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At least 19 recordsLinked to original sources
PubMed1979

Alkenylidene bisphenols, a new class of bisphenol bactericide.

Alkenylidene bisphenols are prepared by condensation of an appropriate phenol with a haloacetaldehyde, followed by base-induced elimination, or by condensation of the corresponding aryl methyl ether, elimination, and deprotection of the phenol with boron tribromide. The resulting compounds may be further elaborated by reactions on the aromatic nucleus. A series of 13 such compounds showed activity against Staphylococcus aureus; the most active was 1,1-dichloro-2-(3-allyl-5-chloro-2-hydroxphenyl)-2-(5-chloro-2-hydroxyphenyl)ethylene (16), MIC 0.16 microgram/mL. 1,1-Dichloro-2,2-bis(5-chloro-2-hydroxyphenyl)ethylene (6) was similar in its activity and spectrum to hexachlorophene.

Anti-Infective Agents, Local↗
PubMed2026

Bisphenols and their role in female infertility and hormone-related cancer.

Various types of external chemicals can disrupt the endocrine system, interfering with normal hormone function and causing a broad spectrum of negative health effects. Endocrine-disrupting chemicals (EDCs) are a diverse group of natural and synthetic chemicals that are known to contaminate the environment. It is postulated that these agents can contribute to the development of many diseases, including infertility and cancer, because of their ability to interfere with estrogen receptors (ERs). Bisphenols (BPs) are a group of compounds that belong to EDCs, the most common of which is bisphenol A (BPA). Due to restrictions on the use of BPA in industry, analogues such as bisphenol S (BPS) and bisphenol F (BPF) have been introduced. However, some reports indicate that BPA analogues also have negative effects on the endocrine system in both humans and animals because of their structural similarity. This review summarises current knowledge related to BPA, its analogues and their role in female infertility and hormone-related cancers. Furthermore, this review also points to the problem of exposure to more than one estrogenic agent and highlights the importance of considering exposure to multiple chemicals when assessing health effects and setting daily limits.

Humans↗
PubMed1978

Simple methods for demonstration of epoxy resins of bisphenol A type.

Low molecular weight oligomers of epoxy resins of bisphenol A type are common sensitizers. For demonstrating the presence of sensitizing oligomers of these resins, two simple methods are described. The first one, a colour reaction, demonstrates the presence of the bisphenol A skeleton. If this test is positive, thin-layer chromatography is carried out to demonstrate the presence of low molecular weight oligomers of epoxy resins. Some practical applications are reported.

Chromatography, Thin Layer↗
PubMed2026

Simultaneous removal of nitrogen, Cu2+, and bisphenol A in a hydrogel-biochar-AQDS immobilized bioreactor with added bicarbonate: Performance and metagenomic insights.

As the complexity of industrial wastewater pollution continues to increase, the simultaneous removal of nitrogen, metal contaminants, and persistent organic pollutants under low carbon conditions has become a key challenge for biological treatment systems. To address the operational instability and dependence on carbon sources observed in immobilized systems when exposed to copper (Cu2+) and bisphenol A (BPA), the Pseudoalteromonas japonicus strain LY0623 was integrated into a hydrogel-biochar-AQDS composite carrier to construct a multifunctional immobilized biofilm system. Notably, under conditions containing only NaHCO3, the R4 system achieved an NH4+-N removal rate of 89%. Under conditions where Cu2+ and BPA coexist, the R4 system achieved removal of NH4+-N (89%), NO3--N (100%), Cu2+ (85%), and BPA (88%). Sediment characterization confirmed that Cu2+ was immobilized through adsorption, complexation, and microbiologically induced carbonate precipitation (MICP). Metagenomic analysis further indicated that the Pseudomonadota phylum remained the dominant phylum, while functional pathways associated with inorganic carbon assimilation, HNAD nitrogen metabolism, endogenous carbon transformation, biomineralization, electron transfer, and aromatic compound degradation were preserved. By combining ammonia oxidation driven energy production, inorganic carbon utilization, redox mediated processes, and biomineralization, this study provides a highly promising low carbon strategy for treating industrial wastewater containing mixed pollutants.

