Identification of Quinone Methide Intermediate Resulting from Metabolic Activation of Icaritin in Vitro and in Vivo.

abstract：:Trans-Resveratrol (tRes) has been shown to have powerful antioxidant, anti-inflammatory, anticarcinogenic, and antiaging properties; however, its use as a therapeutic agent is limited by its rapid metabolism into its conjugated forms by UDP-glucuronosyltransferases (UGTs). The aim of the current study was to test the ...

journal_title：Chemical research in toxicology

authors： Greer AK,Madadi NR,Bratton SM,Eddy SD,Mazerska Z,Hendrickson HP,Crooks PA,Radominska-Pandya A

更新日期：2014-04-21 00:00:00

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

authors： Watson WP,Munter T,Golding BT

更新日期：2004-12-01 00:00:00

abstract：:Rutaevin is one of the major bioactive constituents isolated from Evodia rutaecarpa, a well-known herbal medicine that has been widely prescribed for the treatment of gastrointestinal disorders in China. However, oral administration of rutaevin has been shown to cause hepatotoxicity in mice. Bioactivation was suggeste...

journal_title：Chemical research in toxicology

authors： Liu Y,Liu C,Liu Y,Ge Q,Sun C

更新日期：2020-12-21 00:00:00

abstract：:A well-defined silica nanoparticle model system was developed to study the effect of the size and structure of aggregates on their membranolytic activity. The aggregates were stable and characterized using transmission electron microscopy, dynamic light scattering, nitrogen adsorption, small-angle X-ray scattering, in...

journal_title：Chemical research in toxicology

authors： Thomassen LC,Rabolli V,Masschaele K,Alberto G,Tomatis M,Ghiazza M,Turci F,Breynaert E,Martra G,Kirschhock CE,Martens JA,Lison D,Fubini B

更新日期：2011-11-21 00:00:00

abstract：:The genotoxicity of the dihydrofurans aflatoxin B1 (AFB1), aflatoxin G1 (AFG1), and sterigmatocystin (STG) was examined in a bacterial system in which the induction of SOS repair is monitored with the umuC gene linked to a lacZ reporter gene in plasmid pSK1002. Human liver microsomal cytochrome P-450NF oxidized the di...

journal_title：Chemical research in toxicology

authors： Baertschi SW,Raney KD,Shimada T,Harris TM,Guengerich FP

更新日期：1989-03-01 00:00:00

abstract：:Free-radical oxidation of human plasma low-density lipoprotein (LDL) produces (carboxyalkyl)pyrrole (CAP) epitopes that were detected with enzyme-linked immunosorbent assays using antibodies raised against keyhole limpet hemocyanin (KLH)-bound 2-(omega-carboxyheptyl)-pyrrole (CHP) and 2-(omega-carboxypropyl)pyrrole (C...

journal_title：Chemical research in toxicology

authors： Kaur K,Salomon RG,O'Neil J,Hoff HF

更新日期：1997-12-01 00:00:00

abstract：:Five major products (adducts A(1a), A(1b), A(2), A(3,) and B) from the reaction of guanosine (Guo) with 4-oxo-2(E)-nonenal (ONE) were detected by liquid chromatography-mass spectrometry (LC-MS). Tandem MS (MS/MS) analysis of these compounds suggested that modifications to the nucleoside had been introduced. Adducts A(...

journal_title：Chemical research in toxicology

authors： Zhu P,Lee SH,Wehrli S,Blair IA

更新日期：2006-06-01 00:00:00

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

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

更新日期：2020-07-20 00:00:00

abstract：:A diverse series of polarized alpha,beta-unsaturated and related compounds were evaluated for reactivity with a spectrophotometric assay using the sulfhydryl group in the form of the cysteine residue of the tripeptide GSH as a model nucleophile. The reactive end point (RC 50) calculations were compared to previously d...

journal_title：Chemical research in toxicology

authors： Schultz TW,Yarbrough JW,Hunter RS,Aptula AO

更新日期：2007-09-01 00:00:00

abstract：:Drug induced liver injury (DILI) can require significant risk management in drug development and on occasion can cause morbidity or mortality, leading to drug attrition. Optimizing candidates preclinically can minimize hepatotoxicity risk, but it is difficult to predict due to multiple etiologies encompassing DILI, of...

