Detection of Carbofuran-Protein Adducts in Serum of Occupationally Exposed Pesticide Factory Workers in Pakistan.

Abstract:

:This study was conducted to investigate the protein adducts with pesticides in a cohort of 172 factory workers that were exposed to a mixture of pesticides. The 35 samples showing considerable variation in biochemical parameters, i.e., butyrylcholinestrase (BChE), serum glutamic pyruvic transaminase (SGPT), serum glutamic oxaloacetic transaminase (SGOT), gamma-glutamyl transferase (GGT), serum glutamic pyruvic transaminase (SGPT), alkaline phosphatase (ALP/ALKP), lactate dehydrogenase (LDH), creatine phosphokinase (CPK) enzymes, and controls were analyzed by reversed-phase nanoscale liquid chromatography tandem mass spectrometry (nLC-MS/MS) on an Orbitrap mass spectrometer employing a shotgun proteomics approach. Only protein adducts with carbofuran were found on serum proteins of these workers. These adducts were of carbofuran labeled lysine (Lys-142, Lys-183, Lys-287, and Lys-467), arginine (Arg-210, Arg-242, and Arg-256) from serum albumin, and serine (Ser-07, Ser-54, and Ser-150) from immunoglobulin proteins. The arginine residues (Arg-210, Arg-242, Arg-246, and Arg-434) from albumin were also found to be glycated in serum of workers showing a high level of glucose who also had glycated arginine (Arg-1120) modified with carbofuran in their tankyrase-1-binding protein. The number of tandem mass spectra of modified peptides increased with increasing time of exposure. This is the first report to demonstrate the presence of carbofuran-labeled albumin, immunoglobulin, and glycated arginine, which shows that lysine and arginine of human albumin and serine of immunoglobulin are covalently modified in the serum of workers that were occupationally exposed to carbofuran, and the modification is detectable by tandem mass spectrometry. These peptides modified with carbofuran can potentially be used as a biomarker of carbofuran exposure.

journal_name

Chem Res Toxicol

authors

Rehman T,Khan MM,Shad MA,Hussain M,Oyler BL,Goo YA,Goodlett DR

doi

10.1021/acs.chemrestox.6b00222

subject

Has Abstract

pub_date

2016-10-17 00:00:00

pages

1720-1728

issue

10

eissn

0893-228X

issn

1520-5010

journal_volume

29

pub_type

杂志文章
  • In Vitro Cytotoxicity and Adaptive Stress Responses to Selected Haloacetic Acid and Halobenzoquinone Water Disinfection Byproducts.

    abstract::The process of disinfecting drinking water inadvertently leads to the formation of numerous disinfection byproducts (DBPs). Some of these are mutagenic, genotoxic, teratogenic, and cytotoxic, as well as potentially carcinogenic both in vivo and in vitro. We investigated the in vitro biological activity of five DBPs: t...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.5b00283

    authors: Procházka E,Escher BI,Plewa MJ,Leusch FD

    更新日期:2015-10-19 00:00:00

  • Maillard reaction products modulating the growth of human tumor cells in vitro.

    abstract::We investigated the effect of a series of Maillard reaction products formed from carbohydrates under household heating conditions on the growth of human tumor cells in vitro. 4-Hydroxy-5-methyl-3-(2H)-furanone (1) was found to potently enhance the proliferation of human tumor cells. In contrast, the Maillard-type chro...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx025531a

    authors: Marko D,Habermeyer M,Kemény M,Weyand U,Niederberger E,Frank O,Hofmann T

    更新日期:2003-01-01 00:00:00

  • Chemometric models for toxicity classification based on NMR spectra of biofluids.

    abstract::1H NMR spectroscopic and pattern recognition (PR)-based methods were used to investigate the biochemical variability in urine obtained from control rats and from rats treated with a hydrazine (a model hepatotoxin) or HgCl(2) (a model renal cortical toxin). The 600 MHz (1)H NMR spectra of urine samples obtained from ve...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx990210t

    authors: Holmes E,Nicholls AW,Lindon JC,Connor SC,Connelly JC,Haselden JN,Damment SJ,Spraul M,Neidig P,Nicholson JK

    更新日期:2000-06-01 00:00:00

  • Covalent modification at Cys151 dissociates the electrophile sensor Keap1 from the ubiquitin ligase CUL3.