Bisphenol A Compounds↗
PubMed2026

Multitarget interactions of bisphenol A in polycystic ovary syndrome: evidence from integrated network toxicology, mendelian randomization, and molecular docking.

OBJECTIVE: To study the potential pathogenic mechanisms of bisphenol A (BPA) in polycystic ovary syndrome (PCOS) using an integrative computational strategy. DESIGN: Integrative computational study combining network toxicology, Mendelian randomization (MR), and molecular docking. SUBJECTS: For MR analysis, genetic data were sourced from large European-ancestry cohorts, including plasma protein quantitative trait loci data and genome-wide association study summary statistics for PCOS (3,045 cases and 267,780 controls). EXPOSURE: In silico exposure to BPA for target prediction; genetically predicted plasma protein levels for causal inference. MAIN OUTCOME MEASURES: Identification of overlapping targets between BPA and PCOS; functional enrichment pathways; causal effects of prioritized proteins on PCOS risk (odds ratios with 95% confidence intervals); binding affinities between BPA and core targets (kcal/mol). RESULTS: Network toxicology identified 310 overlapping targets between BPA and PCOS. Enrichment analyses revealed significant involvement in endocrine signaling, inflammatory pathways (eg, IL-17), and cellular processes. MR demonstrated that genetically elevated levels of RET, CXCL8, HTR6, MMP1, MMP9, NTRK1, and TNNI2 were significantly associated with increased PCOS risk, whereas higher PSAP and SHBG levels were protective. Molecular docking confirmed stable binding between BPA and all nine key targets, with strongest affinity for SHBG (-8.4 kcal/mol), followed by NTRK1, TNNI2, and RET. CONCLUSION: This integrative investigation suggests that BPA may contribute to PCOS pathogenesis through multitarget interactions involving inflammatory mediators, endocrine regulators, and tissue remodeling proteins. The findings provide prioritized targets and mechanistic insights for future experimental validation and environmental risk assessment.

Female↗
PubMed2026

Screening of Estrogenic and Antiestrogenic Effects of Estradiol, Bisphenol A, and Fulvestrant Using 2D and 3D Breast Cancer Cell Systems With a Luciferase Reporter Gene Assay.

Endocrine-disrupting chemicals (EDCs) like bisphenol A (BPA) pose health risks by interfering with hormones. This study develops and utilizes in vitro 2D and 3D cell models to evaluate the estrogenic and antiestrogenic properties of compounds. Human breast cancer cell lines T47D and MCF7, stably transfected with a luciferase reporter gene (ERE-LUC), were first compared in 2D. Due to the significantly higher sensitivity and responsiveness observed in the T47D line during preliminary 2D screenings, this cell line was exclusively selected for the development of the 3D spheroid model. Cells were treated with 17β-estradiol (E2), BPA, and Fulvestrant (FUL) to assess cell viability and luciferase activity. In 2D models, T47D ERE-LUC cells showed higher responsiveness than MCF7 ERE-LUC, which failed to show significant luciferase induction with E2. In the 3D T47D model, cells exhibited significant and robust changes in luciferase activity in response to E2 and BPA, highlighting the enhanced fidelity of 3D cultures in replicating tissue conditions compared to their 2D counterparts. The study highlights the effectiveness of 3D models over 2D in evaluating estrogenic activity. Specifically, the 3D T47D ERE-LUC system serves as a superior, sensitive, and reliable platform for screening EDCs, offering benefits in cost, data speed, and reduced in vivo reliance.

Humans↗
PubMed1978

Studies on hemolytic activity of bisphenol A diglycidyl methacrylate (BIS-GMA).

To clarify the high hemolytic activity of BIS-GMA, the molar concentration producing 50% hemolysis (H50) and the partition coefficient inoctanol-water were determined using BIS-GMA and various types of methacrylates. It is suggested that the strong hemolytic potency of BIS-GMA is due to the high hydrophobic nature of the compound.

