intralobular distribution of CYP1A expression.

Journal: Toxicologic pathology 20100601

Title: Determination of heterocyclic amines in urine samples by capillary liquid chromatography with evaporated light-scattering detection.

Journal: Analytical and bioanalytical chemistry 20100501

Title: Meat mutagens and breast cancer in postmenopausal women--a cohort analysis.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20100501

Title: 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.

Journal: Chemical research in toxicology 20100419

Title: A large prospective study of meat consumption and colorectal cancer risk: an investigation of potential mechanisms underlying this association.

Journal: Cancer research 20100315

Title: Inhibition of heterocyclic amine formation in beef patties by ethanolic extracts of rosemary.

Journal: Journal of food science 20100301

Title: Effect of rapid human N-acetyltransferase 2 haplotype on DNA damage and mutagenesis induced by 2-amino-3-methylimidazo-[4,5-f]quinoline (IQ) and 2-amino-3,8-dimethylimidazo-[4,5-f]quinoxaline (MeIQx).

Journal: Mutation research 20100203

Title: Carcinogenic risk assessment: are there dose thresholds for carcinogens?

Journal: Asian Pacific journal of cancer prevention : APJCP 20100101

Title: A review and meta-analysis of prospective studies of red and processed meat intake and prostate cancer.

Journal: Nutrition journal 20100101

Title: Molecular analysis of carcinogen-induced rodent lung tumors: Involvement of microRNA expression and Krαs or Egfr mutations.

Journal: Molecular medicine reports 20100101

Title: Different threshold levels for 2-amino-3,8 dimethylimidazo[4,5-f]quinoxaline (MelQx) initiation of lung and colon carcinogenesis and the effects of an additional initiation by 4 (methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in A/J mice.

Journal: Molecular medicine reports 20100101

Title: Hollow fibre-supported liquid membrane extraction and LC-MS/MS detection for the analysis of heterocyclic amines in urine samples.

Journal: Molecular nutrition & food research 20091201

Title: Effect of N-acetyltransferase 2 polymorphism on tumor target tissue DNA adduct levels in rapid and slow acetylator congenic rats administered 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine or 2-amino-3,8-dimethylimidazo-[4,5-f]quinoxaline.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20091101

Title: Ability of probiotic Lactobacillus casei DN 114001 to bind or/and metabolise heterocyclic aromatic amines in vitro.

Journal: European journal of nutrition 20091001

Title: Lack of Modifying Effects of Intratracheal Instillation of Quartz or Dextran Sulfate Sodium (DSS) in Drinking Water on Lung Tumor Development Initiated with 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in Female A/J Mice.

Journal: Journal of toxicologic pathology 20090901

Title: Biomonitoring of carcinogenic heterocyclic aromatic amines in hair: a validation study.

Journal: Chemical research in toxicology 20090817

Title: Intake of meat, meat mutagens, and iron and the risk of breast cancer in the Prostate, Lung, Colorectal, and Ovarian Cancer Screening Trial.

Journal: British journal of cancer 20090707

Title: Meat and heterocyclic amine intake, smoking, NAT1 and NAT2 polymorphisms, and colorectal cancer risk in the multiethnic cohort study.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20090701

Title: Dietary meat intake in relation to colorectal adenoma in asymptomatic women.

Journal: The American journal of gastroenterology 20090501

Title: Xenobiotic metabolizing gene variants, dietary heterocyclic amine intake, and risk of prostate cancer.

Journal: Cancer research 20090301

Title: Ethanol Does Not Promote MeIQx-initiated Rat Colon Carcinogenesis Based on Evidence from Analysis of a Colon Cancer Surrogate Marker.

Journal: Journal of toxicologic pathology 20090301

Title: Intakes of red meat, processed meat, and meat mutagens increase lung cancer risk.

Journal: Cancer research 20090201

Title: Screening for DNA adducts by data-dependent constant neutral loss-triple stage mass spectrometry with a linear quadrupole ion trap mass spectrometer.

