Synthesis of sialoclusters appended to calix[4]arene platforms via multiple azide-alkyne cycloaddition. New inhibitors of hemagglutination and cytopathic effect mediated by BK and influenza A viruses

Marra, Alberto; Moni, Lisa; Pazzi, Daniele; Corallini, Alfredo; Bridi, Deborah; Dondoni, Alessandro

doi:10.1039/b800598b

Cited by 81 publications

(58 citation statements)

References 137 publications

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“…New inhibitors of hemagglutination and cytopathic effect mediated by BK and influenza A viruses (Marra, et al, 2008b) Calixarenecyclodextrin conjugates β-Cyclodextrin TOF (DHB) Construction of tubular compounds (Hocquelet, et al, 2007) Carbon nanotubes…”

Section: Analysis Of Carbohydrates and Glycoconjugatesmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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Section: Analysis Of Carbohydrates and Glycoconjugatesmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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“…Our study emphasizes the importance of matching particle sizes and ligand densities to mimic biological surfaces and improve interactions; this is a vital concept underlying multivalent interactions. bi-, [10] tetra-, [11] and octavalent [12] sialosides. In the last case, the scaffold used was a polyazido-calix[4]arene.…”

Section: Introductionmentioning

confidence: 99%

Inhibition of Influenza Virus Activity by Multivalent Glycoarchitectures with Matched Sizes

et al. 2011

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We describe the synthesis of a series of sialic acid-conjugated, polyglycerol-based nanoparticles with diameters in the range of 1-100 nm. Particle sizes were varied along with the degree of functionalization to match the corresponding virus size and receptor multiplicity in order to achieve maximum efficiency. To build up these architectures, we used biocompatible, hyperbranched polyglycerols as scaffolds and recently developed polyglycerol-based nanogels, the sizes of which can be varied between 2-4 nm and 40-100 nm, respectively. We demonstrate here that such multivalent nanoparticles inhibit influenza A virus cell binding and fusion and consequently infectivity. The potential of multivalency is evident from larger particles showing very efficient inhibition of viral infection up to 80 %. Indeed, both the size of the nanoparticle and the amount of ligand density are important determinants of inhibition efficiency. The inhibitory activity of the tested polymeric nanoparticles drastically increased with size. Particles with similar dimensions to the virus (50-100 nm) are exceedingly effective. We also observed a saturation point in degree of surface functionalization (i.e. ligand density), above which inhibition was not significantly improved. Our study emphasizes the importance of matching particle sizes and ligand densities to mimic biological surfaces and improve interactions; this is a vital concept underlying multivalent interactions.

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“…The synthesized inhibitors of HA reported to date have been monovalent sialosides (Pritchett and Paulson, 1989;Matrosovich, 1989;Tuzikov et al, 1997;Weiss et al, 1988), bivalent sialosides (Glick et al, 1991), tetravalent sialosides (Chinarev et al, 1999, Marra et al, 2008, octavalent sialoside (Marra et al, 2008) dendrimers (Roy et al, 1993;Reuter et al, 1999;Sakamoto et al, 2007), liposomes (Kingery-Wood et al, 1992;Spevak et al, 1993;Reichert et al, 1995;Charych and Stevens, 1996;Guo et al, 2002), polymeric sialosides (Matrosovich et al, 1990;Spaltenstein and Whitesides et al, 1991;Gamian et al, 1991;Sparks et al, 1993;Mochalova et al, 1994;Lees et al, 1994;Itoh et al, 1995;Choi et al, 1996;Choi et al, 1997;Tuzikov et al, 1997), and self-assembling sialo-glycopeptides (Tuzikov et al, 2003;Bovin et al, 2004).…”

Section: Synthetic Inhibitors Of Hamentioning

confidence: 99%

“…Tetravalent sialosides showed up to 1200-fold enhancement of inhibitory activity over monovalent ligand. Very recently tetra-and octavalent sialosides were prepared as good inhibitors against influenza at submillimolar concentrations (Marra et al, 2008). So it seems that increases of the number of connection points enhance binding affinity and inhibitory activity as well.…”

Section: Synthetic Inhibitors Of Hamentioning

confidence: 99%

Synthetic sialic-acid-containing polyvalent antiviral inhibitors

et al. 2008

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This review gives a brief survey of synthetic inhibitors of influenza virus which have been synthesized to date. It starts with a short introduction which describes the structure and mechanism of action of influenza virus and continues with the main research directions that have been used in order to inhibit the virus. This is followed by discussion of various synthetic materials, including synthesis and antiviral properties, which that have been tested against influenza virus. The most potent inhibitory compounds proved to be polyvalent, because of their high binding affinity and steric stabilization. Finally we conclude with a brief discussion on structural characteristics, a summary, and outlook overview.

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Synthesis of sialoclusters appended to calix[4]arene platforms via multiple azide-alkyne cycloaddition. New inhibitors of hemagglutination and cytopathic effect mediated by BK and influenza A viruses

Cited by 81 publications

References 137 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Inhibition of Influenza Virus Activity by Multivalent Glycoarchitectures with Matched Sizes

Synthetic sialic-acid-containing polyvalent antiviral inhibitors

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