Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18

Autores
Verlinden, Lieve; Verstuyf, Annemieke; Eelen, Guy; Bouillon, Roger; Ordóñez-Morán, Paloma; Larriba, María Jesús; Muñoz, Alberto; Rochel, Natacha; Sato, Yoshiteru; Moras, Dino; Maestro, Miguel; Seoane, Samuel; Dominguez, Fernando; Eduardo, Silvina Laura; Nicoletti, Daniel; Moman, Edelmiro; Mouriño, Antonio
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
An improved synthetic route to 1α,25-dihydroxyvitamin D3 des-side chain analogues 2a and 2b with substituents at C18 is reported, along with their biological activity. These analogues display significant antiproliferative effects toward MCF-7 breast cancer cells and prodifferentiation activity toward SW480-ADH colon cancer cells; they are also characterized by a greatly decreased calcemic profile. The crystal structure of the human vitaminD receptor (hVDR) complexed to one of these analogues, 20(17→18)-abeo-1α,25-dihydroxy-22-homo-21-norvitamin D3 (2a) reveals that the side chain introduced at position C18 adopts the same orientation in the ligand binding pocket as the side chain of 1α,25-dihydroxyvitamin D3. Vitamin D3 supplements: The synthesis and biological activity of des-side chain analogues of 1α,25-dihydroxyvitamin D3 with substituents at C18 are described. Crystallographic analysis revealed that the new side chain introduced at C18 adopts the same orientation as the natural side chain at C17 in the parent molecule 1α,25-dihydroxyvitamin D3. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fil: Verlinden, Lieve. Katholikie Universiteit Leuven; Bélgica
Fil: Verstuyf, Annemieke. Katholikie Universiteit Leuven; Bélgica
Fil: Eelen, Guy. Katholikie Universiteit Leuven; Bélgica
Fil: Bouillon, Roger. Katholikie Universiteit Leuven; Bélgica
Fil: Ordóñez-Morán, Paloma. Universidad Autónoma de Madrid; España
Fil: Larriba, María Jesús. Universidad Autónoma de Madrid; España
Fil: Muñoz, Alberto. Universidad Autónoma de Madrid; España
Fil: Rochel, Natacha. Université de Strasbourg; Francia
Fil: Sato, Yoshiteru. Université de Strasbourg; Francia
Fil: Moras, Dino. Université de Strasbourg; Francia
Fil: Maestro, Miguel. Universidad da Coruña; España
Fil: Seoane, Samuel. Universidad de Santiago de Compostela, Facultad de Medicina;
Fil: Dominguez, Fernando. Universidad de Santiago de Compostela, Facultad de Medicina;
Fil: Eduardo, Silvina Laura. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Santiago de Compostela; España
Fil: Nicoletti, Daniel. Universidad de Santiago de Compostela; España
Fil: Moman, Edelmiro. Universidad de Santiago de Compostela; España
Fil: Mouriño, Antonio. Universidad de Santiago de Compostela; España
Materia
Biological Activity
Cancer
Steroids
Vitamind Analogues
Vitamins
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/69536
Acceder
id CONICETDig_4c03a76c85dd13dc7000e650255627a7
oai_identifier_str oai:ri.conicet.gov.ar:11336/69536
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18Verlinden, LieveVerstuyf, AnnemiekeEelen, GuyBouillon, RogerOrdóñez-Morán, PalomaLarriba, María JesúsMuñoz, AlbertoRochel, NatachaSato, YoshiteruMoras, DinoMaestro, MiguelSeoane, SamuelDominguez, FernandoEduardo, Silvina LauraNicoletti, DanielMoman, EdelmiroMouriño, AntonioBiological ActivityCancerSteroidsVitamind AnaloguesVitaminshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1An improved synthetic route to 1α,25-dihydroxyvitamin D3 des-side chain analogues 2a and 2b with substituents at C18 is reported, along with their biological activity. These analogues display significant antiproliferative effects toward MCF-7 breast cancer cells and prodifferentiation activity toward SW480-ADH colon cancer cells; they are also characterized by a greatly decreased calcemic profile. The crystal structure of the human vitaminD receptor (hVDR) complexed to one of these analogues, 20(17→18)-abeo-1α,25-dihydroxy-22-homo-21-norvitamin D3 (2a) reveals that the side chain introduced at position C18 adopts the same orientation in the ligand binding pocket as the side chain of 1α,25-dihydroxyvitamin D3. Vitamin D3 supplements: The synthesis and biological activity of des-side chain analogues of 1α,25-dihydroxyvitamin D3 with substituents at C18 are described. Crystallographic analysis revealed that the new side chain introduced at C18 adopts the same orientation as the natural side chain at C17 in the parent molecule 1α,25-dihydroxyvitamin D3. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.Fil: Verlinden, Lieve. Katholikie Universiteit Leuven; BélgicaFil: Verstuyf, Annemieke. Katholikie Universiteit Leuven; BélgicaFil: Eelen, Guy. Katholikie Universiteit Leuven; BélgicaFil: Bouillon, Roger. Katholikie Universiteit Leuven; BélgicaFil: Ordóñez-Morán, Paloma. Universidad Autónoma de Madrid; EspañaFil: Larriba, María Jesús. Universidad Autónoma de Madrid; EspañaFil: Muñoz, Alberto. Universidad Autónoma de Madrid; EspañaFil: Rochel, Natacha. Université de Strasbourg; FranciaFil: Sato, Yoshiteru. Université de Strasbourg; FranciaFil: Moras, Dino. Université de Strasbourg; FranciaFil: Maestro, Miguel. Universidad da Coruña; EspañaFil: Seoane, Samuel. Universidad de Santiago de Compostela, Facultad de Medicina;Fil: Dominguez, Fernando. Universidad de Santiago de Compostela, Facultad de Medicina;Fil: Eduardo, Silvina Laura. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Santiago de Compostela; EspañaFil: Nicoletti, Daniel. Universidad de Santiago de Compostela; EspañaFil: Moman, Edelmiro. Universidad de Santiago de Compostela; EspañaFil: Mouriño, Antonio. Universidad de Santiago de Compostela; EspañaWiley VCH Verlag2011-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/69536Verlinden, Lieve; Verstuyf, Annemieke; Eelen, Guy; Bouillon, Roger; Ordóñez-Morán, Paloma; et al.; Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18; Wiley VCH Verlag; Chemmedchem; 6; 5; 5-2011; 788-7931860-7179CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/cmdc.201100021info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/cmdc.201100021info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:18:09Zoai:ri.conicet.gov.ar:11336/69536instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 15:18:09.932CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18
title Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18
spellingShingle Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18
Verlinden, Lieve
Biological Activity
Cancer
Steroids
Vitamind Analogues
Vitamins
title_short Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18
title_full Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18
title_fullStr Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18
title_full_unstemmed Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18
title_sort Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18
dc.creator.none.fl_str_mv Verlinden, Lieve
Verstuyf, Annemieke
Eelen, Guy
Bouillon, Roger
Ordóñez-Morán, Paloma
Larriba, María Jesús
Muñoz, Alberto
Rochel, Natacha
Sato, Yoshiteru
Moras, Dino
Maestro, Miguel
Seoane, Samuel
Dominguez, Fernando
Eduardo, Silvina Laura
Nicoletti, Daniel
Moman, Edelmiro
Mouriño, Antonio
author Verlinden, Lieve
author_facet Verlinden, Lieve
Verstuyf, Annemieke
Eelen, Guy
Bouillon, Roger
Ordóñez-Morán, Paloma
Larriba, María Jesús
Muñoz, Alberto
Rochel, Natacha
Sato, Yoshiteru
Moras, Dino
Maestro, Miguel
Seoane, Samuel
Dominguez, Fernando
Eduardo, Silvina Laura
Nicoletti, Daniel
Moman, Edelmiro
Mouriño, Antonio
author_role author
author2 Verstuyf, Annemieke
Eelen, Guy
Bouillon, Roger
Ordóñez-Morán, Paloma
Larriba, María Jesús
Muñoz, Alberto
Rochel, Natacha
Sato, Yoshiteru
Moras, Dino
Maestro, Miguel
Seoane, Samuel
Dominguez, Fernando
Eduardo, Silvina Laura
Nicoletti, Daniel
Moman, Edelmiro
Mouriño, Antonio
author2_role author
author
author
author
author
author
author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Biological Activity
Cancer
Steroids
Vitamind Analogues
Vitamins
topic Biological Activity
Cancer
Steroids
Vitamind Analogues
Vitamins