Journal: Analytical chemistry 20090115

Title: Short term exposure to cooking fumes and pulmonary function.

Journal: Journal of occupational medicine and toxicology (London, England) 20090101

Title: Optimized HPLC method for analysis of polar and nonpolar heterocyclic amines in cooked meat products.

Journal: Journal of AOAC International 20090101

Title: 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.

Journal: Nutrition journal 20090101

Title: Association between dietary heterocyclic amine levels, genetic polymorphisms of NAT2, CYP1A1, and CYP1A2 and risk of stomach cancer: a hospital-based case-control study in Japan.

Journal: Gastric cancer : official journal of the International Gastric Cancer Association and the Japanese Gastric Cancer Association 20090101

Title: Enhancing effects of a high fat diet on 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline-induced lung tumorigenesis in female A/J mice.

Journal: Molecular medicine reports 20090101

Title: Effect of beer/red wine marinades on the formation of heterocyclic aromatic amines in pan-fried beef.

Journal: Journal of agricultural and food chemistry 20081126

Title: Modifying effects of chitin, chitosan and their related compounds on 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in a rat medium-term hepatocarcinogenesis model, and their post-initiation effects in a female rat 2-stage multi-organ carcinogenesis model.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080801

Title: Quantification of heterocyclic aromatic amines in fried meat by HPTLC/UV-FLD and HPLC/UV-FLD: a comparison of two methods.

Journal: Journal of agricultural and food chemistry 20080625

Title: Quantitative investigation of the role of breast cancer resistance protein (Bcrp/Abcg2) in limiting brain and testis penetration of xenobiotic compounds.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20080601

Title: Carcinogenic risk of heterocyclic amines in combination - assessment with a liver initiation model.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20080601

Title: Suppressive effect of poly-gamma-glutamate on SOS response of Salmonella typhimurium induced by chemical mutagens.

Journal: Journal of bioscience and bioengineering 20080601

Title: Evidence of a threshold-effect for 2-amino-3,8-dimethylimidazo-[4,5-f]quinoxaline liver carcinogenicity in F344/DuCrj rats.

Journal: Toxicologic pathology 20080401

Title: Binding of heterocyclic aromatic amines by lactic acid bacteria: results of a comprehensive screening trial.

Journal: Molecular nutrition & food research 20080301

Title: Modification by N-acetyltransferase 1 genotype on the association between dietary heterocyclic amines and colon cancer in a multiethnic study.

Journal: Mutation research 20080201

Title: Occurrence of mutations in the epidermal growth factor receptor gene in X-ray-induced rat lung tumors.

Journal: Cancer science 20080201

Title: Quantitation of 13 heterocyclic aromatic amines in cooked beef, pork, and chicken by liquid chromatography-electrospray ionization/tandem mass spectrometry.

Journal: Journal of agricultural and food chemistry 20080109

Title: Meat and meat mutagens and risk of prostate cancer in the Agricultural Health Study.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20080101

Title: Effect of oil marinades with garlic, onion, and lemon juice on the formation of heterocyclic aromatic amines in fried beef patties.

Journal: Journal of agricultural and food chemistry 20071212

Title: Inhibitory effect of fruit extracts on the formation of heterocyclic amines.

Journal: Journal of agricultural and food chemistry 20071212

Title: What is a practical threshold?

Journal: Toxicologic pathology 20071001

Title: Meat intake, preparation methods, mutagens and colorectal adenoma recurrence.

Journal: Carcinogenesis 20070901

Title: Inhibitory activities of dietary phenolic compounds on heterocyclic amine formation in both chemical model system and beef patties.

Journal: Molecular nutrition & food research 20070801

Title: Tobacco smoking and urinary levels of 2-amino-9H-pyrido[2,3-b]indole in men of Shanghai, China.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20070801

Title: Processed meat intake, CYP2A6 activity and risk of colorectal adenoma.

