[Lymphomatoid contact dermatitis caused by diaminodiphenylmethane].
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Aged↗
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Results for “Benzhydryl Compounds”
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Structural requirements for 2,4- and 3,6-disubstituted pyran biomimetics of cis-(6-benzhydryl-piperidin-3-yl)-benzylamine compounds to interact with monoamine transporters.
In our effort to delineate novel pharmacophoric configuration of bioisosteric pyran versions of cis-(6-benzhydryl-piperidin-3-yl)-benzylamine derivatives in interacting with the monoamine transporter, further structure-activity relationship study was carried out. Both cis and trans 2,4- and 3,6-disubstituted derivatives were synthesized to determine the positional importance of N-substitution on affinity for monoamine transporters, that is the dopamine transporter (DAT), the serotonin transporter (SERT), and the norepinephrine transporter (NET) in rat brain. For that purpose, the potency of compounds was determined in competing for the binding of [(3)H]WIN 35,428, [(3)H]citalopram, and [(3)H]nisoxetine, respectively. Selected compounds were also evaluated for their activity in inhibiting the uptake of [(3)H]DA by DAT. Our binding results demonstrated potency in 3,6-disubstituted derivatives while 2,4-disubstituted derivatives failed to exhibit any appreciable binding affinity. Further structural exploration of the exocyclic N-atom in 3,6-disubstituted derivatives produced compounds potent at both DAT and NET. Compounds 16h and 16o with hydroxyl and amino groups in the phenyl moiety of the benzyl group produced the highest activity for the NET. In this regard, compound 16e with a methoxy substituent produced weak affinity at NET, which upon conversion into a hydroxyl functionality as in 16h produced potent affinity for the NET. Various indole derivatives displayed different interactions; the 5-substituted indole derivative 16n exerted potent affinity for NET, confirming the bioisosteric equivalence between this indole moiety and the phenyl-4-hydroxy group in 16h.
Animals↗
Determination of the N-acetyl metabolites of 4,4'-methylene dianiline and 4,4'-methylene-bis(2-chloroaniline) in urine.
A sensitive and specific gas chromatographic/mass spectrometric assay is described for the determination of N-acetyl 4,4'-methylene dianiline (N-acetyl MDA) and N-acetyl 4,4'-methylene-bis(2-chloroaniline) (N-acetyl MbOCA) in urine. The method is based on the solvent extraction of the compounds together with deuterium-labelled internal standards, the compounds being separated and detected by capillary gas chromatography/mass spectrometry as their pentafluoropropyl derivatives. The method has been applied to the detection of N-acetyl MbOCA and N-acetyl MDA in the urine of workers occupationally exposed to MbOCA and MDA. The results show that whilst N-acetyl MbOCA is a relatively minor urinary metabolite a significant proportion of MDA is excreted as the N-acetylated compound.
Acetanilides↗
Determination of bisphenol A diglycidyl ether and its hydrolysis and chlorohydroxy derivatives by liquid chromatography-mass spectrometry.
European Legislation establishes that the sum of the migration levels of bisphenol A diglycidyl ether (BADGE), its hydrolysis (BADGE.H2O and BADGE.2H2O) and chlorohydroxy (BADGE.HCl, BADGE.2HCl and BADGE.H2O.HCl) derivatives shall not exceed the limit of 1 mg/kg in foodstuffs or food simulants. A reversed-phase high-performance liquid chromatographic (RP-HPLC) method combined with mass spectrometry detection using atmospheric pressure chemical ionisation (APCI) is developed for the separation, quantification and identification of the interesting compounds. Quantification of the analytes was carried out in the single ion recording mode, once their characteristic masses were selected from their full spectra, by using an external calibration. The optimised method was suitable for the migration evaluation of these compounds in different samples.
Benzhydryl Compounds↗
Metabolism of the environmental estrogen bisphenol A by plant cell suspension cultures.
The metabolism of the environmental estrogen bisphenol A (BPA) was studied in heterotrophic plant cell suspension cultures of soybean (Glycine max), wheat (Triticum aestivum), foxglove (Digitalis purpurea), and thorn apple (Datura stramonium), which were regarded as metabolic model systems for intact plants. Three main metabolic routes of BPA were observed in the tissues. Most of the radioactivity found in the cell extracts consisted of carbohydrate conjugates of BPA amounting to about 85% (foxglove), 80% (wheat), 7% (soybean) and 15% (thorn apple) of applied 14C. The second main route was formation of non-extractable residues. Portions detected were low in foxglove (3.9% of applied 14C), moderate in wheat (13.5%), high in thorn apple (27.4%) and soybean (49.4%). With thorn apple, BPA derived bound residues were preponderantly resistant towards acid treatment; only traces of BPA were released. The third route was the formation of a highly polar, presumably polymeric material detected in media of soybean and thorn apple (29.3% and 36.0% of applied 14C, respectively). The mechanism of its formation remained unknown. In thorn apple, this highly polar material was formed extremely rapidly, and was considerably stable. Only traces of BPA were liberated by hydrolytic treatment with cellulase or acid. During hydrolysis experiments with glycoside fractions, non-extractable residues and highly polar materials, low amounts of presumably primary metabolites of BPA (up to 6% of applied 14C) were detected besides the parent compound; their chemical structures remained unclear.
