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Multivalent Tryptophan‐ and Tyrosine‐Containing [60]Fullerene Hexa‐Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors
Author(s) -
RuizSantaquiteria Marta,
Illescas Beatriz M.,
Abdelnabi Rana,
Boonen Arnaud,
Mills Alberto,
MartíMarí Olaia,
Noppen Sam,
Neyts Johan,
Schols Dominique,
Gago Federico,
SanFélix Ana,
Camarasa MaríaJosé,
Martín Nazario
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202101098
Subject(s) - dendrimer , hexa , adduct , fullerene , tyrosine , chemistry , indole test , tryptophan , stereochemistry , combinatorial chemistry , polymer chemistry , biochemistry , organic chemistry , amino acid
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.