Home Amines 76180-96-6
76180-96-6,MFCD00210316
Catalog No.:AA005FBP

76180-96-6 | 3-Methyl-3H-imidazo[4,5-f]quinolin-2-amine

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50mg
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100mg
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA005FBP
Chemical Name:
3-Methyl-3H-imidazo[4,5-f]quinolin-2-amine
CAS Number:
76180-96-6
Molecular Formula:
C11H10N4
Molecular Weight:
198.2239
MDL Number:
MFCD00210316
SMILES:
Nc1nc2c(n1C)ccc1c2cccn1
Properties
Properties
 
Form:
Solid  
MP:
>200°C (dec.)  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
245  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
XLogP3:
1.5  

Literature

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Title: Oxidative Stress Mechanisms Do Not Discriminate between Genotoxic and Nongenotoxic Liver Carcinogens.

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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: Dammar resin, a non-mutagen, induces [corrected] oxidative stress and metabolic enzymes in the liver of gpt delta transgenic mouse which is different from a mutagen, 2-amino-3-methylimidazo[4,5-f]quinoline.

Journal: Mutation research 20121009

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

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Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120201

Title: 2-Amino-3-methylimidazo[4,5-f]quinoline (IQ) promotes mouse hepatocarcinogenesis by activating transforming growth factor-β and Wnt/β-catenin signaling pathways.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20120201

Title: Inhibition or enhancement by 4 Pacific Island food plants against cancers induced by 2 amino-3-methylimidazo[4,5-f]quinoline in male Fischer 344 rats.

Journal: Nutrition and cancer 20120101

Title: Menopausal status modifies breast cancer risk associated with the myeloperoxidase (MPO) G463A polymorphism in Caucasian women: a meta-analysis.

Journal: PloS one 20120101

Title: Photodegradation of environmental mutagens by visible irradiation in the presence of xanthene dyes as photosensitizers.

Journal: Chemical & pharmaceutical bulletin 20120101

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

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Title: Inhibition of poly(ADP-ribose) polymerase-1 attenuates the toxicity of carbon tetrachloride.

Journal: Journal of enzyme inhibition and medicinal chemistry 20111201

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Title: Validation of a genotoxicity test based on p53R2 gene expression in human lymphoblastoid cells.

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Journal: Cancer science 20110101

Title: Morphological and molecular alterations in 1,2 dimethylhydrazine and azoxymethane induced colon carcinogenesis in rats.

Journal: Journal of biomedicine & biotechnology 20110101

Title: Exposure to isothiocyanates suppresses urinary mutagenicity in rats treated with heterocyclic amine IQ: lack of association with CYP1 activity.

Journal: Nutrition and cancer 20110101

Title: The AOM/DSS murine model for the study of colon carcinogenesis: From pathways to diagnosis and therapy studies.

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Title: Bergamot (Citrus bergamia Risso) fruit extracts and identified components alter expression of interleukin 8 gene in cystic fibrosis bronchial epithelial cell lines.

Journal: BMC biochemistry 20110101

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Title: Inhibition of growth of highly resistant bacterial and fungal pathogens by a natural product.

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Title: Pathobiology and chemoprevention of bladder cancer.

Journal: Journal of oncology 20110101

Title: Fruits and vegetables protect against the genotoxicity of heterocyclic aromatic amines activated by human xenobiotic-metabolizing enzymes expressed in immortal mammalian cells.

Journal: Mutation research 20101221

Title: Assessment of the genotoxic potential of indirect chemical mutagens in HepaRG cells by the comet and the cytokinesis-block micronucleus assays.

Journal: Mutagenesis 20101101

Title: Transcriptomic profile indicative of immunotoxic exposure: in vitro studies in peripheral blood mononuclear cells.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20101101

Title: Evaluation of the genotoxicity of 10 selected dietary/environmental compounds with the in vitro micronucleus cytokinesis-block assay in an interlaboratory comparison.

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Journal: Toxins 20100901

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

Title: In vitro evaluation of baseline and induced DNA damage in human sperm exposed to benzo[a]pyrene or its metabolite benzo[a]pyrene-7,8-diol-9,10-epoxide, using the comet assay.

Journal: Mutagenesis 20100701

Title: Toxicokinetics of the food-toxin IQ in human placental perfusion is not affected by ABCG2 or xenobiotic metabolism.