Benzhydryl Compounds↗
Rational design and synthesis of novel 2,5-disubstituted cis- and trans-piperidine derivatives exhibiting differential activity for the dopamine transporter.
Herein, we report the rational design and synthesis of novel 2,5-disubstituted piperidine derivatives in the cis and trans isomeric forms. Out of these two isomers, the cis-isomer, 7a, was found to exhibit the most potent activity and selectivity for the dopamine transporter. These novel derivatives represent conformationally constrained version of piperidine analogue of GBR compounds.
Benzhydryl Compounds↗
[Studies on the phenolic derivatives from Galeola faberi Rolfe].
Eight phenolic derivatives, p-hydroxybenzaldehyde (I), 4,4'-dihydroxy-diphenyl methane(II), 2,4-bis(4-hydroxybenzyl) phenol (III), 5-methoxy-3-(2-phenyl-E-ethenyl)-2,4-bis (4-hydroxybenzyl) phenol (IV), p-hydroxybenzyl alcohol (V), 4-(beta-D-glucopyranosyloxy) benzyl alcohol (gastrodin) (VI), bis[4-(beta-D-glucopyranosyloxy) benzyl] (S)-2-isopropylmalate (VII), bis [4-(beta-D-glucopyranosyloxy) benzyl] (S)-2-sec-butylmalate (VIII) were isolated from the rhizome of Galeola faberi Rolfe for the first time. IV and VIII are new compounds. III is a new natural compound.
Benzhydryl Compounds↗
A sampling and analytical method for airborne m-phenylenediamine (MPDA) and 4,4'-methylenedianiline (MDA).
A method has been developed and validated for monitoring worker exposure to airborne m-phenylenediamine (MPDA) and 4,4'-methylenedianiline (MDA) in an epoxy resin manufacturing operation. Aerosol and vapor MPDA and MDA are collected on an acid-coated, glass-fiber filter to stabilize them as their amine salts. The amines are extracted from the filter with a mixture of acetonitrile in aqueous base and then treated with acetic anhydride to form the diacetamide derivatives. Studies were performed on the acetylation reaction to establish sample work-up conditions. The derivatives are analyzed by high performance liquid chromatography with UV detection. The method was tested for precision and accuracy using the National Institute for Occupational Safety and Health (NIOSH) criteria for a valid industrial hygiene method. The method may be used with confidence to measure from 0.90 to 755 micrograms of MPDA and/or 0.36 to 55 micrograms of MDA in a total air volume of 200 to 630 L, sampling at a rate of 1.5 to 2.0 L/min. Collected samples remain stable on filters for at least 1 week before analysis. The method will not suffer from interference from high relative humidity or other process volatiles, including diglycidyl ether of bisphenyl A and bis(2,3-epoxycyclopentyl) ether. Test atmospheres of the process materials were prepared in the laboratory for validation of the overall sampling and analytical method. This method can be applied to most aromatic amines and is recommended for monitoring both ambient and workplace air.
Acetylation↗
Liquid chromatographic determination of dimethyl formamide, methylene bisphenyl isocyanate and methylene bisphenyl amine in air samples.
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Air Pollutants↗
Occupational photosensitivity to diaminodiphenylmethane.
A case is reported of occupational exposure to diaminodiphenylmethane leading to acute photosensitivity. Avoidance of sun exposure with cloth has allowed continued employment while preventing further recurrences.
Adult↗
Asthma caused by diphenylmethane diisocyanate in foundry workers. Clinical, bronchial provocation, and immunologic studies.
Eleven foundry workers who developed asthmatic symptoms were studied with inhalation provocation tests with formaldehyde and diphenylmethane diisocyanate (MDI). These latter two chemicals are components of PepSet used for making molds for casting. Six subjects showed specific asthmatic reactions to MDI challenge (more than 20% fall in FEV1), 2 had a combined immediate and late reaction, and 4 had a predominantly late reaction. Four of the 6 subjects experienced recurrent nocturnal asthmatic reactions after a single challenge with MDI that lasted as long as 7 days, and this was associated with a significant increase in bronchial reactivity to methacholine. One subject had an immediate irritant reaction to both MDI and formaldehyde, which was spontaneously reversed in a few minutes. None of the remaining 10 subjects had a positive reaction to formaldehyde challenge. The reactors to MDI showed more evidence of air-flow obstruction in their lung function measurements and had a greater bronchial sensitivity to methacholine than the nonreactors but there was no difference in age, smoking habits, or atopic status. Specific IgE antibodies to MDI-human serum albumin conjugate were detected in 2 subjects, a reactor and a nonreactor. Specific IgG anti-MDI antibodies were detected in 4 subjects, 2 who reacted and 2 who did not. No difference in the pattern of response to MDI inhalation was observed in relation to the different immunologic findings. We conclude that MDI is a cause of asthma in foundry workers.
