Chemical Interaction of Protein Cysteine Residues with Reactive Metabolites of Methyleugenol.

Abstract:

:Methyleugenol (ME), an alkenylbenzene compound, is a natural ingredient of several herbs and is used as flavoring agent in foodstuffs and fragrance in cosmetics. The hepatotoxicity, cytotoxicity, and carcinogenesis of ME have been well documented, and metabolic activation has been suggested to involve in ME-induced toxicities. The objective of this study was to identify chemical identity of interactions of protein with reactive metabolites of ME. Modification of cysteine residues of protein was observed in microsomal incubations and mice after exposure to ME. Three types of protein modification derived from the corresponding epoxide, α,β-unsaturated aldehyde, and carbonium ion of ME were detected in vitro and in vivo. The protein adduction took place in time- and dose-dependent manners. Dexamethasone, ketoconazole, and l-buthionine sulfoximine increased the protein modification induced by ME, which was proportional to the hepatotoxicity of ME. The findings facilitate the understanding of mechanism action of ME toxicities.

journal_name

Chem Res Toxicol

authors

Feng Y,Wang H,Wang Q,Huang W,Peng Y,Zheng J

doi

10.1021/acs.chemrestox.6b00290

subject

Has Abstract

pub_date

2017-02-20 00:00:00

pages

564-573

issue

2

eissn

0893-228X

issn

1520-5010

journal_volume

30

pub_type

杂志文章
  • Reductive activation of mitomycin C by thiols: kinetics, mechanism, and biological implications.

    abstract::The clinically used antitumor antibiotic mitomycin C requires a reductive activation to be converted to a bis-electrophile that forms several covalent adducts with DNA, including an interstrand cross-link which is considered to be the lesion responsible for the cytotoxic effects of the drug. Enzymes such as cytochrome...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx9002758

    authors: Paz MM

    更新日期:2009-10-01 00:00:00

  • Low kinetic hydrogen isotope effects in the dehydrogenation of 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester (nifedipine) by cytochrome P-450 enzymes are consistent with an electron/proton/electron transfer mechan

    abstract::Cytochrome P-450 enzymes have been postulated to oxidize amines through a variety of mechanisms. One of the means of distinguishing among potential pathways involves the use of kinetic hydrogen isotope effects: low isotope effects are characteristic of aminium radical mechanisms while high values are consistent with h...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00013a004

    authors: Guengerich FP

    更新日期:1990-01-01 00:00:00

  • Pivotal role for two electron reduction in 2,3-dimethoxy-1,4-naphthoquinone and 2-methyl-1,4-naphthoquinone metabolism and kinetics in vivo that prevents liver redox stress.

    abstract::2,3-dimethoxy-1,4-naphthoquinone (CAS-RN 6959-96-3) (DMNQ) and 2-methyl-1,4-naphthoquinone (CAS-RN 58-27-5) (MNQ:menadione) are effective one electron redox cycling chemicals in vitro. In addition, in vitro MNQ forms a thioether conjugate with glutathione by nucleophilic attack at the third carbon. In contrast, here w...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx800472z

    authors: Parry JD,Pointon AV,Lutz U,Teichert F,Charlwood JK,Chan PH,Athersuch TJ,Taylor EL,Singh R,Luo J,Phillips KM,Vetillard A,Lyon JJ,Keun HC,Lutz WK,Gant TW

    更新日期:2009-04-01 00:00:00

  • Comparison of the Base Excision and Direct Reversal Repair Pathways for Correcting 1,N6-Ethenoadenine in Strongly Positioned Nucleosome Core Particles.

    abstract::1,N6-ethenoadenine (εA) is a mutagenic lesion and biomarker observed in numerous cancerous tissues. Two pathways are responsible for its repair: base excision repair (BER) and direct reversal repair (DRR). Alkyladenine DNA glycosylase (AAG) is the primary enzyme that excises εA in BER, generating stable intermediates ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.0c00089

    authors: Caffrey PJ,Kher R,Bian K,Li D,Delaney S

    更新日期:2020-07-20 00:00:00

  • Hplc/electrospray ionization mass spectrometric analysis of the heterocyclic aromatic amine carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in human milk.

    abstract::A new procedure has been developed for the extraction of 2-amino-1-methyl-6-phenyl-imidazo[4,5-b]pyridine (PhIP) and other heterocyclic aromatic amines from human breast milk samples. Extracts were analyzed by high-performance liquid chromatography/electrospray ionization/tandem mass spectrometry (HPLC/ESI-MS/MS) with...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0601861

    authors: Scott KA,Turesky RJ,Wainman BC,Josephy PD

    更新日期:2007-01-01 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

  • Identification and quantification of DNA adducts in the oral tissues of mice treated with the environmental carcinogen dibenzo[a,l]pyrene by HPLC-MS/MS.

