当前位置： SCI文献检索 > CHEMICAL RESEARCH IN TOXICOLOGY期刊下所有文献 > Peroxynitrite-dependent tryptophan nitration.

Peroxynitrite-dependent tryptophan nitration.

Abstract：

:Peroxynitrite (ONOO-), the reaction product of superoxide (O2.-) and nitric oxide (.NO), nitrates tyrosine and other phenolics. We report herein that tryptophan is also nitrated by peroxynitrite in the absence of transition metals to one predominant isomer of nitrotryptophan, as determined from spectral characteristics and liquid chromatography-mass spectrometry analysis. At high peroxynitrite to tryptophan ratios, other oxidation products were detected as well. The amount of nitrotryptophan formed from peroxynitrite increased at acidic pH, with an apparent pKa of 7.8. High concentrations of Fe(3+)-EDTA were required to enhance peroxynitrite-induced nitrotryptophan formation, while addition of up to 15 microM Cu/Zn superoxide dismutase had a minimal effect on tryptophan nitration. Cysteine, ascorbate, and methionine decreased nitrotryptophan yield to an extent similar to that predicted by their reaction rates with ground-state peroxynitrite, and typical hydroxyl radical scavengers partially inhibited nitration. Plots of the observed rate constant of nitrotryptophan formation vs tryptophan concentration presented downward curvatures. Thus, the kinetics of metal-independent nitration reactions were interpreted in terms of two parallel mechanisms. In the first one, ground-state peroxynitrous acid nitrated tryptophan with a second-order rate constant of 184 +/- 11 M-1 s-1 at 37 degrees C. The activation enthalpy was 9.1 +/- 0.3 kcal mol-1, and the activation entropy was -19 +/- 1 cal mol-1 K-1. In the second mechanism, ONOOH*, an activated intermediate derived from trans-peroxynitrous acid formed in a steady state, was the nitrating agent.

journal_name

Chem Res Toxicol

journal_title

Chemical research in toxicology

authors

Alvarez B,Rubbo H,Kirk M,Barnes S,Freeman BA,Radi R

doi

10.1021/tx950133b

subject

Has Abstract

pub_date

1996-03-01 00:00:00

pages

390-6

issue

2

eissn

0893-228X

issn

1520-5010

pii

tx950133b

journal_volume

9

pub_type

杂志文章

相关文献

CHEMICAL RESEARCH IN TOXICOLOGY文献大全
  • Framework for identifying chemicals with structural features associated with the potential to act as developmental or reproductive toxicants.

    abstract：:Developmental and reproductive toxicity (DART) end points are important hazard end points that need to be addressed in the risk assessment of chemicals to determine whether or not they are the critical effects in the overall risk assessment. These hazard end points are difficult to predict using current in silico tool...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx400226u

    authors： Wu S,Fisher J,Naciff J,Laufersweiler M,Lester C,Daston G,Blackburn K

    更新日期：2013-12-16 00:00:00

  • Chemical reactivity and skin sensitization potential for benzaldehydes: can Schiff base formation explain everything?

    abstract：:Skin sensitizers chemically modify skin proteins rendering them immunogenic. Sensitizing chemicals have been divided into applicability domains according to their suspected reaction mechanism. The widely accepted Schiff base applicability domain covers aldehydes and ketones, and detailed structure-activity-modeling fo...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx300278t

    authors： Natsch A,Gfeller H,Haupt T,Brunner G

    更新日期：2012-10-15 00:00:00

  • Arsenicals inhibit thioredoxin reductase in cultured rat hepatocytes.

    abstract：:Thioredoxin reductase (TR), an NADPH-dependent flavoenzyme that catalyzes the reduction of many disulfide-containing substrates, plays an important role in the cellular response to oxidative stress. Trivalent arsenicals, especially methyl As that contains trivalent arsenic (MAs(III)), are potent noncompetitive inhibit...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx0001878

    authors： Lin S,Del Razo LM,Styblo M,Wang C,Cullen WR,Thomas DJ

    更新日期：2001-03-01 00:00:00

  • Limited reactivity of formyl chloride with glutathione and relevance to metabolism and toxicity of dichloromethane.