Age Factors↗
Yellow staining: 4,4'-methylenedianiline, or curing agent Z?
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Aniline Compounds↗
Randomized trial of modafinil for the treatment of pathological somnolence in narcolepsy. US Modafinil in Narcolepsy Multicenter Study Group.
Narcolepsy is a central nervous system disorder characterized by excessive daytime sleepiness and cataplexy. This placebo-controlled, double-blind, randomized, parallel-group, 18-center study assessed the efficacy and safety of modafinil, a new wake-promoting drug for treating sleepiness in narcolepsy. Subjects with narcolepsy (n = 283) received daily modafinil, 200 or 400 mg, or placebo, for 9 weeks, followed by an open-label treatment period. Subjective sleepiness was measured with the Epworth Sleepiness Scale. Objective sleepiness was assessed with the Multiple Sleep Latency Test and the Maintenance of Wakefulness Test. Level of illness was measured with the Clinical Global Impression of Change. Modafinil significantly reduced all measures of sleepiness and was associated with significant improvements in level of illness. Medication-related adverse experiences were few, dose-dependent, and mostly rated mild to moderate. Modafinil taken once daily was a very well tolerated and effective wake-promoting agent in the treatment of excessive daytime somnolence associated with narcolepsy. Modafinil demonstrated an excellent safety profile for up to 40 weeks of open-label treatment and efficacy was maintained, suggesting that tolerance will not develop with long-term use. Modafinil is a pharmacologically and clinically promising compound for the treatment of pathological daytime somnolence.
Adolescent↗
Vitellogenesis in male Fundulus heteroclitus (killifish) induced by selected estrogenic compounds.
The response of male Fundulus heteroclitus to estrogenic compounds was assessed in anticipation of using this species in endocrine disrupter field studies in the Chesapeake Bay. Measurements of plasma vitellogenin, gonadosomatic (GSI) and hepatosomatic (HSI) indices, and an assessment of changes in gonadal histology were made. Of the parameters assessed, vitellogenin was found to be the most sensitive biomarker. Plasma vitellogenin production occurred in a dose-dependent manner in males exposed to 4-nonylphenol, 4-(tert-octyl)phenol, bisphenol-A, and 17beta-estradiol. There was some indication that the effect on GSI may be influenced by the season in which the experiments are carried out. Two time course experiments revealed that vitellogenin is a fairly long-lived biomarker in male F. heteroclitus. There was also evidence that fish from two moderately contaminated areas injected with 4-nonylphenol or bisphenol-A produced less vitellogenin than those collected from a more pristine habitat. Production of vitellogenin in male F. heteroclitus appeared similar to two other species dosed with the same compounds.
Analysis of Variance↗
Differential activation of wild-type and variant forms of estrogen receptor alpha by synthetic and natural estrogenic compounds using a promoter containing three estrogen-responsive elements.
Structure-dependent estrogen receptor alpha (ER alpha) agonist and antagonist activities of synthetic and natural estrogenic compounds were investigated in human HepG2, MDA-MB-231 and U2 cancer cell lines. Compounds used in this study include 4'-hydroxytamoxifen, ICI 182,780, bisphenol-A (BPA), 2',4',6'-trichloro-4-biphenylol (3Cl-PCB-OH), 2',3',4',5'-tetrachloro-4-biphenylol (4Cl-PCB-OH), p-t-octylphenol, p-nonylphenol, naringenin, kepone, resveratrol, and 2,2-bis(p-hydroxyphenyl)-1,1,1-trichloroethane (HPTE). Cells were transfected with a construct (pERE(3)) containing three tandem estrogen responsive elements (EREs) and either wild-type estrogen receptor alpha (ER-wt) or variants expressing activation function-1 (ER-AF1) or AF-2 (ER-AF2). The ER agonist activities of the synthetic mono and dihydroxy aromatic compounds are comparable in all three-cell lines, whereas the activities of naringenin, kepone and resveratrol are dependent on cell context and expression of wild-type or variant forms of ER alpha. In contrast, the ER antagonist activities for these compounds were highly complex and, with the exception of 3Cl-PCB-OH, all compounds inhibited E2-induced wild-type or variant ER action. Results of this in vitro study suggest that the estrogenic and antiestrogenic activity of structurally diverse synthetic and natural estrogenic compounds is complex, and this is consistent with published data that often give contradictory results for these compounds.
