Hepatotoxicity after 3'-hydroxyacetanilide administration to buthionine sulfoximine pretreated mice.

Abstract:

:The administration of 3'-hydroxyacetanilide, a regioisomer of acetaminophen, to mice failed to produce hepatotoxicity even after the administration of diethyl maleate. In contrast, hepatotoxicity did occur when 3'-hydroxyacetanilide was administered to buthionine sulfoximine pretreated mice. Although the administration of 3'-hydroxyacetanilide in conjunction with either diethyl maleate or buthionine sulfoximine depleted total hepatic glutathione, only the combined buthionine sulfoximine-3'-hydroxyacetanilide treatment decreased hepatic mitochondrial glutathione concentrations to below 20% of control values. In addition, pretreatment with buthionine sulfoximine increased the amount of 3'-hydroxyacetanilide bound to mitochondrial proteins. These results, in conjunction without previous results on the involvement of mitochondrial damage in the pathogenesis of hepatotoxicity caused by acetaminophen, suggest a probable relationship between mitochondrial damage caused by the buthionine sulfoximine-3'-hydroxyacetanilide treatment and hepatotoxicity caused by this treatment.

journal_name

Chem Res Toxicol

authors

Tirmenstein MA,Nelson SD

doi

10.1021/tx00020a014

subject

Has Abstract

pub_date

1991-03-01 00:00:00

pages

214-7

issue

2

eissn

0893-228X

issn

1520-5010

journal_volume

4

pub_type

杂志文章
  • 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

  • New urinary metabolites formed from ring-oxidized metabolic intermediates of styrene.

    abstract::The urine from mice exposed to styrene vapors (600 and 1200 mg/m(3), 6 h) was analyzed for ring-oxidized metabolites of styrene. To facilitate the identification of metabolites in urine, the following potential metabolites were prepared: 2-, 3-, and 4-vinylphenol (2-, 3-, and 4-VP), 4-vinylpyrocatechol, and 2-, 3-, an...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx9004192

    authors: Linhart I,Mráz J,Scharff J,Krouzelka J,Dusková S,Nohová H,Vodicková L

    更新日期:2010-01-01 00:00:00

  • Biotransformation pathways of biocides and pharmaceuticals in freshwater crustaceans based on structure elucidation of metabolites using high resolution mass spectrometry.

    abstract::So far, there is limited information on biotransformation mechanisms and products of polar contaminants in freshwater crustaceans. In the present study, metabolites of biocides and pharmaceuticals formed in Gammarus pulex and Daphnia magna were identified using liquid chromatography-high resolution mass spectrometry. ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx300457f

    authors: Jeon J,Kurth D,Hollender J

    更新日期:2013-03-18 00:00:00

  • Effect of human glutathione S-transferases on glutathione-dependent inactivation of cytochrome P450-dependent reactive intermediates of diclofenac.

    abstract::Idiosyncratic adverse drug reactions due to the anti-inflammatory drug diclofenac have been proposed to be caused by the generation of reactive acyl glucuronides and oxidative metabolites. For the oxidative metabolism of diclofenac by cytochromes P450 at least five different reactive intermediates have been proposed p...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx400204d

    authors: Dragovic S,Boerma JS,Vermeulen NP,Commandeur JN

    更新日期:2013-11-18 00:00:00

  • Detection and identification of metabolites of microcystins formed in vivo in mouse and rat livers.

    abstract::The hepatic metabolism of microcystins (MCs), potent cyclic peptide hepatotoxins produced by cyanobacteria, was studied by i.p. injection in mice and rats. An immunoaffinity purification method using an anti-MC-LR monoclonal antibody showed a remarkable effect on the removal of contaminants in the hepatic cytosol and ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx960085a

    authors: Kondo F,Matsumoto H,Yamada S,Ishikawa N,Ito E,Nagata S,Ueno Y,Suzuki M,Harada K

    更新日期:1996-12-01 00:00:00

  • Characterization of glutathione conjugates of reactive metabolites of 3'-hydroxyacetanilide, a nonhepatotoxic positional isomer of acetaminophen.

    abstract::3'-Hydroxyacetanilide (AMAP) is a nonhepatotoxic regioisomer of acetaminophen (APAP) that nonetheless does form reactive metabolites which bind to hepatic proteins. Because differences in the nature of reactive metabolites formed from AMAP and APAP may explain differences in their propensity to cause hepatotoxicity, c...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00007a007

    authors: Rashed MS,Nelson SD

    更新日期:1989-01-01 00:00:00

  • In vitro metabolism and covalent binding of enol-carboxamide derivatives and anti-inflammatory agents sudoxicam and meloxicam: insights into the hepatotoxicity of sudoxicam.

