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At least 217 records · Page 12Linked to original sources
PubMed1981

Inhibition of housefly oxidative detoxication by phthaleins, fluoresceins and related compounds.

1. Phenolphthalein, halogenated fluoresceins, and other triphenylmethane and diphenylmethane derivatives inhibited biphenyl hydroxylation, aldrin epoxidation and several O-dealkylations in insect abdomen homogenates. Phenolphthalein and eosin (50 muM) were 2-3 times more effective than SKF 525-A and piperonyl butoxide (50 muM) as inhibitors of biphenyl hydroxylation in vitro. 2. The phthaleins, Aurin and Aluminon, inhibited both epoxidation and hydroxylation to similar extents, but fluoresceins, Rhodamine B, Malachite Green, and basic diphenylmethane derivatives preferentially inhibited hydroxylation. 3. Tetrabromophenolphthalein ethyl ester and bis-(N-dimethyl-4-aminophenyl-methane inhibited biphenyl hydroxylation in vivo. Bis-(N-dimethyl-4-aminophenyl) methane synergized the toxic effects of 1-naphthyl N-methylcarbamate in live houseflies.

Abdomen↗
PubMedDate not supplied

Identification of derivatives of bisphenol A diglycidyl ether and novolac glycidyl ether in can coatings by liquid chromatography/ion trap mass spectrometry.

A reversed-phase liquid chromatographic method combined with fluorescence and multiple mass spectrometric detection in series is presented for the separation and structure elucidation of bisphenol A diglycidyl ether (BADGE) and novolac glycidyl ether (NOGE) derivatives. Atmospheric pressure chemical ionization in the positive ion mode and collision induced fragmentation in the ion trap allowed identification of BADGE- and NOGE-related compounds originating from reactions of the glycidyl ethers with bisphenols, solvents, and chain stoppers. Two extracts from food-can coatings were investigated in detail. It was possible to elucidate the structures of many substances and consequently to draw conclusions about the production of the lacquers.

Acetates↗
PubMed1984

Effects of hypophysectomy on sex differences in the induction and depression of hepatic drug-metabolizing enzymes in the rat.

The role of the pituitary gland in the effects of treatment with phenobarbital, methylcholanthrene and morphine on hepatic drug metabolism in adult male and adult female rats has been investigated. A marked sex difference in the effects of treatment with these three compounds on hepatic drug metabolizing enzymes in intact adult rats was observed. No sex differences in the effects of phenobarbital methylcholanthrene or morphine on hepatic drug metabolizing enzymes were observed after treatment of hypophysectomized adult male and hypophysectomized adult female rats. The results indicate that the pituitary gland plays an important role in the determination of sex differences in the response of hepatic drug metabolizing enzymes to inducing agents.

Aniline Compounds↗
PubMed1997

Chromatographic analysis of water and wine samples for phenolic compounds released from food-contact epoxy resins.

Food-contact epoxy resins can release phenolic compounds such as phenol, m-cresol, bisphenol F, bisphenol A, 4-tert-butylphenol, bisphenol F diglycidyl ether (BFDGE), and bisphenol A diglycidyl ether (BADGE) into foodstuffs. A validated high-performance liquid chromatographic method with fluorometric detection is described for the simultaneous analysis of these compounds in wine and mineral water. Sample preparation by solid-liquid extraction enables detection limits of 2.5 micrograms/L in wine and 0.25 microgram/L in mineral water to be achieved. Recovery rates are close to 100%, except for BFDGE and BADGE (around 60% in wine and 75% in mineral water).

Chromatography, High Pressure Liquid↗
PubMed2000

Toxicity of epoxy fatty acids and related compounds to cells expressing human soluble epoxide hydrolase.