Journal: Carcinogenesis 20070601

Title: Heterocyclic amines in griddled beef steak analysed using a single extract clean-up procedure.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20070401

Title: Analysis of gene expression in different stages of MeIQx-induced rat hepatocarcinogenesis.

Journal: Oncology reports 20070401

Title: Possible application of human c-Ha-ras proto-oncogene transgenic rats in a medium-term bioassay model for carcinogens.

Journal: Toxicologic pathology 20070401

Title: Enhancement of phase II enzyme activity by purpurin resulting in the suppression of MeIQx-DNA-adduct formation in mice.

Journal: Mutation research 20070110

Title: Effects of single nucleotide polymorphisms in human N-acetyltransferase 2 on metabolic activation (O-acetylation) of heterocyclic amine carcinogens.

Journal: International journal of cancer 20060901

Title: Differential effects of heterocyclic amines on poly(ADP-ribose) polymerase-1 and mono-ADP-ribosyltransferase A.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20060901

Title: Existence of a no effect level for MeIQx hepatocarcinogenicity on a background of thioacetamide-induced liver damage in rats.

Journal: Cancer science 20060601

Title: Meat mutagens and risk of distal colon adenoma in a cohort of U.S. men.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20060601

Title: Chemical synthesis of 2'-deoxyguanosine-C8 adducts with heterocyclic amines: an application to synthesis of oligonucleotides site-specifically adducted with 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.

Journal: Chemical research in toxicology 20060601

Title: N-acetylcysteine and S-methylcysteine inhibit MeIQx rat hepatocarcinogenesis in the post-initiation stage.

Journal: Carcinogenesis 20060501

Title: Influence of lignification and feruloylation of maize cell walls on the adsorption of heterocyclic aromatic amines.

Journal: Journal of agricultural and food chemistry 20060308

Title: Lack of modification of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) rat hepatocarcinogenesis by caffeine, a CYP1A2 inducer, points to complex counteracting influences.

Journal: Cancer letters 20060208

Title: Stability and reactivity of 2-nitrosoamino-3,8-dimethylimidazo[4,5-f]quinoxaline.

Journal: Chemical research in toxicology 20060201

Title: Existence of no-observed effect levels for 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline on hepatic preneoplastic lesion development in BN rats.

Journal: Cancer letters 20060118

Title: Existence of no hepatocarcinogenic effect levels of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline with or without coadministration with ethanol.

Journal: Toxicologic pathology 20060101

Title: A prospective study of meat and meat mutagens and prostate cancer risk.

Journal: Cancer research 20051215

Title: Dose-dependence of promotion of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline-induced rat hepatocarcinogenesis by ethanol: evidence for a threshold.

Journal: Cancer science 20051101

Title: Investigation of the separation of heterocyclic aromatic amines by reversed phase ion-pair liquid chromatography coupled with tandem mass spectrometry: the role of ion pair reagents on LC-MS/MS sensitivity.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20051025

Title: Novel antimutagenic factors derived from the edible mushroom Agrocybe cylindracea.

Journal: Mutation research 20051003

Title: PhIP carcinogenicity in breast cancer: computational and experimental evidence for competitive interactions with human estrogen receptor.

Journal: Chemical research in toxicology 20051001

Title: Meat, meat cooking methods and preservation, and risk for colorectal adenoma.

Journal: Cancer research 20050901

Title: Suppression of glutathione S-transferase placental form-positive foci development in rat hepatocarcinogenesis by Chlorella pyrenoidosa.

Journal: Oncology reports 20050801

Title: Nitric oxide-mediated nitrosation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline potentiated by hemin and myeloperoxidase.

Journal: Chemical research in toxicology 20050601

Title: Quantitation of carcinogenic heterocyclic aromatic amines and detection of novel heterocyclic aromatic amines in cooked meats and grill scrapings by HPLC/ESI-MS.