    abstract：:Formyl chloride has been indirectly implicated as an intermediate in the oxidation of CH(2)Cl(2) and proposed to be a product of the oxidation of some other compounds. Formyl chloride was synthesized and added to aqueous solutions, with CO formed as a product. The presence of glutathione (GSH) did not reduce the yield...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx060087n

    authors： Watanabe K,Guengerich FP

    更新日期：2006-08-01 00:00:00

  • Synthesis and characterization of estrogen 2,3- and 3,4-quinones. Comparison of DNA adducts formed by the quinones versus horseradish peroxidase-activated catechol estrogens.

    abstract：:Catechol estrogens (CE) are among the major metabolites of estrone (E1) and 17 beta-estradiol (E2). Oxidation of these metabolites to semiquinones and quinones could generate ultimate carcinogenic forms of E1 and E2. The 2,3- and 3,4-quinones of E1 and E2 were synthesized by MnO2 oxidation of the corresponding CE, fol...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx00030a016

    authors： Dwivedy I,Devanesan P,Cremonesi P,Rogan E,Cavalieri E

    更新日期：1992-11-01 00:00:00

  • Protein modification by acrolein: formation and stability of cysteine adducts.

    abstract：:The toxicity of the ubiquitous pollutant and endogenous metabolite, acrolein, is due in part to covalent protein modifications. Acrolein reacts readily with protein nucleophiles via Michael addition and Schiff base formation. Potential acrolein targets in protein include the nucleophilic side chains of cysteine, histi...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx800465m

    authors： Cai J,Bhatnagar A,Pierce WM Jr

    更新日期：2009-04-01 00:00:00

  • Pharmacodynamics of cytochrome P450 2B induction by phenobarbital, 5-ethyl-5-phenylhydantoin, and 5-ethyl-5-phenyloxazolidinedione in the male rat liver or in cultured rat hepatocytes.

    abstract：:The pharmacodynamics of rat hepatic cytochrome P450 2B (P450 2B) induction by phenobarbital (PB) and two structural congeners, dl-5-ethyl-5-phenylhydantoin (EPH) and dl-5-ethyl-5-phenyloxazolidinedione (EPO), were investigated. The in vivo induction of P450 2B was probed in F344/NCr rats by measuring immunoreactive he...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx00032a008

    authors： Nims RW,Sinclair PR,Sinclair JF,Thomas PE,Jones CR,Mellini DW,Syi JL,Lubet RA

    更新日期：1993-03-01 00:00:00

  • Enhancement of 2'-deoxyguanosine hydroxylation and DNA damage by coal and oil fly ash in relation to particulate metal content and availability.

    abstract：:Epidemiologic studies have shown causal relationships between air pollution particles and adverse health effects in susceptible subpopulations. Fly ash particles (containing water-soluble and insoluble metals) are a component of ambient air particulate pollution and may contribute to particulate-induced health effects...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx000110j

    authors： Prahalad AK,Inmon J,Ghio AJ,Gallagher JE

    更新日期：2000-10-01 00:00:00

  • Etoposide catechol is an oxidizable topoisomerase II poison.

    abstract：:Topoisomerase II regulates DNA topology by generating transient double-stranded breaks. The anticancer drug etoposide targets topoisomerase II and is associated with the formation of secondary leukemias in patients. The quinone and catechol metabolites of etoposide may contribute to strand breaks that trigger leukemic...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx400205n

    authors： Jacob DA,Gibson EG,Mercer SL,Deweese JE

    更新日期：2013-08-19 00:00:00

  • Metabolic Profiles of Tetrabromobisphenol A in Humans Extrapolated from Humanized-Liver Mouse Data Using a Simplified Physiologically Based Pharmacokinetic Model.

    abstract：:Tetrabromobisphenol A, a brominated flame retardant, is increasingly prevalent worldwide and presents a potential health risk. Adjusted animal biomonitoring equivalents of tetrabromobisphenol A after orally administered doses in humanized-liver mice were scaled up to humans using known species allometric scaling facto...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.0c00358

    authors： Miura T,Uehara S,Shigeta K,Yoshizawa M,Kamiya Y,Murayama N,Shimizu M,Suemizu H,Yamazaki H

