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PubMed2003

Synthesis and estrogenic activity of bisphenol a mono- and di-beta-D-glucopyranosides, plant metabolites of bisphenol A.

The syntheses and characterization of bisphenol A mono- and di-beta-D-glucopyranosides were undertaken to confirm that these compounds are major plant metabolities of bisphenol A (BPA) and to allow an assessment of their estrogenicity. Synthesis involved the glucosidation of unprotected BPA with glucose penta-acetate with phosphorus oxychloride as catalyst. The estrogenic activity of BPA and its mono- and di-beta-D-glucopyranosides were measured with an enzyme-linked immunosorbent assay (ELISA)-based estrogen receptor competitive binding assay and with a yeast two-hybrid assay adapted to a chemiluminescent reporter gene (for beta-galactosidase). Both methods showed that the estrogenicity of BPA was eliminated by formation of the di-glucoside, but whereas the ELISA-based method indicated that reduced activity remained in the monoglucoside, the yeast two-hybrid method showed the monoglucoside to be inactive. Presumably these results reflect the more complex interactions of test compound and cellular components required to demonstrate estrogenicity in the yeast two-hybrid assay. As these processes parallel those in mammalian cells, the yeast two-hybrid method is likely to be the more realistic assay. The uptake and metabolism of BPA by plants offers the possibility of phytoremediation of contaminated water, but also provides an additional route for the compound to enter the human food chain.

Benzhydryl Compounds↗
PubMed1995

Decontamination procedures after in vitro topical exposure of human and rat skin to 4,4'-methylenebis[2-chloroaniline] and 4,4'-methylenedianiline.

4,4'-Methylenebis[2-chloroaniline] (MbOCA) and 4,4'-methylenedianiline (MDA) are widely used industrial chemicals classified as suspect human carcinogens. There is considerable occupational skin exposure to these compounds, and consequently, it is important to establish an efficient washing procedure after skin contamination. Four washing solutions were studied (100% ethanol, 100% water, 1 and 10% (v/v) aqueous soap) using fresh human and male F344 rat skin in flow-through diffusion cells. All solutions were equally effective at removing MbOCA and MDA from the surface of human skin, with 21-47% of the applied dose removed at 72 hr. In contrast, with rat skin 100% water and 1% soap solution were significantly less (p < 0.05) effective than 10% soap solution and 100% ethanol at removing MbOCA and MDA. Washing the skin surface at 3 or 30 min significantly reduced (p < 0.05) the absorption of MbOCA and MDA into and through human and rat skin at 72 hr by two- to threefold, compared with control unwashed skin. Washing the skin after this critical time point did not significantly reduce the absorption. These studies suggest that MbOCA and MDA are rapidly absorbed from the skin surface into the skin. Therefore, in order to reduce systemic exposure, the skin must be washed within the first 30 min after contamination has occurred. For human skin, the choice of washing solution employed was not as critical as the time of washing. This is in contrast to the rat, where the higher concentration soap and ethanol solutions were more effective for skin decontamination.

Administration, Topical↗
PubMed1995

Determination of urinary 4,4'-methylenedianiline and its acetylated metabolites by solid-phase extraction and HPLC analysis with UV and electrochemical detection.

An analytical procedure based on solid-phase extraction and high-performance liquid chromatography using both ultraviolet and electrochemical detection was developed to determine, without derivatization, stable urinary forms of 4,4'-methylenedianiline (MDA) and of its acetylated metabolites at the micrograms/l level, in post-shift urine from 63 exposed workers. The determination of MDA, N-acetyl MDA (MAMDA) and N,N'-diacetyl MDA (DAMDA) was achieved on the non-hydrolysed urine samples, and that of total MDA on urine samples after alkaline hydrolysis. It was necessary to protect urine samples with sulfamic acid in order to stabilize amines and to improve the precision and accuracy of the analyses. Under these conditions, unstable labile conjugates were determined as their parent stable amine. The distribution of total MDA, MDA, MAMDA and DAMDA was assessed in 116 urine samples. Their relative concentrations (arithmetic means) were found to be in the following order: total MDA > MAMDA > MDA > DAMDA. While MAMDA represented more than 50% of total MDA, MDA and DAMDA were lower than 15% and 3% respectively. Acetylation of MDA, described as a possible pathway of detoxication, is confirmed to be an important metabolization route in humans, essentially through the monoacetylated metabolite. However, the individual ratio MAMDA/total MDA was found to vary widely (roughly from 0% to 100%).