Journal: Journal of agricultural and food chemistry 20050420

Title: Induction of colon tumors in C57BL/6J mice fed MeIQx, IQ, or PhIP followed by dextran sulfate sodium treatment.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20050401

Title: Meat intake, cooking-related mutagens and risk of colorectal adenoma in a sigmoidoscopy-based case-control study.

Journal: Carcinogenesis 20050301

Title: Formation of a mutagenic heterocyclic aromatic amine from creatinine in urine of meat eaters and vegetarians.

Journal: Chemical research in toxicology 20050301

Title: Inhibitory effects of heterocyclic amine-induced DNA adduct formation in mouse liver and lungs by beer.

Journal: Journal of agricultural and food chemistry 20050209

Title: A comparison of genotoxicity between three common heterocyclic amines and acrylamide.

Journal: Mutation research 20050207

Title: Gene expression profiling of chemically induced rat mammary gland cancer.

Journal: Carcinogenesis 20050201

Title: Colonic adenocarcinomas rapidly induced by the combined treatment with 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and dextran sodium sulfate in male ICR mice possess beta-catenin gene mutations and increases immunoreactivity for beta-catenin, cyclooxygenase-2 and inducible nitric oxide synthase.

Journal: Carcinogenesis 20050101

Title: Heterocyclic amines and genotype of N-acetyltransferases as risk factors for prostate cancer.

Journal: Prostate cancer and prostatic diseases 20050101

Title: Dietary exposure to heterocyclic amines in a Chinese population.

Journal: Nutrition and cancer 20050101

Title: Global gene expression profiling of chemically induced rat mammary gland carcinomas and adenomas.

Journal: Toxicologic pathology 20050101

Title: Addition of various carbohydrates to beef burgers affects the formation of heterocyclic amines during frying.

Journal: Journal of agricultural and food chemistry 20041215

Title: The cooked food derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine is a potent oestrogen: a mechanistic basis for its tissue-specific carcinogenicity.

Journal: Carcinogenesis 20041201

Title: Induction of DNA-adducts and increase of 8-hydroxy-2-deoxyguanosine, but no development of preneoplastic lesions in offspring liver with transplacental and trans-breast milk exposure to 2-amino-3,8-dimethylimidazo [4,5-f ]quinoxaline (MeIQx) in rats.

Journal: Cancer science 20041201

Title: Lactoperoxidase-catalyzed activation of carcinogenic aromatic and heterocyclic amines.

Journal: Chemical research in toxicology 20041201

Title: Effect of the South African traditional meat, biltong, on cancer-associated enzymes CYP2E1 and CYP1A2.

Journal: South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde 20041101

Title: Embryonic turkey liver: activities of biotransformation enzymes and activation of DNA-reactive carcinogens.

Journal: Archives of toxicology 20041001

Title: No-observed effect levels for carcinogenicity and for in vivo mutagenicity of a genotoxic carcinogen.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20041001

Title: Heterocyclic amines in some Swedish cooked foods industrially prepared or from fast food outlets and restaurants.

Journal: Molecular nutrition & food research 20040901

Title: Rapid biomonitoring of heterocyclic aromatic amines in human urine by tandem solvent solid phase extraction liquid chromatography electrospray ionization mass spectrometry.

Journal: Chemical research in toxicology 20040801

Title: Randomized controlled trial of dietary intervention: association between level of urinary phenolics and anti-mutagenicity.

Journal: Mutation research 20040711

Title: Modulation of cytochrome P450 1A1 by food-derived heterocyclic aromatic amines.

Journal: Toxicology 20040701

Title: Disruption of beta-catenin pathway or genomic instability define two distinct categories of liver cancer in transgenic mice.

Journal: Gastroenterology 20040501

Title: Inhibitory effects of beer on heterocyclic amine-induced mutagenesis and PhIP-induced aberrant crypt foci in rat colon.