Acrylates↗
PubMed2024

Epigenetic footprints: Investigating placental DNA methylation in the context of prenatal exposure to phenols and phthalates.

BACKGROUND: Endocrine disrupting compounds (EDCs) such as phthalates and phenols can affect placental functioning and fetal health, potentially via epigenetic modifications. We investigated the associations between pregnancy exposure to synthetic phenols and phthalates estimated from repeated urine sampling and genome wide placental DNA methylation. METHODS: The study is based on 387 women with placental DNA methylation assessed with Infinium MethylationEPIC arrays and with 7 phenols, 13 phthalates, and two non-phthalate plasticizer metabolites measured in pools of urine samples collected twice during pregnancy. We conducted an exploratory analysis on individual CpGs (EWAS) and differentially methylated regions (DMRs) as well as a candidate analysis focusing on 20 previously identified CpGs. Sex-stratified analyses were also performed. RESULTS: In the exploratory analysis, when both sexes were studied together no association was observed in the EWAS. In the sex-stratified analysis, 114 individual CpGs (68 in males, 46 in females) were differentially methylated, encompassing 74 genes (36 for males and 38 for females). We additionally identified 28 DMRs in the entire cohort, 40 for females and 42 for males. Associations were mostly positive (for DMRs: 93% positive associations in the entire cohort, 60% in the sex-stratified analysis), with the exception of several associations for bisphenols and DINCH metabolites that were negative. Biomarkers associated with most DMRs were parabens, DEHP, and DiNP metabolite concentrations. Some DMRs encompassed imprinted genes including APC (associated with parabens and DiNP metabolites), GNAS (bisphenols), ZIM2;PEG3;MIMT1 (parabens, monoethyl phthalate), and SGCE;PEG10 (parabens, DINCH metabolites). Terms related to adiposity, lipid and glucose metabolism, and cardiovascular function were among the enriched phenotypes associated with differentially methylated CpGs. The candidate analysis identified one CpG mapping to imprinted LGALS8 gene, negatively associated with ethylparaben. CONCLUSIONS: By combining improved exposure assessment and extensive placental epigenome coverage, we identified several novel genes associated with the exposure, possibly in a sex-specific manner.

Humans↗
PubMed1977

Allergenicity of epoxy resins in the guinea pig.

The sensitizing capacity of epoxy resins of diglycidylether-Bisphenol A type was investigated using the "guinea pig maximization test". One isolated resin had a molecular weight (MW) of 340, which is the lowest among this type of epoxy resin. The other resins were mixtures with different MWs. Their distribution is not known, but only their average MW. The low molecular weight resin sensitized all of the animals and can be classified as an extreme allergen. The sensitizing capacity decreased in inverse proportion to the increase in the average MW of the resin mixtures. The cross-testing also indicated that the resin mixtures with higher average MW contained enough of the low MW resin (MW 340) to render this resin a sensitizer. Bisphenol A did not sensitize the animals at all but epichlorhydrin sensitized 60%. It is evident that in order to formulate hypoallergenic epoxy resins it will be necessary to achieve sensitization of animals with isolated resins of varying molecular weight.

Allergens↗
PubMed2026

Prenatal BPA exposure perturbs RNA-binding protein-mediated splicing regulation and synaptogenesis in the developing cerebellum in a sex-dependent manner.