Journal: Placenta 20100701

Title: The C8-2'-deoxyguanosine adduct of 2-amino-3-methylimidazo[1,2-d]naphthalene, a carbocyclic analogue of the potent mutagen 2-amino-3-methylimidazo[4,5-f]quinoline, is a block to replication in vitro.

Journal: Chemical research in toxicology 20100621

Title: Biological profile of erucin: a new promising anticancer agent from cruciferous vegetables.

Journal: Toxins 20100401

Title: Antimutagenic and anticarcinogenic effect of methanol extracts of Petasites japonicus Maxim leaves.

Journal: Journal of veterinary science 20100301

Title: Evaluation of chrono-amperometric signal detection for the analysis of genotoxicity by a whole cell biosensor.

Journal: Analytica chimica acta 20100205

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: Pivotal role of curcuminoids on the antimutagenic activity of Curcuma zedoaria extracts.

Journal: Drug and chemical toxicology 20100101

Title: Effects of apples and specific apple components on the cecal environment of conventional rats: role of apple pectin.

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Title: Beneficial effects of green tea: a literature review.

Journal: Chinese medicine 20100101

Title: A dietary supplement to improve the quality of sleep: a randomized placebo controlled trial.

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Title: Replication Past the γ-Radiation-Induced Guanine-Thymine Cross-Link G[8,5-Me]T by Human and Yeast DNA Polymerase η.

Journal: Journal of nucleic acids 20100101

Title: Anti-cancer and potential chemopreventive actions of ginseng by activating Nrf2 (NFE2L2) anti-oxidative stress/anti-inflammatory pathways.

Journal: Chinese medicine 20100101

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: Flavonoids inhibit the genotoxicity of hydrogen peroxide (H(2)O(2)) and of the food mutagen 2-amino-3-methylimadazo[4,5-f]-quinoline (IQ) in lymphocytes from patients with inflammatory bowel disease (IBD).

Journal: Mutagenesis 20090901

Title: Characterization of new metabolites from in vivo biotransformation of 2-amino-3-methylimidazo[4,5-f]quinoline in mouse by mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20090901

Title: Identification of new 2-amino-3-methylimidazo[4,5-f]quinoline urinary metabolites from beta-naphthoflavone-treated mice.

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Title: Antimutagenic effect of phenethyl isothiocyanate.

Journal: Central European journal of public health 20090601

Title: Development of a freeze-drying protocol for the long-term storage of S9-fraction at ambient temperatures.

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Title: Tissue differences in the modulation of rat cytochromes P450 and phase II conjugation systems by dietary doses of phenethyl isothiocyanate.

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Title: Mass spectrometric investigation of the sequence selectivity for adduction of heterocyclic aromatic amines on single-strand oligonucleotides.

Journal: Rapid communications in mass spectrometry : RCM 20081001

Title: Impairment of human CYP1A2-mediated xenobiotic metabolism by Antley-Bixler syndrome variants of cytochrome P450 oxidoreductase.

Journal: Archives of biochemistry and biophysics 20080715

Title: N-Demethylation is a major route of 2-amino-3-methylimidazo[4,5-f]quinoline metabolism in mouse.

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

Title: Antimutagenicity of hops (Humulus lupulus L.): bioassay-directed fractionation and isolation of xanthohumol.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20080301

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

Journal: Molecular nutrition & food research 20080301

Title: Anti-clastogenic effect of magnolol on benzo(a)pyrene-induced clastogenicity in mice.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 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: The use of cultured primary bovine colon epithelial cells as a screening model to detect genotoxic effects of heterocyclic aromatic amines in the comet assay.

Journal: Journal of toxicology and environmental health. Part A 20080101

Title: Protective effects of epigallocatechin gallate on colon preneoplastic lesions induced by 2-amino-3-methylimidazo[4,5-f ] quinoline in mice.

Journal: Molecular medicine (Cambridge, Mass.) 20080101

Title: Synthesis of oligonucleotides containing the N2-deoxyguanosine adduct of the dietary carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline.

Journal: Chemical research in toxicology 20071201

Title: New insights in the formation of deoxynucleoside adducts with the heterocyclic aromatic amines PhIP and IQ by means of ion trap MSn and accurate mass measurement of fragment ions.

Journal: Journal of the American Society for Mass Spectrometry 20071201

Title: Beta-glucuronidase in human intestinal microbiota is necessary for the colonic genotoxicity of the food-borne carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline in rats.