Journal: Mutation research 20040411

Title: Determination of heterocyclic aromatic amines (HAs) content in samples of household-prepared meat dishes.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040325

Title: 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: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040325

Title: Rapid analysis of gene expression changes caused by liver carcinogens and chemopreventive agents using a newly developed three-dimensional microarray system.

Journal: Cancer science 20040201

Title: Cytochrome P450 1A2 (CYP1A2) activity, mammographic density, and oxidative stress: a cross-sectional study.

Journal: Breast cancer research : BCR 20040101

Title: Selected heterocyclic amines.

Journal: Report on carcinogens : carcinogen profiles 20040101

Title: Prevention of heterocyclic amine-induced DNA damage in colon and liver of rats by different lactobacillus strains.

Journal: Carcinogenesis 20031201

Title: Potent genotoxicity of aminophenylnorharman, formed from non-mutagenic norharman and aniline, in the liver of gpt delta transgenic mouse.

Journal: Carcinogenesis 20031201

Title: Low dose genotoxicity of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in gpt delta transgenic mice.

Journal: Mutation research 20031110

Title: Mutagenic activity and heterocyclic amine carcinogens in commercial pet foods.

Journal: Mutation research 20030805

Title: Effect of high water-holding capacity on the formation of heterocyclic amines in fried beefburgers.

Journal: Journal of agricultural and food chemistry 20030716

Title: Post-initiation inhibition of MeIQx hepatocarcinogenesis in rats by cysteine.

Journal: Osaka city medical journal 20030601

Title: Enhancing risk of ethanol on MeIQx-induced rat hepatocarcinogenesis is accompanied with increased levels of cellular proliferation and oxidative stress.

Journal: Cancer letters 20030320

Title: Inhibition of mutagenicity of food-derived heterocyclic amines by sulforaphane--a constituent of broccoli.

Journal: Indian journal of experimental biology 20030301

Title: Lack of initiation activity in rat liver of low doses of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline.

Journal: Cancer letters 20030227

Title: Effects of cigarette smoke and a heterocyclic amine, MeIQx on cytochrome P-450, mutagenic activation of various carcinogens and glucuronidation in rat liver.

Journal: Mutagenesis 20030101

Title: Effect of high sucrose diet on cytochrome P450 1A and heterocyclic amine mutagenesis.

Journal: Anticancer research 20030101

Title: Inhibitory effect of dibenzoylmethane on mutagenicity of food-derived heterocyclic amine mutagens.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20030101

Title: A model system study of the inhibition of heterocyclic aromatic amine formation by organosulfur compounds.

Journal: Journal of agricultural and food chemistry 20021218

Title: Inhibitory effect of curcumin and its natural analogues on genotoxicity of heterocyclic amines from cooked food.

Journal: Indian journal of experimental biology 20021201

Title: Lack of modification of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx)-induced hepatocarcinogenesis in rats by fenbendazole--a CYP1A2 inducer.

Journal: Cancer letters 20021108

Title: Inhibition of heterocyclic aromatic amine formation in fried ground beef patties by garlic and selected garlic-related sulfur compounds.

Journal: Journal of food protection 20021101

Title: Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin.

Journal: Mutation research 20021031

Title: Development of a short questionnaire to assess the dietary intake of heterocyclic aromatic amines.

Journal: Public health nutrition 20021001

Title: Lack of a dose-response relationship for carcinogenicity in the rat liver with low doses of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline or N-nitrosodiethylamine.

Journal: Japanese journal of cancer research : Gann 20021001

Title: Mammary gland carcinogenesis by food-derived heterocyclic amines and studies on the mechanisms of carcinogenesis of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).

Journal: Mutation research 20020930

Title: Analysis of total meat intake and exposure to individual heterocyclic amines in a case-control study of colorectal cancer: contribution of metabolic variation to risk.

Journal: Mutation research 20020930

Title: Metabolism of heterocyclic aromatic amines by human hepatocytes and cytochrome P4501A2.