    abstract::Sudoxicam and meloxicam are nonsteroidal anti-inflammatory drugs (NSAIDs) from the enol-carboxamide class. While the only structural difference between the two NSAIDs is the presence of a methyl group on the C5-position of the 2-carboxamidothiazole motif in meloxicam, a marked difference in their toxicological profile...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx800185b

    authors: Obach RS,Kalgutkar AS,Ryder TF,Walker GS

    更新日期:2008-09-01 00:00:00

  • Aromatic Residues at the Dimer-Dimer Interface in the Peroxiredoxin Tsa1 Facilitate Decamer Formation and Biological Function.

    abstract::To prevent the accumulation of reactive oxygen species and limit associated damage to biological macromolecules, cells express a variety of oxidant-detoxifying enzymes, including peroxiredoxins. In Saccharomyces cerevisiae, the peroxiredoxin Tsa1 plays a key role in peroxide clearance and maintenance of genome stabili...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.8b00346

    authors: Loberg MA,Hurtig JE,Graff AH,Allan KM,Buchan JA,Spencer MK,Kelly JE,Clodfelter JE,Morano KA,Lowther WT,West JD

    更新日期:2019-03-18 00:00:00

  • Human serum albumin-benzo[a]pyrene anti-diol epoxide adduct structure elucidation by fluorescence line narrowing spectroscopy.

    abstract::Cryogenic (4-10 K) laser-induced vibrationless ground state and vibronic excited state fluorescence emission spectra of the adducts resulting from reaction in vitro of human serum albumin and the carcinogen (+-)-r-7,t-8-dihydroxy-c-9,c-10-epoxy-7,8,9,10- tetrahydrobenzo[a]-pyrene were recorded in order to determine th...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00025a012

    authors: Day BW,Doxtader MM,Rich RH,Skipper PL,Singh K,Dasari RR,Tannenbaum SR

    更新日期:1992-01-01 00:00:00

  • Alkylation of DNA by 1,3-dialkyl-3-acyltriazenes: correlation of biological activity with chemical behavior.

    abstract::The reactions of calf thymus DNA with four 1,3-dialkyl-3-acyltriazenes were studied alone or in the presence of pig liver esterase in pH 7.4 phosphate buffer for varying lengths of time. The best alkylating agent in the absence of esterase was determined to be 1,3-dimethyl-3-carbethoxytriazene (DMC), followed in order...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00028a013

    authors: Kroeger-Koepke MB,Michejda CJ,Smith RH Jr

    更新日期:1992-07-01 00:00:00

  • Impact of Physicochemical Properties on Dose and Hepatotoxicity of Oral Drugs.

    abstract::A database containing maximum daily doses of 1841 marketed oral drugs was used to examine the influence of physicochemical properties on dose and hepatotoxicity (drug induced liver injury, DILI). Drugs in the highest ∼20% dose range had significantly reduced mean lipophilicity and molecular weight, increased fractiona...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.8b00044

    authors: Leeson PD

    更新日期:2018-06-18 00:00:00

  • Kinetics of DNA Adducts and Abasic Site Formation in Tissues of Mice Treated with a Nitrogen Mustard.

    abstract::Nitrogen mustards (NM) are an important class of chemotherapeutic drugs used in the treatment of malignant tumors. The accepted mechanism of action of NM is through the alkylation of DNA bases. NM-adducts block DNA replication in cancer cells by forming cytotoxic DNA interstrand cross-links. We previously characterize...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.0c00012

    authors: Chen H,Cui Z,Hejazi L,Yao L,Walmsley SJ,Rizzo CJ,Turesky RJ

    更新日期:2020-04-20 00:00:00

  • Bioisosteric Replacement of Amide Group with 1,2,3-Triazoles in Acetaminophen Addresses Reactive Oxygen Species-Mediated Hepatotoxic Insult in Wistar Albino Rats.

    abstract::Acetaminophen (AP) is a popularly recommended over-the-counter analgesic-antipyretic in clinical use. However, the drug is handicapped by the occurrence of hepatotoxic insult following acute ingestion. Consequently, AP-induced hepatotoxicity is often implicated in accidental or suicidal overdose. In the current study,...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.9b00392

    authors: Sahu A,Das D,Sahu P,Mishra S,Sakthivel A,Gajbhiye A,Agrawal R

    更新日期:2020-02-17 00:00:00

  • Synthesis of a hapten to be used in development of immunoassays for trans-3'-hydroxycotinine, a major metabolite of cotinine.