Journal: Carcinogenesis 20071101

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Title: Protective effects of xanthohumol against the genotoxicity of benzo(a)pyrene (BaP), 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and tert-butyl hydroperoxide (t-BOOH) in HepG2 human hepatoma cells.

Journal: Mutation research 20070815

Title: Organ-dependent susceptibility of p53 knockout mice to 2-amino-3-methylimidazo[4,5-f]quinoline (IQ).

Journal: Cancer science 20070801

Title: DNA sequence modulates the conformation of the food mutagen 2-amino-3-methylimidazo[4,5-f]quinoline in the recognition sequence of the NarI restriction enzyme.

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Title: Metabolism of a heterocyclic amine colon carcinogen in young and old rats.

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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: Conformational differences of the C8-deoxyguanosine adduct of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) within the NarI recognition sequence.

Journal: Chemical research in toxicology 20070301

Title: 2-(4-Carboxyphenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide potentiates nitrosation of a heterocyclic amine carcinogen by nitric oxide.

Journal: Life sciences 20070123

Title: Increased susceptibility to hepatocarcinogenicity of Nrf2-deficient mice exposed to 2-amino-3-methylimidazo[4,5-f]quinoline.

Journal: Cancer science 20070101

Title: Chemoprevention of aberrant crypt foci in the colon of rats by dietary onion.

Journal: European journal of cancer (Oxford, England : 1990) 20070101

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Journal: BMC cancer 20070101

Title: Translesion synthesis past the C8- and N2-deoxyguanosine adducts of the dietary mutagen 2-Amino-3-methylimidazo[4,5-f]quinoline in the NarI recognition sequence by prokaryotic DNA polymerases.

Journal: Chemical research in toxicology 20061101

Title: In vitro anti-mutagenic effect of magnolol against direct and indirect mutagens.

Journal: Mutation research 20061010

Title: Biochemical basis of genotoxicity of heterocyclic arylamine food mutagens: Human DNA polymerase eta selectively produces a two-base deletion in copying the N2-guanyl adduct of 2-amino-3-methylimidazo[4,5-f]quinoline but not the C8 adduct at the NarI G3 site.

Journal: The Journal of biological chemistry 20060901

Title: Lack of formation of heterocyclic amines in fumes from frying French fries.

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

Title: Base-displaced intercalated structure of the food mutagen 2-amino-3-methylimidazo[4,5-f]quinoline in the recognition sequence of the NarI restriction enzyme, a hotspot for -2 bp deletions.

Journal: Journal of the American Chemical Society 20060809

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Journal: The Prostate 20060601

Title: N-Acetyltransferase and sulfotransferase activity in human prostate: potential for carcinogen activation.

Journal: Pharmacogenetics and genomics 20060601

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Journal: Chemical research in toxicology 20060601

Title: Enhancing effects of simultaneous treatment with sodium nitrite on 2-amino-3-methylimidazo[4,5-f]quinoline-induced rat liver, colon and Zymbal's gland carcinogenesis after initiation with diethylnitrosamine and 1,2-dimethylhydrazine.

Journal: International journal of cancer 20060515

Title: Parp-1 deficiency does not enhance liver carcinogenesis induced by 2-amino-3-methylimidazo[4,5-f]quinoline in mice.

Journal: Cancer letters 20060508

Title: Lung as a new target in rats of 2-amino-3-methylimidazo[4,5-f]quinoline carcinogenesis: results of a two-stage model initiated with N-bis(2-hydroxypropyl)nitrosamine.

Journal: Cancer science 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: Breast cancer resistance protein (Bcrp1/Abcg2) reduces systemic exposure of the dietary carcinogens aflatoxin B1, IQ and Trp-P-1 but also mediates their secretion into breast milk.

Journal: Carcinogenesis 20060101

Title: Post-initiation chlorophyllin exposure does not modulate aflatoxin-induced foci in the liver and colon of rats.

Journal: Journal of carcinogenesis 20060101

Title: A 26-week carcinogenicity study of 2-amino-3-methylimidazo[4,5-f]quinoline in rasH2 mice.

Journal: Toxicologic pathology 20060101

Title: Modest induction of phase 2 enzyme activity in the F-344 rat prostate.

Journal: BMC cancer 20060101

Title: IGF-II transgenic mice display increased aberrant colon crypt multiplicity and tumor volume after 1,2-dimethylhydrazine treatment.

