Synthesis of giant globular multivalent glycofullerenes as potent inhibitors in a model of Ebola virus infection

Muñoz, Antonio; Sigwalt, David; Illescas, Beatriz M.; Luczkowiak, Joanna; Rodríguez‐Pérez, Laura; Nierengarten, Iwona; Holler, Michel; Rémy, Jean-Serge; Buffet, Kévin; Vincent, Stéphane; Rojo, Javier; Delgado, Rafaël; Nierengarten, Jean‐François; Martı́n, Nazario

doi:10.1038/nchem.2387

Cited by 258 publications

(192 citation statements)

References 37 publications

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“…Hexakis adducts of [60]fullerene have been tested as gene transfection vectors, 6 multiplying units for photodynamic therapy, 7 glycosidase and glycosyltransferase inhibitors, 8 or efficient antibacterial 9 or antiviral systems. 10 The synthesis of these adducts was first studied by Hirsch by the one-pot addition of malonates templated by 9,10-dimethylanthracene 11 and later modified by Sun. 12 However, these procedures are often limited by the size of the malonates, as the steric aspects limit the yield of the reaction.…”

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confidence: 99%

Cyclooctyne [60]fullerene hexakis adducts: a globular scaffold for copper-free click chemistry

et al. 2016

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The synthesis of a new highly symmetric hexakis adduct of C60 appended with 12 cyclooctyne moieties has been carried out. This compound has been used for the copper-free strain-promoted cycloaddition reaction to a series of azides with excellent yields. This strategy for the obtention of clicked adducts of [60]fullerene is of special interest for biological applications.[60]Fullerene hexakis adducts with Th symmetry constitute an attractive class of compounds that allow the globular disposition of substituents around the C60 core. 1 These compounds have attracted much attention in the last recent years, both in the areas of materials science and biomedicine. Thus, some of them present liquid crystal behavior, 2 have been employed for the study of electronic and energy transfer processes, 3 as organic connectivity centers for the synthesis of Metal Organic Frameworks (MOFs), 4 or as catalysts. 5 On the other hand, in the area of biological applications, their activity has been tested in different fields showing interesting properties and good biocompatibility. Hexakis adducts of [60]fullerene have been tested as gene transfection vectors, 6 multiplying units for photodynamic therapy, 7 glycosidase and glycosyltransferase inhibitors, 8 or efficient antibacterial 9 or antiviral systems. 10 The synthesis of these adducts was first studied by Hirsch by the one-pot addition of malonates templated by 9,10-dimethylanthracene 11 and later modified by Sun. 12 However, these procedures are often limited by the size of the malonates, as the steric aspects limit the yield of the reaction. To overcome this drawback, Nierengarten proposed the employment of an azide appended malonate to obtain a clickable hexakis adduct of C60 to effectively allow the covalent functionalization of [60]fullerene by Cu(I) alkyne-azide cycloaddition (CuAAC) reaction. 13 Lately, Nierengarten and we described the 12-alkyne modified hexakis adduct of [60]fullerene and its use in the click chemistry addition of azides and alkynes. 14 This effective reaction requires, however, the use of copper (I) as catalyst, which involves a subsequent purification step for the removal of copper, especially with those materials for bio-medical applications, owing to its high cytotoxicity. This step can be hampered by the presence in the final products of functional groups, and even the triazole rings themselves, capable of binding copper, thus limiting their biological applications. 15 A strategy to avoid this purification step is to employ of strain promoted alkyne-azide cycloaddition (SPAAC) click reaction. This reaction, developed by Bertozzi and coworkers, 16 consists of the reaction of strained cyclooctynes with azides and has received considerable attention owing to its simplicity and faster reaction rates, avoiding the use of a metal as catalyst. As it does not require the use of copper, it has especial relevance for biological applications. In the present communication we report the synthesis of a new hexakis adduct of [60]fullerene substituted with twelve c...

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Cyclooctyne [60]fullerene hexakis adducts: a globular scaffold for copper-free click chemistry

et al. 2016

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“…One is surely that of bio-sensing, especially in those cases where target detection is measured via its ability to drive self-assembly via ligand-receptor bond formation, 144 e.g., functionalised nanoparticles for DNA 145 or enzyme 146 recognition. Another is the fast advancing field of nanoparticles as anti-viral drugs, [147][148][149][150] where multivalent particles are used that mimic, and compete with, cell receptors. Both these applications can benefit from the same approaches and techniques used to understand targeting selectivity, [70][71][72]79 and indeed some initial step in that direction have already been taken.…”

Section: Discussionmentioning

confidence: 99%

Theory, simulations and the design of functionalized nanoparticles for biomedical applications: A Soft Matter Perspective

Angioletti‐Uberti

2017

npj Comput Mater

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Functionalised nanoparticles for biomedical applications represents an incredibly exciting and rapidly growing field of research. Considering the complexity of the nano-bio interface, an important question is to what extent can theory and simulations be used to study these systems in a realistic, meaningful way. In this review, we will argue for a positive answer to this question. Approaching the issue from a "Soft Matter" perspective, we will consider those properties of functionalised nanoparticles that can be captured within a classical description. We will thus not concentrate on optical and electronic properties, but rather on the way nanoparticles' interactions with the biological environment can be tuned by functionalising their surface and exploited in different contexts relevant to applications. In particular, we wish to provide a critical overview of theoretical and computational coarsegrained models, developed to describe these interactions and present to the readers some of the latest results in this fascinating area of research.

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“…In 2016 Muñoz et al . 12 reported the synthesis of hexakis adducts of fullerene C 60 , with the most effective dendrimeric growth (compounds 26 - 28 ) (Fig. 5).…”

Section: Antiviral Activitymentioning

confidence: 99%

“…5 Since then, efficient synthetic methods for fullerene functionalization have been developed. 6, 7 Functionalization with bioactive compounds that exhibit affinity to certain nucleic acids, proteins or cell receptors such as peptides 8-10 or saccharides, 11, 12 functionalization with polar or ionic groups such as hydroxyl, 13, 14 carbonyl 15-17 or quaternary ammonium salts, 18, 19 and encapsulation with macromolecules 20, 21 are the most common approaches to synthesize water-soluble fullerene derivatives for biomedical applications. 22-26 …”

Section: Introductionmentioning

confidence: 99%

Fullerenes in biology and medicine

et al. 2017

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Synthesis of giant globular multivalent glycofullerenes as potent inhibitors in a model of Ebola virus infection

Cited by 258 publications

References 37 publications

Cyclooctyne [60]fullerene hexakis adducts: a globular scaffold for copper-free click chemistry

Cyclooctyne [60]fullerene hexakis adducts: a globular scaffold for copper-free click chemistry

Theory, simulations and the design of functionalized nanoparticles for biomedical applications: A Soft Matter Perspective

Fullerenes in biology and medicine

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