The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition

Durka, Maxime; Buffet, Kévin; Iehl, Julien; Holler, Michel; Nierengarten, Jean‐François; Vincent, Stéphane

doi:10.1002/chem.201102052

Cited by 101 publications

(83 citation statements)

References 107 publications

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“…For example, CuAAC functionalizations of C 60 derivatives have been achieved [196] and improved their solubility. Recent examples include the preparation of fullerene sugar balls [197], C 60 -containing polymers [198], viral M a n u s c r i p t 38 nanoparticle (VNP)-C 60 conjugates [199], supramolecular interactions between molecular tweezers and macrocycles, functionalization of C 70 fullerenes [200], and biotinylation of fullerene vesicle via CuAAC and conjugation with avidin [201]. Functionalized graphene and partially reduced graphene oxide (rGO) functionalized on the surface provide possibilities for improving the electrical strength recovery and utilization in devices.…”

Section: Applications Of the Cuaac "Click" Reactionsmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

293

162

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Highlights-The review is focused on the mechanistic aspects and recent trends (since 2012) of the metal-catalyzed azide-alkyne cycloaddition (MAAC) so-called "click" reactions with catalysts based on various metals (Cu, Ru, Ag, Au, Ir, Ni, Zn, Ln), although Cu (I) catalysts are still the most used ones.-These MAAC reactions are by far the most common click reactions relevant to the "green chemistry" concept.-Mechanistic investigations are essential to reaction improvements and subsequent applications, and indeed as shown in this review the proposed mechanisms have been multiple during the last decade based on theoretical computations and experimental search of intermediates.-New trends are also presented here often representing both exciting approaches for various applications and new challenges for further mechanistic investigations.

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Section: Applications Of the Cuaac "Click" Reactionsmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

293

162

View full text Add to dashboard Cite

show abstract

“…26 The unambiguous structural characterization of 17a-c was, however, greatly facilitated by their high symmetry. Indeed, 13 C NMR spectroscopy was particularly helpful for the characterization of hexakis-adducts of [60]fullerene, as only two signals are usually observed for the sp 2 carbons of C60, evidencing the octahedral symmetry of the fullerene core.…”

Section: Synthesismentioning

confidence: 99%

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

et al. 2015

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“…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.…”

mentioning

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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The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition

Cited by 101 publications

References 107 publications

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

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

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

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