当前位置： SCI文献检索 > CHEMICAL RESEARCH IN TOXICOLOGY期刊下所有文献 > Is Isoeugenol a Prehapten? Characterization of a Thiol-Reactive Oxidative Byproduct of Isoeugenol and Potential Implications for Skin Sensitization.

Is Isoeugenol a Prehapten? Characterization of a Thiol-Reactive Oxidative Byproduct of Isoeugenol and Potential Implications for Skin Sensitization.

Abstract：

:Isoeugenol is widely used by the cosmetic and fragrance industries, but it also represents a known cause of skin sensitization adverse effects. Although devoid of a structural alert, isoeugenol has been classified as prehapten in virtue of the presence of a pre-Michael acceptor domain. Isoeugenol oxidation could theoretically lead to the generation of reactive toxic quinones, and photoinduced oxidative degradation of isoeugenol was reported to generate strongly thiol reactive byproducts. Nonetheless, the isoeugenol degradation product responsible for increased reactivity was found to be elusive. In the present study, an aged isoeugenol sample was subjected to reactivity-guided experiments to trap elusive thiol reactive species with a fluorescent nucleophile, viz. dansyl cysteamine (DCYA). The results herein presented demonstrate that photo-oxidation of isoeugenol led to the formation of a dimeric 7,4'-oxyneolignan with strong chemical reactivity, capable of nucleophilic substitution with thiols. The results were confirmed by isolation, structural characterization, and further NMR reactivity studies. Isoeugenol is already well-known as moderately reactive in thiol depletion assays, and was herein demonstrated to be capable of converting to more potent electrophilic species upon degradation, thus acting as a prehapten. The application of the reactivity-guided strategy described herein was shown to serve as an effective tool to investigate elusive skin sensitizers.

journal_name

Chem Res Toxicol

journal_title

Chemical research in toxicology

authors

Ahn J,Avonto C,Chittiboyina AG,Khan IA

doi

10.1021/acs.chemrestox.9b00501

subject

Has Abstract

pub_date

2020-04-20 00:00:00

pages

948-954

issue

4

eissn

0893-228X

issn

1520-5010

journal_volume

33

pub_type

杂志文章

相关文献

CHEMICAL RESEARCH IN TOXICOLOGY文献大全
  • 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 glut...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.6b00222

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

    更新日期：2016-10-17 00:00:00

  • Identification of antrocin from Antrodia camphorata as a selective and novel class of small molecule inhibitor of Akt/mTOR signaling in metastatic breast cancer MDA-MB-231 cells.

    abstract：:The PI3K/Akt/mTOR pathway is considered to be an attractive target for the development of novel anticancer molecules. This paper reports for the first time that a small molecule, antrocin (MW = 234), from Antrodia camphorata was a potent antagonist in various cancer types, being highest in metastatic breast cancer MDA...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx100318m

    authors： Rao YK,Wu AT,Geethangili M,Huang MT,Chao WJ,Wu CH,Deng WP,Yeh CT,Tzeng YM

    更新日期：2011-02-18 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

  • 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

  • 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

  • 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

  • Ferroptosis: The Greasy Side of Cell Death.

    abstract：:Ferroptosis is a form of cell death that requires phospholipid peroxidation and has attracted increased attention, both as a means to eradicate tumors resistant to standard chemotherapy and for its potential contribution to tissue damage such as in ischemia/reperfusion. The center stage taken by phospholipid peroxidat...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章,评审

    doi：10.1021/acs.chemrestox.8b00349

    authors： Friedmann Angeli JP,Miyamoto S,Schulze A

    更新日期：2019-03-18 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

  • Structure-toxicity relationships for the effects to Tetrahymena pyriformis of aliphatic, carbonyl-containing, alpha,beta-unsaturated chemicals.

    abstract：:Toxicity data for 82 aliphatic chemicals with an alpha,beta-unsaturated substructure were compiled. Toxicity was assessed in the 2-day Tetrahymena pyriformis population growth impairment assay. Toxic potency [log(IGC50(-1))] for most of these chemicals was in excess of baseline narcosis as quantified by the 1-octanol/...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx049833j

    authors： Schultz TW,Netzeva TI,Roberts DW,Cronin MT

    更新日期：2005-02-01 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

  • 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

  • Benzo[a]pyrene-induced changes in microRNA-mRNA networks.