Journal: Journal of carcinogenesis 20060101

Title: 2-Nitrosoamino-3-methylimidazo[4,5-f]quinoline activated by the inflammatory response forms nucleotide adducts.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 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: 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: Characterization of antimutagenic mechanism of 3-allyl-5-substituted 2-thiohydantoins against 2-amino-3-methylimidazo[4,5-f]quinoline.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20050401

Title: The effects of thyme volatiles on the induction of DNA damage by the heterocyclic amine IQ and mitomycin C.

Journal: Mutation research 20050307

Title: The stimulatory role of human cytochrome b5 in the bioactivation activities of human CYP1A2, 2A6 and 2E1: a new cell expression system to study cytochrome P450 mediated biotransformation.

Journal: Mutagenesis 20050301

Title: Hemin potentiates nitric oxide-mediated nitrosation of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) to 2-nitrosoamino-3-methylimidazo[4,5-f]quinoline.

Journal: Chemical research in toxicology 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: A comparison of genotoxicity between three common heterocyclic amines and acrylamide.

Journal: Mutation research 20050207

Title: Myeloperoxidase potentiates nitric oxide-mediated nitrosation.

Journal: The Journal of biological chemistry 20050121

Title: In vivo mutational analysis of liver DNA in gpt delta transgenic rats treated with the hepatocarcinogens N-nitrosopyrrolidine, 2-amino-3-methylimidazo[4,5-f]quinoline, and di(2-ethylhexyl)phthalate.

Journal: Molecular carcinogenesis 20050101

Title: Genotoxicity of environmental agents assessed by the alkaline comet assay.

Journal: Basic & clinical pharmacology & toxicology 20050101

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

Journal: Nutrition and cancer 20050101

Title: Synthesis of the N2-deoxyguanosine adduct of the potent dietary mutagen IQ.

Journal: Organic letters 20041223

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

Journal: Chemical research in toxicology 20041201

Title: Sucrose and IQ induced mutations in rat colon by independent mechanism.

Journal: Mutation research 20041004

Title: Site-specific synthesis and properties of oligonucleotides containing C8-deoxyguanosine adducts of the dietary mutagen IQ.

Journal: Journal of the American Chemical Society 20040915

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

Journal: Molecular nutrition & food research 20040901

Title: Short-term black tea intake modulates the excretion of urinary mutagens in rats treated with 2-amino-3-methylimidazo-[4,5-f]quinoline (IQ): role of CYP1A2 upregulation.

Journal: Archives of toxicology 20040801

Title: Characterization of a peptide adduct formed by N-acetoxy-2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), a reactive intermediate of the food carcinogen PhIP.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20040801

Title: Effects of sucrose and cornstarch on 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)-induced colon and liver carcinogenesis in F344 rats.

Journal: Cancer letters 20040608

Title: 2-Nitrosoamino-3-methylimidazo[4,5-f]quinoline stability and reactivity.

Journal: Chemical research in toxicology 20040501

Title: An improved method for the extraction of mutagens from human urine and cooked meat using blue rayon.

Journal: Mutation research 20040411

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

Journal: Mutation research 20040411

Title: Formation and reduction of aryl and heterocyclic nitroso compounds and significance in the flux of hydroxylamines.

Journal: Chemical research in toxicology 20040401

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: Mechanisms by which resistant starches and non-starch polysaccharide sources affect the metabolism and disposition of the food carcinogen, 2-amino-3-methylimidazo[4,5-f]quinoline.

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

Title: Effect of intestinal microfloras from vegetarians and meat eaters on the genotoxicity of 2-amino-3-methylimidazo[4,5-f]quinoline, a carcinogenic heterocyclic amine.

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

Title: Effect of common Brassica vegetables (Brussels sprouts and red cabbage) on the development of preneoplastic lesions induced by 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in liver and colon of Fischer 344 rats.

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

Title: Protective effects of Brussels sprouts, oligosaccharides and fermented milk towards 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)-induced genotoxicity in the human flora associated F344 rat: role of xenobiotic metabolising enzymes and intestinal microflora.

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

Title: Anti-genotoxic activity of the mushroom Lactarius vellereus extract in bacteria and in mammalian cells in vitro.

Journal: Die Pharmazie 20040301

Title: Uptake of heterocyclic aromatic amine by insoluble dietary fiber in artificial gastric and intestinal juice.

Journal: Environmental health and preventive medicine 20040301

Title: Functional characterization of four allelic variants of human cytochrome P450 1A2.

