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Abstract
Based on the benzo[b]naphtho[1,2-d]furan and benzo[b]naphtho[1,2-d]thiophene frameworks, a series of ligands with different basic side chains (BSCs) has been synthesized and pharmacologically evaluated. Also, their binding modes have been modelled using docking techniques. It was found that the introduction of a BSC in these systems brings about a decrease of affinity for both estrogen receptors α and β in an in vitro competitive binding assay. However, two full antagonists of the estrogen receptor β (9c and 9f) have been discovered, with potency in the low micromolar concentration in a cell-based luciferase reporter assay, and completely devoid of activity against the α receptor at the same concentration range. Differences in the ERα/ERβ binding modes have also been rationalized with the help of molecular modelling techniques. This interesting functional profile could be used to elucidate the physiological role of each ER subtype.
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Authors (9)
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Jose Juan Rodríguez
- Universidad CEU San Pablo Departamento de Química, Facultad de Farmacia
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Kamila Filipiak
- The John Paul II Catholic University of Lublin, Department of Molecular Biology, Faculty of Mathematics and Natural Sciences
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Maciej Maslyk
- The John Paul II Catholic University of Lublin, Department of Molecular Biology, Faculty of Mathematics and Natural Sciences
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Jakub Ciepielski
- The John Paul II Catholic University of Lublin, Department of Environmental Biochemistry and Chemistry, Faculty of Mathematics and Natural Sciences
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Sonia de Pascual-Teresa
- Spanish National Research Council (CSIC) Institute of Food Science, Food Technology and Nutrition (ICTAN)
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Sonsoles Martín-Santamaría
- Universidad CEU San Pablo Departamento de Química, Facultad de Farmacia
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Beatriz de Pascual-Teresa ..
- Universidad CEU San Pablo Departamento de Química, Facultad de Farmacia
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Ana Ramos
- Universidad CEU San Pablo Departamento de Química, Facultad de Farmacia
Cite as
Full text
- Publication version
- Accepted or Published Version
- DOI:
- Digital Object Identifier (open in new tab) 10.1039/c2ob26062j
- License
- Copyright (2012 The Royal Society of Chemistry)
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Details
- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
ORGANIC & BIOMOLECULAR CHEMISTRY
no. 10,
edition 36,
pages 7334 - 7346,
ISSN: 1477-0520 - Language:
- English
- Publication year:
- 2012
- Bibliographic description:
- Rodríguez J., Filipiak K., Maslyk M., Ciepielski J., Demkowicz S., De Pascual-Teresa S., Martín-Santamaría S., .. ., Ramos A.: Towards β-selectivity in functional estrogen receptor antagonists// ORGANIC & BIOMOLECULAR CHEMISTRY. -Vol. 10, iss. 36 (2012), s.7334-7346
- DOI:
- Digital Object Identifier (open in new tab) 10.1039/c2ob26062j
- Verified by:
- Gdańsk University of Technology
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