    abstract::Tobacco smoking is one of the leading causes for oral cancer. Dibenzo[a,l]pyrene (DB[a,l]P), an environmental pollutant and a tobacco smoke constituent, is the most carcinogenic polycyclic aromatic hydrocarbon (PAH) tested to date in several animal models (target organs: skin, lung, ovary, and mammary tissues). We hav...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx200188j

    authors: Zhang SM,Chen KM,Aliaga C,Sun YW,Lin JM,Sharma AK,Amin S,El-Bayoumy K

    更新日期:2011-08-15 00:00:00

  • A novel method for the isolation and identification of stable DNA adducts formed by Dibenzo[a,l]pyrene and Dibenzo[a,l]pyrene 11, 12-dihydrodiol 13,14-epoxides in vitro.

    abstract::Our laboratory previously reported the identification and quantification of depurinating DNA adducts of dibenzo[a,l]pyrene (DB[a,l]P) in vitro, which comprise about 84% of all the DNA adducts that are formed [Li, K.-M., et al. (1995) Biochemistry 34, 8043-8049]. To determine a complete adduct profile and identify both...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx980203p

    authors: Devanesan P,Ariese F,Jankowiak R,Small GJ,Rogan EG,Cavalieri EL

    更新日期:1999-09-01 00:00:00

  • Common E-Cigarette Flavoring Chemicals Impair Neutrophil Phagocytosis and Oxidative Burst.

    abstract::E-cigarette flavorings have not been thoroughly evaluated for inhalational toxicity. We have shown that the flavoring chemical cinnamaldehyde impairs human neutrophils, macrophages, and natural killer cells. Here we investigated the effects of other common e-liquid flavoring chemicals on phagocytosis and oxidative bur...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.9b00171

    authors: Hickman E,Herrera CA,Jaspers I

    更新日期:2019-06-17 00:00:00

  • Proteins modified by the lipid peroxidation aldehyde 9,12-dioxo-10(E)-dodecenoic acid in MCF7 breast cancer cells.

    abstract::The hydroperoxide of linoleic acid (13-HPODE) degrades to 9,12-dioxo-10(E)-dodecenoic acid (DODE), which readily modifies proteins. This study identified the major proteins in MCF7 cells modified by DODE. To reduce false positives, three methods were used to identify DODE-modified proteins. First, cells were treated w...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx9002808

    authors: Slade PG,Williams MV,Brahmbhatt V,Dash A,Wishnok JS,Tannenbaum SR

    更新日期:2010-03-15 00:00:00

  • Oncometabolites d- and l-2-Hydroxyglutarate Inhibit the AlkB Family DNA Repair Enzymes under Physiological Conditions.

    abstract::Cancer-associated mutations often lead to perturbed cellular energy metabolism and accumulation of potentially harmful oncometabolites. One example is the chiral molecule 2-hydroxyglutarate (2HG); its two stereoisomers (d- and l-2HG) have been found at abnormally high concentrations in tumors featuring anomalous metab...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.7b00009

    authors: Chen F,Bian K,Tang Q,Fedeles BI,Singh V,Humulock ZT,Essigmann JM,Li D

    更新日期:2017-04-17 00:00:00

  • Relative Propensities of Cytochrome c Oxidase and Cobalt Corrins for Reaction with Cyanide and Oxygen: Implications for Amelioration of Cyanide Toxicity.

    abstract::In aqueous media at neutral pH, the binding of two cyanide molecules per cobinamide can be described by two formation constants, Kf1 = 1.1 (±0.6) × 105 M-1 and Kf2 = 8.5 (±0.1) × 104 M-1, or an overall cyanide binding constant of ∼1 × 1010 M-2. In comparison, the cyanide binding constants for cobalamin and a fully oxi...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.7b00275

    authors: Yuan Q,Pearce LL,Peterson J

    更新日期:2017-12-18 00:00:00

  • Assessment of DNA Epigenetic Modifications.

    abstract::DNA molecules utilize adenine, thymine, cytosine, and guanine for coding genetic information. In addition to these four canonical nucleobases, DNA molecules also contain a variety of modified nucleobases that can control and regulate gene expression and chromosome structure. Elucidating the functions of DNA modificati...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.9b00372

    authors: Yuan BF

    更新日期:2020-03-16 00:00:00

  • Biotransformation and clearance of 3-(phenylamino)propane-1,2-diol, a compound present in samples related to toxic oil syndrome, in C57BL/6 and A/J mice.