    abstract::The regulation of cellular stress responses to electrophiles and oxidants is mediated by the transcription factor NF-E2-related factor 2 (Nrf2), which, in turn, is regulated by CUL-E3 (CUL3) ligase-mediated ubiquitylation. The Kelch-like ECH-associated protein 1 (Keap1) serves as an adapter between CUL3 and Nrf2. We u...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx700302s

    authors: Rachakonda G,Xiong Y,Sekhar KR,Stamer SL,Liebler DC,Freeman ML

    更新日期:2008-03-01 00:00:00

  • Alkylating potential of styrene oxide: reactions and factors involved in the alkylation process.

    abstract::The chemical reactivity of styrene-7,8-oxide (SO), an alkylating agent with high affinity for the guanine–N7 position and a probable carcinogen for humans, with 4-(p-nitrobenzyl)pyridine (NBP), a trap for alkylating agents with nucleophilic characteristics similar to those of DNA bases, was investigated kinetically in...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx5002892

    authors: González-Pérez M,Gómez-Bombarelli R,Pérez-Prior MT,Arenas-Valgañón J,García-Santos MP,Calle E,Casado J

    更新日期:2014-10-20 00:00:00

  • Protein binding and metabolism influence the relative skin sensitization potential of cinnamic compounds.

    abstract::Skin protein modification (haptenation) is thought to be a key step in the manifestation of sensitization to low molecular mass chemicals (<500 g/mol). For sensitizing chemicals that are not protein reactive, it is hypothesised that metabolic activation can convert such chemicals into protein reactive toxins within th...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0341456

    authors: Elahi EN,Wright Z,Hinselwood D,Hotchkiss SA,Basketter DA,Pease CK

    更新日期:2004-03-01 00:00:00

  • Role of cytochrome P450 enzyme induction in the metabolic activation of benzo[c]phenanthrene in human cell lines and mouse epidermis.

    abstract::The environmental contaminant benzo[c]phenanthrene (B[c]Ph) has weak carcinogenic activity in rodent bioassays; however, the fjord region diol epoxides of B[c]Ph, B[c]Ph-3,4-diol 1,2-epoxides (B[c]PhDE), are potent carcinogens. To determine the role of cytochrome P450 isozymes in the activation of B[c]Ph in MCF-7 cell...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx960174n

    authors: Einolf HJ,Story WT,Marcus CB,Larsen MC,Jefcoate CR,Greenlee WF,Yagi H,Jerina DM,Amin S,Park SS,Gelboin HV,Baird WM

    更新日期:1997-05-01 00:00:00

  • Oxidative Release of Thiol-Conjugated Forms of the Mycotoxin 4-Deoxynivalenol.

    abstract::Deoxynivalenol (DON) is a trichothecene mycotoxin that is produced by several species of Fusarium, which may infect grain crops. DON, as well as other type-B trichothecenes, contain an α,β-unsaturated carbonyl group that may react with sulfhydryl groups in, for example, amino acids and peptides. Such conjugates have b...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.9b00385

    authors: Uhlig S,Ivanova L,Miles CO

    更新日期:2020-02-17 00:00:00

  • Effects of intracerebroventricular administration of 5-(glutathion-S-yl)-alpha-methyldopamine on brain dopamine, serotonin, and norepinephrine concentrations in male Sprague-Dawley rats.

    abstract::alpha-Methyldopamine (alpha-MeDA) is a metabolite of the serotonergic neurotoxicants 3,4-(+/-)-(methylenedioxy)amphetamine (MDA) and 3,4-(+/-)-(methylenedioxy)methamphetamine (MDMA). alpha-MeDA readily oxidizes, and in the presence of glutathione (GSH) it forms 5-(glutathion-S-yl)-alpha-methyldopamine [5-(glutathion-S...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx9501546

    authors: Miller RT,Lau SS,Monks TJ

    更新日期:1996-03-01 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

  • Identification of tamoxifen-DNA adducts formed by alpha-sulfate tamoxifen and alpha-acetoxytamoxifen.

    abstract::alpha-Sulfate trans-tamoxifen and alpha-sulfate cis-tamoxifen were synthesized as proposed active metabolites of tamoxifen that react with DNA. alpha-Acetoxytamoxifen was prepared as a model-activated form to produce a reactive carbocation. Calf thymus DNA was reacted with alpha-hydroxytamoxifen or the activated forms...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx960114h

    authors: Dasaradhi L,Shibutani S

    更新日期:1997-02-01 00:00:00

  • A Multiplatform Approach for the Discovery of Novel Drug-Induced Kidney Injury Biomarkers.