    abstract::4-Carboxyl-substituted analogues of trans-3'-hydroxycotinine were synthesized to be covalently linked to macromolecules for antibody production. 3-Pyridyl-N-methylnitrone was condensed with dimethyl fumarate to give two isomeric isoxazolidines. Hydrogenolysis of the major product [2RS-(2 alpha,3 alpha,3 beta)]-3-carbo...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00023a006

    authors: Desai DH,Amin S

    更新日期:1991-09-01 00:00:00

  • Identification of 4-S-Cysteinyltetrodotoxin from the liver of the puffer fish, Fugu pardalis, and formation of thiol adducts of tetrodotoxin from 4,9-anhydrotetrodotoxin.

    abstract::The metabolic pathway of tetrodotoxin (TTX), a powerful and specific voltage-gated sodium channel blocker, has not been well-clarified either in TTX-poisoned patients or in puffer fish. 4-S-CysteinylTTX (4-CysTTX) was isolated from the liver of the puffer fish, Fugu pardalis, as the first adduct of TTX with thiol. The...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx050015g

    authors: Yotsu-Yamashita M,Goto A,Nakagawa T

    更新日期:2005-05-01 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

  • Nanomaterials and Innate Immunity: A Perspective of the Current Status in Nanosafety.

    abstract::Human exposure to engineered nanomaterials (ENMs) is inevitable due to the plethora of applications for which they are being manufactured and integrated within. ENMs demonstrate plentiful advantages in terms of industrial approaches as well as from a consumer perspective. However, despite such positives, doubts remain...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.0c00051

    authors: Cronin JG,Jones N,Thornton CA,Jenkins GJS,Doak SH,Clift MJD

    更新日期:2020-05-18 00:00:00

  • Guanine-adenine DNA cross-linking by 1,2,3,4-diepoxybutane: potential basis for biological activity.

    abstract::1,2,3,4-Diepoxybutane (DEB) is a prominent carcinogenic metabolite of 1,3-butadiene (1,3-BD), an important industrial chemical and an environmental pollutant found in cigarette smoke and automobile exhaust. DEB is capable of inducing a variety of genotoxic effects, including point mutations, large deletions, and chrom...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0498206

    authors: Park S,Hodge J,Anderson C,Tretyakova N

    更新日期:2004-12-01 00:00:00

  • Biochemical characterization of two hemorrhagic proteases from the venom of Lachesis muta (bushmaster).

    abstract::Two hemorrhagic proteases, Lachesis hemorrhagic toxins a and b (LHTa and LHTb), were isolated from the venom of Lachesis muta, which is distributed in Central and South America. One protease showed strong hemorrhagic action, while the other showed weak hemorrhagic activity even though the two enzymes are very similar ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00006a003

    authors: Ran YL,Zheng SD,Tu AT

    更新日期:1988-11-01 00:00:00

  • Molecular recognition between oligopeptides and nucleic acids: DNA binding selectivity of a series of 1,2,4-triazole-containing lexitropsins.

    abstract::The synthesis of a series of 1,2,4-triazole-containing oligopeptide lexitropsins related to the natural antitumor antibiotic distamycin is described. The binding properties of these new agents to both native DNAs and synthetic polydeoxyribonucleotides were determined by UV absorption and circular dichroism studies. Th...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00020a019

    authors: Rao KE,Krowicki K,Burckhardt G,Zimmer C,Lown JW

    更新日期:1991-03-01 00:00:00

  • Computational models for predicting the binding affinities of ligands for the wild-type androgen receptor and a mutated variant associated with human prostate cancer.

    abstract::In the present study, values of the binding energy (BE) were calculated for the rat androgen receptor on a data set of 25 steroidal and nonsteroidal compounds for which published values of the observed binding affinity (K(i)) are available. A correlation between BE and pK(i) was evident (r(2) = 0.50) for the entire da...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx034168k

    authors: Ai N,DeLisle RK,Yu SJ,Welsh WJ

    更新日期:2003-12-01 00:00:00

  • Coumarin metabolism by rat esophageal microsomes and cytochrome P450 2A3.

    abstract::The rat esophagus is strikingly sensitive to tumor induction by nitrosamines, and it has been hypothesized that this tissue contains cytochrome P450 enzymes (P450s) which catalyze the metabolic activation of these carcinogens. The metabolic capacity of the esophagus is not well characterized. In the study described he...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx010065v

    authors: von Weymarn LB,Murphy SE

    更新日期:2001-10-01 00:00:00

  • Peroxidase-catalyzed oxidation of pentachlorophenol.

