Multivalent Tryptophan- and Tyrosine-Containing [60] Fullerene Hexa-Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors

Unprecedented 3D hexa-adducts of [60]fullerene peripherally decorated with twelve tryptophan (Trp) or tyrosine (Tyr) residues have been synthesized. Studies on the antiviral activity of these novel compounds against HIV and EV71 reveal that they are much more potent against HIV and equally active ag...

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Autores: Ruiz-Santaquiteria, Marta, Illescas, Beatriz M., Abdelnabi, Rana, Boonen, Arnaud, Mills, Alberto, Martí-Marí, Olaia, Noppen, Sam, Neyts, Johan, Schols, Dominique, Gago, Federico, San-Félix, Ana, Camarasa Rius, María José, Martín, Nazario
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2021
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/244578
Acceso en línea:http://hdl.handle.net/10261/244578
Access Level:acceso abierto
Palabra clave:Antiviral agents
EV71
Fullerenes
Hexa-adduct
HIV
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spelling Multivalent Tryptophan- and Tyrosine-Containing [60] Fullerene Hexa-Adducts as Dual HIV and Enterovirus A71 Entry InhibitorsRuiz-Santaquiteria, MartaIllescas, Beatriz M.Abdelnabi, RanaBoonen, ArnaudMills, AlbertoMartí-Marí, OlaiaNoppen, SamNeyts, JohanSchols, DominiqueGago, FedericoSan-Félix, AnaCamarasa Rius, María JoséMartín, NazarioAntiviral agentsEV71FullerenesHexa-adductHIVUnprecedented 3D hexa-adducts of [60]fullerene peripherally decorated with twelve tryptophan (Trp) or tyrosine (Tyr) residues have been synthesized. Studies on the antiviral activity of these novel compounds against HIV and EV71 reveal that they are much more potent against HIV and equally active against EV71 than the previously described dendrimer prototypes AL-385 and AL-463, which possess the same number of Trp/Tyr residues on the periphery but attached to a smaller and more flexible pentaerythritol core. These results demonstrate the relevance of the globular 3D presentation of the peripheral groups (Trp/Tyr) as well as the length of the spacer connecting them to the central core to interact with the viral envelopes, particularly in the case of HIV, and support the hypothesis that [60]fullerene can be an alternative and attractive biocompatible carbon-based scaffold for this type of highly symmetrical dendrimers. In addition, the functionalized fullerenes here described, which display twelve peripheral negatively charged indole moieties on their globular surface, define a new and versatile class of compounds with a promising potential in biomedical applications.This work has been supported by the Spanish MINECO/FEDER (Projects CTQ2017-84327-P and CTQ2017-83531-R), the Spanish MICINN (Projects PID2019-104070RB-C21 and PID2019- 104070RB-C22), the Spanish Agencia Estatal Consejo Superior de Investigaciones Científicas (CSIC, Projects CSIC-PIE- 201980E100 and CSIC-PIE-201980E028), “The Centers of Excellence” of the KU Leuven (EF-05/15 and PF-10/18), EU FP7 (FP7/ 2007–2013) Project EUVIRNA (Grant 408 Agreement 264286), EU FP7 SILVER (Contract HEALTH-F3-2010-260644), a grant from the Belgian Interuniversity Attraction Poles (IAP) Phase VII-P7/45 (BELVIR) and the EU FP7 Industry-Academia Partnerships and Pathways Project AIROPICO. The Spanish MEC/MINECO is also acknowledged for a grant to O. M.-M. We also thank Charlotte Vanderheydt, Caroline Collard, Kim Donckers, Sandra Claes and Evelyne Van Kerckhove for help with the processing of the antiviral data.Peer reviewedWiley-VCHMinisterio de Ciencia, Innovación y Universidades (España)European CommissionConsejo Superior de Investigaciones Científicas (España)San-Félix, Ana [0000-0003-4271-7598]Camarasa, María-José [0000-0002-4978-6468]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202120212021info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/244578reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-84327-Pinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-83531-Rinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-104070RB-C21info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019- 104070RB-C22eu-repo/grantAgreement/EC/FP7/264286HEALTH-F3-2010-260644https://doi.org/10.1002/chem.202101098Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2445782026-05-22T06:33:51Z
