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

Abstract:

:Both cooked red meat intake and chronic inflammation/infection are thought to play a role in the etiology of colon cancer. The heterocyclic amine 2-amino-3-methylimidazo[4,5-f ]quinoline (IQ) is formed during cooking of red meat and may be involved in initiation of colon cancer. Reactive nitrogen oxygen species (RNOS), components of the inflammatory response, contribute to the deleterious effects attributed to inflammation on normal tissues. This study assessed the possible chemical transformation of IQ by RNOS. RNOS were generated by various conditions to react with (14)C-IQ, and samples were evaluated by HPLC. Myeloperoxidase (MPO)-catalyzed reaction was dependent upon both H(2)O(2) and NO(2)(-). This reaction produced an azo-IQ dimer and IQ dimer along with two nitrated IQ products identified by ESI/MS. 2-Nitro-IQ was not detected. Product formation was inhibited by 2 mM cyanide. Reduction in nitrated products observed with 100 mM chloride was not altered with 0.5 mM taurine. Nitrated products were also produced by other conditions, ONOO(-) and NO(2)(-) + HOCl, which generate nitrogen dioxide radical. In contrast, conditions which generate N(2)O(3), such as diethylamine NONOate, produced only small amounts of nitrated products with the major product identified by MS and NMR as N-nitroso-IQ. MPO activation of IQ to bind DNA was dependent upon both H(2)O(2) and NO(2)(-). RNOS generated by ONOO(-) and DEA NONOate also activated IQ DNA binding. The nitrated IQ products were not activated by MPO to bind DNA. In contrast, N-nitroso-IQ was activated to bind DNA by MPO +/- NO(2)(-). HOCl activated N-nitroso-IQ, but not IQ. RAW cells produced N-nitroso-IQ and increased amounts of NO(2)(-)/NO(3)(-), when incubated with 0.1 mM IQ and stimulated with lipopolysaccharide and interferon gamma. Results demonstrate chemical transformation and activation of IQ by RNOS and activation of its N-nitroso product by biological oxidants, events which may contribute to initiation of colon cancer.

journal_name

Chem Res Toxicol

authors

Lakshmi VM,Hsu FF,Zenser TV

doi

10.1021/tx020008h

subject

Has Abstract

pub_date

2002-08-01 00:00:00

pages

1059-68

issue

8

eissn

0893-228X

issn

1520-5010

pii

tx020008h

journal_volume

15

pub_type

杂志文章
  • Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives.

    abstract::Structure-function relationships for the inhibition of human cytochrome P450s (P450s) 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives were studied. Thirty-two of the 33 flavonoids tested produced reverse type I binding spectra with P450 1B1, and the potencies of binding were correlated with the abilities to in...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx100286d

    authors: Shimada T,Tanaka K,Takenaka S,Murayama N,Martin MV,Foroozesh MK,Yamazaki H,Guengerich FP,Komori M

    更新日期:2010-12-20 00:00:00

  • Microprobe X-ray absorption spectroscopic determination of the oxidation state of intracellular chromium following exposure of V79 Chinese hamster lung cells to genotoxic chromium complexes.

    abstract::The oxidation state of intracellular chromium has been determined directly in mammalian lung cells exposed to mutagenic and carcinogenic chromium compounds. Microprobe X-ray absorption spectroscopy (XAS) experiments on single V79 Chinese hamster lung cells showed that Cr(VI) and Cr(V) complexes were reduced completely...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx970010m

    authors: Dillon CT,Lay PA,Cholewa M,Legge GJ,Bonin AM,Collins TJ,Kostka KL,Shea-McCarthy G

    更新日期:1997-05-01 00:00:00

  • Orientation of the crotonaldehyde-derived N2-[3-Oxo-1(S)-methyl-propyl]-dG DNA adduct hinders interstrand cross-link formation in the 5'-CpG-3' sequence.

    abstract::The conformation of the crotonaldehyde-derived N(2)-[3-oxo-1(S)-methyl-propyl]-dG adduct in the oligodeoxynucleotide 5'-d(G(1)C(2)T(3)A(4)G(5)C(6)X(7)A(8)G(9)T(10)C(11)C(12))-3'.5'-d(G(13)G(14)A(15)C(16)T(17)C(18)G(19)C(20)T(21)A(22)G(23)C(2)(4))-3', where X = N(2)-[3-oxo-1(S)-methyl-propyl]-dG, is reported. This addu...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0600604

    authors: Cho YJ,Wang H,Kozekov ID,Kozekova A,Kurtz AJ,Jacob J,Voehler M,Smith J,Harris TM,Rizzo CJ,Lloyd RS,Stone MP