Acetylation↗
PubMed1990

Determination of 4,4'-methylenedianiline in hydrolysed human urine using liquid chromatography with UV detection and peak identification by absorbance ratio.

A liquid chromatographic method using multi-wavelength UV detection (258 and 285 nm) is presented for the determination of 4,4'-methylenedianiline (MDA) in hydrolysed human urine. The method is based on hydrolysis under strongly acidic conditions followed by derivatization with pentafluoropropionic anhydride. The perfluoro fatty acid amide derivative formed was analysed on a bonded octadecylsilyl column using isocratic elution with acetonitrile-water (67:33, v/v) as mobile phase. The overall recovery for urine samples containing 115 micrograms/l of MDA was 97 +/- 3%. The calibration graph was linear in the investigated range (12-122 micrograms/l) with a correlation coefficient of 0.998. The precision was 2.3% for urine samples containing 122 micrograms/l and the detection limit was 8 micrograms/l. The chromatograms were evaluated using a combination of retention time data and absorbance ratio by the simultaneous monitoring of the wavelengths 285 and 258 nm. The absorbance ratio (285/258 nm) was virtually constant (0.28 +/- 0.04) in the range 78-10,000 micrograms/l. The precision for the absorbance ratio was 6.1% for urine samples containing 124 micrograms/l and the lowest amount of MDA to give an absorbance ratio was 50 micrograms/l. The procedure for the hydrolysis of urine spiked with MDA and N,N'-diacetyl-MDA and urine from skin-exposed workers was studied under strongly acidic, weakly acidic and basic conditions. MDA was found in hydrolysed urines from skin-exposed epoxy resin workers in the concentration range 8-700 micrograms/l.

Aniline Compounds↗
PubMed2001

Differentiation of the mechanism of micronuclei induced by cysteine and glutathione conjugates of methylenedi-p-phenyl diisocyanate from that of 4,4'-methylenedianiline.

Methylenedi-p-phenyl diisocyanate (MDI) is widely used in the production of polyurethane products. Diisocyanates are reactive compounds, MDI can react under physiological conditions with various functional groups found on biological molecules resulting in conjugate formation or undergo non-enzymatic hydrolysis to form 4,4'-methylenedianiline (MDA). We have previously reported that addition of MDI directly to Chinese hamster lung fibroblasts (V79) cultures did not induce micronuclei (MN), but MDA, and the glutathione and cysteine conjugates of MDI (BisGS-MDI and BisCYS-MDI), induced a concentration-dependent increase in the frequency of MN. The conventional MN assay does not discriminate between MN produced by acentric chromosome fragments from those arising due to whole lagging chromosomes that were not incorporated into daughter nuclei at the time of cell division. The mechanism of MN induction from these potential MDI metabolites/reaction products was explored in the present study using immunofluorescent staining of kinetochore in MN of cytokinesis-blocked V79 cells. This assay discerns the presence of centromere within the MN to distinguish the MN containing centric chromosomes from those containing acentric fragments. Eighty five percent of MDA-induced MN were negative with respect to anti-kinetochore antibody binding (KC(-)). This is consistent with an interaction between MDA and DNA resulting in chromosome breakage. However, BisGS-MDI and BisCYS-MDI induced a higher percentage of MN that were positively stained by the anti-kinetochore antibody (KC(+)). These results suggest that the mechanism of MN formation induced by BisGS-MDI and BisCYS-MDI is mediated through disruption and/or by affecting the function of the mitotic spindle. This mechanism is distinctly different from the mechanism of MN induction by MDA.

Aniline Compounds↗
PubMed1997

Workers exposed to thermal degradation products of TDI- and MDI-based polyurethane: biomonitoring of 2,4-TDA, 2,6-TDA, and 4,4'-MDA in hydrolyzed urine and plasma.

