{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,15]],"date-time":"2026-01-15T00:49:11Z","timestamp":1768438151141,"version":"3.49.0"},"reference-count":16,"publisher":"Springer Science and Business Media LLC","issue":"S4","content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["BMC Bioinformatics"],"published-print":{"date-parts":[[2005,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n          <jats:sec>\n            <jats:title>Background<\/jats:title>\n            <jats:p>The organic polychlorinated compounds like dichlorodiphenyltrichloroethane with its metabolites and polychlorinated biphenyls are a class of highly persistent environmental contaminants. They have been recognized to have detrimental health effects both on wildlife and humans acting as endocrine disrupters due to their ability of mimicking the action of the steroid hormones, and thus interfering with hormone response. There are several experimental evidences that they bind and activate human steroid receptors. However, despite the growing concern about the toxicological activity of endocrine disrupters, molecular data of the interaction of these compounds with biological targets are still lacking.<\/jats:p>\n          <\/jats:sec>\n          <jats:sec>\n            <jats:title>Results<\/jats:title>\n            <jats:p>We have used a flexible docking approach to characterize the molecular interaction of seven endocrine disrupting chemicals with estrogen, progesterone and androgen receptors in the ligand-binding domain. All ligands docked in the buried hydrophobic cavity corresponding to the hormone steroid pocket. The interaction was characterized by multiple hydrophobic contacts involving a different number of residues facing the binding pocket, depending on ligands orientation. The EDC ligands did not display a unique binding mode, probably due to their lipophilicity and flexibility, which conferred them a great adaptability into the hydrophobic and large binding pocket of steroid receptors.<\/jats:p>\n          <\/jats:sec>\n          <jats:sec>\n            <jats:title>Conclusion<\/jats:title>\n            <jats:p>Our results are in agreement with toxicological data on binding and allow to describe a pattern of interactions for a group of ECD to steroid receptors suggesting the requirement of a hydrophobic cavity to accommodate these chlorine carrying compounds. Although the affinity is lower than for hormones, their action can be brought about by a possible synergistic effect.<\/jats:p>\n          <\/jats:sec>","DOI":"10.1186\/1471-2105-6-s4-s10","type":"journal-article","created":{"date-parts":[[2005,12,3]],"date-time":"2005-12-03T19:13:49Z","timestamp":1133637229000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Modelling the interaction of steroid receptors with endocrine disrupting chemicals"],"prefix":"10.1186","volume":"6","author":[{"given":"Pasqualina","family":"D'Ursi","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Erika","family":"Salvi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Paola","family":"Fossa","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Luciano","family":"Milanesi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ermanna","family":"Rovida","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2005,12,1]]},"reference":[{"key":"725_CR1","doi-asserted-by":"publisher","first-page":"137","DOI":"10.1016\/j.taap.2004.05.007","volume":"201","author":"R Villa","year":"2004","unstructured":"Villa R, Bonetti E, Penza ML, Iacobello C, Bugari G, Bailo M, Parolini O, Apostoli P, Caimi L, Ciana P, Maggi A, Di Lorenzo D: Target-specific action of organochlorine compounds in reproductive and nonreproductive tissues of estrogen-reporter male mice. Toxicol Appl Pharmacol 2004, 201: 137\u2013148. 10.1016\/j.taap.2004.05.007","journal-title":"Toxicol Appl Pharmacol"},{"key":"725_CR2","doi-asserted-by":"publisher","first-page":"71","DOI":"10.1080\/10408440091159176","volume":"30","author":"JG Vos","year":"2000","unstructured":"Vos JG, Dybing E, Greim HA, Ladefoged O, Lambre C, Tarazona JV, Brandt I, Vethaak AD: Health effects of endocrine-disrupting chemicals on wildlife, with special reference to the European situation. Crit Rev Toxicol 2000, 30: 71\u2013133. 10.1080\/10408440091159176","journal-title":"Crit Rev Toxicol"},{"key":"725_CR3","doi-asserted-by":"publisher","first-page":"4252","DOI":"10.1210\/en.139.10.4252","volume":"139","author":"GG Kuiper","year":"1998","unstructured":"Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA: Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology 1998, 139: 4252\u20134263. 10.1210\/en.139.10.4252","journal-title":"Endocrinology"},{"key":"725_CR4","doi-asserted-by":"publisher","first-page":"664","DOI":"10.1007\/s00216-003-2251-0","volume":"378","author":"ML Scippo","year":"2004","unstructured":"Scippo ML, Argiris C, Van De Weerdt C, Muller M, Willemsen P, Martial J, Maghuin-Rogister G: Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors. Anal Bioanal Chem 2004, 378: 664\u2013669. 10.1007\/s00216-003-2251-0","journal-title":"Anal Bioanal Chem"},{"key":"725_CR5","doi-asserted-by":"publisher","first-page":"581","DOI":"10.1038\/375581a0","volume":"375","author":"WR Kelce","year":"1995","unstructured":"Kelce WR, Stone CR, Laws SC, Gray LE, Kemppainen JA, Wilson EM: Persistent DDT metabolite p,p'-DDE is a potent androgen receptor antagonist. Nature 1995, 375: 581\u2013585. 