    更新日期:2006-08-01 00:00:00

  • Application of capillary liquid chromatography coupled with tandem mass spectrometric methods to the rapid screening of adducts formed by the reaction of N-acetoxy-N-acetyl-2-aminofluorene with calf thymus DNA.

    abstract::Capillary liquid chromatography-continuous-flow fast atom bombardment mass spectrometry is applied to the detection of deoxynucleoside adducts of N-acetoxy-N-acetyl-2-aminofluorene. In such a configuration, normal scan and tandem mass spectrometric techniques are shown to provide useful structural information for an N...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00037a013

    authors: Wolf SM,Vouros P

    更新日期:1994-01-01 00:00:00

  • Arsenic exposure through drinking water is associated with longer telomeres in peripheral blood.

    abstract::Inorganic arsenic is a strong carcinogen, possibly by interaction with the telomere length. The aim of the study was to evaluate how chronic arsenic exposure from drinking water as well as the arsenic metabolism efficiency affect the individual telomere length and the expression of telomere-related genes. Two hundred ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx300222t

    authors: Li H,Engström K,Vahter M,Broberg K

    更新日期:2012-11-19 00:00:00

  • Biomarkers of furan exposure by metabolic profiling of rat urine with liquid chromatography-tandem mass spectrometry and principal component analysis.

    abstract::Furan has been found in a number of heated food items and is carcinogenic in the liver of rats and mice. Estimates of human exposure on the basis of concentrations measured in food are not reliable because of the volatility of furan. A biomarker approach is therefore indicated. We searched for metabolites excreted in ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx7004212

    authors: Kellert M,Wagner S,Lutz U,Lutz WK

    更新日期:2008-03-01 00:00:00

  • Inhibition of skeletal sarcoplasmic reticulum Ca2+-ATPase activity by deferoxamine nitroxide free radical.

    abstract::Deferoxamine is an inhibitor of iron-dependent free radical reactions. Despite the antioxidant roles, prolonged clinical use of the chelator is far from benign, and paradoxically, deferoxamine has been shown to promote lipid peroxidation. The possible toxicity of the drug's metabolites, such as deferoxamine nitroxide ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx980212y

    authors: Kiyose M,Lee CI,Okabe E

    更新日期:1999-02-01 00:00:00

  • Antibody recognition of melphalan adducts characterized using immobilized DNA: enhanced alkylation of G-Rich regions in cells compared to in vitro.

    abstract::The bifunctional alkylating agent, melphalan, forms adducts on DNA that are recognized by two previously described monoclonal antibodies, MP5/73 and Amp4/42. Immunoreactivity to MP5/73 was lost when alkylated DNA was exposed to alkaline pH, while Amp4/42 only recognized the structures formed after the alkali treatment...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx000178z

    authors: McCartney H,Martin AM,Middleton PG,Tilby MJ

    更新日期:2001-01-01 00:00:00

  • Immunochemical Detection of Protein Modification Derived from Metabolic Activation of 8-Epidiosbulbin E Acetate.

    abstract::Furanoid 8-epidiosbulbin E acetate (EEA) is one of the most abundant diterpenoid lactones in herbal medicine Dioscorea bulbifera L. (DB). Our early work proved that EEA could be metabolized to EEA-derived cis-enedial (EDE), a reactive intermediate, which is required for the hepatotoxicity observed in experimental anim...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.0c00016

    authors: Zhou S,Zhang N,Hu Z,Lin D,Li W,Peng Y,Zheng J

    更新日期:2020-07-20 00:00:00

  • Dominant contribution of P450 3A4 to the hepatic carcinogenic activation of aflatoxin B1.

