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Abnormal sex hormone levels in utero have been associated with child behavioral problems, but it is unclear if normal variation in prenatal sex hormones is associated with subsequent behavior in childhood. We assessed maternal sex hormones, including serum estrone (E1), estradiol (E2), estriol (E3), free testosterone (FT), and total testosterone (TT), during early pregnancy (gestational week 6-21 (mean = 11.1)) and evaluated child behavior at ages 4-5 using the Behavioral Assessment System for Children (BASC-2) and Social Responsiveness Scale (SRS-2) in 404 mother/child pairs (211 girls, 193 boys) within The Infant Development and Environment Study, a multi-site pregnancy cohort study. Associations between hormones and composite scores were evaluated using multiple linear regressions in both sexes combined, and separate models assessed effect modification by sex with the addition of interaction terms. A 10-fold increase in maternal FT or TT was associated in both sexes with a 4.3-point (95 % CI: 0.5, 8.2) or 4.4-point (0.8, 8.0) higher BASC-2 internalizing composite T score, respectively. In addition, a 10-fold increase in FT or TT was associated with a 3.8-point (0.04, 7.5) or 4.0-point (0.5, 7.5) higher behavioral symptoms index composite score. In models evaluating effect modification by sex, a 10-fold increase in E1 was associated with a 4.3-point (1.2, 7.4) decrease in adaptive skills composite score in girls only (interaction p = 0.04). We observed associations between testosterone and internalizing behaviors and behavioral symptoms index in both sexes, as well as a female-specific association between E1 and adaptive skills. Sex hormones during pregnancy may play a key role in influencing later-life behavior, and additional studies should further examine different periods of susceptibility to hormonal signals., Competing Interests: Declaration of Competing Interest The authors have no conflicts of interest to declare with respect to this manuscript., (Copyright © 2019 Elsevier Ltd. All rights reserved.)

Removal of six phenolic endocrine disrupting compounds (EDCs) (estrone, 17β-estradiol, 17α-ethinylestradiol, estriol, bisphenol A, and 4-nonylphenols) from waste activated sludge (WAS) was investigated using calcium peroxide (CaO2) oxidation. Effects of initial pH and CaO2 dosage were investigated. The impacts of CaO2 treatment on sludge solubilization and anaerobic digestion were also evaluated. Specifically, the role of reactive oxygen species (ROS) in EDC degradation during CaO2 oxidation was tested. Effects of 6 metal ions contained in the sludge matrix on EDC degradation were also evaluated. The results showed that CaO2 treatment can be a promising technology for EDC removal and facilitating sludge reuse. The EDC removal efficiencies increased with the increase in CaO2 dosage. At CaO2 doses of more than 0.34 g per gram of total solid (g g(-1) TS), more than 50% of EDCs were removed in a wide pH range of 2-12. Higher removal efficiencies were achieved at initial pH values of 12 and 2. The products of EDCs during CaO2 oxidation had less estrogenic activity than the originals. Under the conditions of neutral pH and CaO2 dosage = 0.34 g g(-1) TS, the sludge solubilization can be improved by increasing the soluble total organic carbon (STOC) and volatile suspended solids (VSS) reduction by 25% and 27% in 7 d, respectively; the volatile fatty acid (VFA) production was enhanced by 96% in the 15 d following anaerobic digestion. The ROS released by CaO2 are the main factors contributing to EDC removal, among which, hydroxyl radicals (OH) play the most important role. Metal ions contained in the sludge matrix also affected EDC removal. For most cases, Fe, Cu, and Zn had positive effects; Mn and Ag had negative effects; and Mg had an insignificant effect on EDC removal., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