    abstract::In May 1981, a massive food-borne intoxication occurred in Spain. The so-called toxic oil syndrome (TOS) was associated with the consumption of aniline-denatured and refined rapeseed oil that was illegally sold as edible olive oil. Fatty acid anilides and fatty acid derivatives of 3-(phenylamino)propane-1,2-diol were ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx990105j

    authors: Ladona MG,Bujons J,Messeguer A,Ampurdanés C,Morató A,Corbella J

    更新日期:1999-12-01 00:00:00

  • Synthesis and sequence-specific DNA binding of a topoisomerase inhibitory analog of Hoechst 33258 designed for altered base and sequence recognition.

    abstract::The preparation and DNA binding characteristics of a structural analog of Hoechst 33258 bearing two pyridinic nitrogen atoms are described. The 1H NMR signals of the complex formed between the new ligand 1 and decadeoxyribonucleotide d(CATGGCCATG)2 were assigned by employing one- and two-dimensional NMR techniques. In...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00029a003

    authors: Singh MP,Joseph T,Kumar S,Bathini Y,Lown JW

    更新日期:1992-09-01 00:00:00

  • Kinetic study of the reaction of glutathione peroxidase with peroxynitrite.

    abstract::Glutathione peroxidases and their mimics, e.g., ebselen or diaryl tellurides, efficiently reduce peroxynitrite/peroxynitrous acid (ONOO-/ONOOH) to nitrite and protect against oxidation and nitration reactions. Here, we report the second-order rate constant for the reaction of the reduced form of glutathione peroxidase...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx980086y

    authors: Briviba K,Kissner R,Koppenol WH,Sies H

    更新日期:1998-12-01 00:00:00

  • Mechanisms of nitrogen oxide-mediated disruption of metalloprotein function: an examination of the copper-responsive yeast transcription factor Ace1.

    abstract::Nitric oxide (NO) has been found to inhibit the copper-responsive yeast transcription factor Ace1 in an oxygen-dependent manner. However, the mechanism responsible for NO-dependent inhibition of Ace1 remains unestablished. In the present study, the chemical interaction of nitrogen oxide species with Ace1 was examined ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx010102i

    authors: Shinyashiki M,Pan CJ,Switzer CH,Fukuto JM

    更新日期:2001-12-01 00:00:00

  • Ethyl octylphosphonofluoridate and analogs: optimized inhibitors of neuropathy target esterase.

    abstract::The relation between organophosphorus-induced delayed neuropathy (OPIDN) and brain neuropathy target esterase (NTE) inhibition is further examined in hens by structure-activity studies leading to the most potent in vitro NTE inhibitors known, which are then examined for their neuropathic effects in vivo in hens. The p...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00050a011

    authors: Wu SY,Casida JE

    更新日期:1995-12-01 00:00:00

  • Reactive sulfur species: kinetics and mechanism of the hydrolysis of cysteine thiosulfinate ester.

    abstract::The kinetics and mechanisms of the hydrolysis of cysteine thiosulfinate ester (CyS(O)SCy ( x- ), x = 0-2) have been investigated by stopped-flow spectrophotometry between pH 6 and pH 14. The rate-limiting reaction of hydroxide is observed for pH < 13. More complicated kinetics are observed above pH 13, where the hydro...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx700168z

    authors: Nagy P,Ashby MT

    更新日期:2007-09-01 00:00:00

  • Assessing Toxicity and in Vitro Bioactivity of Smoked Cigarette Leachate Using Cell-Based Assays and Chemical Analysis.

    abstract::Smoked cigarettes are the most prevalent form of litter worldwide, often finding their way into oceans and inland waterways. Cigarette smoke contains more than 4000 individual chemicals, some of them carcinogenic or otherwise toxic. We examined the cytotoxicity, genotoxicity, aryl hydrocarbon receptor (AhR), estrogen ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.9b00201

    authors: Xu EG,Richardot WH,Li S,Buruaem L,Wei HH,Dodder NG,Schick SF,Novotny T,Schlenk D,Gersberg RM,Hoh E

    更新日期:2019-08-19 00:00:00

  • Identification of 14 quercetin phase II mono- and mixed conjugates and their formation by rat and human phase II in vitro model systems.

    abstract::In this study, the HPLC, UV-vis, LC-MS, and 1H NMR characteristics of 14 different phase II mono- and mixed conjugates of quercetin were determined, providing a useful tool in the identification of quercetin phase II metabolite patterns in various biological systems. Using these data, the phase II metabolism of querce...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx049826v

    authors: van der Woude H,Boersma MG,Vervoort J,Rietjens IM

    更新日期:2004-11-01 00:00:00

  • 16α-Hydroxyestrone: Mass Spectrometry-Based Methodologies for the Identification of Covalent Adducts Formed with Blood Proteins.

