Rapid Screening of Human Transthyretin Disruptors through a Tiered in Silico Approach

In silico models have been considered as a promising tool that can be used to screen and identify potential endocrine disrupting chemicals (EDCs) effectively and assist finally realizing the sustai...

[1]  Liang-Hong Guo,et al.  Binding and activity of polybrominated diphenyl ether sulfates to thyroid hormone transport proteins and nuclear receptors. , 2019, Environmental science. Processes & impacts.

[2]  I. Meerts,et al.  Potent competitive interactions of some brominated flame retardants and related compounds with human transthyretin in vitro. , 2000, Toxicological sciences : an official journal of the Society of Toxicology.

[3]  Paola Gramatica,et al.  QSAR modeling and prediction of the endocrine-disrupting potencies of brominated flame retardants. , 2010, Chemical research in toxicology.

[4]  P. Gramatica,et al.  QSAR prediction of the competitive interaction of emerging halogenated pollutants with human transthyretin£ , 2013, SAR and QSAR in environmental research.

[5]  I. Sylte,et al.  In Vitro and in Silico Competitive Binding of Brominated Polyphenyl Ether Contaminants with Human and Gull Thyroid Hormone Transport Proteins. , 2018, Environmental science & technology.

[6]  Henner Hollert,et al.  Endocrine disruptor screening: regulatory perspectives and needs , 2011 .

[7]  E. Simon,et al.  Evaluation of a panel of in vitro methods for assessing thyroid receptor β and transthyretin transporter disrupting activities. , 2020, Reproductive Toxicology.

[8]  M. Saraiva,et al.  Iodination of salicylic acid improves its binding to transthyretin. , 2008, Biochimica et biophysica acta.

[9]  Fei Li,et al.  Integration of Computational Toxicology, Toxicogenomics Data Mining, and Omics Techniques to Unveil Toxicity Pathways , 2021, ACS Sustainable Chemistry & Engineering.

[10]  Melanie Gross,et al.  Current Limitations and Recommendations to Improve Testing for the Environmental Assessment of Endocrine Active Substances , 2017 .

[11]  Laura N. Vandenberg,et al.  Endocrine-disrupting chemicals: economic, regulatory, and policy implications. , 2020, The lancet. Diabetes & endocrinology.

[12]  Károly Héberger,et al.  Why is Tanimoto index an appropriate choice for fingerprint-based similarity calculations? , 2015, Journal of Cheminformatics.

[13]  Jingwen Chen,et al.  Anionic phenolic compounds bind stronger with transthyretin than their neutral forms: nonnegligible mechanisms in virtual screening of endocrine disrupting chemicals. , 2013, Chemical research in toxicology.

[14]  R. Slama,et al.  Endocrine-disrupting chemicals: implications for human health. , 2020, The lancet. Diabetes & endocrinology.

[15]  Kevin M. Crofton,et al.  Thyroid-Disrupting Chemicals: Interpreting Upstream Biomarkers of Adverse Outcomes , 2009, Environmental health perspectives.

[16]  K. P. Kepp,et al.  Molecular Mechanism of Alternative P450-Catalyzed Metabolism of Environmental Phenolic Endocrine-Disrupting Chemicals. , 2018, Environmental science & technology.

[17]  L. Hoffmann,et al.  New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors. , 2012, Toxicological sciences : an official journal of the Society of Toxicology.

[18]  Liang-Hong Guo,et al.  Assessment of the binding of hydroxylated polybrominated diphenyl ethers to thyroid hormone transport proteins using a site-specific fluorescence probe. , 2012, Environmental science & technology.

[19]  Timo Hamers,et al.  Quantitative structure‐activity relationship modeling on in vitro endocrine effects and metabolic stability involving 26 selected brominated flame retardants , 2007, Environmental toxicology and chemistry.

[20]  W. Tong,et al.  Computational prediction models for assessing endocrine disrupting potential of chemicals , 2018, Journal of environmental science and health. Part C, Environmental carcinogenesis & ecotoxicology reviews.

[21]  J. Braun,et al.  Early-life exposure to EDCs: role in childhood obesity and neurodevelopment , 2017, Nature Reviews Endocrinology.

[22]  H. Hong,et al.  Development of classification models for predicting inhibition of mitochondrial fusion and fission using machine learning methods. , 2020, Chemosphere.

[23]  Jerzy Leszczynski,et al.  Endocrine-disrupting activity of per- and polyfluoroalkyl substances: Exploring combined approaches of ligand and structure based modeling. , 2017, Chemosphere.

