Effect of glutathione depletion and inhibition of glucuronidation and sulfation on 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) metabolism, PhIP-DNA adduct formation and unscheduled DNA synthesis in primary rat hepatocytes.

No abstract is available for this paper.

• Publication year

  1994

• Venue

  Carcinogenesis

• Publication date

  1994-08-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1093/CARCIN/15.8.1711PMID 8055653
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Glucuronidation of N-hydroxy heterocyclic amines by human and rat liver microsomes.

  1994cited by this paper
• 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.

  1992cited by this paper
• Identification of N-(Deoxyguanosin-8-yl)-2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine as the major adduct formed by the food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, with DNA.

  1992cited by this paper
• Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) with 2'-deoxyguanosine and DNA. Synthesis and identification of N2-(2'-deoxyguanosin-8-yl)-PhIP.

  1992cited by this paper
• A new colon and mammary carcinogen in cooked food, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).

  1991cited by this paper
• Presence of carcinogenic heterocyclic amines in urine of healthy volunteers eating normal diet, but not of inpatients receiving parenteral alimentation.

  1991cited by this paper
• 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.

  1991cited by this paper
• Detection of a carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), in cigarette smoke condensate.

  1991cited by this paper
• Metabolic activation of carcinogenic heterocyclic aromatic amines by human liver and colon.

  1991cited by this paper
• The formation of heart DNA adducts in F344 rat following dietary administration of heterocyclic amines.

  1991cited by this paper
• Formation of a glutathione conjugate and a semistable transportable glucuronide conjugate of N2-oxidized species of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in rat liver.

  1991cited by this paper
• Re: "Fried foods and the risk of colon cancer".

  1990cited by this paper
• Aromatic amine acetyltransferase as a marker for colorectal cancer: Environmental and demographic associations

  1990cited by this paper
• Enhancement by cysteinyl thiols of acetyltransferase-mediated, but not of sulfotransferase-mediated, binding of a pyrolysate-derived N-hydroxyarylamine, 2-hydroxyamino-6-methyldipyrido[1,2-a:3',2'-d]imidazole, to DNA.

  1990cited by this paper
• Simple methods for quantifying mutagenic heterocyclic aromatic amines in food products.

  1990cited by this paper
• DNA Adducts Formed by 2‐Amino‐3,8‐dimethylimidazo[4,5‐f]quinoxaline in Rat Liver: Dose‐Response on Chronic Administration

  1990cited by this paper
• Metabolism of 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP) by liver microsomes and isolated rabbit cytochrome P450 isozymes.

  1990cited by this paper
• Role of sulfation and acetylation in the activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine to intermediates which bind DNA.

  1990cited by this paper
• The contribution of N-oxidation to the metabolism of the food-borne carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in rat hepatocytes.

  1990cited by this paper
• Effect of pretreatment with hepatic mixed-function oxidase inducers on the genotoxicity of four rat carcinogens in the hepatocyte/DNA repair assay.

  1990cited by this paper
• Differential rates of metabolic activation and detoxication of the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by different cytochrome P450 enzymes.

  1990cited by this paper
• DNA Modification by 2‐Amino‐1‐methyl‐6‐phenylimidazo[4,5‐b]pyridine in Rats

  1989cited by this paper
• 4-(2-amino-1-methylimidazo[4,5-b]pyrid-6-yl)phenyl sulfate--a major metabolite of the food mutagen 2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine (PhIP) in the rat.

  1989cited by this paper
• Genotoxicity of the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP): formation of 2-hydroxamino-PhIP, a directly acting genotoxic metabolite.

  1989cited by this paper
• Identification of the mutagens in cooked beef.

  1986cited by this paper
• The isolation and identification of a new mutagen from fried ground beef: 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).

  1986cited by this paper
• Nonrandom binding of the carcinogen N-hydroxy-2-acetylaminofluorene to repetitive sequences of rat liver DNA in vivo.

  1984cited by this paper
• Effect of glutathione and uridine-5'-diphosphoglucuronic acid on the mutagenicity of tryptophan pyrolysis products (Trp-P-1 and Trp-P-2) by rat-liver and -intestine S9 fraction.

