Fluorescent Labelled Thiourea‐Bridged Glycodendrons

Krist, Pavel; Vannucci, Luca; Kuzma, Marek; Man, Petr; Sadalapure, Kashinath; Patel, A.; Bezouška, Karel; Pospı́šil, M.; Petruš, Ladislav; Lindhorst, Thisbe K.; Křen, Vladimı́r

doi:10.1002/cbic.200300669

Cited by 31 publications

(17 citation statements)

References 39 publications

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“…Animal model cells were studied by the group of Kren who described the activation of rat natural killer (NK) cells by glycodendrimers. [19] Another study by Lee et al reports on the grafting of multi-lineage haematopoietic factor human interleukin-3 (hIL-3) on a fifth-generation poly(amidoamine) PAMAM dendrimer. The in vitro immunostimulating properties of this conjugate were reported to be lower than those of free hIL-3.…”

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confidence: 99%

Tailored Control and Optimisation of the Number of Phosphonic Acid Termini on Phosphorus‐Containing Dendrimers for the Ex‐Vivo Activation of Human Monocytes

Rolland

Griffe

Poupot

et al. 2008

Chemistry A European J

103

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The syntheses of a series of phosphonic acid-capped dendrimers is described. This collection is based on a unique set of dendritic structural parameters-cyclo(triphosphazene) core, benzylhydrazone branches and phosphonic acid surface-and was designed to study the influence of phosphonate (phosphonic acid) surface loading towards the activation of human monocytes ex vivo. Starting from the versatile hexachloro-cyclo(triphosphazene) N(3)P(3)Cl(6), six first-generation dendrimers were obtained, bearing one to six full branches, that lead to 4, 8, 12, 16, 20 and 24 phosphonate termini, respectively. The surface loading was also explored at the limit of dense packing by means of a first-generation dendrimer having a cyclo(tetraphosphazene) core and bearing 32 termini, and with a first-generation dendrimer based on a AB(2)/CD(5) growing pattern and bearing 60 termini. Human monocyte activation by these dendrimers confirms the requirement of the whole dendritic structure for bioactivity and identifies the dendrimer bearing four branches, thus 16 phosphonate termini, as the most bioactive.

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confidence: 99%

Tailored Control and Optimisation of the Number of Phosphonic Acid Termini on Phosphorus‐Containing Dendrimers for the Ex‐Vivo Activation of Human Monocytes

Rolland

Griffe

Poupot

et al. 2008

Chemistry A European J

103

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“…Among these architectural categories, glycodendrons were chosen for our study, because (i) a relatively large number of carbohydrates can be displayed with a high density, (ii) their valency and size can be easily adjusted, and (iii) they can be selectively functionalized for conjugation to other biomolecules. Over the past several years, many groups have found that glycodendrimers/ glycodendrons exhibit strikingly enhanced affinity against target proteins (23,31,32). More recently, different synthetic approaches and applications of these macromolecules have been explored (33)(34)(35)(36).…”

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confidence: 99%

Targeting the carbohydrates on HIV-1: Interaction of oligomannose dendrons with human monoclonal antibody 2G12 and DC-SIGN

Wang

Liang

Astronomo

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

274

175

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It is widely accepted that the heavily glycosylated glycoprotein gp120 on the surface of HIV-1 shields peptide epitopes from recognition by the immune system and may promote infection in vivo by interaction with dendritic cells and transport to tissue rich in CD4 ؉ T cells such as lymph nodes. A conserved cluster of oligomannose glycans on gp120 has been identified as the epitope recognized by the broadly HIV-1-neutralizing monoclonal antibody 2G12. Oligomannose glycans are also the ligands for DC-SIGN, a C-type lectin found on the surface of dendritic cells. Multivalency is fundamental for carbohydrate-protein interactions, and mimicking of the high glycan density on the virus surface has become essential for designing carbohydrate-based HIV vaccines and antiviral agents. We report an efficient synthesis of oligomannose dendrons, which display multivalent oligomannoses in high density, and characterize their interaction with 2G12 and DC-SIGN by a glycan microarray binding assay. The solution and the surface binding analysis of 2G12 to a prototype oligomannose dendron clearly demonstrated the efficacy of dendrimeric display. We further showed that these glycodendrons inhibit the binding of gp120 to 2G12 and recombinant dimeric DC-SIGN with IC 50 in the nanomolar range. A second-generation Man 9 dendron was identified as a potential immunogen for HIV vaccine development and as a potential antiviral agent.glycodendron ͉ high mannose ͉ multivalency ͉ HIV vaccine ͉ antiviral agent

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“…Several low molecular weight and low valence glycodendrimers (dimers, trimers and tetramers) are very potent and, sometimes, even more potent than higher valency analogs in their interaction with lectins. [4][5][6][7] This is very important from the medicinal chemistry point of view, since low molecular dendrimers are expected to have favorable physicochemical properties comparing to the high molecular weight, multivalent ones.…”

Section: Introductionmentioning

confidence: 99%

An efficient synthesis of D-galactose-based multivalent neoglycoconjugates

Andrade

Figueiredo²,

Filho

et al. 2012

J. Braz. Chem. Soc.

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Este trabalho descreve a síntese de neoglicoconjugados diméricos, triméricos e tetraméricos derivados de D-galactose. O ligante monossacarídico foi preparado em cinco etapas utilizando-se a modificação de Doebner da reação de Knoevenagel na etapa de extensão da cadeia lateral. O ligante foi acoplado a 1,4-butanodiamina, tris-(2-etilamino)amina, pentaeritritiltetramina e dendrímeros PAMAM (núcleo 1,4-butanodiamina G0 e núcleo 1,12-dodecanodiamina G0). Os glicodendrímeros desprotegidos foram purificados por cromatografia por exclusão de tamanho (SEC). Esta foi a única etapa em que um método cromatográfico foi empregado em toda rota sintética. Essa é uma estratégia nova e eficiente para a preparação de neoglicoconjugados.In this work, the synthesis of dimeric, trimeric and tetrameric D-galactose-based neoglycoconjugates is reported. The monosaccharide ligand was prepared in 5 straightforward steps from D-galactose using the Doebner modification of the Knoevenagel reaction for chain elongation. The ligand was coupled to 1,4-butanediamine, tris-(2-ethylamino)amine, pentaerythrityltetramine and PAMAM dendrimers (1,4-butanodiamine core G0 and 1,12-dodecanediamine core G0). The unprotected glycodendrimers were purified by size-exclusion chromatography (SEC). This was the only step in which a chromatographic method was employed throughout the synthetic route. This is a new and efficient strategy for the preparation of neoglycoconjugates.

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Fluorescent Labelled Thiourea‐Bridged Glycodendrons

Cited by 31 publications

References 39 publications

Tailored Control and Optimisation of the Number of Phosphonic Acid Termini on Phosphorus‐Containing Dendrimers for the Ex‐Vivo Activation of Human Monocytes

Tailored Control and Optimisation of the Number of Phosphonic Acid Termini on Phosphorus‐Containing Dendrimers for the Ex‐Vivo Activation of Human Monocytes

Targeting the carbohydrates on HIV-1: Interaction of oligomannose dendrons with human monoclonal antibody 2G12 and DC-SIGN

An efficient synthesis of D-galactose-based multivalent neoglycoconjugates

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