[24]  A C Gore,et al.  EDC-2: The Endocrine Society's Second Scientific Statement on Endocrine-Disrupting Chemicals. , 2015, Endocrine reviews.

[25]  Ruili Huang,et al.  Development and Validation of a Computational Model for Androgen Receptor Activity , 2016, Chemical research in toxicology.

[26]  P. Heikkinen,et al.  Toxicological Profile of Ultrapure 2,2′,3,4,4′,5,5′-Heptachlorbiphenyl (PCB 180) in Adult Rats , 2014, PloS one.

[27]  Laura N. Vandenberg,et al.  Consensus on the key characteristics of endocrine-disrupting chemicals as a basis for hazard identification , 2019, Nature Reviews Endocrinology.

[28]  Jürgen Bajorath,et al.  From Qualitative to Quantitative Analysis of Activity and Property Landscapes. , 2020, Journal of chemical information and modeling.

[29]  D. Muir,et al.  Toward a Global Understanding of Chemical Pollution: A First Comprehensive Analysis of National and Regional Chemical Inventories. , 2020, Environmental science & technology.

[30]  K. Main,et al.  Thyroid effects of endocrine disrupting chemicals , 2012, Molecular and Cellular Endocrinology.

[31]  Xiangru Zhang,et al.  Application of (LC/)MS/MS precursor ion scan for evaluating the occurrence, formation and control of polar halogenated DBPs in disinfected waters: A review. , 2019, Water research.

[32]  J. Sacchettini,et al.  Hydroxylated polychlorinated biphenyls selectively bind transthyretin in blood and inhibit amyloidogenesis: rationalizing rodent PCB toxicity. , 2004, Chemistry & biology.

[33]  H. Hong,et al.  Applicability Domains Enhance Application of PPARγ Agonist Classifiers Trained by Drug-like Compounds to Environmental Chemicals. , 2020, Chemical research in toxicology.

[34]  Timo Hamers,et al.  In vitro profiling of the endocrine-disrupting potency of brominated flame retardants. , 2006, Toxicological sciences : an official journal of the Society of Toxicology.

[35]  Patience Browne,et al.  Application of Adverse Outcome Pathways to U.S. EPA’s Endocrine Disruptor Screening Program , 2017, Environmental health perspectives.

[36]  Timo Hamers,et al.  Effect-directed analysis to explore the polar bear exposome: identification of thyroid hormone disrupting compounds in plasma. , 2013, Environmental science & technology.

[37]  Feifei Yang,et al.  Binding interactions of halo-benzoic acids, halo-benzenesulfonic acids and halo-phenylboronic acids with human transthyretin. , 2020, Chemosphere.

[38]  T. Hamers,et al.  In vitro toxicity profiling of ultrapure non-dioxin-like polychlorinated biphenyl congeners and their relative toxic contribution to PCB mixtures in humans. , 2011, Toxicological sciences : an official journal of the Society of Toxicology.

[39]  Na Li,et al.  Hormone Activity of Hydroxylated Polybrominated Diphenyl Ethers on Human Thyroid Receptor-β: In Vitro and In Silico Investigations , 2009, Environmental health perspectives.

[40]  Paola Gramatica,et al.  QSAR classification models for the prediction of endocrine disrupting activity of brominated flame retardants. , 2011, Journal of hazardous materials.

[41]  T. Visser,et al.  Biotransformation of brominated flame retardants into potentially endocrine-disrupting metabolites, with special attention to 2,2',4,4'-tetrabromodiphenyl ether (BDE-47). , 2008, Molecular nutrition & food research.

[42]  Laura N. Vandenberg,et al.  Designing Endocrine Disruption Out of the Next Generation of Chemicals. , 2013, Green chemistry : an international journal and green chemistry resource : GC.

[43]  R. Judson,et al.  Evaluation of androgen assay results using a curated Hershberger database. , 2018, Reproductive toxicology.

[44]  Shaoyong Lu,et al.  Pentabromoethylbenzene Exposure Induces Transcriptome Aberration and Thyroid Dysfunction: in Vitro, in Silico and in Vivo Investigations. , 2020, Environmental science & technology.

[45]  T. Hamers,et al.  In Silico Approach To Identify Potential Thyroid Hormone Disruptors among Currently Known Dust Contaminants and Their Metabolites. , 2015, Environmental science & technology.

[46]  J. McLachlan,et al.  Potential mechanisms of thyroid disruption in humans: interaction of organochlorine compounds with thyroid receptor, transthyretin, and thyroid-binding globulin. , 1999, Environmental health perspectives.