Journal: Archives of biochemistry and biophysics 20040201

Title: Cigarette smoking, cytochrome P4501A1 polymorphisms, and breast cancer among African-American and white women.

Journal: Breast cancer research : BCR 20040101

Title: Antimutagenic activity of spearmint.

Journal: Environmental and molecular mutagenesis 20040101

Title: Selected heterocyclic amines.

Journal: Report on carcinogens : carcinogen profiles 20040101

Title: Bacterial antimutagenesis by hydroxycinnamic acids from plant cell walls.

Journal: Mutation research 20031209

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

Journal: Carcinogenesis 20031201

Title: Effects of dietary antioxidants and 2-amino-3-methylimidazo[4,5-f]- quinoline (IQ) on preneoplastic lesions and on oxidative damage, hormonal status, and detoxification capacity in the rat.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20031001

Title: Regional mutagenicity of heterocyclic amines in the intestine: mutation analysis of the cII gene in lambda/lacZ transgenic mice.

Journal: Mutation research 20030805

Title: The disposition and metabolism of 2-amino-3-methylimidazo-[4,5-f]quinoline in the F344 rat at high versus low doses of indole-3-carbinol.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030801

Title: Dietary low-dose sucrose modulation of IQ-induced genotoxicity in the colon and liver of Big Blue rats.

Journal: Mutation research 20030619

Title: Contrasting effects of non-starch polysaccharide and resistant starch-based diets on the disposition and excretion of the food carcinogen, 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), in a rat model.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20030601

Title: Modulation of the mutagenicity of heterocyclic amines by organophosphate insecticides and their metabolites.

Journal: Mutation research 20030420

Title: Mutational analysis of Ctnnb1 and Apc in tumors from rats given 1,2-dimethylhydrazine or 2-amino-3-methylimidazo[4,5-f]quinoline: mutational 'hotspots' and the relative expression of beta-catenin and c-jun.

Journal: Molecular carcinogenesis 20030401

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

Journal: Indian journal of experimental biology 20030301

Title: Chemoprevention of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)-induced colonic and hepatic preneoplastic lesions in the F344 rat by cruciferous vegetables administered simultaneously with the carcinogen.

Journal: Carcinogenesis 20030201

Title: Use of human liver S9 in the Ames test: assay of three procarcinogens using human S9 derived from multiple donors.

Journal: Regulatory toxicology and pharmacology : RTP 20030201

Title: Development and characterization of CHO repair-proficient cell lines for comparative mutagenicity and metabolism of heterocyclic amines from cooked food.

Journal: Environmental and molecular mutagenesis 20030101

Title: Promotion versus suppression of rat colon carcinogenesis by chlorophyllin and chlorophyll: modulation of apoptosis, cell proliferation, and beta-catenin/Tcf signaling.

Journal: Mutation research 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: Effect of dietary constituents with chemopreventive potential on adduct formation of a low dose of the heterocyclic amines PhIP and IQ and phase II hepatic enzymes.

Journal: Nutrition and cancer 20030101

Title: Modulation by flavonoids of the effects of a food mutagen in different thalassaemia genotypes in the Comet assay.

Journal: Teratogenesis, carcinogenesis, and mutagenesis 20030101

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: Effect of CYP1A2 deficiency on heterocyclic amine DNA adduct levels in mice.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 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: Induction of tumors in the colon and liver of the immunodeficient (SCID) mouse by 2-amino-3-methylimidazo[4,5-f ]quinoline (IQ)-modulation by long-chain fatty acids.

Journal: Carcinogenesis 20020901

Title: Heterologous expression of human N-acetyltransferases 1 and 2 and sulfotransferase 1A1 in Salmonella typhimurium for mutagenicity testing of heterocyclic amines.

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

Title: DNA damage and metallothionein synthesis in human hepatoma cells (HepG2) exposed to cadmium.

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

Title: Mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline in colon and liver of Big Blue rats: role of DNA adducts, strand breaks, DNA repair and oxidative stress.

Journal: Carcinogenesis 20020801

Title: Nitrosation and nitration of 2-amino-3-methylimidazo[4,5-f]quinoline by reactive nitrogen oxygen species.

Journal: Chemical research in toxicology 20020801

Title: Reactivity and selectivity of the N-acetyl-Glu-P-1, N-acetyl-Glu-P-2, N-acetyl-MeIQx, and N-acetyl-IQx nitrenium ions: comparison to carbocyclic N-arylnitrenium ions.