BACKGROUND: Autism spectrum disorder (ASD) is a pervasive neurodevelopmental condition characterized by social communication deficits, exhibiting a male bias in prevalence. Emerging evidence suggests that prenatal exposure to bisphenol A (BPA) may perturb neurodevelopmental trajectories relevant to ASD. While the cerebellum is increasingly recognized as a brain region implicated in ASD pathophysiology, the impact of gestational BPA exposure on its post-transcriptional alternative splicing machinery remains fundamentally undefined. METHODS: Here, we investigated sex-dependent effects of prenatal BPA exposure on the alternative splicing landscape of the neonatal rat cerebellum. We utilized RNA-seq to profile differential alternative splicing (DAS) events. Ingenuity Pathway Analysis (IPA) was used to predict biological functions and canonical pathways, and to construct the interactome network of DAS genes. To explore candidate upstream regulatory mechanisms, we performed in silico molecular docking and used high-resolution melting (HRM) qRT-PCR to validate selected splicing events. Furthermore, we assessed in vitro cellular phenotypes in primary cerebellar neurons by measuring MTS-based viability and Syn1/Psd95 puncta colocalization. RESULTS: Prenatal BPA exposure was associated with widespread DAS in genes enriched for ASD-relevant pathways in the neonatal rat cerebellum. To our knowledge, this study is the first to report molecular docking analyses predicting favorable interactions between BPA and several candidate RNA-binding proteins (RBPs), including CPEB1, RALYL, HNRNPDL, and ACO1. Our findings support a model in which BPA may perturb RBP-associated splicing regulation, including altered splicing of chromatin regulators such as Ccar1 in males. These molecular and cellular findings were accompanied by sex-stratified differences in neuronal viability and synaptic puncta measurements. BPA exposure was associated with an increased MTS viability signal in male primary cerebellar neurons, together with significant reductions in Psd95 and Syn1 puncta density, whereas female neurons showed significantly increased synaptic puncta colocalization together with reduced viability. CONCLUSIONS: In this study, we propose that prenatal BPA may be relevant to ASD-related neurodevelopmental pathways through sex-dependent changes in RBP-associated alternative splicing, including altered splicing of Ccar1 in males, together with distinct cellular outcomes. Together, these findings identify the developing cerebellum as a sensitive target of prenatal BPA exposure and highlight alternative splicing as a candidate pathway relevant to ASD biology.

Animals↗
PubMed1979

Persistent photosensitivity following occupational exposure to epoxy resin.

Persistent photosensitivity developed in eight men following occupational exposure to hot epoxy resin fumes. The condition was limited to sites the resin contacted. Small doses of ultraviolet-A light (2 to 5 joules/sq cm) evoked abnormal reactions consisting of erythema, edema, and papules in the clinically involved skin. Positive photopatch tests to epoxy resin were observed in four subjects, and to 4, 4'-isopropylidenediphenol (Bisphenol A) in all. The photosensitivity is most probably due to photocontact allergy to 4,4'-isopropylidenediphenol or to a closely related chemical.

Adult↗
PubMed1978

Surface area of dental enamel, bone, and hydroxyapatite: chemisorption from solution.

The surface areas of three different samples of hydroxyapatite, samples of deproteinized bone, and samples of whole and deproteinized enamel were determined by adsorption of an adduct (the diglycidyl ether of bisphenol A with N-phe-nylglycine) from methylene chloride solution. In all cases, the surface areas of these samples agree well with those obtained by the BET (N2) method.

Adsorption↗
PubMed1976

Direct bonding of orthodontic brackets.

The direct adhesive bonding of orthodontic brackets to enamel was investigated. For a number of resin systems, all based on a bisphenol-GMA type of resin, commercially available or synthesized, the adhesive bonding to the enamel as well as to the bracket was studied. The maximum average bond strength to enamel was 121 Kg. per square centimeter; the maximum adhesion to the bracket material was 53 Kg. per square centimeter. Consequently, the attachment of the adhesive to the bracket material is the bottleneck of the direct-bonding procedure. Special attention has been given to preconditioning procedures to enhance the bonding between adhesive and bracket. The best results were obtained when the bracket base was roughened by means of a small amount of resin powder. Because all adhesives studied show large standard deviations of the bond strength, criteria of reliability are discussed. They show that future approaches should aim not only for higher average bonds strengths but also for a smaller standard deviation. The setting process, one of the factors influencing reliability, has been considered in some detail. Results of different mixing ratios as well as the influence of the amount of catalyst are presented.

Animals↗
PubMed1977

Hemolysis due to chemical contamination of clinical perfusion apparatus.

