Second generation of fucose-based DC-SIGN ligands : affinity improvement and specificity versus Langerin

Andreini, Manuel; Doknic, Daniela; Sutkevičiūtė, Ieva; Reina, José J.; Duan, Janxin; Chabrol, E; Thépaut, Michel; Moroni, Elisabetta; Doro, Fábio Gorzoni; Belvisi, Laura; Weiser, Joerg; Rojo, Javier; Fieschi, Franck; Bernardi, Anna

doi:10.1039/c1ob05573a

Cited by 64 publications

(89 citation statements)

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“…Extensive work on the design of fucose-based glycomimetics has been reported [76]; these molecules are characterized by the presence of an unnatural α-fucosylamide anchor and bind DC-SIGN with an affinity similar to that of the Lewis X oligosaccharide. The simplest of these mimics, an α-fucosyl-β-alanyl amide, loaded on a gold nanoparticle platform, gave rise to a potent DC-SIGN targeting device (38, Figure 6) that did not induce dendritic cell maturation and IL-10 production, thus suggesting a possible use as targeted imaging or antigen delivery tool [77].…”

Section: Figurementioning

confidence: 99%

Glycoconjugates and Glycomimetics as Microbial Anti-Adhesives

Sattin

Bernardi

2016

Trends in Biotechnology

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Microbial adhesion is an essential step of infections and is mediated primarily by proteincarbohydrate interactions. Antagonists of such interactions have become a promising target for antiadhesive therapy in a number of infective diseases. Monovalent protein-sugar interactions are often weak, and most successful antiadhesive materials consist of multivalent glycoconjugates.Although often very effective in hampering microbial adhesion, natural epitopes often show limited resistance to enzymatic degradation. The use of carbohydrate mimics (glycomimetics) as a replacement for natural sugars potentially allows to achieve higher metabolic stability and also higher selectivity towards the desired protein target. In this review we will describe the state of the art on the design and synthesis of glycoconjugates and glycomimetics employed for the construction of antiadhesive biomaterials.

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Section: Figurementioning

confidence: 99%

Glycoconjugates and Glycomimetics as Microbial Anti-Adhesives

Sattin

Bernardi

2016

Trends in Biotechnology

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“…21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 Flow cytometry analysis of DC surface molecules and cytokine production. Suspensions of 100 µL immature DCs (1.10 6 cells/mL) were stimulated by addition of AuNPs (1 µg/mL) for [16][17][18][19][20] hours at 37°C in the presence of 5% CO 2 . 10 ng/mL LPS (E. coli, Sigma-Aldrich) served as a control.…”

Section: Stable K562/dc-sign Ll/y Transfectantsmentioning

confidence: 99%

“…[16][17] Most of these molecules bind DC-SIGN with an affinity similar to or better than that of the Le X trisaccharide (Galβ1-4[Fucα1-3]GlcNAcβ1), one of its natural fucose-containing ligands. [4][5] In particular, N-α-fucosyl-β-alanylamide 1a (Figure 1), which can be prepared in a single step from fucosyl azide, binds to DC-SIGN with almost the same affinity as Le X , that has often been used as a DC-SIGN targeting unit in the context of polyvalent constructs.…”

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Effective Targeting of DC-SIGN by α-Fucosylamide Functionalized Gold Nanoparticles

et al. 2014

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Abstract:Dendritic Cells (DCs), the most potent antigen-presenting cells, play a critical role in the detection of invading pathogens, which are recognized also by multiple carbohydrate-specific receptors.Among them, DC-SIGN is one of the best characterized, with high-mannose and Lewis-type glycan specifity. In this study, we present a potent DC-SIGN targeting device developed using gold nanoparticles functionalized with α-fucosyl-β-alanyl amide. The nanoparticles bound to cellular DC-SIGN and induced internalization as effectively as similar particles coated with comparable amounts of Lewis X oligosaccharide. They were found to be neutral towards dendritic cell maturation and IL-10 production, thus envisaging a possible use as targeted imaging tools and antigen delivery devices.