The aim of the study was to investigate biomarkers of exposure to thermal degradation products of 2,4- and 2,6-toluene diisocyanate (TDI)- and 4,4'-methylenediphenyl diisocyanate (MDI)-based polyurethane and the toxicokinetics of these products. Blood and urine were collected from 15 factory workers exposed to thermal degradation products of MDI-based polyurethane glue and TDI-based flexible foam. Four of these workers were also studied during an exposure-free period. Urine and plasma were analyzed after acidic hydrolysis and the concentrations of the isocyanates' corresponding amines, 2,4-, 2,6-toluenediamine (TDA), and 4,4'-methylenedianiline (MDA), were determined as derivatives of pentafluoropropionic anhydride by gas chromatography using chemical ionization mass spectrometry monitoring negative ions. Urinary elimination rates were in the range of < 0.01-5.7 micrograms of 2,4-TDA per hour, < 0.01-3.5 micrograms of 2,6-TDA per hour, and < 0.01-1.6 micrograms of 4,4'-MDA per hour. Plasma levels were in the range of < 0.1-5.5 ng of 2,4-TDA per mL, < 0.1-2.3 ng of 2,6-TDA per mL, and < 0.1-45 ng of 4,4'-MDA per mL. The urinary half-lives of 4,4'-MDA for four of the workers were found to be 59, 61, 73, and 82 hours. The half-lives of 4,4'-MDA in plasma were 10, 14, 16, and 22 days. Elimination rate peaks of 2,4-TDA, 2,6-TDA, and 4,4'-MDA in urine varied during and between workdays. The individual variation in plasma concentrations of 2,4-TDA, 2,6-TDA, and 4,4'-MDA with time was small, but between individuals the variation was great.

Air Pollutants↗
PubMed1984

Modification of the development of N-nitrosomorpholine-induced hepatic lesions by 2-acetylaminofluorene, phenobarbital and 4,4'-diaminodiphenylmethane: a sequential histological and histochemical analysis.

The effects of 2-acetylaminofluorene (2-AAF), sodium phenobarbital (PB) and 4,4'-diaminodiphenylmethane (DDPM) on the developmental sequence of N-nitrosomorpholine (NNM) induced changes in the rat liver was investigated using a histological, histochemical and morphometric approach. Male Sprague-Dawley rats were treated with NNM for 3 weeks, maintained on basal diet for 1 week and then fed on diets containing either 0.005% 2-AAF, 0.05% PB, 0.08% DDPM or, as carcinogen controls, no addition (basal diet, BD) for a further 48 weeks. Control and experimental groups were sacrificed at weeks 4, 16, 28, 40 and 52 of the investigation. The incidence of the hepatocellular carcinomas observed at weeks 40 and 52 was markedly enhanced by 2-AAF treatment and slightly increased after PB administration. 2-AAF also exerted a positive influence on the development of angiosarcomas, benign hemangioendotheliomas and cystic cholangiomas. DDPM did not show clear effects on the development of liver cell carcinoma but enhanced the induction of cholangiofibromas, cholangiofibrosis and, very markedly, spongiosis hepatis. No neoplastic lesions were observed in animals treated with 2-AAF, PB or DDPM without prior application of NNM. Morphometric analysis of enzyme-altered foci revealed contrasting effects of 2-AAF, PB and DDPM, not only on number and size of lesion but also on their histochemical phenotype. Thus whilst 2-AAF administration was primarily linked with increase in number of lesions, PB appeared to stabilise their phenotypic cellular changes and increased the activity of G6PDH. DDPM did not significantly influence the number of focal lesions but seemed to effect a decrease in phenotypic alteration within foci. The results suggest that changes in the nature of enzyme-altered foci may be correlated with enhancement or inhibition of tumorigenesis.

2-Acetylaminofluorene↗
PubMed1998

Proposal for the assessment to quantitative dermal exposure limits in occupational environments: Part 2. Feasibility study for application in an exposure scenario for MDA by two different dermal exposure sampling methods.

