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 Martínez, Beatriz María, Abdelnabi, Rana, Boonen, Arnaud, Mills, Alberto, Martí‐Marí, Olaia, Noppen, Sam, Neyts, Johan, Schols, Dominique, Gago, Federico, San‐Félix, Ana, Camarasa, María‐José, Martín, Nazario
Tipo de recurso: artículo
Fecha de publicación:2021
País:España
Institución:Universidad Complutense de Madrid (UCM)
Repositorio:Docta Complutense
Idioma:inglés
OAI Identifier:oai:docta.ucm.es:20.500.14352/6752
Acceso en línea:https://hdl.handle.net/20.500.14352/6752
Access Level:acceso abierto
Palabra clave:547
antiviral agents
EV71
fullerenes
hexa-adduct
HIV
Química orgánica (Química)
2306 Química Orgánica
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oai_identifier_str oai:docta.ucm.es:20.500.14352/6752
network_acronym_str ES
network_name_str España
repository_id_str
spelling Multivalent Tryptophan‐ and Tyrosine‐Containing [60]Fullerene Hexa‐Adducts as Dual HIV and Enterovirus A71 Entry InhibitorsRuiz Santaquiteria, MartaIllescas Martínez, Beatriz MaríaAbdelnabi, RanaBoonen, ArnaudMills, AlbertoMartí‐Marí, OlaiaNoppen, SamNeyts, JohanSchols, DominiqueGago, FedericoSan‐Félix, AnaCamarasa, María‐JoséMartín, Nazario547antiviral agentsEV71fullereneshexa-adductHIVQuímica orgánica (Química)2306 Química OrgánicaUnprecedented 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.WileyUniversidad Complutense de Madrid20212021-04-1420212021-04-14journal articlehttp://purl.org/coar/resource_type/c_6501info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/20.500.14352/6752reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2Atribución-NoComercial-SinDerivadas 3.0 Españahttps://creativecommons.org/licenses/by-nc-nd/3.0/es/info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/67522026-06-02T12:44:21Z
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
547
antiviral agents
EV71
fullerenes
hexa-adduct
HIV
Química orgánica (Química)
2306 Química Orgánica
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 Martínez, Beatriz María
Abdelnabi, Rana
Boonen, Arnaud
Mills, Alberto
Martí‐Marí, Olaia
Noppen, Sam
Neyts, Johan
Schols, Dominique
Gago, Federico
San‐Félix, Ana
Camarasa, María‐José
Martín, Nazario
author Ruiz Santaquiteria, Marta
author_facet Ruiz Santaquiteria, Marta
Illescas Martínez, Beatriz María
Abdelnabi, Rana
Boonen, Arnaud
Mills, Alberto
Martí‐Marí, Olaia
Noppen, Sam
Neyts, Johan
Schols, Dominique
Gago, Federico
San‐Félix, Ana
Camarasa, María‐José
Martín, Nazario
author_role author
author2 Illescas Martínez, Beatriz María
Abdelnabi, Rana
Boonen, Arnaud
Mills, Alberto
Martí‐Marí, Olaia
Noppen, Sam
Neyts, Johan
Schols, Dominique
Gago, Federico
San‐Félix, Ana
Camarasa, María‐José
Martín, Nazario
author2_role author
author
author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 547
antiviral agents
EV71
fullerenes
hexa-adduct
HIV
Química orgánica (Química)
2306 Química Orgánica
topic 547
antiviral agents
EV71
fullerenes
hexa-adduct
HIV
Química orgánica (Química)
2306 Química Orgánica
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
2021-04-14
2021
2021-04-14
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/6752
url https://hdl.handle.net/20.500.14352/6752
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Atribución-NoComercial-SinDerivadas 3.0 España
https://creativecommons.org/licenses/by-nc-nd/3.0/es/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Atribución-NoComercial-SinDerivadas 3.0 España
https://creativecommons.org/licenses/by-nc-nd/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Docta Complutense
instname:Universidad Complutense de Madrid (UCM)
instname_str Universidad Complutense de Madrid (UCM)
reponame_str Docta Complutense
collection Docta Complutense
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869413964994052096
score 15.300724

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