    abstract::The hepatic carcinogen aflatoxin B1 (AFB1) is metabolized in the liver by at least four different P450s, all of which exhibit large interindividual differences in the expression levels. These differences could affect the individual risk of hepatocellular carcinoma (HCC). We investigated the metabolism of AFB1 in a pan...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx050358e

    authors: Kamdem LK,Meineke I,Gödtel-Armbrust U,Brockmöller J,Wojnowski L

    更新日期:2006-04-01 00:00:00

  • Can Galactose Be Converted to Glucose in HepG2 Cells? Improving the in Vitro Mitochondrial Toxicity Assay for the Assessment of Drug Induced Liver Injury.

    abstract::Human hepatocellular carcinoma cells, HepG2, are often used for drug mediated mitochondrial toxicity assessments. Glucose in HepG2 culture media is replaced by galactose to reveal drug-induced mitochondrial toxicity as a marked shift of drug IC50 values for the reduction of cellular ATP. It has been postulated that ga...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.9b00033

    authors: Xu Q,Liu L,Vu H,Kuhls M,Aslamkhan AG,Liaw A,Yu Y,Kaczor A,Ruth M,Wei C,Imredy J,Lebron J,Pearson K,Gonzalez R,Mitra K,Sistare FD

    更新日期:2019-08-19 00:00:00

  • Highly Predictive Reprogramming of tRNA Modifications Is Linked to Selective Expression of Codon-Biased Genes.

    abstract::Cells respond to stress by controlling gene expression at several levels, with little known about the role of translation. Here, we demonstrate a coordinated translational stress response system involving stress-specific reprogramming of tRNA wobble modifications that leads to selective translation of codon-biased mRN...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.5b00004

    authors: Chan CT,Deng W,Li F,DeMott MS,Babu IR,Begley TJ,Dedon PC

    更新日期:2015-05-18 00:00:00

  • Identification and characterization of deoxyguanosine adducts of methyl vinyl ketone and ethyl vinyl ketone. Genotoxicity of the ketones in the SOS Chromotest.

    abstract::The reaction of the alpha, beta-unsaturated ketones methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) with nucleosides and 5'-mononucleotides was studied. The genotoxic activity of MVK and EVK in the SOS Chromotest was investigated. Three different types of adducts with deoxyguanosine were found and their structu...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00019a007

    authors: Eder E,Hoffman C,Deininger C

    更新日期:1991-01-01 00:00:00

  • Use of electrochemical oxidation and model peptides to study nucleophilic biological targets of reactive metabolites: the case of rimonabant.

    abstract::Electrochemical oxidation of drug molecules is a useful tool to generate several different types of metabolites. In the present study we developed a model system involving electrochemical oxidation followed by characterization of the oxidation products and their propensity to modify peptides. The CB1 antagonist rimona...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx500255r

    authors: Thorsell A,Isin EM,Jurva U

    更新日期:2014-10-20 00:00:00

  • Model system to study the influence of aggregation on the hemolytic potential of silica nanoparticles.

    abstract::A well-defined silica nanoparticle model system was developed to study the effect of the size and structure of aggregates on their membranolytic activity. The aggregates were stable and characterized using transmission electron microscopy, dynamic light scattering, nitrogen adsorption, small-angle X-ray scattering, in...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx2002178

    authors: Thomassen LC,Rabolli V,Masschaele K,Alberto G,Tomatis M,Ghiazza M,Turci F,Breynaert E,Martra G,Kirschhock CE,Martens JA,Lison D,Fubini B

    更新日期:2011-11-21 00:00:00

  • Lateral Flow Assessment and Unanticipated Toxicity of Kratom.

    abstract::The leaves of the Mitragynine speciosia tree (also known as Kratom) have long been chewed, smoked, or brewed into a tea by people in Southeastern Asian countries, such as Malaysia and Thailand. Just this past year, the plant Kratom gained popularity in the United States as a "legal opioid" and scheduling it as a drug ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.8b00218

    authors: Smith LC,Lin L,Hwang CS,Zhou B,Kubitz DM,Wang H,Janda KD

    更新日期:2019-01-22 00:00:00

  • Structure-activity relationships for contact allergenic potential of gamma,gamma-dimethyl-gamma-butyrolactone derivatives. 1. Synthesis and electrophilic reactivity studies of alpha-(omega-substituted-alkyl)-gamma,gamma-dimethyl-gamma-butyrolacton es and

    abstract::A series of alpha-(X-substituted-methyl)-gamma,gamma-dimethyl-gamma-butyrolactones (series 1), a series of alpha-(2-X-substituted-ethyl)-gamma,gamma-dimethyl-gamma-butyrolactones (series 2), where X is a leaving group, and the compound alpha-(3-bromopropyl)-gamma,gamma-butyrolactone (3) were synthesized. Their reactio...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00039a005

    authors: Franot C,Roberts DW,Smith RG,Basketter DA,Benezra C,Lepoittevin JP

    更新日期:1994-05-01 00:00:00

  • Interactions of TiO2 Nanoparticles with Ingredients from Modern Lifestyle Products and Their Effects on Human Skin Cells.