OBJECTIVE: To evaluate two different techniques for assessing dermal exposure to 4,4'-methylene dianiline (MDA) in a field study. The results were used to test the applicability of a recently proposed quantitative dermal occupational exposure limit (DOEL) for MDA in a workplace scenario. METHODS: For two consecutive weeks six workers were monitored for exposure to MDA in a factory that made glass fibre reinforced resin pipes. Dermal exposure of the hands and forearms was assessed during week 1 by a surrogate skin technique (cotton monitoring gloves) and during week 2 by a removal technique (hand wash). As well as the dermal exposure sampling, biological monitoring, measurement of MDA excretion in urine over 24 hours, occurred during week 2. Surface contamination of the workplace and equipment was monitored qualitatively by colorimetric wipe samples. RESULTS AND CONCLUSIONS: Geometric means of daily exposure ranged from 81-1762 micrograms MDA for glove monitoring and from 84-1783 micrograms MDA for hand washes. No significant differences, except for one worker, were found between exposure of the hands in weeks 1 and 2. Significant differences between the mean daily exposure of the hands (for both weeks and sampling methods) were found for all workers. The results of the colorimetric wipe samples indicated a general contamination of the workplace and equipment. Excretion of MDA in 24 hour urine samples ranged from 8 to 249 micrograms MDA, whereas cumulative MDA excretion over a week ranged from 82 to 717 micrograms MDA. Cumulative hand wash and MDA excretion results over a week showed a high correlation (R2 = 0.94). The highest actual daily dermal exposure found seemed to be about 4 mg (hand wash worker A on day 4), about 25% of the external DOEL. Testing of compliance by means of a biological limit value (BLV) led to similar results for the same worker. It is concluded that both dermal exposure monitoring methods were applicable and showed a compatible performance in the present exposure scenario, where the exposure relevant to dermal absorption is considered mainly restricted to hands. The concept for a DOEL seemed to be relevant and applicable for compliance testing and health surveillance in the situation under investigation.

Adult↗
PubMed1996

A new haemocompatible phospholipid polyurethane based on hydrogenated poly(isoprene) soft segment.

A new haemocompatible phospholipid polyurethane based on hydrogenated poly(isoprene) glycol (HPIP) and 4,4'-methylendiphenyl diisocyanate (MDI) was synthesized using 2-[bis(2-hydroxyethyl)methyl-ammonio]ethylstearylphosphate (BESP) and 1,4-butanediol (BD) as chain extender. The bulk and surface characteristics of this material was investigated by differential scanning calorimetry (DSC), dynamic viscoelasticity and tensile property measurements, attenuated total reflectance-Fourier transform infrared spectroscopy (ATR-FTIR), and contact angle measurement. This polymer possessed a hydrophobic surface revealed by contact angle measurement. The haemocompatibility of this polyurethane was evaluated by platelet rich plasma (PRP) contacting studies and scanning electron microscopy (SEM) observation using medical grade poly(vinyl chloride) (PVC) as the reference. The results show that this new polyurethane had relatively lower platelet adhesion and limited shape change for the attached platelets compared to PVC. The clotting time of the materials in contact with platelet poor plasma (PPP) was 99, 75, and 62 s and in contact with PRP was more than 240, 100, and 86 s for new polyurethane, PVC, and glass, respectively. This new phospholipid polyurethane is expected to have wide applications as coating or structural material for blood-contacting medical equipment due to its outstanding haemocompatibility and excellent mechanical strength.

Biocompatible Materials↗
PubMedDate not supplied

[Change in the allergen spectrum in contact eczema 1975-1984].

The patch test results in 8247 patients tested in the years from 1975 to 1984 at the Department of Dermatology at the University of Graz were evaluated and a trend analysis was performed. The most conspicuous results were: Increase of contact allergy to nickel in young women; Decrease of contact allergy to chromate; Frequent occurrence of contact allergy to 4,4-diaminodiphenylmethane.

Adult↗
PubMed1984

4,4'-Diaminodiphenylmethane: promoting effect on the development of thyroid tumors in rats treated with N-bis(2-hydroxypropyl)nitrosamine.