[47]  Liang-Hong Guo,et al.  Binding interactions of perfluoroalkyl substances with thyroid hormone transport proteins and potential toxicological implications. , 2016, Toxicology.

[48]  David Dix,et al.  Computational Toxicology as Implemented by the U.S. EPA: Providing High Throughput Decision Support Tools for Screening and Assessing Chemical Exposure, Hazard and Risk , 2010, Journal of toxicology and environmental health. Part B, Critical reviews.

[49]  Paola Gramatica,et al.  Real External Predictivity of QSAR Models. Part 2. New Intercomparable Thresholds for Different Validation Criteria and the Need for Scatter Plot Inspection , 2012, J. Chem. Inf. Model..

[50]  Jacob de Boer,et al.  Miniaturization of a transthyretin binding assay using a fluorescent probe for high throughput screening of thyroid hormone disruption in environmental samples. , 2017, Chemosphere.

[51]  W. Notten,et al.  Interactions of halogenated industrial chemicals with transthyretin and effects on thyroid hormone levels in vivo , 2005, Archives of Toxicology.

[52]  Weida Tong,et al.  Estrogenic activity data extraction and in silico prediction show the endocrine disruption potential of bisphenol A replacement compounds. , 2015, Chemical research in toxicology.

[53]  J. Wheeler,et al.  A review of the evidence for endocrine disrupting effects of current-use chemicals on wildlife populations , 2018, Critical reviews in toxicology.

[54]  F. Lyakurwa,et al.  Different binding mechanisms of neutral and anionic poly-/perfluorinated chemicals to human transthyretin revealed by In silico models. , 2017, Chemosphere.

[55]  CHUN WEI YAP,et al.  PaDEL‐descriptor: An open source software to calculate molecular descriptors and fingerprints , 2011, J. Comput. Chem..

[56]  K. Roy,et al.  How important is to detect systematic error in predictions and understand statistical applicability domain of QSAR models , 2017 .

[57]  Liang-Hong Guo,et al.  Structure-based investigation on the binding interaction of hydroxylated polybrominated diphenyl ethers with thyroxine transport proteins. , 2010, Toxicology.

[58]  Rebecca Kusko,et al.  Molecular Modeling Method Applications: Probing the Mechanism of Endocrine Disruptor Action , 2019, Challenges and Advances in Computational Chemistry and Physics.

[59]  Daniel P. Russo,et al.  Construction of a Virtual Opioid Bioprofile: A Data-Driven QSAR Modeling Study to Identify New Analgesic Opioids. , 2021, ACS sustainable chemistry & engineering.

[60]  R. Grabic,et al.  Bisphenols emerging in Norwegian and Czech aquatic environments show transthyretin binding potency and other less-studied endocrine-disrupting activities. , 2020, The Science of the total environment.

[61]  Ralph Kühne,et al.  Quantitative read-across for predicting the acute fish toxicity of organic compounds. , 2011, Environmental science & technology.

[62]  G Chen,et al.  Development of classification models for predicting chronic toxicity of chemicals to Daphnia magna and Pseudokirchneriella subcapitata , 2018, SAR and QSAR in environmental research.

[63]  Fabian A. Grimm,et al.  Sulfated Metabolites of Polychlorinated Biphenyls Are High-Affinity Ligands for the Thyroid Hormone Transport Protein Transthyretin , 2013, Environmental health perspectives.

[64]  G. Jiang,et al.  Chlorinated Polyfluoroalkylether Sulfonates Exhibit Similar Binding Potency and Activity to Thyroid Hormone Transport Proteins and Nuclear Receptors as Perfluorooctanesulfonate. , 2018, Environmental science & technology.

[65]  M Vracko,et al.  Integration of in silico methods and computational systems biology to explore endocrine-disrupting chemical binding with nuclear hormone receptors. , 2017, Chemosphere.

[66]  E. B. Wedebye,et al.  Organophosphate ester flame retardants have antiandrogenic potential and affect other endocrine related endpoints in vitro and in silico. , 2020, Chemosphere.

[67]  Ana M Soto,et al.  Minireview: Endocrine Disruptors: Past Lessons and Future Directions. , 2016, Molecular endocrinology.

[68]  Yikai Zhou,et al.  Structure-directed screening and analysis of thyroid-disrupting chemicals targeting transthyretin based on molecular recognition and chromatographic separation. , 2020, Environmental science & technology.

[69]  P. Gramatica,et al.  QSAR classification models for the screening of the endocrine-disrupting activity of perfluorinated compounds , 2012, SAR and QSAR in environmental research.