    更新日期：2020-11-16 00:00:00

  • Sex dependence of the components and structure of urinary calculi induced by biphenyl administration in rats.

    abstract：:To obtain definitive information about the mechanisms of urinary calculus formation and the structural characteristics of the calculi induced by biphenyl administration in rats, with a focus on the sex dependency, the constituents of the urinary calculi were analyzed by HPLC, inductively coupled plasma spectroscopy (I...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx0000163

    authors： Ohnishi M,Yajima H,Yamamoto S,Matsushima T,Ishii T

    更新日期：2000-08-01 00:00:00

  • Synthesis, characterization, and quantitation of a 4-aminobiphenyl-DNA adduct standard.

    abstract：:32P-Postlabeling is a powerful technique for the detection of DNA adducts; however, quantitation of DNA adducts by this method can result in errors due to differences in hydrolysis and labeling efficiencies between adducted and normal nucleotides. We have synthesized a DNA sample modified with 4-aminobiphenyl to serve...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx980172y

    authors： Beland FA,Doerge DR,Churchwell MI,Poirier MC,Schoket B,Marques MM

    更新日期：1999-01-01 00:00:00

  • Accurate and efficient bypass of 8,5'-cyclopurine-2'-deoxynucleosides by human and yeast DNA polymerase η.

    abstract：:Reactive oxygen species (ROS), which can be produced during normal aerobic metabolism, can induce the formation of tandem DNA lesions, including 8,5'-cyclo-2'-deoxyadenosine (cyclo-dA) and 8,5'-cyclo-2'-deoxyguanosine (cyclo-dG). Previous studies have shown that cyclo-dA and cyclo-dG accumulate in cells and can block ...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx3001576

    authors： Swanson AL,Wang J,Wang Y

    更新日期：2012-08-20 00:00:00

  • Quartz Disrupts Iron Homeostasis in Alveolar Macrophages To Impact a Pro-Inflammatory Effect.

    abstract：:The biological response of bronchial epithelial cells to particles is associated with a sequestration of cell metal by the particle surface and a subsequent disruption in host iron homeostasis. The macrophage is the cell type resident in the respiratory tract that is most likely to make initial contact with inhaled pa...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.8b00301

    authors： Ghio AJ,Soukup JM,Stonehuerner J,Tong H,Richards J,Gilmour MI,Madden MC,Shen Z,Kantrow SP

    更新日期：2019-09-16 00:00:00

  • Identification of protein targets of 4-hydroxynonenal using click chemistry for ex vivo biotinylation of azido and alkynyl derivatives.

    abstract：:Polyunsaturated fatty acids (PUFA) are primary targets of free radical damage during oxidative stress. Diffusible electrophilic alpha,beta-unsaturated aldehydes, such as 4-hydroxynonenal (HNE), have been shown to modify proteins that mediate cell signaling (e.g., IKK and Keap1) and alter gene expression pathways respo...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx700347w

    authors： Vila A,Tallman KA,Jacobs AT,Liebler DC,Porter NA,Marnett LJ

    更新日期：2008-02-01 00:00:00

  • Synthesis and characterization of enantiomeric anti-2-fluorobenzo[a]pyrene-7,8-dihydrodiol-9,10-epoxides and their 2'-deoxyguanosine and oligodeoxynucleotide adducts.

    abstract：:Benzo[a]pyrene diol epoxides (BPDEs) are the ultimate carcinogenic species of benzo[a]pyrene, a prototype polycyclic aromatic hydrocarbon (PAH). BPDE-modified DNA duplexes can adopt multiple conformations depending on the nature of the modified bases, the stereochemistry at the location of the covalent linkage, and th...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx050308+

    authors： Yang T,Huang Y,Cho BP

    更新日期：2006-02-01 00:00:00

  • Formation, solvolysis, and transcarbamoylation reactions of bis(S-glutathionyl) adducts of 2,4- and 2,6-diisocyanatotoluene.