Soluble epoxide hydrolase (sEH) is suggested to alter the mode of action and increase the toxic potency of fatty acid epoxides. To characterize the structural features necessary for sEH-dependent epoxy fatty acid toxicity, 75 aliphatic compounds were assayed for cytotoxicity in the presence and absence of sEH. Three groups of aliphatic epoxide-diol pairs were described by their observed differential toxicity. Group I compounds were typified by terminal epoxides whose toxicity was reduced in the presence of sEH. Group II compounds were toxic in either their epoxide or diol form, but toxicity was unaffected by sEH. Group III compounds exhibited sEH-dependent toxicity and were therefore used to investigate the structural elements required for cytotoxicity in this study. The optimal structure for group III compounds appeared to be a fatty acid 18-20 atoms long (e.g., a carbon backbone plus a terminal heteroatom) with an epoxide positioned between C-7 and C-12. In the absence of sEH, replacement of epoxides with a vicinal diol was required for toxicity. While diol stereochemistry was unimportant, vicinal diol-induced toxicity exhibited fewer positional constraints to toxicity than sEH-dependent epoxide toxicity. Tested fatty acids and esters with neither an epoxide nor a vicinal diol were not toxic. These data support the hypothesis that long-chain epoxy fatty acid methyl esters are potential pro-toxins metabolized by sEH to more toxic diols. Furthermore, our results suggest that the endogenous compounds, leukotoxin methyl ester, 9,10(Z)-epoxyoctadec-12(Z)-enoic acid methyl ester, and isoleukotoxin methyl ester, 12, 13(Z)-epoxyoctadec-9(Z)-enoic acid methyl ester, are structurally optimized to elicit the observed effect.

Epoxide Hydrolases↗
PubMed1997

Delayed and immediate allergy caused by methylhexahydrophthalic anhydride.

Epoxy resin compounds (ERC) include a large number of chemicals, such as epoxy resins (ER), reactive diluents and hardeners. Many hardeners, e.g., aliphatic polyamines, are well-known sensitizers. Another type of ER hardeners are the phthalic anhydrides, such as methylhexahydrophthalic anhydride (MHHPA) and methyltetrahydrophthalic anhydride (MTHPA), which have been reported as causing immunologically-mediated respiratory diseases and contact urticaria, but not allergic contact dermatitis. Here, we present a horizontal boring-machine worker who developed allergic contact dermatitis, as well as allergic rhinitis and an immediate contact skin reaction from MHHPA. Patch testing with a dilution series of MHHPA in pet. elicited the following results: 2%, 1% and 0.5%, +2; 0.25% and 0.125%, + (3- to 6-day readings). An immunohistochemical and electron microscopic study also indicated that the patch test reactions were conventional-delayed allergic reactions. Interleukin 8 was observed in the epidermal cells, whereas interleukin 4 immunoreactivity was detected in the dermal cells. Immunoreactivity to-interleukin 5, granulocyte/macrophage-colophony stimulating factor (GM-CSF) or eosinophil cationic protein was not seen. In conclusion, the patient developed both Type I and Type IV allergy to MHHPA. The clinical data, patch test results, immunohistochemical and electron microscopic observations indicated that the MHHPA allergy detected by the patch test reaction was a conventional delayed-type hypersensitivity reaction. The patient also had an allergic patch test reaction to para-phenylenediamine and diaminodiphenylmethane, possibly representing occupational sensitization.

Allergens↗
PubMed1979

Isoepoxydon, a new metabolite of the patulin pathway in Penicillium urticae.