[70]  Timo Hamers,et al.  Competitive binding of poly- and perfluorinated compounds to the thyroid hormone transport protein transthyretin. , 2009, Toxicological sciences : an official journal of the Society of Toxicology.

[71]  Timo Hamers,et al.  Blood plasma sample preparation method for the assessment of thyroid hormone-disrupting potency in effect-directed analysis. , 2011, Environmental science & technology.

[72]  Hongxia Yu,et al.  Activation of steroid hormone receptors: Shed light on the in silico evaluation of endocrine disrupting chemicals. , 2018, The Science of the total environment.

[73]  Ruili Huang,et al.  CERAPP: Collaborative Estrogen Receptor Activity Prediction Project , 2016, Environmental health perspectives.

[74]  Fei Li,et al.  The critical factors affecting typical organophosphate flame retardants to mimetic biomembrane: An integrated in vitro and in silico study. , 2019, Chemosphere.

[75]  Ruili Huang,et al.  CoMPARA: Collaborative Modeling Project for Androgen Receptor Activity , 2020, Environmental health perspectives.

[76]  Mineyuki Mizuguchi,et al.  Biosensor discovery of thyroxine transport disrupting chemicals. , 2008, Toxicology and applied pharmacology.

[77]  Hongbin Yang,et al.  In Silico Prediction of Endocrine Disrupting Chemicals Using Single-Label and Multilabel Models , 2019, J. Chem. Inf. Model..

[78]  H. Hong,et al.  Structures of endocrine-disrupting chemicals determine binding to and activation of the oestrogen receptor α (ERα) and androgen receptor (AR). , 2020, Environmental science & technology.

[79]  Timo Hamers,et al.  Tracing thyroid hormone-disrupting compounds: database compilation and structure-activity evaluation for an effect-directed analysis of sediment , 2015, Analytical and Bioanalytical Chemistry.

[80]  Mineyuki Mizuguchi,et al.  Biosensor recognition of thyroid-disrupting chemicals using transport proteins. , 2006, Analytical chemistry.

[81]  Jingwen Chen,et al.  Emerging Polar Phenolic Disinfection Byproducts Are High-Affinity Human Transthyretin Disruptors: An in Vitro and in Silico Study. , 2019, Environmental science & technology.

[82]  C. Grundström,et al.  Structure-Based Virtual Screening Protocol for in Silico Identification of Potential Thyroid Disrupting Chemicals Targeting Transthyretin. , 2016, Environmental science & technology.

[83]  F. Lyakurwa,et al.  In silico model for predicting soil organic carbon normalized sorption coefficient (K(OC)) of organic chemicals. , 2015, Chemosphere.

[84]  Jianjie Fu,et al.  Evaluation of the Estrogenic/Antiestrogenic Activities of Perfluoroalkyl Substances and Their Interactions with the Human Estrogen Receptor by Combining In Vitro Assays and In Silico Modeling. , 2020, Environmental science & technology.

[85]  I. Meerts,et al.  Identification of 4-Hydroxyheptachlorostyrene in Polar Bear Plasma and Its Binding Affinity to Transthyretin: A Metabolite of Octachlorostyrene? , 2000 .

[86]  S. Safe,et al.  Structure-dependent, competitive interaction of hydroxy-polychlorobiphenyls, -dibenzo-p-dioxins and -dibenzofurans with human transthyretin. , 1993, Chemico-biological interactions.

[87]  K. J. Berg.  Interaction of chlorinated phenols with thyroxine binding sites of human transthyretin, albumin and thyroid binding globulin. , 1990 .

[88]  Xianhai Yang,et al.  Development of liposome/water partition coefficients predictive models for neutral and ionogenic organic chemicals. , 2019, Ecotoxicology and environmental safety.

[89]  A. Kortenkamp,et al.  Transthyretin-Binding Activity of Complex Mixtures Representing the Composition of Thyroid-Hormone Disrupting Contaminants in House Dust and Human Serum , 2020, Environmental health perspectives.

[90]  Shulin Zhuang,et al.  Thyroid Disruption by Bisphenol S Analogues via Thyroid Hormone Receptor β: in Vitro, in Vivo, and Molecular Dynamics Simulation Study. , 2018, Environmental science & technology.

[91]  Hongxia Yu,et al.  Structure–activity relationship study on the binding of PBDEs with thyroxine transport proteins , 2011, Environmental toxicology and chemistry.

[92]  Qinghua Zhang,et al.  Binding and Activity of Tetrabromobisphenol A Mono-Ether Structural Analogs to Thyroid Hormone Transport Proteins and Receptors , 2020, Environmental health perspectives.