    abstract::Drug-induced kidney injury (DIKI) is a common toxicity observed in pharmaceutical development. We demonstrated the use of label-free liquid chromatography-mass spectrometry (LC-MS) and multiplex liquid chromatography-single reaction monitoring (LC-SRM) as practical extensions of standard immunoassay based safety bioma...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.7b00159

    authors: Chen L,Smith J,Mikl J,Fryer R,Pack F,Williams BJ,Phillips JA,Papov VV Jr

    更新日期:2017-10-16 00:00:00

  • Influence of DNA Lesions on Polymerase-Mediated DNA Replication at Single-Molecule Resolution.

    abstract::Faithful replication of DNA is a critical aspect in maintaining genome integrity. DNA polymerases are responsible for replicating DNA, and high-fidelity polymerases do this rapidly and at low error rates. Upon exposure to exogenous or endogenous substances, DNA can become damaged and this can alter the speed and fidel...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章,评审

    doi:10.1021/acs.chemrestox.7b00224

    authors: Gahlon HL,Romano LJ,Rueda D

    更新日期:2017-11-20 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

  • Serum metabolomics reveals irreversible inhibition of fatty acid beta-oxidation through the suppression of PPARalpha activation as a contributing mechanism of acetaminophen-induced hepatotoxicity.

    abstract::Metabolic bioactivation, glutathione depletion, and covalent binding are the early hallmark events after acetaminophen (APAP) overdose. However, the subsequent metabolic consequences contributing to APAP-induced hepatic necrosis and apoptosis have not been fully elucidated. In this study, serum metabolomes of control ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx800464q

    authors: Chen C,Krausz KW,Shah YM,Idle JR,Gonzalez FJ

    更新日期:2009-04-01 00:00:00

  • Comparison of crystal structure and theory for 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine.

    abstract::The crystal structure of the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine (PhIP) has been determined by single-crystal X-ray crystallography. Crystals grown by evaporation of an aqueous solution form in the monoclinic space group P2(1)/n with two molecules of PhIP per asymmetric unit, along with six w...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx950168b

    authors: Parkin S,Marsch GA,Hope H,Whitney E,Winter NW,Colvin ME,Felton JS,Turteltaub KW

    更新日期:1996-04-01 00:00:00

  • Prostaglandin H synthase-1-catalyzed bioactivation of neurotransmitters, their precursors, and metabolites: oxidative DNA damage and electron spin resonance spectroscopy studies.

    abstract::The role of prostaglandin H synthase-1 (PHS-1) and a related model enzyme, horseradish peroxidase (HRP), in catalyzing the bioactivation of dopamine (DA) and epinephrine and their precursors and metabolites to potential neurodegenerative free radical intermediates was examined. To determine the potential contribution ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx800423s

    authors: Gonçalves LL,Ramkissoon A,Wells PG

    更新日期:2009-05-01 00:00:00

  • Sustained systemic delivery of green tea polyphenols by polymeric implants significantly diminishes benzo[a]pyrene-induced DNA adducts.

    abstract::The polyphenolics in green tea are believed to be the bioactive components. However, poor bioavailability following ingestion limits their efficacy in vivo. In this study, polyphenon E (poly E), a standardized green tea extract, was administered by sustained-release polycaprolactone implants (two, 2-cm implants; 20% d...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx2000625

    authors: Cao P,Vadhanam MV,Spencer WA,Cai J,Gupta RC

    更新日期:2011-06-20 00:00:00

  • Formation of malonaldehyde-acetaldehyde conjugate adducts in calf thymus DNA.

    abstract::It has previously been shown that malonaldehyde forms conjugates with acetaldehyde and that these conjugates react with nucleobases forming so-called conjugate adducts. In the current study, it is shown that conjugate adducts are also formed in calf thymus DNA when incubated simultaneously with malonaldehyde and aceta...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx060027h

    authors: Pluskota-Karwatka D,Pawłowicz AJ,Kronberg L

    更新日期:2006-07-01 00:00:00

  • 12-OH-nevirapine sulfate, formed in the skin, is responsible for nevirapine-induced skin rash.