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv An improved synthetic route to 1α,25-dihydroxyvitamin D3 des-side chain analogues 2a and 2b with substituents at C18 is reported, along with their biological activity. These analogues display significant antiproliferative effects toward MCF-7 breast cancer cells and prodifferentiation activity toward SW480-ADH colon cancer cells; they are also characterized by a greatly decreased calcemic profile. The crystal structure of the human vitaminD receptor (hVDR) complexed to one of these analogues, 20(17→18)-abeo-1α,25-dihydroxy-22-homo-21-norvitamin D3 (2a) reveals that the side chain introduced at position C18 adopts the same orientation in the ligand binding pocket as the side chain of 1α,25-dihydroxyvitamin D3. Vitamin D3 supplements: The synthesis and biological activity of des-side chain analogues of 1α,25-dihydroxyvitamin D3 with substituents at C18 are described. Crystallographic analysis revealed that the new side chain introduced at C18 adopts the same orientation as the natural side chain at C17 in the parent molecule 1α,25-dihydroxyvitamin D3. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fil: Verlinden, Lieve. Katholikie Universiteit Leuven; Bélgica
Fil: Verstuyf, Annemieke. Katholikie Universiteit Leuven; Bélgica
Fil: Eelen, Guy. Katholikie Universiteit Leuven; Bélgica
Fil: Bouillon, Roger. Katholikie Universiteit Leuven; Bélgica
Fil: Ordóñez-Morán, Paloma. Universidad Autónoma de Madrid; España
Fil: Larriba, María Jesús. Universidad Autónoma de Madrid; España
Fil: Muñoz, Alberto. Universidad Autónoma de Madrid; España
Fil: Rochel, Natacha. Université de Strasbourg; Francia
Fil: Sato, Yoshiteru. Université de Strasbourg; Francia
Fil: Moras, Dino. Université de Strasbourg; Francia
Fil: Maestro, Miguel. Universidad da Coruña; España
Fil: Seoane, Samuel. Universidad de Santiago de Compostela, Facultad de Medicina;
Fil: Dominguez, Fernando. Universidad de Santiago de Compostela, Facultad de Medicina;
Fil: Eduardo, Silvina Laura. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Santiago de Compostela; España
Fil: Nicoletti, Daniel. Universidad de Santiago de Compostela; España
Fil: Moman, Edelmiro. Universidad de Santiago de Compostela; España
Fil: Mouriño, Antonio. Universidad de Santiago de Compostela; España
description An improved synthetic route to 1α,25-dihydroxyvitamin D3 des-side chain analogues 2a and 2b with substituents at C18 is reported, along with their biological activity. These analogues display significant antiproliferative effects toward MCF-7 breast cancer cells and prodifferentiation activity toward SW480-ADH colon cancer cells; they are also characterized by a greatly decreased calcemic profile. The crystal structure of the human vitaminD receptor (hVDR) complexed to one of these analogues, 20(17→18)-abeo-1α,25-dihydroxy-22-homo-21-norvitamin D3 (2a) reveals that the side chain introduced at position C18 adopts the same orientation in the ligand binding pocket as the side chain of 1α,25-dihydroxyvitamin D3. Vitamin D3 supplements: The synthesis and biological activity of des-side chain analogues of 1α,25-dihydroxyvitamin D3 with substituents at C18 are described. Crystallographic analysis revealed that the new side chain introduced at C18 adopts the same orientation as the natural side chain at C17 in the parent molecule 1α,25-dihydroxyvitamin D3. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
publishDate 2011
dc.date.none.fl_str_mv 2011-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/69536
Verlinden, Lieve; Verstuyf, Annemieke; Eelen, Guy; Bouillon, Roger; Ordóñez-Morán, Paloma; et al.; Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18; Wiley VCH Verlag; Chemmedchem; 6; 5; 5-2011; 788-793
1860-7179
CONICET Digital
CONICET
url http://hdl.handle.net/11336/69536
identifier_str_mv Verlinden, Lieve; Verstuyf, Annemieke; Eelen, Guy; Bouillon, Roger; Ordóñez-Morán, Paloma; et al.; Synthesis, structure, and biological activity of des-side Chain analogues of 1α,25-Dihydroxyvitamin D3 with substituents at C18; Wiley VCH Verlag; Chemmedchem; 6; 5; 5-2011; 788-793
1860-7179
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/cmdc.201100021
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/cmdc.201100021
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.22299

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