    abstract::Pentachlorophenol (PCP) was shown to function as a reducing substrate for horseradish peroxidase (HRP) and to stimulate the HRP-catalyzed reduction of 5-phenyl-4-penten-1-yl hydroperoxide (PPHP) to 5-phenyl-4-penten-1-ol. HRP catalyzed the hydroperoxide-dependent oxidation of PCP, using H2O2, PPHP, or ethyl hydroperox...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00045a005

    authors: Samokyszyn VM,Freeman JP,Maddipati KR,Lloyd RV

    更新日期:1995-04-01 00:00:00

  • Mutagenic Replication of N2-Deoxyguanosine Benzo[a]pyrene Adducts by Escherichia coli DNA Polymerase I and Sulfolobus solfataricus DNA Polymerase IV.

    abstract::Benzo[a]pyrene, a potent human carcinogen, is metabolized in vivo to a diol epoxide that reacts with the N2-position of guanine to produce N2-BP-dG adducts. These adducts are mutagenic causing G to T transversions. These adducts block replicative polymerases but can be bypassed by the Y-family translesion synthesis po...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.6b00466

    authors: Gowda ASP,Krzeminski J,Amin S,Suo Z,Spratt TE

    更新日期:2017-05-15 00:00:00

  • Formation and structure of cross-linking and monomeric pyrrole autoxidation products in 2,5-hexanedione-treated amino acids, peptides, and protein.

    abstract::2,5-Hexanedione (2,5-HD) is the neurotoxic gamma-diketone metabolite of the industrial solvent n-hexane. Substantial evidence indicates that 2,5-HD reacts with neurofilament protein lysine epsilon-amines to yield 2,5-dimethylpyrrole adducts and that this reaction is critical to the mechanism of toxicity. Alkylpyrroles...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00040a011

    authors: Zhu M,Spink DC,Yan B,Bank S,DeCaprio AP

    更新日期:1994-07-01 00:00:00

  • Reactivity with Tris(hydroxymethyl)aminomethane confounds immunodetection of acrolein-adducted proteins.

    abstract::The toxic alpha,beta-unsaturated aldehyde acrolein readily attacks proteins, generating adducts at cysteine, histidine, and lysine residues. In this study, rabbit antiserum was raised against acrolein-modified keyhole limpet hemocyanin in the expectation that it would allow immunodetection of adducted proteins in biol...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0341106

    authors: Burcham PC,Fontaine FR,Petersen DR,Pyke SM

    更新日期:2003-10-01 00:00:00

  • The Impact of the COVID-19 Pandemic on the Future of Science Careers.

    abstract::As COVID-19 swept across the world, it created a global pandemic and an unpredictable and challenging job market. This article discusses the future of the 2020-2021 job market in both academia and industry in the midst and aftermath of this pandemic. ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.0c00436

    authors: Perera HM,Griffin WC,Kankanamage RNT,Pathira Kankanamge LS

    更新日期:2020-12-23 00:00:00

  • Metabolism and mutagenicity of dibenzo[a,e]pyrene and the very potent environmental carcinogen dibenzo[a,l]pyrene.

    abstract::Dibenzo[a,l]pyrene (DB[a,l]P) is one of the most potent carcinogens ever tested in mouse skin and rat mammary gland. DB[a,l]P is present in cigarette smoke and, presumably, in other environmental pollutants. Metabolism and mutagenicity studies of this compound compared to the weak carcinogen dibenzo[a,e]pyrene (DB[a,e...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00018a014

    authors: Devanesan PD,Cremonesi P,Nunnally JE,Rogan EG,Cavalieri EL

    更新日期:1990-11-01 00:00:00

  • Dityrosine cross-linked Abeta peptides: fibrillar beta-structure in Abeta(1-40) is conducive to formation of dityrosine cross-links but a dityrosine cross-link in Abeta(8-14) does not induce beta-structure.

    abstract::Recent reports by Galeazzi and co-workers demonstrated the susceptibility of Abeta(1-42) to undergo dityrosine formation via peroxidase-catalyzed tyrosine cross-linking. We have formed dityrosine cross-links in Abeta(1-40) using these enzymatic conditions as well as a copper-H(2)O(2) method. The efficiency of dityrosi...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx025666g

    authors: Yoburn JC,Tian W,Brower JO,Nowick JS,Glabe CG,Van Vranken DL

    更新日期:2003-04-01 00:00:00

  • Heterocyclic derivatives of 3-substituted-1,1,1-trifluoro-2-propanones as inhibitors of esterolytic enzymes.

    abstract::A series of (alkylthio)trifluoropropanones containing a heterocyclic moiety was synthesized. The compounds were tested for in vitro inhibition of four hydrolytic enzymes including insect juvenile hormone esterase (JHE), eel acetylcholinesterase (AChE), yeast lipase (LP), and bovine alpha-chymotrypsin. The I50 values r...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00016a009

    authors: Székács A,Halarnkar PP,Olmstead MM,Prag KA,Hammock BD

    更新日期:1990-07-01 00:00:00