10.1038\/375581a0","journal-title":"Nature"},{"key":"725_CR6","doi-asserted-by":"publisher","first-page":"165","DOI":"10.1006\/prep.2001.1409","volume":"22","author":"S Eiler","year":"2001","unstructured":"Eiler S, Gangloff M, Duclaud S, Moras D, Ruff M: Overexpression, purification, and crystal structure of native ER alpha LBD. Protein Expr Purif 2001, 22: 165\u2013173. 10.1006\/prep.2001.1409","journal-title":"Protein Expr Purif"},{"key":"725_CR7","doi-asserted-by":"publisher","first-page":"392","DOI":"10.1038\/30775","volume":"393","author":"SP Williams","year":"1998","unstructured":"Williams SP, Sigler PB: Atomic structure of progesterone complexed with its receptor. Nature 1998, 393: 392\u2013396. 10.1038\/30775","journal-title":"Nature"},{"key":"725_CR8","doi-asserted-by":"publisher","first-page":"4904","DOI":"10.1073\/pnas.081565498","volume":"98","author":"JS Sack","year":"2001","unstructured":"Sack JS, Kish KF, Wang C, Attar RM, Kiefer SE, An Y, Wu GY, Scheffler JE, Salvati ME, Krystek SR Jr, Weinmann R, Einspahr HM: Crystallographic structures of the ligand-binding domains of the androgen receptor and its T877A mutant complexed with the natural agonist dihydrotestosterone. Proc Natl Acad Sci U S A 2001, 98: 4904\u20134909. 10.1073\/pnas.081565498","journal-title":"Proc Natl Acad Sci U S A"},{"key":"725_CR9","doi-asserted-by":"publisher","first-page":"53","DOI":"10.1038\/39645","volume":"389","author":"AM Brzozowski","year":"1997","unstructured":"Brzozowski AM, Pike AC, Dauter Z, Hubbard RE, Bonn T, Engstrom O, Ohman L, Greene GL, Gustafsson JA, Carlquist M: Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 1997, 389: 53\u201358. 10.1038\/39645","journal-title":"Nature"},{"key":"725_CR10","doi-asserted-by":"publisher","first-page":"1639","DOI":"10.1002\/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B","volume":"19","author":"GM Morris","year":"1998","unstructured":"Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ: Automated Docking Using a Lamarckian Genetic Algorithm and Empirical Binding Free Energy Function. J Computational Chemistry 1998, 19: 1639\u20131662. Publisher Full Text 10.1002\/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B","journal-title":"J Computational Chemistry"},{"key":"725_CR11","first-page":"401","volume-title":"Pac Symp Biocomput","author":"MF Sanner","year":"1999","unstructured":"Sanner MF, Duncan BS, Carillo CJ, Olson AJ: Integrating computation and visualization for biomolecular analysis: an example using Python and AVS. Pac Symp Biocomput 1999, 401\u2013412."},{"key":"725_CR12","doi-asserted-by":"publisher","first-page":"333","DOI":"10.1023\/A:1007907728892","volume":"11","author":"C McMartin","year":"1997","unstructured":"McMartin C, Bohacek R: QXP: powerful, rapid computer algorithms for structure-based drug design. J Comput Aided-Mol Des 1997, 11: 333\u2013344. 10.1023\/A:1007907728892","journal-title":"J Comput Aided-Mol Des"},{"key":"725_CR13","doi-asserted-by":"publisher","first-page":"127","DOI":"10.1093\/protein\/8.2.127","volume":"8","author":"AC Wallace","year":"1995","unstructured":"Wallace AC, Laskowski RA, Thornton JM: LIGPLOT:a program to generate schematic diagrams of protein-ligand interactions. Protein Eng 1995, 8: 127\u2013134. 10.1093\/protein\/8.2.127","journal-title":"Protein Eng"},{"key":"725_CR14","doi-asserted-by":"publisher","first-page":"1338","DOI":"10.1021\/tx030011g","volume":"16","author":"H Fang","year":"2003","unstructured":"Fang H, Tong W, Branham WS, Moland CL, Dial SL, Hong H, Xie Q, Perkins R, Owens W, Sheehan D: Study of 202 Natural, Synthetic, and Environmental Chemicals for Binding to the Androgen Receptor. Chem Res Toxicol 2003, 16: 1338\u20131358. 10.1021\/tx030011g","journal-title":"Chem Res Toxicol"},{"key":"725_CR15","doi-asserted-by":"publisher","first-page":"138","DOI":"10.1093\/toxsci\/54.1.138","volume":"54","author":"RM Blair","year":"2000","unstructured":"Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, Tong W, Shi L, Perkins R, Sheehan DM: The Estrogen Receptor Relative Binding Affinities of 188 Natural and Xenochemicals: Structural Diversity of Ligands. Toxicol Science 2000, 54: 138\u2013153. 10.1093\/toxsci\/54.1.138","journal-title":"Toxicol Science"},{"key":"725_CR16","doi-asserted-by":"publisher","first-page":"440","DOI":"10.1002\/jcc.540110405","volume":"11","author":"F Mohamadi","year":"1990","unstructured":"Mohamadi F, Richards NGJ, Guida WC, Liskamp R, Lipton M, Caufield C, Chang G, Hendrickson T, Still WC: MacroModel \u2013 an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J Comput Chem 1990, 11: 440\u2013467. 10.1002\/jcc.540110405","journal-title":"J Comput Chem"}],"container-title":["BMC Bioinformatics"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1186\/1471-2105-6-S4-S10.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,9,1]],"date-time":"2021-09-01T08:18:43Z","timestamp":1630484323000},"score":1,"resource":{"primary":{"URL":"https:\/\/bmcbioinformatics.biomedcentral.com\/articles\/10.1186\/1471-2105-6-S4-S10"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2005,12]]},"references-count":16,"journal-issue":{"issue":"S4","published-print":{"date-parts":[[2005,12]]}},"alternative-id":["725"],"URL":"https:\/\/doi.org\/10.1186\/1471-2105-6-s4-s10","relation":{},"ISSN":["1471-2105"],"issn-type":[{"value":"1471-2105","type":"electronic"}],"subject":[],"published":{"date-parts":[[2005,12]]},"assertion":[{"value":"1 December 2005","order":1,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}}],"article-number":"S10"}}