journal_title：Chemical research in toxicology

authors： Williams DP,Lazic SE,Foster AJ,Semenova E,Morgan P

更新日期：2020-01-21 00:00:00

abstract：:"Krokodil" is the street name for a homemade injectable drug that has been used as a cheap substitute for heroin. Codeine is the opioid starting material for krokodil synthesis, and desomorphine is claimed to be the main opioid of krokodil and the main component responsible for its addictive and psychoactive character...

journal_title：Chemical research in toxicology

authors： Soares JX,Alves EA,Silva AMN,de Figueiredo NG,Neves JF,Cravo SM,Rangel M,Netto ADP,Carvalho F,Dinis-Oliveira RJ,Afonso CM

更新日期：2017-08-21 00:00:00

abstract：:Today much is known about cytochrome P450 (P450) enzymes and their catalytic specificity, but the range of reactions catalyzed by each still continues to surprise. Historically, P450s had been considered to be involved in either the metabolism of xenobiotics or endogenous chemicals, in the former case playing a genera...

journal_title：Chemical research in toxicology

authors： Guengerich FP

更新日期：2017-01-17 00:00:00

abstract：:Induction of Phase II enzymes of the [Ah] gene battery by L-buthionine (S,R)-sulfoximine (BSO) and other agents was examined in mouse hepatoma Hepa-1c1c7 cells. BSO, a nonelectrophilic inhibitor of gamma-glutamylcysteine synthetase (GCS), is routinely used to examine the toxicological implications of GSH depletion. Ex...

journal_title：Chemical research in toxicology

authors： Shertzer HG,Vasiliou V,Liu RM,Tabor MW,Nebert DW

更新日期：1995-04-01 00:00:00

abstract：:Reaction of lysine with estrone 3,4-o-quinone gave a complex mixture of products. Six compounds were isolated and identified using spectroscopic techniques. Among the reaction products isolated were 4-hydroxyestrone (2), 3-aminoisoestrone (3), 3-(N-pentyl-5-amino)-isoestrone (4), 1-lysylestrone 3,4-o-iminoquinone (5),...

journal_title：Chemical research in toxicology

authors： Tabakovic K,Abul-Hajj YJ

更新日期：1994-09-01 00:00:00

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

authors： Reddy GR,Marnett LJ

更新日期：1996-01-01 00:00:00

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 theor...

journal_title：Chemical research in toxicology

authors： Ahn J,Avonto C,Chittiboyina AG,Khan IA

更新日期：2020-04-20 00:00:00

abstract：:Autophagy is a "self-eating" destructive process that eliminates damaged organelles to maintain cellular homeostasis. Polychlorinated biphenyls (PCBs) are one of the most infamous industrial pollutants, which are ubiquitous in nature. In the present study, we found that an active, quinone-type PCB metabolite (PCB29-pQ...

journal_title：Chemical research in toxicology

authors： Shi Q,Song X,Liu Z,Wang Y,Wang Y,Fu J,Su C,Xia X,Song E,Song Y

更新日期：2016-07-18 00:00:00

abstract：:Structure-function relationships for the inhibition of human cytochrome P450s (P450s) 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives were studied. Thirty-two of the 33 flavonoids tested produced reverse type I binding spectra with P450 1B1, and the potencies of binding were correlated with the abilities to in...

journal_title：Chemical research in toxicology

authors： Shimada T,Tanaka K,Takenaka S,Murayama N,Martin MV,Foroozesh MK,Yamazaki H,Guengerich FP,Komori M

更新日期：2010-12-20 00:00:00

abstract：:In order to better understand the skin sensitization mechanism of allylic hydroperoxides, linalyl hydroperoxide (1) and several of its potential rearrangement products-epoxylinalool (2), epoxynerol (3), epoxygeraniol (4), and furan (5) and pyran (6) derivatives-were synthesized. The sensitizing properties of these mol...

journal_title：Chemical research in toxicology

authors： Bezard M,Karlberg AT,Montelius J,Lepoittevin JP

更新日期：1997-09-01 00:00:00

abstract：:The leaves of the Mitragynine speciosia tree (also known as Kratom) have long been chewed, smoked, or brewed into a tea by people in Southeastern Asian countries, such as Malaysia and Thailand. Just this past year, the plant Kratom gained popularity in the United States as a "legal opioid" and scheduling it as a drug ...

journal_title：Chemical research in toxicology

authors： Smith LC,Lin L,Hwang CS,Zhou B,Kubitz DM,Wang H,Janda KD

更新日期：2019-01-22 00:00:00

abstract：:8-Aminoguanine had previously been identified as one of the nucleic acid base modifications produced in livers of rats by treatment with the hepatocarcinogen 2-nitropropane (2-NP), and a hypothetical mechanism of activation of 2-NP to hydroxylamine-O-sulfonate or acetate that would lead to NH2+, an aminating species, ...