    abstract::The number of consumer products containing nanoparticles (NPs) experienced a rapid increase during the past decades. However, most studies of nanosafety have been conducted using only pure NPs produced in the laboratory, while the interactions with other ingredients in consumer products have rarely been considered so ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.9b00428

    authors: Geppert M,Schwarz A,Stangassinger LM,Wenger S,Wienerroither LM,Ess S,Duschl A,Himly M

    更新日期:2020-05-18 00:00:00

  • Peroxynitrite-initiated oxidation of acetoacetate and 2-methylacetoacetate esters by oxygen: potential sources of reactive intermediates in keto acidoses.

    abstract::Oxidative stress is believed to play a role in the pathogenesis of several diseases, including diabetes and inborn errors of metabolism. The types of oxidative damage observed in these pathologies have been attributed to the excessive production of reactive intermediates relating to the accumulation of toxic metabolit...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx049821y

    authors: Royer LO,Knudsen FS,de Oliveira MA,Tavares MF,Bechara EJ

    更新日期:2004-12-01 00:00:00

  • Efficient synthesis of the benzo[a]pyrene metabolic adducts of 2'-deoxyguanosine and 2'-deoxyadenosine and their direct incorporation into DNA.

    abstract::A new and efficient method is described for the synthesis in gram quantities of the benzo[a]pyrene (B[a]P) metabolic adducts of 2'-deoxyguanosine (dG) and 2'-deoxyadenosine (dA) substituted, respectively, at the N(2)- and N(6)- positions. When the racemic form of the tris(benzoyloxy)amine 5 (related to the notoriously...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0256174

    authors: Johnson F,Bonala R,Tawde D,Torres MC,Iden CR

    更新日期:2002-12-01 00:00:00

  • Toxicant Deposition and Transport in Alveolus: A Classical Density Functional Prediction.

    abstract::The deposition and transport of toxicants on pulmonary surfactant are important processes in human health and medical care. We have introduced classical density functional theory (CDFT) to provide insight into this process. Nine typical toxicants in PM2.5 were considered, and their free energy and structural informati...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.8b00272

    authors: Liu H,Liu Y,Shang Y,Liu H

    更新日期:2018-12-17 00:00:00

  • Systematic investigation of the physicochemical factors that contribute to the toxicity of ZnO nanoparticles.

    abstract::ZnO nanoparticles (NPs) are prone to dissolution, and uncertainty remains whether biological/cellular responses to ZnO NPs are solely due to the release of Zn(2+) or whether the NPs themselves have additional toxic effects. We address this by establishing ZnO NP solubility in dispersion media (Dulbecco's modified Eagl...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx4004243

    authors: Mu Q,David CA,Galceran J,Rey-Castro C,Krzemiński L,Wallace R,Bamiduro F,Milne SJ,Hondow NS,Brydson R,Vizcay-Barrena G,Routledge MN,Jeuken LJ,Brown AP

    更新日期:2014-04-21 00:00:00

  • Indirect cytotoxicity of flucloxacillin toward human biliary epithelium via metabolite formation in hepatocytes.

    abstract::Flucloxacillin, an isoxazolyl-penicillin, causes cholestasis and biliary epithelium injury. The aim of the study was to determine whether flucloxacillin, either directly or through metabolite formation, may induce cytotoxicity in hepatic or biliary cells. Cytotoxicity was assessed by lactate dehydrogenase release in p...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0002435

    authors: Lakehal F,Dansette PM,Becquemont L,Lasnier E,Delelo R,Balladur P,Poupon R,Beaune PH,Housset C

    更新日期:2001-06-01 00:00:00

  • Binding of nickel(II) and copper(II) to the N-terminal sequence of human protamine HP2.