Estrogenic hormones (estrone (E1), 17β-estradiol (E2), estriol (E3), 17α-ethinylestradiol (EE2)) are the major contributor to the total estrogenicity in waterways. Presence of these compounds in biosolids is also causing concern in terms of their use as soil amendment. In comparison with wastewater treatment, removal of estrogenic compounds in sewage sludge has received less attention. This paper presents a literature review regarding the source and occurrence of these pollutants in our environment. The removal pathways of estrogenic compounds in engineered systems, such as full-scale wastewater treatment plants (WWTPs), are also discussed. Review of the fate studies revealed that activated sludge system with nutrient removal shows very high (>90%) removal of estrogenic hormones in most of the cases. Although, aerobic digestion showed better attenuation of estrogenic compounds, anaerobic digestion increased the overall estrogenicity of biosolids. Finally, this paper highlights the challenges involved in analytical determination of these compounds in sewage sludge matrix., (Copyright © 2012 Elsevier Ltd. All rights reserved.)

Assignment of ecological impacts of contamination to specific classes of contaminants is a prerequisite for risk assessment and remediation. In this study, the combination of polarity-based fractionation, two-hybrid yeast bioassay, and chemical analysis were used to evaluate and identify estrogen receptor agonists (ER-agonists) in sediments from Wenyu River, Beijing, China. By bioassay, organic raw sediment extracts could induce significant estrogenicity and the bioassay-derived 17β-estradiol equivalents (EEQs) of raw extracts (EEQ(raw)s) ranged from 0.8 to 19.8 ng/g dry weight. By polarity-based fractionation, the raw extracts were separated into three fractions, i.e. non-polar, moderately polar, and polar fractions, which were subjected to bioassay and chemical analysis. The highest estrogenicity was observed in the polar fraction, which accounted for more than 78% of the total. The medium polar fraction contains PAHs and OCPs, and the estrogenic activities in this fraction contributed 3%-12% of the total in raw extract. An estrogenic activity of non-polarity fraction was negligible in compare to other two fractions. By chemical analysis and toxic equivalent calculation, major part of the estrogenicity in polar fraction could be attributed to six natural/synthetic estrogens (16%-63%), i.e. 17β-estradiol, estrone, estriol, 17α-ethynylestradiol, diethylstilbestrol, and β-estradiol-17-valerate, and to nonylphenols (26%-55%). The proposed approach has been successfully used for characterization of ER-agonists in this case study., (Copyright © 2011 Elsevier Ltd. All rights reserved.)

The primary objective of our research was to establish the technical feasibility of using the horseradish peroxidase (HRP) enzyme for natural and synthetic estrogens-estrone (E1), 17beta-estradiol (E2), estriol (E3), and 17alpha-ethinylestradiol (EE2)-removal. The effects of temperature and pH on enzymatic treatment kinetics were investigated. Residual estrogen concentrations were quantified by liquid chromatography, coupled with mass spectrometry analysis. In a synthetic solution at pH 7 and 25+/-1 degrees C, the HRP enzyme-catalyzed process was capable of achieving 92-100% removal of E1, E2, E3, and EE2 within 1h of treatment with an HRP activity of 0.017 U/ml. The influence of the pH (5-9) and temperature (5-35 degrees C) on estrogen removal was observed to be significant, with the optimum pH near neutral conditions. The results also showed that wastewater constituents significantly impact the HRP-catalyzed estrogen removal. The experimental research proved that the HRP-catalyzed system is technically feasible for the removal of the main estrogens present in the environment at low concentrations.

In pooled amniotic fluid obtained between the 15th and 17th weeks of gestation the concentration of free steroids and steroid glucuronides was found to be 40 micrograms/dl. The concentration of steroid monosulfates and disulfates was 19 micrograms/dl. About half of the characterized steroids are progesterone metabolites. The "fetal type" 3 beta-hydroxy-5-ene steroids were found exclusively in the sulfoconjugated form. Their concentration represents 20% of the total steroid content. The identification of two 15 beta-hydroxylated C21 steroids, 3 beta,15 beta,17 alpha-tridoxy-5-pregnen-20-one and 5-pregnene-3 beta,15 beta,17 alpha,20 alpha-tetrol isolated from mid-pregnancy amniotic fluid is reported here. Metabolites of cortisol and 17-deoxycorticosteroid metabolites had similar quantitative importance, 8.6 and 9.4%, respectively.