    abstract：:Toxicological studies assessing the safety of compounds for humans frequently use in vitro systems to characterize toxic responses in combination with transcriptomic analyses. Thus far, changes have mostly been investigated at the mRNA level. Recently, microRNAs have attracted attention because they are powerful negat...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx2003799

    authors： Lizarraga D,Gaj S,Brauers KJ,Timmermans L,Kleinjans JC,van Delft JH

    更新日期：2012-04-16 00:00:00

  • In vitro model of mammary estrogen metabolism: structural and kinetic differences between catechol estrogens 2- and 4-hydroxyestradiol.

    abstract：:Estrogens and their oxidative metabolites, the catechol estrogens, have been implicated in the development of breast cancer; yet, relatively little is known about estrogen metabolism in the breast. To determine how the parent hormone, 17 beta-estradiol (E(2)), is metabolized, we used recombinant, purified phase I enzy...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx0498657

    authors： Dawling S,Hachey DL,Roodi N,Parl FF

    更新日期：2004-09-01 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

  • The efficiencies of damage recognition and excision correlate with duplex destabilization induced by acetylaminofluorene adducts in human nucleotide excision repair.

    abstract：:Nucleotide excision repair (NER) removes lesions caused by environmental mutagens or UV light from DNA. A hallmark of NER is the extraordinarily wide substrate specificity, raising the question of how one set of proteins is able to recognize structurally diverse lesions. Two key features of good NER substrates are tha...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx3003033

    authors： Yeo JE,Khoo A,Fagbemi AF,Schärer OD

    更新日期：2012-11-19 00:00:00

  • Enzyme-linked immunosorbent assay for the specific detection of the mercapturic acid metabolites of naphthalene.

    abstract：:The measurement of metabolites constitutes a useful tool for detection of exposure and in pharmacokinetic studies. Epoxidation with subsequent glutathione conjugation and mercapturic acid formation is an important deactivation pathway for naphthalene, a toxin which presumably causes lung disease. The mercapturic acid ...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx00033a006

    authors： Marco MP,Nasiri M,Kurth MJ,Hammock BD

    更新日期：1993-05-01 00:00:00

  • Analysis of 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB)-releasing DNA adducts in human exfoliated oral mucosa cells by liquid chromatography-electrospray ionization-tandem mass spectrometry.

    abstract：:Quantitation of DNA adducts could provide critical information on the relationship between exposure to tobacco smoke and cancer risk in smokers. In this study, we developed a robust and sensitive liquid chromatography-tandem mass spectrometry method for the analysis of 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB)-releasin...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx300282k

    authors： Stepanov I,Muzic J,Le CT,Sebero E,Villalta P,Ma B,Jensen J,Hatsukami D,Hecht SS

    更新日期：2013-01-18 00:00:00

  • Double-strand breaks from a radical commonly produced by DNA-damaging agents.

    abstract：:Double-strand breaks are widely accepted to be the most toxic form of DNA damage. Molecules that produce double-strand breaks via a single chemical event are typically very cytotoxic and far less common than those that form single-strand breaks. It was recently reported that a commonly formed C4'-radical produces doub...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.5b00032

    authors： Taverna Porro ML,Greenberg MM

    更新日期：2015-04-20 00:00:00

  • Chalcone inhibition of anthracycline secondary alcohol metabolite formation in rabbit and human heart cytosol.

    abstract：:Antineoplastic therapy with anthracyclines like doxorubicin (DOX) and daunorubicin (DNR) is limited by the possible development of a dose-related cardiomyopathy. Secondary alcohol metabolites like doxorubicinol (DOXol) and daunorubicinol (DNRol), formed by cytoplasmic two-electron reductases, have been implicated as p...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx060159a

    authors： Silvestrini A,Meucci E,Vitali A,Giardina B,Mordente A

    更新日期：2006-11-01 00:00:00

  • Stereostructure and biological activity of 42-hydroxy-palytoxin: a new palytoxin analogue from Hawaiian Palythoa subspecies.

    abstract：:This paper reports on the analysis of the toxin content from Palythoa tuberculosa and Palythoa toxica samples collected off of the Hawaiian coast. Our work, based on in-depth high-resolution liquid chromatography-mass spectrometry analysis along with extensive NMR study, led us to structurally characterize 42-hydroxy-...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx900259v

    authors： Ciminiello P,Dell'aversano C,Dello Iacovo E,Fattorusso E,Forino M,Grauso L,Tartaglione L,Florio C,Lorenzon P,De Bortoli M,Tubaro A,Poli M,Bignami G