A chemical contaminant found on the interior surface of the extracorporeal apparatus manufactured by the William Harvey Corporation was believed to have caused severe hematuria in 2 children. The biological activity of the contaminant was tested by mixing 50 ml of whole blood in contaminated cardiotomies; after 5 minutes of exposure lysis of one-sixth of the red blood cells was found. This hemolytic agent was concluded to be bisphenol A dissolved in an organic solvent, but the mechanism of contamination was never found.

Benzhydryl Compounds↗
PubMed1978

Rat alpha-foetoprotein. Purification, physicochemical characterization, oestrogen-binding properties and chemical modification of the thiol group.

1. Rat alpha-foetoprotein, an oestrogen-binding foetal globulin, was isolated in large quantities from amniotic fluid and serum by preparative electrophoresis on polyacrylamide slab gels or by chromatography on an immunoadsorbent column. Subsequently the two electrophoretic forms of this protein were separated by electrophoresis on the same medium. 2. Both forms were found to show identical binding with oestradiol. From the extrinsic fluorescence of the bound dye 8-anilinonaphthalene-1-sulphonic acid it was shown that the polarity of the binding site is practically identical for both forms. One residue of tryptophan was determined for both forms. The two electrophoretic variants display the same amount of secondary structure as demonstrated by circular dichroism. 3. The affinity of total alpha-foetoprotein for oestradiol as a function of pH was studied by using a Sephadex G-25 gel-equilibration method. Maximal binding occurred at pH8.5. Only a fractional number of binding sites per molecule could be measured at pH7.4, whereas at higher pH the number of sites was very close to unity. There was no significant effect of pH on the value of the association constant (K(a)=4.3x10(7)+/-1.2x10(7)m(-1)). 4. Displacement experiments of bound labelled oestradiol with various steroids have permitted investigation of the specificity of alpha-foetoprotein. This foetal globulin binds rather strongly compounds that display the rigid structure of the oestratriene skeleton (oestradiol, oestrone). Diminished binding for diethylstilboestrol and a diethylstilboestrol affinity label was observed. No binding was measured with a more flexible structure such as hexoestrol [4,4'-(1,2-diethylethane-1,2-diyl)bisphenol]. 5. Chemical modification of cysteine residues of alpha-foetoprotein with two alkylating reagents [iodoacetic acid and 8-[N-(iodoacetylaminoethyl)amino]naphthalene-1-sulphonic acid] has very little effect on the oestrogen binding. It is suggested that the oestrogen-binding site does not contain a cysteine residue. From the kinetics of alkylation and from the fluorescence properties of the chemically bound thiol reagent 8-[N-(iodoacetylaminoethyl)amino]naphthalene-1-sulphonic acid], it was demonstrated that the very-slow-reacting thiol group is probably located in a non-polar region of the molecule.

Alkylation↗
PubMed1976

Sensitivity to epoxy resins and triethylenetetramine.

The present studies concerned 31 work sites in eight factories at which 422 persons were employed. In the course of seven years there were 126 cases of dermatitis, 99 of whom were patch-tested. Positive reactions to epoxy resin and/or to triethylenetetramine were found in 65.7% of the subjects. The aetiology of the other cases is discussed. Some of the patients who were positive to epoxy resin were tested with Bisphenol A and modified resins with blocked epoxy groups. The latency period of dermatitis and the localization were recorded, as well as the influence of the season and of certain working conditions on the occurrence of sensitization. Of the 80 patients who changed their occupation, there were relapses in 50 within one year. Relapses were more frequent in persons who continued to work with epoxy resins for more than three months after the appearance of dermatitis and in those simultaneously sensitive to allergens in the standard series.

Dermatitis, Contact↗
PubMed1979

Penetration of protective gloves by epoxy resin.

A gas jointer developed dermatitis from epoxy resin of Bisphenol A type. This substance penetrates plastic and rubber gloves. The man was compelled to change his job. There is a need for new types of gloves which are impermeable. The wearing of the existing types of glove by those not sensitised may be worthwhile because it probably lessens the dose of allergen absorbed and hence lessens the incidence of sensitisation.

Adult↗