    abstract::Elevated levels of the estrone metabolite, 16α-hydroxyestrone (16αOHE1), have been linked with multiple diseases. As an electrophilic reactive metabolite, covalent binding to proteins is thought to constitute one of the possible mechanisms in the onset of deleterious health outcomes associated with 16αOHE1. Whereas ma...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.0c00171

    authors: Charneira C,Nunes J,Antunes AMM

    更新日期:2020-08-17 00:00:00

  • Bone as target organ for metals: the case of f-elements.

    abstract::The skeleton is a target organ for most metals. This leads to their bioaccumulation, either as storage of useful oligoelements or as a protection against damage by toxic elements. The different events leading to their accumulation in this organ, under constant remodeling, are not fully understood, nor the full subsequ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章,评审

    doi:10.1021/tx300064m

    authors: Vidaud C,Bourgeois D,Meyer D

    更新日期:2012-06-18 00:00:00

  • A new role for glutathione: protection of vitamin B12 from depletion by xenobiotics.

    abstract::NADPH in microsomes reduces the hydroxocob(III)alamin form of vitamin B12 to cob(II)alamin and the supernucleophilic cob(I)alamin, which are both highly reactive toward xenobiotic epoxides formed by mammalian metabolism of dienes such as the industrially important chemicals chloroprene and 1,3-butadiene. With styrene,...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0497898

    authors: Watson WP,Munter T,Golding BT

    更新日期:2004-12-01 00:00:00

  • Photoaddition of fluphenazine to nucleophiles in peptides and proteins. Possible cause of immune side effects.

    abstract::By the action of UVA light, fluphenazine reacted with nucleophiles through a mechanism involving defluorination of its trifluoromethyl group, giving rise to carboxylic acid derivatives that were easily detected by electrospray mass spectrometry. This photoreaction took place with alcohols, sulphydryls, and amines. Whe...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx700123u

    authors: Caffieri S,Miolo G,Seraglia R,Dalzoppo D,Toma FM,van Henegouwen GM

    更新日期:2007-10-01 00:00:00

  • Synthesis and characterization of adducts derived from the syn-diastereomer of benzo[a]pyrene 7,8-dihydrodiol 9,10-epoxide and the 5'-d(CCTATAGATATCC) oligonucleotide.

    abstract::5'-d(CCTATAGATATCC) was reacted with each syn-enantiomer of trans-7,8-dihydroxy 9,10-epoxy 7,8,9,10-tetrahydrobenzo[a]pyrene (syn-BPDE). The (-)-enantiomer yielded one dominating adduct, whereas the (+)-enantiomer resulted in two major adducts. As indicated by optical spectroscopic methods, the major adduct derived fr...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx950041m

    authors: Pontén I,Seidel A,Gräslund A,Jernström B

    更新日期:1996-01-01 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

  • Slow-binding inhibition of carboxylesterase and other serine hydrolases by chlorodifluoroacetaldehyde.

    abstract::The chlorofluorocarbon substitute 1,2-dichloro-1,1-difluoroethane (HCFC-132b) undergoes oxidative metabolism in rats to give a range of metabolites, including chlorodifluoroacetaldehyde [Harris and Anders (1991) Chem. Res. Toxicol. 4, 180]. The present experiments were undertaken after studies to characterize an unide...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00035a007

    authors: Yin H,Jones JP,Anders MW

    更新日期:1993-09-01 00:00:00

  • Bisphenol A increases BeWo trophoblast survival in stress-induced paradigms through regulation of oxidative stress and apoptosis.

    abstract::Bisphenol A (BPA) is ubiquitous in the environment and is reported to be present at high concentrations in placental tissue, where its presence raises concerns over its potential to disrupt placental function. This report investigates how BPA interferes with the survival of human choriocarcinoma BeWo cells (a model of...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.5b00093

    authors: Ponniah M,Billett EE,De Girolamo LA

    更新日期:2015-09-21 00:00:00

  • Structural determinant of chemical reactivity and potential health effects of quinones from natural products.

    abstract::Although many phenols and catechols found as polyphenol natural products are antioxidants and have putative disease-preventive properties, others have deleterious health effects. One possible route to toxicity is the bioactivation of the phenolic function to quinones that are electrophilic, redox-agents capable of mod...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx200140s

    authors: Tu T,Giblin D,Gross ML

    更新日期:2011-09-19 00:00:00