    abstract：:During our ongoing studies of the reactions of toluene diisocyanate (2,4- and 2,6-diisocyanatotoluene, TDI) in vivo, it became apparent that reactive form(s) of these diisocyanates reach(es) the circulatory system after passage through the respiratory system. Based on recent work by others regarding the transcarbamoyl...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx960201+

    authors： Day BW,Jin R,Basalyga DM,Kramarik JA,Karol MH

    更新日期：1997-04-01 00:00:00

  • Mass spectrometric methods for the analysis of nucleoside-protein cross-links: application to oxopropenyl-deoxyadenosine.

    abstract：:Electrophilic DNA adducts produced following oxidative stress can form DNA-protein cross-links (DPCs), dramatically altering genomic maintenance pathways. Complete characterization of DPCs has been hindered, in part, because of a lack of comprehensive techniques for their analysis. We have, therefore, established a pr...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx400384e

    authors： Shuck SC,Rose KL,Marnett LJ

    更新日期：2014-01-21 00:00:00

  • Cytochrome P450 2A-catalyzed metabolic activation of structurally similar carcinogenic nitrosamines: N'-nitrosonornicotine enantiomers, N-nitrosopiperidine, and N-nitrosopyrrolidine.

    abstract：:N'-Nitrosonornicotine (NNN) and N-nitrosopiperidine (NPIP) are potent esophageal and nasal cavity carcinogens in rats and pulmonary carcinogens in mice. N-Nitrosopyrrolidine (NPYR) induces mainly liver tumors in rats and is a weak pulmonary carcinogen in mice. These nitrosamines may be causative agents in human cancer...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx0497696

    authors： Wong HL,Murphy SE,Hecht SS

    更新日期：2005-01-01 00:00:00

  • Synthesis, microsome-mediated metabolism, and identification of major metabolites of environmental pollutant naphtho[8,1,2-ghi]chrysene.

    abstract：:Naphtho[8,1,2- ghi]chrysene, commonly known as naphtho[1,2- e]pyrene (N[1,2- e]P) is a widespread environmental pollutant, identified in coal tar extract, air borne particulate matter, marine sediment, cigarette smoke condensate, and vehicle exhaust. Herein, we determined the ability of rat liver microsomes to metabol...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx8000384

    authors： Sharma AK,Gowdahalli K,Gimbor M,Amin S

    更新日期：2008-05-01 00:00:00

  • Synthesis and monoamine oxidase B catalyzed oxidation of C-4 heteroaromatic substituted 1,2,3,6-tetrahydropyridine derivatives.

    abstract：:The monoamine oxidase B (MAO-B) catalyzed oxidation of amines has been proposed to proceed via a polar pathway, an initial single-electron transfer pathway and an initial hydrogen atom transfer pathway. Results from previous studies on selected N-cyclopropyl-4-substituted-1,2,3,6-tetrahydropyridine derivatives have le...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx960063o

    authors： Nimkar SK,Anderson AH,Rimoldi JM,Stanton M,Castagnoli KP,Mabic S,Wang YX,Castagnoli N Jr

    更新日期：1996-09-01 00:00:00

  • The mechanism of the peroxynitrite-mediated oxidation of myoglobin in the absence and presence of carbon dioxide.

    abstract：:Among the cellular components that can react directly with peroxynitrite in the presence of physiological CO(2) concentrations are sulfur-, selenium-, and metal-containing proteins, in particular hemoproteins. We have previously shown that the reactions of peroxynitrite with oxymyoglobin (MbFeO(2)) and oxyhemoglobin p...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx025595l

    authors： Herold S,Exner M,Boccini F

    更新日期：2003-03-01 00:00:00

  • Notopterygium forbesii boiss extract and its active constituents increase reactive species and heme oxygenase-1 in human fetal hepatocytes: mechanisms of action.

    abstract：:Notopterygium forbesii Boiss (NF) has been used as a traditional Chinese medicine for the treatment of common cold and rheumatism. However, there has been limited research on the biological properties of NF, and the mechanisms of action remain unknown. Here, we aimed to study the mechanism of NF-induced heme oxygenase...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx800301f

    authors： Tang SY,Wang H,Zhang W,Halliwell B

    更新日期：2008-12-01 00:00:00

  • (-)-Epigallocatechin gallate, a major constituent of green tea, poisons human type II topoisomerases.