    更新日期：2009-11-01 00:00:00

  • 42,43,44,45,46,47,55-Heptanor-41-oxohomoyessotoxin, a new biotoxin from mussels of the northern Adriatic sea.

    abstract：:The diarrhetic shellfish toxin composition in the digestive glands of mussels from the northern Adriatic sea was investigated. Along with known yessotoxins, identified by comparison of their chromatographic and spectral properties with those reported in the literature, we isolated a new analogue of yessotoxin, 42,43,4...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx000259v

    authors： Ciminiello P,Fattorusso E,Forino M,Poletti R

    更新日期：2001-05-01 00:00:00

  • Distinct endoplasmic reticulum signaling pathways regulate apoptotic and necrotic cell death following iodoacetamide treatment.

    abstract：:Environmental stress induces the synthesis of glucose-regulated proteins (Grps) in the endoplasmic reticulum (ER) and heat shock proteins (Hsps) in the cytoplasm. Iodoacetamide (IDAM), a prototypical alkyating agent, induces both Grp and Hsp synthesis in renal epithelial cells and causes necrosis which is prevented by...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx990054q

    authors： van De Water B,Wang Y,Asmellash S,Liu H,Zhan Y,Miller E,Stevens JL

    更新日期：1999-10-01 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

  • Quantitative structure-metabolism relationship analyses of MAO-mediated toxication of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and analogues.

    abstract：:The 1-octanol/water partition coefficients of a number of toxic and nontoxic analogues of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) were determined using centrifugal partition chromatography (CPC), a novel and effective technique for measuring lipophilicity, and found to be highly correlated with values calc...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx00027a008

    authors： Altomare C,Carrupt PA,Gaillard P,el Tayar N,Testa B,Carotti A

    更新日期：1992-05-01 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

  • Mechanism of reaction of beta-(aryloxy)acroleins with nucleosides.

    abstract：:The mechanism of DNA adduct formation by acroleins substituted with good leaving groups in the beta-position was investigated using [3-2H]-3-(p-nitrophenoxy)acrolein (1). Reaction of 1 with guanosine at acidic pH produced 9-beta-D-ribofuranosylpyrimido[1,2-alpha]purin-10(3H)-one containing equal amounts of deuterium a...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx950105t

    authors： Reddy GR,Marnett LJ

    更新日期：1996-01-01 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

  • Radicals derived from histone hydroperoxides damage nucleobases in RNA and DNA.

    abstract：:Exposure of individual histone proteins (H1, H2A, H2B, H3, or H4) and histone octamers (consisting of two molecules each of H2A, H2B, H3, and H4) to hydroxyl radicals, generated by gamma-irradiation, in the presence of O(2) generates protein-bound hydroperoxides in a dose-dependent fashion; this is in accord with prev...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx000053u

    authors： Luxford C,Dean RT,Davies MJ

    更新日期：2000-07-01 00:00:00

  • Hydroxyl Radicals in E-Cigarette Vapor and E-Vapor Oxidative Potentials under Different Vaping Patterns.

    abstract：:Available studies, while limited in number, suggest that e-cigarette vaping induces oxidative stress, with one potential mechanism being the direct formation of reactive oxygen species (ROS) in e-vapor. In the present studies, we measured the formation of hydroxyl radical (•OH), the most destructive ROS, in e-vapor un...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.8b00400

    authors： Son Y,Mishin V,Laskin JD,Mainelis G,Wackowski OA,Delnevo C,Schwander S,Khlystov A,Samburova V,Meng Q

    更新日期：2019-06-17 00:00:00

  • Modeling liver-related adverse effects of drugs using knearest neighbor quantitative structure-activity relationship method.

    abstract：:Adverse effects of drugs (AEDs) continue to be a major cause of drug withdrawals in both development and postmarketing. While liver-related AEDs are a major concern for drug safety, there are few in silico models for predicting human liver toxicity for drug candidates. We have applied the quantitative structure-activi...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx900451r

    authors： Rodgers AD,Zhu H,Fourches D,Rusyn I,Tropsha A

    更新日期：2010-04-19 00:00:00