ERRγ tethers strongly bisphenol A and 4-α-cumylphenol in an induced-fit manner

Matsushima, Ayami; Teramoto, Takamasa; Okada, Hiroyuki; Liu, Xiaohui; Tokunaga, Takatoshi; Kakuta, Yoshimitsu; Shimohigashi, Yasuyuki

doi:10.1016/j.bbrc.2008.06.050

Cited by 72 publications

(45 citation statements)

References 22 publications

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“…The structure of ERRc in complex with BPA ( Fig. 4b) has been solved, revealing an overall protein conformation indistinguishable from that of the unliganded receptor [72][73][74]. A close look at the LBP shows that, as previously anticipated, one of the two phenol-hydroxyl groups of BPA forms hydrogen bonds with residues E275 (H3) and R316 (H5) while the second is hydrogen bonded to N346 in H7.…”

Section: Structure Of Bpa-bound Errcmentioning

confidence: 74%

A structural view of nuclear hormone receptor: endocrine disruptor interactions

Maire

Bourguet

Balaguer

2010

Cell. Mol. Life Sci.

111

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Endocrine-disrupting chemicals (EDCs) represent a broad class of exogenous substances that cause adverse effects in the endocrine system by interfering with hormone biosynthesis, metabolism, or action. The molecular mechanisms of EDCs involve different pathways including interactions with nuclear hormone receptors (NHRs) which are primary targets of a large variety of environmental contaminants. Here, based on the crystal structures currently available in the Protein Data Bank, we review recent studies showing the many ways in which EDCs interact with NHRs and impact their signaling pathways. Like the estrogenic chemical diethylstilbestrol, some EDCs mimic the natural hormones through conserved protein-ligand contacts, while others, such as organotins, employ radically different binding mechanisms. Such structure-based knowledge, in addition to providing a better understanding of EDC activities, can be used to predict the endocrine-disrupting potential of environmental pollutants and may have applications in drug discovery.

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Section: Structure Of Bpa-bound Errcmentioning

confidence: 74%

A structural view of nuclear hormone receptor: endocrine disruptor interactions

Maire

Bourguet

Balaguer

2010

Cell. Mol. Life Sci.

111

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“…Furthermore, receptor binding assays show that BPA has higher affinity for ESR2 than ESR1 (Matthews et al 2001). Also, receptor binding assays and X-ray crystal structure analyses have demonstrated that BPA binds strongly to human estrogen-related receptor g (ESRRG/ ERRg; Takayanagi et al 2006, Matsushima et al 2008. Animal studies have shown that prenatal and neonatal exposure to low environmentally relevant doses of BPA (25 and 250 mg/kg) cause numerous abnormalities in the ovary and uterus (Maffini et al 2006).…”

Section: Chemicals That Alter Hormone Receptor Binding and Actionmentioning

confidence: 99%

Endocrine-disrupting chemicals in ovarian function: effects on steroidogenesis, metabolism and nuclear receptor signaling

Craig¹,

Wang²,

Flaws³

2011

Reproduction

225

123

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Endocrine-disrupting chemicals (EDCs) are exogenous agents with the ability to interfere with processes regulated by endogenous hormones. One such process is female reproductive function. The major reproductive organ in the female is the ovary. Disruptions in ovarian processes by EDCs can lead to adverse outcomes such as anovulation, infertility, estrogen deficiency, and premature ovarian failure among others. This review summarizes the effects of EDCs on ovarian function by describing how they interfere with hormone signaling via two mechanisms: altering the availability of ovarian hormones, and altering binding and activity of the hormone at the receptor level. Among the chemicals covered are pesticides (e.g. dichlorodiphenyltrichloroethane and methoxychlor), plasticizers (e.g. bisphenol A and phthalates), dioxins, polychlorinated biphenyls, and polycyclic aromatic hydrocarbons (e.g. benzo[a]pyrene).

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“…For the method development and validation experiments, 4.0 g dried samples were transferred into Teflon lined extraction vessels and spiked with 100 ng of phenolic EDCs. 100 ng of BPA-d 16 were added in order to correct the possible losses in the procedure. The samples were carefully mixed with a spatula and then left for 48 h to allow sorption processes to occur, as in nature.…”

Section: Microwave-assisted Extractionmentioning

confidence: 99%

“…The estrogenicity of BPA is about 500 times stronger than 4-t-OP [14]. 4-CP lacks one of two phenol-hydroxyl groups of BPA, but it has been noted that 4-CP has an intense estrogenic activity [15,16].…”

Section: Introductionmentioning

confidence: 99%

Analysis of Six Phenolic Endocrine Disrupting Chemicals in Surface Water and Sediment

et al. 2011

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An efficient and reliable method based on gas chromatography-mass spectrometry (GC-MS) was developed for the extraction and analysis of six phenolic endocrine disrupting chemicals (EDCs), such as 4-nonylphenol (4-NP), nonylphenol-mono-ethoxylate (NP1EO), nonylphenol-diethoxylate (NP2EO), 4-tert-octylphenol (4-t-OP), bisphenol A (BPA) and 4-cumylphenol (4-CP) in surface water and sediment. The method was developed by using microwaveassisted extraction (MAE), solid phase extraction (SPE) and derivatization procedure. The MAE procedures were performed by optimizing three key process factors, consisted of extraction solvent, extraction temperature and holding time, affecting the extraction efficiency from sediment samples. For SPE, various parameters that may affect the recovery efficiency of water samples, such as SPE phase cartridge, elution solvent, as well as pH of water samples, were investigated. A series of derivatization conditions, such as derivatization reagent, reaction temperature and reaction time, were improved. The method achieved good repeatability and reproducibility with relative standard deviations\13% for all target EDCs in the both samples. Satisfactory recoveries for spiked water and sediment samples ranged from 85 to 101% and 74 to 105%, respectively. The limits of quantification varied from 0.20 (4-t-OP) to 11.50 ng L -1 (NP2EO) and from 0.31 (4-t-OP) to 9.50 ng g -1 dry weight (dw) (NP2EO) for water samples and sediment samples, respectively. The established method was successfully applied to the analysis of target EDCs in surface water and sediment samples collected from Caohai site of Dianchi Lake, China. The results showed that NP1EO, NP2EO and BPA were the three dominant phenolic EDCs in the site, reaching 114, 97 and 149 ng L -1 in surface water, while 444, 186 and 178 ng g -1 dw in surface sediment, respectively.

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ERRγ tethers strongly bisphenol A and 4-α-cumylphenol in an induced-fit manner

Cited by 72 publications

References 22 publications

A structural view of nuclear hormone receptor: endocrine disruptor interactions

A structural view of nuclear hormone receptor: endocrine disruptor interactions

Endocrine-disrupting chemicals in ovarian function: effects on steroidogenesis, metabolism and nuclear receptor signaling

Analysis of Six Phenolic Endocrine Disrupting Chemicals in Surface Water and Sediment

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