    abstract::A potentiometric and spectroscopic (UV/vis and CD) study of Cu(II) and Ni(II) binding to the N-terminal pentadecapeptide of human protamine HP2 (HP2(1-15)) was performed. The results indicate that the N-terminal tripeptide motif Arg-Thr-His is the exclusive binding site for both metal ions at a metal to HP2(1-15) mola...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx970028x

    authors: Bal W,Jezowska-Bojczuk M,Kasprzak KS

    更新日期:1997-08-01 00:00:00

  • Mapping serum albumin adducts of the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by data-dependent tandem mass spectrometry.

    abstract::2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) is a heterocyclic aromatic amine that is formed during the cooking of meats. PhIP is a potential human carcinogen: it undergoes metabolic activation to form electrophilic metabolites that bind to DNA and proteins, including serum albumin (SA). The structures of Ph...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx300253j

    authors: Peng L,Dasari S,Tabb DL,Turesky RJ

    更新日期:2012-10-15 00:00:00

  • Highly galloylated tannin fractions from witch hazel (Hamamelis virginiana) bark: electron transfer capacity, in vitro antioxidant activity, and effects on skin-related cells.

    abstract::Witch hazel ( Hammamelis virginiana) bark is a rich source of both condensed and hydrolizable oligomeric tannins. From a polyphenolic extract soluble in both ethyl acetate and water, we have generated fractions rich in pyrogallol-containing polyphenols (proanthocyanidins, gallotannins, and gallates). The mixtures were...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx700425n

    authors: Touriño S,Lizárraga D,Carreras A,Lorenzo S,Ugartondo V,Mitjans M,Vinardell MP,Juliá L,Cascante M,Torres JL

    更新日期:2008-03-01 00:00:00

  • In vitro replication and repair studies of tandem lesions containing neighboring thymidine glycol and 8-oxo-7,8-dihydro-2'-deoxyguanosine.

    abstract::Reactive oxygen species can induce the formation of tandem DNA lesions. We recently showed that the treatment of calf thymus DNA with Cu2+/H2O2/ascorbate could result in the efficient formation of a tandem lesion where a 5,6-dihydroxy-5,6-dihydrothymidine (or thymidine glycol) is situated on the 5' side of an 8-oxo-7,...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx8003449

    authors: Jiang Y,Wang Y,Wang Y

    更新日期:2009-03-16 00:00:00

  • Large-scale synthesis of the catechol metabolites of diethylstilbestrol and hexestrol.

    abstract::Diethylstilbestrol (DES) and hexestrol (HES) are carcinogenic synthetic estrogens. The major metabolites of these compounds are their catechol derivatives, 3'-OH-DES and 3'-OH-HES. Oxidation of these metabolites leads to the electrophilic quinones, which are presumably involved in the tumor-initiating process. A synth...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx970140v

    authors: Jan ST,Rogan EG,Cavalieri EL

    更新日期:1998-05-01 00:00:00

  • Characterization of benzo[a]pyrene anti-diol epoxide adducts to human histones.

    abstract::Nuclei from human lymphoblast cells grown in culture were treated with [7-14C]-(+/-)-r-7,t-8-dihydroxy-t-9,t-10-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene (anti-BPDE), and the nucleosomal core histones were isolated for adduct studies by cryogenic fluorescence line narrowing spectroscopy. The four core histones H2A, H2B...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00038a004

    authors: SooHoo CK,Singh K,Skipper PL,Tannenbaum SR,Dasari RR

    更新日期:1994-03-01 00:00:00

  • Benomyl, aldehyde dehydrogenase, DOPAL, and the catecholaldehyde hypothesis for the pathogenesis of Parkinson's disease.

    abstract::The dopamine metabolite 3,4-dihydroxyphenylacetaldehyde (DOPAL) is detoxified mainly by aldehyde dehydrogenase (ALDH). We find that the fungicide benomyl potently and rapidly inhibits ALDH and builds up DOPAL in vivo in mouse striatum and in vitro in PC12 cells and human cultured fibroblasts and glial cells. The in vi...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx5002223

    authors: Casida JE,Ford B,Jinsmaa Y,Sullivan P,Cooney A,Goldstein DS

    更新日期:2014-08-18 00:00:00