Journal: Journal of the American Chemical Society 20020710

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: Chemoprotective effects of garden cress (Lepidium sativum) and its constituents towards 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ)-induced genotoxic effects and colonic preneoplastic lesions.

Journal: Carcinogenesis 20020701

Title: One dose of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) or 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) induces tumours in Min/+ mice by truncation mutations or LOH in the Apc gene.

Journal: Mutation research 20020527

Title: Antimutagenic activity of selenium-enriched green tea toward the heterocyclic amine 2-amino-3-methylimidazo[4,5-f]quinoline.

Journal: Biological trace element research 20020501

Title: Antimutagenic activities of various lactic acid bacteria against food mutagens: heterocyclic amines.

Journal: The Journal of dairy research 20020501

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: Sequencing of the rat beta-catenin gene (Ctnnb1) and mutational analysis of liver tumors induced by 2-amino-3-methylimidazo[4,5-f]quinoline.

Journal: Gene 20020123

Title: Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1.

Journal: Mutagenesis 20020101

Title: Tobacco smoke carcinogens and breast cancer.

Journal: Environmental and molecular mutagenesis 20020101

Title: Studies on mammary carcinogenesis induced by a heterocyclic amine, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, in mice and rats.

Journal: Environmental and molecular mutagenesis 20020101

Title: Inhibition of colonic aberrant crypt formation by the dietary flavonoids (+)-catechin and hesperidin.

Journal: Advances in experimental medicine and biology 20020101

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

Journal: Nutrition and cancer 20020101

Title: Diet modulates the genotoxicity of IQ (2-amino-3-methylimidazo[4,5-f]quinoline) in rats associated with a human faecal flora.

Journal: IARC scientific publications 20020101

Title: IQ (2-amino-3-methylimidazo[4,5-f]quinoline)-induced aberrant crypt foci and colorectal tumour development in rats fed two different carbohydrate diets.

Journal: IARC scientific publications 20020101

Title: 2-Amino-3-methylimidazo[4,5-f]quinolone (IQ).

Journal: Report on carcinogens : carcinogen profiles 20020101

Title: IQ (2-amino-3-methylimidazo[4,5-f]quinoline)-induced aberrant crypt foci and colorectal tumour development in rats fed two different carbohydrate diets.

Journal: European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 20011201

Title: Evaluation of the cytotoxicity, mutagenicity and antimutagenicity of emerging edible plants.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20011101

Title: Intestinal microflora plays a crucial role in the genotoxicity of the cooked food mutagen 2-amino-3-methylimidazo [4,5-f]quinoline.

Journal: Carcinogenesis 20011001

Title: Contributions of major components to the antimutagenic effect of Hsian-tsao (Mesona procumbens Hemsl.).

Journal: Journal of agricultural and food chemistry 20011001

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

Journal: Mutation research 20010822

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: Urinary excretion of N-OH-2-amino-3-methylimidazo[4,5-f]quinoline-N-glucuronide in F344 rats is enhanced by green tea.

Journal: Carcinogenesis 20010701

Title: Quantification of the heterocyclic aromatic amine DNA adduct N-(deoxyguanosin-8-yl)-2-amino-3-methylimidazo[4,5-f]quinoline in livers of rats using capillary liquid chromatography/microelectrospray mass spectrometry: a dose-response study.

Journal: Analytical chemistry 20010701

Title: Assessing carcinogen exposure with MS.

Journal: Analytical chemistry 20010701

Title: N-Acetyltransferases, sulfotransferases and heterocyclic amine activation in the breast.

Journal: Pharmacogenetics 20010701

Title: Green tea and the metabolism of 2-amino-3-methylimidazo.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20010601

Title: Detection of in vivo formed DNA adducts at the part-per-billion level by capillary liquid chromatography/microelectrospray mass spectrometry.

Journal: Analytical chemistry 20010601

Title: Isolation and characterization of structurally novel antimutagenic flavonoids from spinach (Spinacia oleracea).

Journal: Journal of agricultural and food chemistry 20010601

Title: Metabolic activation of heterocyclic amines and other procarcinogens in Salmonella typhimurium umu tester strains expressing human cytochrome P4501A1, 1A2, 1B1, 2C9, 2D6, 2E1, and 3A4 and human NADPH-P450 reductase and bacterial O-acetyltransferase.

Journal: Mutation research 20010531

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: Colonic cell proliferation, apoptosis and aberrant crypt foci development in rats given 2-amino-3-methylimidaz.

