Abstract
Molecules with potent estrogenic activity are ~270 Å3 hydrophobic structures that encompass two hydroxyls among which is at least one phenol. However, compounds with only one phenol or devoid of such a ring have been shown to enhance ERα-mediated transcription at concentrations much larger than those measured with E2. In this context, we show here that benzopyrans sharing one hydroxyl/methoxyl and containing an additional benzylidenyl or a spirocyclohexyl motif are able to induce ERE-dependent transcription in breast carcinoma cells.
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Acknowledgments
This study was supported in part by grants from La Ligue Nationale contre le Cancer (comité de Montbéliard) and the Fonds J.C. Heuson de Cancérologie Mammaire. We are very grateful to Denis Lesage (UMR 7201, the Université Pierre et Marie Curie, Paris6) for mass spectrometry experiments. We are also grateful to Kamal Boubekeur of the Laboratoire de Chimie Inorganique et Matériaux Moléculaires, CNRS UMR 7071 (Université Pierre et Marie Curie, Paris6) for X-ray experiments; and to Olivier Lequin for 2D NMR experiments. Further, we are grateful to Dominique Gallo, Ioanna Laios, and Anny Cleeren for their precious participation in the biological assays.
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Jacquot, Y., Byrne, C., Xicluna, A. et al. Synthesis, structure, and estrogenic activity of 2- and 3-substituted 2,3-dihydro-4H-1-benzopyran-4-ones. Med Chem Res 22, 681–691 (2013). https://doi.org/10.1007/s00044-012-0058-2
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DOI: https://doi.org/10.1007/s00044-012-0058-2