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“…In particular, stereoselective synthesis of α-N-glycosides is one of the most challenging issues despite their potentials as therapeutic compounds. [9][10][11] In 2003, DeShong's group has reported a highly α-selective synthesis of N-glycosides through a Cu-mediated acylation of glycopyranosyl isoxazoline intermediates generated from the corresponding azides, 5) while anomerization of 1-aminoglycopyranosyl derivatives is generally a significant problem. 4) Direct N-glycosylation of amides has emerged as an alternative approaches, 6-8) but those reports relied on the neighboring group participation to give β-N-glycosides (Chart 1a).…”

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Organocatalytic Direct α-Selective <i>N</i>-Glycosylation of Amide with Glycosyl Trichloroacetimidate

Kobayashi

Takemoto

2018

Chem. Pharm. Bull.

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Through the synergistic catalytic effect of the halogen bond (XB) donor and thiourea catalyst, a direct α-selective N-glycosylation of the amide residue of asparagine derivative was achieved using readily accessible glycosyl trichloroacetimidate. n-Butyl methyl ether was found to be the most suitable solvent for the α-selectivity.Key words glycosylation; organocatalyst; halogen bond; hydrogen bond; green chemistry N-Glycosides are found in a variety of bioactive compounds, including natural products. 1) Sugar moieties are known to extend the diversity of molecules, altering their property, structure, and biological activities. 2) However, synthetic methods for N-glycosides have not been well developed, [3][4][5][6][7][8] as compared with the preparation of O-glycosides. In particular, stereoselective synthesis of α-N-glycosides is one of the most challenging issues despite their potentials as therapeutic compounds. [9][10][11] In 2003, DeShong's group has reported a highly α-selective synthesis of N-glycosides through a Cu-mediated acylation of glycopyranosyl isoxazoline intermediates generated from the corresponding azides, 5) while anomerization of 1-aminoglycopyranosyl derivatives is generally a significant problem. 4) Direct N-glycosylation of amides has emerged as an alternative approaches, 6-8) but those reports relied on the neighboring group participation to give β-N-glycosides (Chart 1a).Herein, we report the first direct α-N-glycosylation of amide with glycosyl trichloroacetimidate 12) using halogen bond (XB) donor 13) /Schreiner thiourea 14) co-catalytic system. We envisioned that α-selectivity would be achieved through the double inversion strategy (Chart 1b). The initial S N 2 addition of an appropriate solvent, such as etheric solvent, and/or additive 15) to α-donor 1 would form a β-linked intermediate A, to which the following S N 2 attacked by an employed amide would afford the desired α-linked product. As in our previous report, 8) we have chosen an XB-donor/thiourea co-catalytic system for the activation of the leaving group (LG) of 1, mainly due to the following reasons: 1) XB interaction would be effective in relatively polar etheric solvent, and 2) tuning of both HB donor and XB donor would improve their ability to trap the LG via anion binding, 16) preventing the undesired rearrangement of the LG.We first screened the reaction conditions for the direct α-N-glycosylation of asparagine derivative 3 with glycosyl donor 1 (Table 1). According to our previous work, 2-iodoimidazolium salt (XB1) 13) was examined in conjunction with HB1 in dichloromethane. 8) As we expected, the combination of HB1 and XB1 was essential for the production of desired N-glycoside 2a (entries 1-3), although almost no α/β selectivity was observed (entry 3). A control experiment with non-halogenated azolium 5 did not furnish 2a at all (entry 4), indicating that XB interaction would play an important role. The chemical yields were slightly improved using XB2 and XB3 (entries 5 and 6), whereas the undesired glycosyl trichl...

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Second generation of fucose-based DC-SIGN ligands : affinity improvement and specificity versus Langerin

Cited by 64 publications

References 50 publications

Glycoconjugates and Glycomimetics as Microbial Anti-Adhesives

Glycoconjugates and Glycomimetics as Microbial Anti-Adhesives

Effective Targeting of DC-SIGN by α-Fucosylamide Functionalized Gold Nanoparticles

Organocatalytic Direct α-Selective <i>N</i>-Glycosylation of Amide with Glycosyl Trichloroacetimidate

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