Journal: Mutation research 20020930

Title: An epidemiologic approach to studying heterocyclic amines.

Journal: Mutation research 20020930

Title: Estimation of dietary HCA intakes in a large-scale population-based prospective study in Japan.

Journal: Mutation research 20020930

Title: Biomarkers of exposure to heterocyclic amines: approaches to improve the exposure assessment.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20020801

Title: Screening for heterocyclic amines in chicken cooked in various ways.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20020801

Title: Effects of soy sauce and sugar on the formation of heterocyclic amines in marinated foods.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20020701

Title: Down-regulation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx)-induced CYP1A2 expression is associated with bovine lactoferrin inhibition of MeIQx-induced liver and colon carcinogenesis in rats.

Journal: Japanese journal of cancer research : Gann 20020601

Title: Role of oxidative DNA damage caused by carbon tetrachloride-induced liver injury -- enhancement of MeIQ-induced glutathione S-transferase placental form-positive foci in rats.

Journal: Cancer letters 20020508

Title: Natural variations of precursors in pig meat affect the yield of heterocyclic amines--effects of RN genotype, feeding regime, and sex.

Journal: Journal of agricultural and food chemistry 20020508

Title: Analysis and quantification of DNA adducts of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in liver of rats by liquid chromatography/electrospray tandem mass spectrometry.

Journal: Chemical research in toxicology 20020401

Title: Genetic polymorphisms in heterocyclic amine metabolism and risk of colorectal adenomas.

Journal: Pharmacogenetics 20020301

Title: 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.

Journal: The journal of medical investigation : JMI 20020201

Title: Human prostate epithelial cells metabolize chemicals of dietary origin to mutagens.

Journal: Cancer letters 20020125

Title: Mutational spectra of benzo[a]pyrene and MeIQx in rpsL transgenic zebrafish embryos.

Journal: Mutation research 20020115

Title: Enhancement by cigarette smoke exposure of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline-induced rat hepatocarcinogenesis in close association with elevation of hepatic CYP1A2.

Journal: Japanese journal of cancer research : Gann 20020101

Title: Mutagenicity of food-derived carcinogens and the effect of antioxidant vitamins.

Journal: Nutrition and cancer 20020101

Title: Clean-up procedures for the analysis of heterocyclic aromatic amines (aminoazaarenes) from heat-treated meat samples.

Journal: Journal of chromatography. A 20011214

Title: Effect of cruciferous vegetable consumption on heterocyclic aromatic amine metabolism in man.

Journal: Carcinogenesis 20010901

Title: Potent antimutagenic activity of white tea in comparison with green tea in the Salmonella assay.

Journal: Mutation research 20010822

Title: Characterization of phenolic compounds in virgin olive oil and their effect on the formation of carcinogenic/mutagenic heterocyclic amines in a model system.

Journal: Journal of agricultural and food chemistry 20010801

Title: A comparison of whole wheat, refined wheat and wheat bran as inhibitors of heterocyclic amines in the Salmonella mutagenicity assay and in the rat colonic aberrant crypt focus assay.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20010701

Title: Regioselective differences in C(8)- and N-oxidation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline by human and rat liver microsomes and cytochromes P450 1A2.

Journal: Chemical research in toxicology 20010701

Title: Dietary intake of heterocyclic amines, meat-derived mutagenic activity, and risk of colorectal adenomas.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20010501

Title: The food mutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline: a conformational analysis of its major DNA adduct and comparison with the 2-amino-3-methylimidazo[4,5-f]quinoline adduct.

Journal: Chemical research in toxicology 20010501

Title: Reporter gene transgenic mice as a tool for analyzing the molecular mechanisms underlying experimental carcinogenesis.

Journal: Journal of experimental & clinical cancer research : CR 20010301

Title: Induction of liver preneoplastic lesions by aminophenylnorharman, formed from norharman and aniline, in male F344 rats.

Journal: Cancer letters 20010226

Title: 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.