4,4'-Diaminodiphenylmethane (4,4'-methylenedianiline) (DDPM) promoted the development of thyroid tumors in rats treated with a subeffective dose of N-bis(2-hydroxypropyl)nitrosamine (2,2'-dihydroxy-N-nitrosodipropylamine) (DHPN) for thyroid tumorigenesis. Male inbred W rats were given a single ip injection of 280 mg DHPN/100 g body weight and fed diets with or without 1,000 ppm DDPM. Thyroid tumor incidences at the end of week 20 of the experiment were 90% (19/21) in rats given DHPN and then DDPM and 28% (6/21) in rats given DHPN alone. The incidence of thyroid cancers was 9.5% (2/21) in rats first given DHPN and then DDPM. Untreated rats and rats given DDPM alone had no thyroid tumors after 20 weeks. Incidences of kidney tumors were 38% (8/21) in rats given DHPN and then DDPM and 28% (6/21) in rats given DHPN alone. No tumors were found in the kidneys and lungs of rats given DDPM alone and in those of control rats. Treatment with DDPM alone slightly but not significantly decreased the serum concentrations of thyroxine and triiodothyronine; treatment with DHPN plus DDPM had no such effect.

Aniline Compounds↗
PubMed1983

[Infrahepatic bile duct proliferation in the gestating rat treated with 4,4'-diaminodiphenylmethane (4,4DDPM)].

We have attempted to produce experimentally the histological hepatic lesions observed in the case of biliary infant atresia. Though the etiopathogeny of this disease remains uncertain, the possibility of a toxic origin for the liver was evoked. Female rats were treated per os from the 10th to the 20th day of gestation with 44' DDPM, a molecule able to provoke an intra-hepatic biliary ductular proliferation. If we always observed hepatic lesions in pregnant rats sacrificed 24 hours before delivery, in some cases we also noticed the existence of macro- and microscopic hepatic lesions in the foetus. With a dose superior to LD 50, we have sometimes observed neural tube defects without hepatic lesions.

Aniline Compounds↗
PubMed2004

Glycosylation of bisphenol A by tobacco BY-2 cells.

Tobacco BY-2 cells in suspension culture absorbed and transformed bisphenol A dissolved in the culture medium. Major products were bisphenol A mono-O-beta D-gentiobioside and the trisaccharide bisphenol A mono-O-beta-D-glucopyranosyl-(1-->4)-[beta-D-glucopyranosyl-(1 --> 6)] beta-D-glucopyranoside. Also produced were the mono- and di- O-beta-D-glucopyranosides. As glycosides of bisphenol A lack the estrogenic activity of the parent compound, these findings enhance the possibilities of phytoremediation of natural waters contaminated by bisphenol A. .

Benzhydryl Compounds↗
PubMed2005

Transformation and removal of bisphenol A from aqueous phase via peroxidase mediated oxidative coupling reactions: efficacy, products, and pathways.

A systematic investigation of the feasibility of and mechanisms for transformation and removal of bisphenol A (BPA) from aqueous phase via oxidative coupling mediated by horseradish peroxidase is described. It is demonstrated that BPA can be effectively transformed into precipitable solid products in HRP-mediated oxidative coupling reactions. A total of 13 reaction intermediates and products are identified using LC/MS and GC/MS techniques, and with the help of ab initio molecular modeling, detailed reaction pathways are proposed. It is postulated that two BPA radicals are coupled primarily by the interaction of an oxygen atom on one radical and propyl-substituted aromatic carbon atom on another, followed by elimination of an isopropylphenol carboncation. All intermediates or products detected can be interpreted as resulting from either coupling or substitution reactions between BPA and other intermediates or products. The efficacy of the reaction at low substrate concentrations is demonstrated using a sensitive analytical procedure involving solid-phase extractions. The results suggest that catalyzed oxidative coupling reactions may be important natural transformation pathways for estrogenic phenolic compounds and indicate their potential use as an efficient means for removal of estrogenicity from waters and wastewaters.

Benzhydryl Compounds↗