  1984cited by this paper
• Effect of glutathione levels, sulfate levels, and metabolic inhibitors on covalent binding of 2-amino-3-methylimidazo[4,5-f]quinoline and 2-acetylaminofluorene to cell macromolecules in primary monolayer cultures of adult rat hepatocytes.

  1984cited by this paper
• Activation and detoxication of N-hydroxy-Trp-P-2 by glutathione and glutathione transferases.

  1983cited by this paper
• Mutagens-carcinogens in foods.

  1983cited by this paper
• Dependence of glucuronidation rate on UDP-glucuronic acid levels in isolated hepatocytes.

  1981cited by this paper
• A rapid and simple synthesis of reactive metabolites of carcinogenic aromatic amines in high yield.

  1981cited by this paper
• Inhibition of sulfate conjugation of N-hydroxy-2-acetylaminofluorene in isolated perfused rat liver and in the rat in vivo by pentachlorophenol and low sulfate.

  1980cited by this paper
• Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n-butyl homocysteine sulfoximine).

  1979cited by this paper
• Protein measurement with the Folin phenol reagent.

  1951cited by this paper

• Multi-DNA Adduct and Abasic Site Quantitation In Vivo by Nano-Liquid Chromatography/High-Resolution Orbitrap Tandem Mass Spectrometry: Methodology for Biomonitoring Colorectal DNA Damage.

  2022cites this paper
• Metabolism and biomarkers of heterocyclic aromatic amines in humans

  2021cites this paper
• Mouse models of colorectal cancer: Past, present and future perspectives

  2020cites this paper
• Phenethyl isothiocyanate and indole-3-carbinol from cruciferous vegetables, but not furanocoumarins from apiaceous vegetables, reduced PhIP-induced DNA adducts in Wistar rats.

  2016cites this paper
• Updated recommended lists of genotoxic and non-genotoxic chemicals for assessment of the performance of new or improved genotoxicity tests.

  2016cites this paper
• Apiaceous vegetable consumption decreases PhIP-induced DNA adducts and increases methylated PhIP metabolites in the urine metabolome in rats.

  2015cites this paper
• Modulation of prostate and pancreatic PhIP-DNA adducts by consumption of cruciferous and apiaceous vegetables in male wistar rats

  2013cites this paper
• Accelerated Cytotoxicity Mechanism Screening of 4-Aminobiphenyl in an in vitro Hepatocyte Inflammation Model

  2011cites this paper
• Metabolism and biomarkers of heterocyclic aromatic amines in molecular epidemiology studies: lessons learned from aromatic amines.

  2011cites this paper
• Pharmacokinetics of liquiritigenin and its two glucuronides, M1 and M2, in rats with acute hepatitis induced by d-galactosamine/lipopolysaccharide or CCl4

  2010cites this paper
• Amodiaquine-induced oxidative stress in a hepatocyte inflammation model.

  2009cites this paper
• Liquiritigenin, a flavonoid aglycone from licorice, has a choleretic effect and the ability to induce hepatic transporters and phase-II enzymes.

  2009cites this paper
• Reactions of Nitrosoarenes with SH Groups

  2009cites this paper
• PSA-Based Screening Outcomes, Dietary Heterocyclic Amine Exposure, and Prostate Cancer Risk in African Americans

  2008cites this paper
• Recommended lists of genotoxic and non-genotoxic chemicals for assessment of the performance of new or improved genotoxicity tests: a follow-up to an ECVAM workshop.

  2008cites this paper
• UGT1A1 and UGT1A9 functional variants, meat intake, and colon cancer, among Caucasians and African-Americans.

  2008cites this paper
• Chapter 3 Glucuronidation-Dependent Toxicity and Bioactivation

  2008cites this paper
• Mechanisms of drug-induced oxidative stress in the hepatocyte inflammation model.