A patulin-negative mutant (J1) of Penicillium urticae (N.R.R.L. 2159A) was known to accumulate about 100mg per litre quantities of the 5,6-epoxygentisyl quinone, (-)-phyllostine and another metabolite (UIII). Both were derived from acetate and hence were polyketides. Purified UIII (m.p. 53 degrees C, [alpha](32) (D)+206 degrees , lambda(methanol) (max.) 240nm; epsilon 3806 litre.mol(-1).cm(-1)) was characterized as a partially reduced derivative of (-)-phyllostine and was found to be a diastereoisomer of the known phytotoxin, (+)-epoxydon. Hence its designation as (+)-iso- or epi-epoxydon. From (1)H n.m.r. and c.d. data the stereochemistry of the epoxide ring in (+)-isoepoxydon was determined to be identical with that in (+)-epoxydon (i.e. R,R) but the configuration of the secondary alcohol at C-4 was S rather than R as in (+)-epoxydon. Isoepoxydon (compound UIII) is therefore (4S,5R,6R)-5,6-epoxy-4-hydroxy-2-hydroxymethylcyclohex-2-en-1-one. The boat conformation in which the C-4 hydroxy group is axial is preferred. In the range of 1mm to 5mm, the antibiotic activity of (+)-isoepoxydon against Bacillus subtilis sp. was 56% of that obtained with patulin. Over a period of 1 to 3h, [(14)C]isoepoxydon was efficiently converted into patulin by a shake culture of the parent strain of P. urticae. The precursor relationship of isoepoxydon to patulin was confirmed by feeding unlabelled isoepoxydon (1mm) to a washed-cell suspension of a mutant (J2) in which, over a period of 3 to 5h, a better than 60% conversion into patulin was attained. The enzymic relationship between isoepoxydon and phyllostine and their positions in the late portion of the patulin biosynthetic pathway are discussed.

Acetylation↗
PubMed1990

[CNS-active substances: synthesis of epoxybenzoxocines].

The 2-(2-Bromophenyl)-acetaldehyde acetals 8 are treated with n-BuLi and the aldehydes 7 and 11 to form the hydroxyacetales 9 and 12, respectively. 9 is cyclized under acidic conditions to the epoxybenzoxocine 2; analogously 12 yields the epoxydibenzoxocine 14.

Bridged Bicyclo Compounds↗
PubMed1987

Responses of the L5178Y tk+/tk- mouse lymphoma cell forward mutation assay to coded chemicals. I: Results for nine compounds.

Nine substances were tested for their mutagenic potential in the L5178Y tk+/tk- mouse lymphoma cell forward mutation assay, by means of procedures based upon those described by Clive and Spector (Mutat Res 44:269-278, 1975) and Clive et al (Mutat Res 59:61-108, 1979). Cultures were exposed to the chemicals for 4 hr, then cultured for 2 days before plating in soft agar with or without trifluorothymidine (TFT), 3 micrograms/ml. The coded chemicals were tested at least twice. Significant responses were obtained with calcium chromate, 3-(chloromethyl)pyridine, 1,2-epoxybutane, monochloroacetic acid, dicyclohexylthiourea, 2,4-diaminophenol hydrochloride, and pentachloroanisole. Apart from pentachloroanisole, rat liver S9 mix was not a requirement for the clearly mutagenic activity of any of these compounds. Compounds not identified as mutagens were 3-amino-1,2,4-triazole and sucrose.

Acetates↗
PubMed1981

Carcinogenicity and mutagenicity of solvents. I. Glycidyl ethers, dioxane, nitroalkanes, dimethylformamide and allyl derivatives.

The carcinogenicity and/or mutagenicity as well as structural features and relationships of the glycidylethers (principally phenyl-, butyl-, allyl-, and isopropyl-), dioxane, nitroalkanes (nitro methane, ethane and propane), dimethylformamide and allyl derivatives (chloride, alcohol and amine) were examined. Additionally, considerations of the production, use patterns, estimated populations at risk, TLV's and metabolism of the above agents were discussed.

Allyl Compounds↗
PubMed2005

Determination of bisphenol diglycidyl ether residues in canned foods by pressurized liquid extraction and liquid chromatography-tandem mass spectrometry.