Journal: European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 20010401

Title: Investigation of commercial Mitolife as an antioxidant and antimutagen.

Journal: Nutrition (Burbank, Los Angeles County, Calif.) 20010401

Title: Synthesis of the C8-deoxyguanosine adduct of the food mutagen IQ.

Journal: Organic letters 20010222

Title: Post-initiation effects of chlorophyllin and indole-3-carbinol in rats given 1,2-dimethylhydrazine or 2-amino-3-methyl- imidazo.

Journal: Carcinogenesis 20010201

Title: beta-Catenin mutation in rat colon tumors initiated by 1,2-dimethylhydrazine and 2-amino-3-methylimidazo[4,5-f]quinoline, and the effect of post-initiation treatment with chlorophyllin and indole-3-carbinol.

Journal: Carcinogenesis 20010201

Title: DNA adduct formation by 2-amino-3-methylimidazo [4,5-f] quinoline (IQ) in rat colon.

Journal: The journal of medical investigation : JMI 20010201

Title: Contrasting effects of acute and chronic dietary exposure to 2-amino-3-methyl-imidazo[4,5-f]quinoline (IQ) on xenobiotic metabolising enzymes in the male Fischer 344 rat: implications for chemoprevention studies.

Journal: European journal of nutrition 20010201

Title: Effects of heterocyclic amines with mammary gland carcinogenic potential on estrogenic response of uterus in ovariectomized rats.

Journal: Cancer letters 20010110

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

Journal: Carcinogenesis 20010101

Title: Metabolism of ochratoxin A: absence of formation of genotoxic derivatives by human and rat enzymes.

Journal: Chemical research in toxicology 20010101

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

Journal: Cancer letters 19990901

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

Journal: Cancer research 19980501

Title: High frequency of beta-catenin (ctnnb1) mutations in the colon tumors induced by two heterocyclic amines in the F344 rat.

Journal: Cancer research 19980315

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

Journal: Carcinogenesis 19971001

Title: Differential effect of acetyltransferase expression on the genotoxicity of heterocyclic amines in CHO cells.

Journal: Mutation research 19970424

Title: Genetic alterations in rat colon tumors induced by heterocyclic amines.

Journal: Cancer 19960415

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: Specific 5'-GGGA-3'-->5'-GGA-3' mutation of the Apc gene in rat colon tumors induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19950131

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: Chemopreventive effects of beta-carotene, alpha-tocopherol and five naturally occurring antioxidants on initiation of hepatocarcinogenesis by 2-amino-3-methylimidazo[4,5-f]quinoline in the rat.

Journal: Japanese journal of cancer research : Gann 19941201

Title: Heterocyclic amines formed by cooking food: comparison of bioassay results with other chemicals in the Carcinogenic Potency Database.

Journal: Cancer letters 19940815

Title: Absence of p53 mutations in rat colon tumors induced by 2-amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole, 2-amino-3-methylimidazo[4,5-f]quinoline, or 2-amino-1-methyl-6-phenylimidazo]4,5-b]pyridine.

Journal: Japanese journal of cancer research : Gann 19940501

Title: Rare frequency of activation of the Ki-ras gene in rat colon tumors induced by heterocyclic amines: possible alternative mechanisms of human colon carcinogenesis.

Journal: Molecular carcinogenesis 19930101

Title: Introduction of cytochrome P450IA2 metabolic capability into cell lines genetically matched for DNA repair proficiency/deficiency.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19910501

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: Carcinogenic potential of cooked food mutagens (IQ and MeIQ) in Wistar rats after short-term exposure.

Journal: Pharmacology & toxicology 19891101

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: Dose-dependent induction of liver and thyroid neoplastic lesions by short-term administration of 2-amino-3-methylimidazo[4,5-f]quinoline combined with partial hepatectomy followed by phenobarbital or low dose 3'-methyl-4-dimethylaminoazobenzene promotion.

Journal: Japanese journal of cancer research : Gann 19880601

Title: Carcinogenicity in mice and rats of heterocyclic amines in cooked foods.

Journal: Environmental health perspectives 19860801

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

Journal: Princess Takamatsu symposia 19850101

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Tags:76180-96-6 Molecular Formula|76180-96-6 MDL|76180-96-6 SMILES|76180-96-6 3-Methyl-3H-imidazo[4,5-f]quinolin-2-amine |Heterocyclic_Building_Blocks