journal_title：Chemical research in toxicology

authors： Sodum RS,Sohn OS,Nie G,Fiala ES

更新日期：1994-05-01 00:00:00

abstract：:Purine deoxyribonucleoside 3'-phosphates were reacted separately with the four configurational isomers of benzo[c]phenanthrene 3,4-dihydrodiol 1,2-epoxide. Products resulting from the cis and trans opening of the epoxide ring by the exocyclic amino groups of deoxyadenosine and deoxyguanosine 3'-phosphates were separat...

journal_title：Chemical research in toxicology

authors： Canella KA,Peltonen K,Yagi H,Jerina DM,Dipple A

更新日期：1992-09-01 00:00:00

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 administratio...

journal_title：Chemical research in toxicology

authors： Tirmenstein MA,Nelson SD

更新日期：1991-03-01 00:00:00

abstract：:The major plant growth regulator ethephon degrades to ethylene and phosphate in aqueous solutions and plants and is spontaneously activated to a butyrylcholinesterase (BChE) inhibitor in alkaline solutions and animal tissues. In the present (31)P NMR kinetic study of the reactions of ethephon in pH 7.4 carbonate buffe...

journal_title：Chemical research in toxicology

authors： Lantz SR,Casida JE

更新日期：2013-09-16 00:00:00

abstract：:In recent years, there has been an increase in the production of shellfish and in global demand for seafood as nutritious and healthy food. Unfortunately, a significant number of incidences of shellfish poisoning occur worldwide, and microalgae that produce phycotoxins are responsible for most of these. Phycotoxins in...

journal_title：Chemical research in toxicology

authors： Otero A,Chapela MJ,Atanassova M,Vieites JM,Cabado AG

更新日期：2011-11-21 00:00:00

abstract：:A series of alpha-(X-substituted-methyl)-gamma,gamma-dimethyl-gamma-butyrolactones (series 1), a series of alpha-(2-X-substituted-ethyl)-gamma,gamma-dimethyl-gamma-butyrolactones (series 2), where X is a leaving group, and the compound alpha-(3-bromopropyl)-gamma,gamma-butyrolactone (3) were synthesized. Their reactio...

journal_title：Chemical research in toxicology

authors： Franot C,Roberts DW,Smith RG,Basketter DA,Benezra C,Lepoittevin JP

更新日期：1994-05-01 00:00:00

abstract：:Quantum dots (QDs) are a novel class of inorganic fluorophores which are gaining widespread recognition as a result of their exceptional photophysical properties and their applications as a biomarker and in molecular biomedical imaging. The aim of this study was to evaluate the in vivo genotoxicity in mice exposed to ...

journal_title：Chemical research in toxicology

authors： Khalil WK,Girgis E,Emam AN,Mohamed MB,Rao KV

更新日期：2011-05-16 00:00:00

abstract：:This study addresses the detection and characterization of the modification of human serum albumin (HSA) by amoxicillin (AX) in ex vivo samples from healthy subjects under oral amoxicillin administration (acute intake of 1 g every 8 h for 48 h). To reach this goal, we used an analytical strategy based on targeted and ...

journal_title：Chemical research in toxicology

authors： Garzon D,Ariza A,Regazzoni L,Clerici R,Altomare A,Sirtori FR,Carini M,Torres MJ,Pérez-Sala D,Aldini G

更新日期：2014-09-15 00:00:00

abstract：:Acetaminophen (APAP), a commonly used analgesic, is catalyzed by cytochrome P450 (P450) enzymes to a toxic intermediate which can be trapped by glutathione. Using this approach, involvement of enzymes in the activation of APAP and their kinetics were studied. With human liver microsomes, there were three apparent Km v...

journal_title：Chemical research in toxicology

authors： Patten CJ,Thomas PE,Guy RL,Lee M,Gonzalez FJ,Guengerich FP,Yang CS

更新日期：1993-07-01 00:00:00

abstract：:Catalase is an important antioxidant enzyme, which has been shown to provide cardiac protection from acute toxicity induced by doxorubicin, a most effective anticancer agent. Because cumulative dose-dependent chronic cardiomyopathy due to a long-term administration of doxorubicin is a significant clinical problem, the...

journal_title：Chemical research in toxicology

authors： Kang YJ,Sun X,Chen Y,Zhou Z

更新日期：2002-01-01 00:00:00