  2008cites this paper
• Highly elevated PSA and dietary PhIP intake in a prospective clinic-based study among African Americans

  2007cites this paper
• 14 – The possible involvement of mutagenic and carcinogenic heterocyclic amines in human cancer

  2006cites this paper
• Biochemical and Molecular Roles of Nutrients Dietary Components Modify the Ability of Garlic to Suppress 7,12-Dimethylbenz(a)anthracene-Induced Mammary DMA Adducts1'2'3

  2006cites this paper
• 16 – Metabolic factors affecting the mutagenicity of heterocyclic amines

  2006cites this paper
• Effects of alpha-naphthyl isothiocyanate and a heterocyclic amine, PhIP, on cytochrome P-450, mutagenic activation of various carcinogens and glucuronidation in rat liver.

  2005cites this paper
• Cigarette smoking, metabolic activation and carcinogenesis.

  2004cites this paper
• Potential toxicity of flavonoids and other dietary phenolics: significance for their chemopreventive and anticancer properties.

  2004cites this paper
• The Effect of Dietary Restriction on PhIP-Induced Mutation in the Distal Colon and B[a]P- and ENU-Induced Mutation in the Liver of the Rat

  2004cites this paper
• The role of genetic polymorphisms in metabolism of carcinogenic heterocyclic aromatic amines.

  2004cites this paper
• Association of SULT1A1 Phenotype and Genotype with Prostate Cancer Risk in African-Americans and Caucasians

  2004cites this paper
• Enzyme polymorphisms influencing the metabolism of heterocyclic aromatic amines.

  2004cites this paper
• Meat‐related mutagens/carcinogens in the etiology of colorectal cancer

  2004cites this paper
• The effects of coffee on enzymes involved in metabolism of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in rats.

  2003cites this paper
• Effects of cigarette smoke and a heterocyclic amine, MeIQx on cytochrome P-450, mutagenic activation of various carcinogens and glucuronidation in rat liver.

  2003influential citation
• Metabolic activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Syrian hamsters congenic at the N-acetyltransferase 2 (NAT2) locus.

  2003influential citation
• Metabolism of heterocyclic aromatic amines by human hepatocytes and cytochrome P4501A2.

  2002cites this paper
• Mammary gland carcinogenesis by food‐derived heterocyclic amines: Metabolism and additional factors influencing carcinogenesis by 2‐amino‐1‐methyl‐6‐phenylimidazo[4,5‐b]pyridine (PhIP)

  2002cites this paper
• 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

  2002cites this paper
• Cytosolic enzymes from rat tissues that activate the cooked meat mutagen metabolite N-Hydroxyamino-1-methyl-6- phenylimidazo[4,5-b]pyridine (N-OH-PhIP).

  2001cites this paper
• Increased bioavailability of the food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in MRP2-deficient rats.

  2001cites this paper
• Mrp2-deficiency in the rat impairs biliary and intestinal excretion and influences metabolism and disposition of the food-derived carcinogen 2-amino-1-methyl-6-phenylimidazo.

  2001cites this paper
• Oral administration of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) yields PhIP-DNA adducts but not tumors in male Syrian hamsters congenic at the N-acetyltransferase 2 (NAT2) locus.

  2001cites this paper
• U.S. dietary exposures to heterocyclic amines*

  2001cites this paper
• Evaluation of fecal mutagenicity and colorectal cancer risk.

  2000cites this paper
• DEVELOPMENT AND UTILIZATION OF PRIMARY HEPATOCYTE CULTURE SYSTEMS TO EVALUATE METABOLISM, DNA BINDING, AND DNA REPAIR OF XENOBIOTICS*

  2000cites this paper
• Indole-3-carbinol as a chemopreventive agent in 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) carcinogenesis: inhibition of PhIP-DNA adduct formation, acceleration of PhIP metabolism, and induction of cytochrome P450 in female F344 rats.

  2000cites this paper
• Creatine and creatinine metabolism.

  2000cites this paper
• 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine induces a higher number of aberrant crypt foci in Fischer 344 (rapid) than in Wistar Kyoto (slow) acetylator inbred rats.