    abstract：:(-)-Epigallocatechin gallate (EGCG) is the most abundant and biologically active polyphenol in green tea, and many of the therapeutic benefits of the beverage have been attributed to this compound. High concentrations of EGCG are cytotoxic and trigger genotoxic events in mammalian cells. Although this catechin affects...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx700434v

    authors： Bandele OJ,Osheroff N

    更新日期：2008-04-01 00:00:00

  • A metabolite of equine estrogens, 4-hydroxyequilenin, induces DNA damage and apoptosis in breast cancer cell lines.

    abstract：:Estrogen replacement therapy has been correlated with an increased risk of developing breast or endometrial cancer. 4-Hydroxyequilenin (4-OHEN) is a catechol metabolite of equilenin which is a minor component of the estrogen replacement formulation marketed under the name of Premarin (Wyeth-Ayerst). Previously, we sho...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx990186j

    authors： Chen Y,Liu X,Pisha E,Constantinou AI,Hua Y,Shen L,van Breemen RB,Elguindi EC,Blond SY,Zhang F,Bolton JL

    更新日期：2000-05-01 00:00:00

  • Photomutagenicity of anhydroretinol and 5,6-epoxyretinyl palmitate in mouse lymphoma cells.

    abstract：:Retinyl palmitate (RP) is frequently used as an ingredient in cosmetics and other retail products. We previously reported that, under UVA light irradiation, RP is facilely decomposed into multiple products, including anhydroretinol (AR) and 5,6-epoxyretinyl palmitate (5,6-epoxy-RP). We also determined that combined tr...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx0600907

    authors： Mei N,Xia Q,Chen L,Moore MM,Chen T,Fu PP

    更新日期：2006-11-01 00:00:00

  • Synthesis and structural characterization of the N2G-mitomycin C-N2G interstrand cross-link in a model synthetic 23 base pair oligonucleotide DNA duplex.

    abstract：:Mitomycin C (MMC) is a genotoxic cancer chemotherapeutic agent that reacts principally at the N2 position of guanine to form one of two predominant monoadducts, or a G-G interstrand cross-link at CpG sites, or a G-G intrastrand cross-link at GpG sites. Previous studies of MMC adduction have principally used very short...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx960070c

    authors： Warren AJ,Hamilton JW

    更新日期：1996-10-01 00:00:00

  • Rapid screening of glutathione-trapped reactive metabolites by linear ion trap mass spectrometry with isotope pattern-dependent scanning and postacquisition data mining.

    abstract：:The present study describes a novel integrated approach for rapid analysis of reactive metabolites with a linear ion trap mass spectrometer (LTQ). In this approach, an isotope pattern-dependent scanning method was applied to the data acquisition of glutathione (GSH)-trapped reactive metabolites. Recorded full-scan MS ...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx8001115

    authors： Ma L,Wen B,Ruan Q,Zhu M

    更新日期：2008-07-01 00:00:00

  • The design of agents to control DNA methylation adducts. Enhanced major groove methylation of DNA by an N-methyl-N-nitrosourea functionalized phenyl neutral red intercalator.

    abstract：:An N-methyl-N-nitrosourea (MNU) moiety [CH3N(N=O)C(=O)NH-] linked to the C4'-position of the 5-substituted phenyl ring of phenyl neutral red (PNR), 2-methyl-3-amino-5-[p-[[2-[(N-nitroso-N-methylcarbamoyl)amino]ethy l] carbamoyl]phenyl]-7-(dimethylamino)phenazenium chloride (MNU-PNR), has been synthesized as an approac...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx960007n

    authors： Mehta P,Church K,Williams J,Chen FX,Encell L,Shuker DE,Gold B

    更新日期：1996-09-01 00:00:00

  • The influence of delivery rate on the chemistry and biological effects of nitric oxide.

    abstract：:Nitric oxide can be introduced slowly and steadily into aqueous solutions, including cell culture media, over extended periods of time via semipermeable Silastic (a registered trademark of the Dow Corning Corp.) polymer membranes. The rates of introduction are predictable and reproducible and can approach rates of nit...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx00036a021

    authors： Tamir S,Lewis RS,de Rojas Walker T,Deen WM,Wishnok JS,Tannenbaum SR

    更新日期：1993-11-01 00:00:00