Journal: Chemical research in toxicology 20010201

Title: Carcinogen substrate specificity of human COX-1 and COX-2.

Journal: Carcinogenesis 20010101

Title: Recombinant human P450 forms 1A1, 1A2, and 1B1 catalyze the bioactivation of heterocyclic amine mutagens in Escherichia coli lacZ strains.

Journal: Environmental and molecular mutagenesis 20010101

Title: Metabolism of the food mutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in human hepatocytes.

Journal: Advances in experimental medicine and biology 20010101

Title: Interspecies differences in metabolism of heterocyclic aromatic amines by rat and human P450 1A2.

Journal: Cancer letters 19990901

Title: Establishment of a Salmonella tester strain highly sensitive to mutagenic heterocylic amines.

Journal: Cancer letters 19990901

Title: Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats.

Journal: Cancer letters 19990901

Title: Heterozygous p53-deficient mice are not susceptible to 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) carcinogenicity.

Journal: Cancer letters 19990524

Title: Establishment of a Salmonella tester strain highly sensitive to mutagenic heterocyclic amines.

Journal: Cancer research 19980501

Title: Marmoset CYP1A2: primary structure and constitutive expression in livers.

Journal: Carcinogenesis 19971001

Title: Assessing human risk to heterocyclic amines.

Journal: Mutation research 19970512

Title: Effects of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine on intestinal polyp development in Apc delta 716 knockout mice.

Journal: Molecular carcinogenesis 19960101

Title: Simultaneous expression of human CYP3A7 and N-acetyltransferase in Chinese hamster CHL cells results in high cytotoxicity for carcinogenic heterocyclic amines.

Journal: Archives of biochemistry and biophysics 19950710

Title: Studies on the carcinogenic and myocardial effects of 2-amino-3-methylimidazo [4,5-f] quinoline (IQ) in nonhuman primates.

Journal: Princess Takamatsu symposia 19950101

Title: Genetic alterations in HCA-induced tumors.

Journal: Princess Takamatsu symposia 19950101

Title: Effects of human and rat glutathione S-transferases on the covalent DNA binding of the N-acetoxy derivatives of heterocyclic amine carcinogens in vitro: a possible mechanism of organ specificity in their carcinogenesis.

Journal: Cancer research 19940915

Title: Cytochrome P450 forms in the rodent lung involved in the metabolic activation of food-derived heterocyclic amines.

Journal: Carcinogenesis 19930901

Title: Enhancement of GST-P positive liver cell foci development by combined treatment of rats with five heterocyclic amines at low doses.

Journal: Carcinogenesis 19910501

Title: Mutational activation of c-Ha-ras gene in squamous cell carcinomas of rat Zymbal gland induced by carcinogenic heterocyclic amines.

Journal: Molecular carcinogenesis 19910101

Title: Metabolism of 2-acetylaminofluorene and benzo(a)pyrene and activation of food-derived heterocyclic amine mutagens by human cytochromes P-450.

Journal: Cancer research 19900601

Title: Comparison of initiation potential of 2-amino-3-methylimidazo[4,5-f]quinoline and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in an in vivo carcinogen bioassay system.

Journal: Carcinogenesis 19900401

Title: Human liver microsomal cytochrome P-450 enzymes involved in the bioactivation of procarcinogens detected by umu gene response in Salmonella typhimurium TA 1535/pSK1002.

Journal: Cancer research 19890615

Title: Streptozotocin-induced diabetes modulates the metabolic activation of chemical carcinogens.

Journal: Chemico-biological interactions 19880101

Title: Carcinogenicities in mice and rats of IQ, MeIQ, and MeIQx.

Journal: Princess Takamatsu symposia 19850101

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Tags:77500-04-0 Molecular Formula|77500-04-0 MDL|77500-04-0 SMILES|77500-04-0 3,8-Dimethyl-3H-imidazo[4,5-f]quinoxalin-2-amine |Heterocyclic_Building_Blocks