dc.title.none.fl_str_mv Multivalent Tryptophan- and Tyrosine-Containing [60] Fullerene Hexa-Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors
title Multivalent Tryptophan- and Tyrosine-Containing [60] Fullerene Hexa-Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors
spellingShingle Multivalent Tryptophan- and Tyrosine-Containing [60] Fullerene Hexa-Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors
Ruiz-Santaquiteria, Marta
Antiviral agents
EV71
Fullerenes
Hexa-adduct
HIV
title_short Multivalent Tryptophan- and Tyrosine-Containing [60] Fullerene Hexa-Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors
title_full Multivalent Tryptophan- and Tyrosine-Containing [60] Fullerene Hexa-Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors
title_fullStr Multivalent Tryptophan- and Tyrosine-Containing [60] Fullerene Hexa-Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors
title_full_unstemmed Multivalent Tryptophan- and Tyrosine-Containing [60] Fullerene Hexa-Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors
title_sort Multivalent Tryptophan- and Tyrosine-Containing [60] Fullerene Hexa-Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors
dc.creator.none.fl_str_mv Ruiz-Santaquiteria, Marta
Illescas, Beatriz M.
Abdelnabi, Rana
Boonen, Arnaud
Mills, Alberto
Martí-Marí, Olaia
Noppen, Sam
Neyts, Johan
Schols, Dominique
Gago, Federico
San-Félix, Ana
Camarasa Rius, María José
Martín, Nazario
author Ruiz-Santaquiteria, Marta
author_facet Ruiz-Santaquiteria, Marta
Illescas, Beatriz M.
Abdelnabi, Rana
Boonen, Arnaud
Mills, Alberto
Martí-Marí, Olaia
Noppen, Sam
Neyts, Johan
Schols, Dominique
Gago, Federico
San-Félix, Ana
Camarasa Rius, María José
Martín, Nazario
author_role author
author2 Illescas, Beatriz M.
Abdelnabi, Rana
Boonen, Arnaud
Mills, Alberto
Martí-Marí, Olaia
Noppen, Sam
Neyts, Johan
Schols, Dominique
Gago, Federico
San-Félix, Ana
Camarasa Rius, María José
Martín, Nazario
author2_role author
author
author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia, Innovación y Universidades (España)
European Commission
Consejo Superior de Investigaciones Científicas (España)
San-Félix, Ana [0000-0003-4271-7598]
Camarasa, María-José [0000-0002-4978-6468]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Antiviral agents
EV71
Fullerenes
Hexa-adduct
HIV
topic Antiviral agents
EV71
Fullerenes
Hexa-adduct
HIV
description Unprecedented 3D hexa-adducts of [60]fullerene peripherally decorated with twelve tryptophan (Trp) or tyrosine (Tyr) residues have been synthesized. Studies on the antiviral activity of these novel compounds against HIV and EV71 reveal that they are much more potent against HIV and equally active against EV71 than the previously described dendrimer prototypes AL-385 and AL-463, which possess the same number of Trp/Tyr residues on the periphery but attached to a smaller and more flexible pentaerythritol core. These results demonstrate the relevance of the globular 3D presentation of the peripheral groups (Trp/Tyr) as well as the length of the spacer connecting them to the central core to interact with the viral envelopes, particularly in the case of HIV, and support the hypothesis that [60]fullerene can be an alternative and attractive biocompatible carbon-based scaffold for this type of highly symmetrical dendrimers. In addition, the functionalized fullerenes here described, which display twelve peripheral negatively charged indole moieties on their globular surface, define a new and versatile class of compounds with a promising potential in biomedical applications.
publishDate 2021
dc.date.none.fl_str_mv 2021
2021
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/244578
url http://hdl.handle.net/10261/244578
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-84327-P
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-83531-R
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-104070RB-C21
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019- 104070RB-C22
eu-repo/grantAgreement/EC/FP7/264286
HEALTH-F3-2010-260644
https://doi.org/10.1002/chem.202101098
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
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