Benzhydryl Compounds↗
Correlation between induction of DNA fragmentation and micronuclei formation in kidney cells from rats and humans and tissue-specific carcinogenic activity.
Five chemicals, known to induce kidney tumors in rats, were assayed for their ability to induce DNA damage and formation of micronuclei in primary cultures of rat and human kidney cells and in the kidney of intact rats. Significant dose-dependent increases of DNA fragmentation, as measured by the Comet assay, and of micronuclei frequency were obtained in primary kidney cells from both rats and humans with the following concentrations of the five test compounds: lead acetate (not tested for micronuclei induction) and potassium bromate from 0.56 to 1.8 mM, phenacetin from 1 to 3.2 mM, and 1, 4-dichlorobenzene and nitrilotriacetic acid from 1.8 to 5.6 mM. In terms of DNA-damaging potency all the five chemicals were more active in rat than in human kidney cells, whereas the potencies in inducing micronuclei formation were similar in the two species with the exception of 1,4-dichlorobenzene, which was slightly more potent in human than in rat cells. Consistently with the results observed in vitro, statistically significant increases in the average frequency of both DNA breaks and micronucleated cells were detected in the kidney of rats given po a single (12 LD50) or three successive daily doses (13 LD50) of the five test compounds. 4, 4'-Methylenedianiline, a carcinogen which does not induce kidney tumors in rats, gave negative responses in both in vitro and in vivo assays. These findings give evidence that kidney carcinogens may be identified by short-term genotoxicity assays using as target kidney cells and show that the five chemicals tested produce in primary cultures of kidney cells from human donors effects similar to those observed in rats.
Adult↗
Determination of 4,4'-methylenedianiline in hydrolysed human urine by micro liquid chromatography with ultraviolet detection.
4,4'-Methylenedianiline was determined in human urine by micro liquid chromatography with ultraviolet detection. The combination of a thorough work-up and the high mass sensitivity of micro liquid chromatography gave the method very high sensitivity. Derivatization with pentafluoropropionic anhydride enhanced the resolution of the 4,4'-dimethylenedianiline peak. The detection limit, defined as blank plus three times the standard deviation of the blank, was 2 nmol/l of urine, for 10-microliters injection volumes. The detection limit, defined as three times the noise, was about ten times better. The within- and between-assay coefficients of variation were 4 and 6%, respectively, for samples containing 40 nmol/l. The method was applied for the monitoring of excreted 4,4'-methylenedianiline in urine, during epicutaneous skin hypersensitivity testing (patch testing).
Aniline Compounds↗
Effects of endocrine disruptors on prosobranch snails (Mollusca: Gastropoda) in the laboratory. Part I: Bisphenol A and octylphenol as xeno-estrogens.
The effects of suspected endocrine disrupting chemicals on freshwater and marine prosobranch species were analysed in laboratory experiments. In this first publication, the responses of the freshwater snail Marisa cornuarietis and of the marine prosobranch Nucella lapillus to the xeno-estrogenic model compounds bisphenol A (BPA) and octylphenol (OP) are presented at nominal concentration ranges between 1 and 100 micrograms/L. Marisa was exposed during 5 months using adult specimens and in a complete life-cycle test for 12 months. In both experiments, the xeno-estrogens induced a complex syndrome of alterations in female Marisa referred to as "superfemales" at the lowest concentrations. Affected specimens were characterised by the formation of additional female organs, an enlargement of the accessory pallial sex glands, gross malformations of the pallial oviduct section resulting in an increased female mortality, and a massive stimulation of oocyte and spawning mass production. The effects of BPA and OP were comparable at the same nominal concentrations. An exposure to OP resulted in inverted U-type concentration response relationships for egg and spawning mass production. Adult Nucella from the field were tested for three months in the laboratory. As in Marisa, superfemales with enlarged accessory pallial sex glands and an enhancement of oocyte production were observed. No oviduct malformations were found probably due to species differences in the gross anatomical structure of the pallial oviduct. A lower percentage of exposed specimens had ripe sperm stored in their vesicula seminalis and additionally male Nucella exhibited a reduced length of penis and prostate gland when compared to the control. Because statistically significant effects were observed at the lowest nominal test concentrations (1 microgram BPA or OP/L), it can be assumed that even lower concentrations may have a negative impact on the snails. The results show that prosobranchs are sensitive to endocrine disruption at environmentally relevant concentrations and that especially M. cornuarietis is a promising candidate for a future organismic invertebrate model to identify endocrine-mimetic test compounds.
Animals↗