Although cystic lesions of the breast are not precancerous per se, statistical studies have indicated that this condition predisposes a 2- to 4-fold greater risk for breast cancer. Seeking a hormonal etiology to this correlation, investigators have analyzed breast cyst fluid ( BCF ) for steroids and have compared the levels to those in the blood. The 17-ketosteroids-androsterone, dehydroisoandrosterone and their sulfates are elevated in BCF . The same is true for estrone sulfate and estradiol-3-sulfate. We have found the most dramatic differences with estriol-3-sulfate (E3-3S), the concentration of which ranged from 187-6134 pg/ml in over 40 specimens analyzed, whereas in 12 serum specimens from normal women, E3-3S was barely detectable. The origin of E3-3S is not known. [3H]E3-3S is not concentrated in BCF following its injection into an arm vein. The blood half-life of [3H]E3-3S is much lower than that of estrone sulfate. Samples of breast nipple aspirates from normal women were also analyzed for E3-3S. None could be detected. The best explanation of the data accumulated thus far is that E3-3S is synthesized at the epithelial lining of the cyst and released into the BCF , from which its efflux is inefficient.

The preparation and antigenic properties of estrone-3-glucuronide- and estriol-3-glucuronide-bovine serum albumin conjugates in which the hapten is linked to the carrier protein through an (O-carboxymethyl)oxime bridge at the C-6 position on the steroid nucleus, have been described. Antibodies raised against the two immunogens in the rabbit possessed high specificity to estrone-3-glucuronide and estriol-3-glucuronide, respectively, exhibiting little cross-reactivities with other estrogen conjugates and no cross-reactions with related steroids except for free estrogens, their 3-methyl ethers and 3-sulfates. The cross-reactive antibodies were eliminated by partial immunoadsorption on affinity chromatographic media using the estrone-3-methyl ether 17-(O-carboxymethyl)oxime- and estriol-3-methyl ether 16 (or 17)-hemisuccinate-aminohexyl Sepharose conjugates, respectively. The purified antisera exhibited no cross-reactivities with free estrogens and ring A conjugates of estrone and estriol.

Conjugated and unconjugated oestrone, oestradiol and oestriol were measured in simultaneous milk and plasma samples obtained from 21 women in the early post-partum period. Conjugated oestrogens comprised more than 90% of the total oestrogen content of both milk and plasma. Oestrone glucosiduronate was the major oestrogen metabolite in milk (33%), the levels being significantly higher (P less than 0.01) than in plasma. Oestriol glucosiduronates were the predominant oestrogen metabolites (63%) in plasma.

The preparation and antigenic properties of estriol 3-sulfate 16-glucuronide-bovine serum albumin (BSA) conjugate in which the hapten is linked to the carrier through an (O-carboxymethyl)oxime bridge at the C-6 position on the steroid nucleus, have been described. Coupling of 6-oxoestriol 3-sulfate 16-glucuronide acetate-methyl ester 6-(O-carboxymethyl)oxime with BSA by the activated ester method followed by removal of the protecting groups with alkali provided the desired conjugate. The antisera raised against the conjugate in rabbits were highly specific to the double conjugate, estriol 3-sulfate 16-glucuronide, discriminating from ring A or D monoconjugated and unconjugated estrogens. The specificity of antisera elicited has been discussed on the basis of stereochemistry of the hapten-[C-6]-BSA conjugate.

During the last few years non-isotopic techniques have been developed to measure steroid hormones. One of these methods is the luminescence immunoassay. Three classes of substances have been found to yield reasonable results, i.e. aminophthalhydrazides, aminonaphthohydrazides and acridiniumesters. Examples of application are shown.