  2000cites this paper
• Major inter-species differences in the rates of O-sulphonation and O-glucuronylation of alpha-hydroxytamoxifen in vitro: a metabolic disparity protecting human liver from the formation of tamoxifen-DNA adducts.

  2000cites this paper
• Evaluation of fecal mutagenicity and colorectal cancer risk 1 Manuscript requested by Paul A. White.

  2000cites this paper
• N-acetyltransferase-dependent activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine: formation of 2-amino-1-methyl-6-(5-hydroxy)phenylimidazo [4,5-b]pyridine, a possible biomarker for the reactive dose of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.

  2000cites this paper
• Inhibition of DNA adduct formation of 2‐amino‐1‐methyl‐6‐phenylimidazo[4,5‐b]pyridine and 2‐amino‐3‐methylimidazo[4,5‐f]quinoline by dietary indole‐3‐carbinol in female rats

  1999cites this paper
• DNA adducts of heterocyclic amine food mutagens: implications for mutagenesis and carcinogenesis.

  1999cites this paper
• Glucuronidation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4, 5-b]pyridine by human microsomal UDP-glucuronosyltransferases: identification of specific UGT1A family isoforms involved.

  1999cites this paper
• 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.

  1999cites this paper
• Metabolism and Cytotoxicity of Chlorpropham (CIPC) and Its Essential Metabolites in Isolated Rat Hepatocytes During a Partial Inhibition of Sulphation and Glucuronidation Reactions: A Comparative Study

  1998cites this paper
• Effect of some cooked food mutagens on unscheduled DNA synthesis in cultured precision-cut rat, mouse and human liver slices.

  1998cites this paper
• Effects of Selected Polycyclic Aromatic Hydrocarbons on Cell Proliferation, Protein Phosphorylation, and Intracellular Calcium Concentration in Lepomis Macrochirus.

  1998cites this paper
• Mutagenicity of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) when activated by hamster pancreatic duct epithelial cells: a chemopreventive role for glutathione.

  1997cites this paper
• Colon cancer from etiology to prevention

  1997cites this paper
• Metabolic differences and their impact on human disease Sulfotransferase and colorectal cancer.

  1997cites this paper
• Estimation of exposure to two potent heterocyclic aromatic amines in various human populations and their role in colorectal cancer

  1997cites this paper
• Thomas G. Orr Memorial Lectureship. Colon cancer from etiology to prevention.

  1997cites this paper
• DNA adduct formation, cell proliferation and aberrant crypt focus formation induced by PhIP in male and female rat colon with relevance to carcinogenesis.

  1996cites this paper
• Formation and processing of reactive metabolites of the heterocyclic amines.

  1996cites this paper
• Enzymic and interindividual differences in the human metabolism of heterocyclic amines.

  1996cites this paper
• Dissociation of DDVP-induced DNA strand breaks from oxidative damage in isolated rat hepatocytes.

  1996cites this paper
• Dietary components modify the ability of garlic to suppress 7,12-dimethylbenz(a)anthracene-induced mammary DNA adducts.

  1996cites this paper
• Role of glutathione modulation in acrylonitrile-induced gastric DNA damage in rats

  1996cites this paper
• Strong anti-mutagenic activity of the novel lipophilic antioxidant 1-O-hexyl-2,3,5-trimethylhydroquinone against heterocyclic amine-induced mutagenesis in the Ames assay and its effect on metabolic activation of 2-amino-6-methyldipyrido[1,2-a:3',2'-d] imidazole (Glu-p-1).

  1995cites this paper
• Determination of in vitro formed DNA adducts of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine using capillary liquid chromatography/electrospray ionization/tandem mass spectrometry.

  1995cites this paper
• Protective effect of N-acetylcysteine against heterocyclic amine-induced cardiotoxicity in cultured myocytes and in rats.

  1995cites this paper
• Metabolic activation of N-hydroxy arylamines and N-hydroxy heterocyclic amines by human sulfotransferase(s).

  1995cites this paper
• 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.

  1994cites this paper
• Metabolic activation pathway for the formation of DNA adducts of the carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in rat extrahepatic tissues.

  1994cites this paper