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

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Ruiz Santaquiteria, Marta and Illescas Martínez, Beatriz M. and Abdelnabi, Rana and Boonen, Arnaud and Mills, Alberto and Martí‐Marí, Olaia and Noppen, Sam and Neyts, Johan and Schols, Dominique and Gago, Federico and San‐Félix, Ana and Camarasa, María‐José and Martín, Nazario (2021) Multivalent Tryptophan‐ and Tyrosine‐Containing [60]Fullerene Hexa‐Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors. Chemistry – A European Journal, 27 (41). pp. 10700-10710. ISSN 0947-6539

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Official URL: https://doi.org/10.1002/chem.202101098



Abstract

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.


Item Type:Article
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CRUE-CSIC (Acuerdos Transformativos 2021)

Uncontrolled Keywords:antiviral agents, EV71, fullerenes, hexa-adduct, HIV
Subjects:Sciences > Chemistry > Chemistry, Organic
ID Code:70134
Deposited On:07 Feb 2022 11:07
Last Modified:22 Feb 2022 09:58

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