A new confirmatory method for simultaneous determination of bisphenol diglycidyl ether residues (BADGE, BADGE.H(2)O, BADGE.2H(2)O, BADGE.H(2)O.HCl, BADGE.HCl, BADGE.2HCl, BFDGE and BFDGE.2HCl) from canned food has been developed. The proposed method includes extraction by pressurized liquid extraction (PLE) followed by liquid-liquid partition and purification by solid phase extraction (SPE). Several solvent systems and different operating conditions (time, temperature) have been investigated for PLE optimization. A reversed-phase high-performance liquid chromatography (RP-HPLC) coupled to atmospheric pressure chemical ionisation tandem mass spectrometry (APCI-MS-MS) method was developed for the separation, quantification and confirmation. The ion source settings were optimized using a design of experiments (DOE). The optimized method was applied to the determination of these chemicals at very low levels in different samples with a quantification limit of 5 ng/g. Recoveries ranged between 82 and 101% and standard deviations were less than 10%.

Atmospheric Pressure↗
PubMed2006

Single laboratory validation of a method for the determination of Bisphenol A, Bisphenol A diglycidyl ether and its derivatives in canned foods by reversed-phase liquid chromatography.

A method was developed and validated for the simultaneous determination of Bisphenol A (BPA), Bisphenol A diglycidyl ether (BADGE), BADGE-H2O, BADGE-2H2O, BADGE-H2O-HCl, BADGE-HCl, and BADGE-2HCl in canned food using reversed phase high-performance liquid chromatography (HPLC) with fluorescence detection; chromatographic separation of all seven analytes was achieved (Rs > or = 1.08) using HPLC gradient elution technique. Acetonitrile was used to extract the analytes from the food matrix before subjecting the samples to liquid-liquid extraction, solid-phase extraction for further clean-up and preconcentration prior to HPLC analysis. Excellent inter-day precision data (n = 10) and intra-day precision data (n = 5) were obtained on a 200 microg/kg spiked sample. The RSD ranged from 0.20% to 2.96% for the inter-day precision tests, and 0.04% to 2.82% for the intra-day precision tests. Accuracy was measured at three concentration levels: 200, 1000, and 2000 microg/kg; recoveries ranged from 86.07% to 114.06%. The excellent validation data suggests that this method can be applied on canned foods for the determination of migration of BPA, BADGE and its derivatives from can coatings into food.

Acetonitriles↗
PubMed2004

Development of parenteral formulation for a novel angiogenesis inhibitor, CKD-732 through complexation with hydroxypropyl-beta-cyclodextrin.

The effect of hydroxypropyl-beta-cyclodextrin (HP-beta-CyD) on the aqueous solubility and chemical stability of O-(4-Dimethylaminoethoxycinnamoyl)fumagillol (CKD-732), a new angiogenesis inhibitor, was investigated with an aim of preparing a stable and effective parenteral formulation. The CKD-732/HP-beta-CyD inclusion complex was obtained in solid state by freeze-drying and characterized in solution by proton nuclear magnetic resonance (1H NMR). Then, the pharmacokinetic profile in rats and the in vivo tumor growth inhibitory activity in mice following the parenteral administration of aqueous CKD-732/HP-beta-CyD complex were compared to those of CKD-732.hemioxalate solution having an equivalent concentration. The aqueous solubility of CKD-732 was markedly increased by the combination of pH adjustment and HP-beta-CyD complexation through a soluble 1:1 inclusion complex formation, which was supported by NMR spectroscopy. The hydrolysis of CKD-732 following pseudo first-order kinetics was decelerated moderately but significantly in acidic and basic solutions in the presence of HP-beta-CyD. The stability of lyophilized CKD-732/HP-beta-CyD complex was also drastically improved after storage in various conditions. The intravenous pharmacokinetic profile and the subcutaneous in vivo tumor growth inhibitory activity of aqueous CKD-732/HP-beta-CyD complex were not significantly different from those of CKD-732.hemioxalate solution with the favorable reduction of irritation. These results demonstrate that the CKD-732/HP-beta-CyD complex is an attractive formulation for use in the parenteral delivery of CKD-732.

2-Hydroxypropyl-beta-cyclodextrin↗