    abstract::Nevirapine (NVP) treatment is associated with a significant incidence of skin rash in humans, and it also causes a similar immune-mediated skin rash in Brown Norway (BN) rats. We have shown that the sulfate of a major oxidative metabolite, 12-OH-NVP, covalently binds in the skin. The fact that the sulfate metabolite i...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx400098z

    authors: Sharma AM,Novalen M,Tanino T,Uetrecht JP

    更新日期:2013-05-20 00:00:00

  • Renal elimination of perfluorocarboxylates (PFCAs).

    abstract::Sex-, species-, and chain length-dependent renal elimination is the hallmark of mammalian elimination of perfluorocarboxylates (PFCAs) and has been extensively studied for almost 30 years. In this review, toxicokinetic data of PFCAs (chain lengths ranging from 4 to 10) in different species are compared with an emphasi...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章,评审

    doi:10.1021/tx200363w

    authors: Han X,Nabb DL,Russell MH,Kennedy GL,Rickard RW

    更新日期:2012-01-13 00:00:00

  • The major metabolite of equilin, 4-hydroxyequilin, autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone.

    abstract::The risk factors for women developing breast and endometrial cancers are all associated with a lifetime of estrogen exposure. Estrogen replacement therapy in particular has been correlated with a slight increased cancer risk. Previously, we showed that equilenin, a minor component of Premarin (Wyeth-Ayerst), was metab...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx980217v

    authors: Zhang F,Chen Y,Pisha E,Shen L,Xiong Y,van Breemen RB,Bolton JL

    更新日期:1999-02-01 00:00:00

  • Effects of hepatotoxic doses of acetaminophen and furosemide on tissue concentrations of CoASH and CoASSG in vivo.

    abstract::The effects of hepatotoxic doses of acetaminophen on tissue concentrations of CoA in the thiol form (CoASH) and as the corresponding mixed disulfide with GSH (CoASSG) were determined to test the hypotheses that early oxidant effects of acetaminophen are expressed principally in the mitochondrial compartment and that o...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0000926

    authors: Rogers LK,Valentine CJ,Szczpyka M,Smith CV

    更新日期:2000-09-01 00:00:00

  • Identification and Profiling of Environmental Chemicals That Inhibit the TGFβ/SMAD Signaling Pathway.

    abstract::The transforming growth factor beta (TGFβ) superfamily of secreted signaling molecules and their cognate receptors regulate cell fate and behaviors relevant to many developmental and disease processes. Disruption of TGFβ signaling during embryonic development can, for example, affect morphogenesis and differentiation ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.9b00228

    authors: Wei Z,Sakamuru S,Zhang L,Zhao J,Huang R,Kleinstreuer NC,Chen Y,Shu Y,Knudsen TB,Xia M

    更新日期:2019-12-16 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

  • Directed evolution reveals requisite sequence elements in the functional expression of P450 2F1 in Escherichia coli.

    abstract::Cytochrome P450 2F1 (P450 2F1) is expressed exclusively in the human respiratory tract and is implicated in 3-methylindole (3MI)-induced pneumotoxicity via dehydrogenation of 3MI to a reactive electrophilic intermediate, 3-methyleneindolenine (3-MEI). Studies of P450 2F1 to date have been limited by the failure to exp...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx300281g

    authors: Behrendorff JB,Moore CD,Kim KH,Kim DH,Smith CA,Johnston WA,Yun CH,Yost GS,Gillam EM

    更新日期:2012-09-17 00:00:00

  • Ring addition of the alpha-amino group of glutathione increases the reactivity of benzoquinone thioethers.

    abstract::2-(Glutathion-S-yl)-1,4-benzoquinone was found to be remarkably unstable in phosphate buffer (pH 7.4) even in the absence of oxygen. Intramolecular addition of the alpha-amino group of the glutamate residue to the quinone ring yielded ultimately 2,3-(glutathion-N, S-yl)-1,4-benzoquinone and 2,6-(glutathion-N,S-yl)-1,4...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx9800699

    authors: Alt C,Eyer P

    更新日期:1998-10-01 00:00:00

  • Metabolites and safety: What are the concerns, and how should we address them?

    abstract::The issue of the safety of drug metabolites in humans is a complex one. In this commentary, a proposal is made regarding how to deal with drug metabolites observed in humans such that the safety of these molecules can be assured. The human radiolabeled ADME study, in which metabolites are identified and quantified in ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0602012

    authors: Smith DA,Obach RS

    更新日期:2006-12-01 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

  • 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