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<title lang=en>Estrogenic potency of benzophenone UV filters in breast cancer cells: proliferative and transcriptional activity substantiated by docking analysis.</title>
<creator>Kerdivel, Gwenneg</creator>
<creator>Le Guevel, Remy</creator>
<creator>Habauzit, Denis</creator>
<creator>Brion, François</creator>
<creator>Ait-Aissa, Selim</creator>
<creator>Pakdel, Farzad</creator>
<contributor>TREC : Transcription, Environment and Cancer ; Institut de recherche, santé, environnement et travail [Rennes] (Irset) ; Université d'Angers (UA) - Université des Antilles et de la Guyane (UAG) - Université de Rennes 1 (UR1) - École des Hautes Études en Santé Publique [EHESP] (EHESP) - Institut National de la Santé et de la Recherche Médicale (INSERM) - Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique ) - Université d'Angers (UA) - Université des Antilles et de la Guyane (UAG) - Université de Rennes 1 (UR1) - École des Hautes Études en Santé Publique [EHESP] (EHESP) - Institut National de la Santé et de la Recherche Médicale (INSERM) - Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique )</contributor>
<contributor>Génétique fonctionnelle, agronomie et santé (GFAS) ; Institut National de la Recherche Agronomique (INRA) - Université de Rennes 1 (UR1) - Institut National de la Santé et de la Recherche Médicale (INSERM) - Centre National de la Recherche Scientifique (CNRS)</contributor>
<contributor>Institut National de l'Environnement Industriel et des Risques (INERIS)</contributor>
<contributor>Région Bretagne ; Ministère de l'écologie, du développement durable et de l'énergie ; INSERM ; Ligue contre le cancer ; IFR140 Biosit ; Université de Rennes 1 ; Université européenne de Bretagne</contributor>
<description>International audience</description>
<source>ISSN: 1932-6203</source>
<source>PLoS ONE</source>
<publisher>Public Library of Science</publisher>
<identifier>inserm-00838323</identifier>
<identifier>http://www.hal.inserm.fr/inserm-00838323</identifier>
<identifier>http://www.hal.inserm.fr/inserm-00838323/document</identifier>
<identifier>http://www.hal.inserm.fr/inserm-00838323/file/journal.pone.0060567.pdf</identifier>
<source>http://www.hal.inserm.fr/inserm-00838323</source>
<source>PLoS ONE, Public Library of Science, 2013, 8 (4), pp.e60567. 〈10.1371/journal.pone.0060567〉</source>
<identifier>DOI : 10.1371/journal.pone.0060567</identifier>
<relation>info:eu-repo/semantics/altIdentifier/doi/10.1371/journal.pone.0060567</relation>
<identifier>PUBMED : 23593250</identifier>
<relation>info:eu-repo/semantics/altIdentifier/pmid/23593250</relation>
<language>en</language>
<subject>[SDV.CAN] Life Sciences [q-bio]/Cancer</subject>
<type>info:eu-repo/semantics/article</type>
<type>Journal articles</type>
<description lang=en>The results from recent studies show that some benzophenones (BPs) and their hydroxylated metabolites can function as weak estrogens (E2) in the environment. However, little is known about the structure-activity relationship of these molecules. We have examined the effects of exposure to ten different BPs on the proliferation of estrogen receptor (ER)-positive breast cancer cells and on the transcriptional activity of E2-target genes. We analyzed two genes that are tightly linked with estrogen-mediated proliferation, the CXCL12 and amphiregulin genes and two classical estrogen-responsive genes, the pS2 and progesterone receptor. Significant differences in the BPs efficiency to induce cell proliferation and endogenous E2-target gene expressions were observed. Using ERE-, Sp1-, AP1- and C3-reporter genes that contain different ER-binding sites in their promoter, we also showed significant differences in the BPs efficiency in activation of the ER transactivation. Together, our analyzes showed that the most active molecule is 4-hydroxy-BP. Docking analysis of the interaction of BPs in the ligand-binding pocket of ERα suggests that the minimum structural requirement for the estrogenic activity of BPs is a hydroxyl (OH) group in the phenyl A-ring that allows interaction with Glu-353, Arg-394 or Phe-404, which enhances the stability between BPs and ERα. Our modeling also indicates a loss of interaction between the OH groups of the phenyl B-ring and His-524. In addition, the presence of some OH groups in the phenyl B-ring can create repulsion forces, which may constrain helix 12 in an unfavorable position, explaining the differential estrogenic effects of BPs. These results, together with our analysis of BPs for their potency in activation of cell proliferation and ER-mediated transcription, report an improved understanding of the mechanism and structure-activity relationship of BPs.</description>
<date>2013</date>
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