A molecular-diversity-oriented approach for the preparation of well-defined polycationic amphiphilic cyclodextrins (paCDs) as gene-delivery systems is reported. The synthetic strategy takes advantage differential reactivity primary versus secondary hydroxyl groups on CD torus to regioselectively decorate each rim with cationic elements and lipophilic tails, respectively. Both charge density hydrophobic-hydrophilic balance can be finely tuned in a highly symmetrical architecture that...

(6AR,6DR)-6A,6D-di-C-cyano-β-cyclodextrin (3) was synthesized and shown to catalyze hydrolysis of nitrophenyl glycosides with the reaction following Michaelis−Menten kinetics. At pH 7.4 25 °C, 4-nitrophenyl-β-glucopyranoside (2) catalyzed KM = 15 mM, kcat 8.2 × 10-6 s-1, kcat/kuncat 1217. Catalysis observed concentration 3 as low 10 μM. Hydrolysis corresponding α-glucoside, α-galactoside, α-mannoside, 2-nitrophenyl-β-galactoside also by 3, ranging from 283 2147. A series analogues prepared...

The vision of multivalency as a strategy limited to achieve affinity enhancements between protein receptor and its putative sugar ligand (glycotope) has proven too simplistic. On the one hand, binding glycotope in dense glycocalix-like construct lectin partner been shown be sensitive presence third entity (heterocluster effect). other several carbohydrate processing enzymes (glycosidases glycosyltransferases) have found also responsive multivalent presentations partners (multivalent enzyme...

An efficient general strategy for the incorporation of functional elements onto secondary hydroxyl rim β-cyclodextrin has been developed and applied to synthesis a novel series C7-symmetric homogeneous macromolecular polycations with improved DNA complexing delivery properties.

This review concentrates on both the protein receptor and guest binding abilities of carbohydrate clusters based a cyclodextrin core. The combination complexation is basis one pursued approaches for developing site-specific drug delivery systems. Influence molecular recognition properties number appended saccharides, type clustering spacer arms, among other factors, are discussed. Keywords: Cyclodextrins, neoglycoconjugates, glycoclusters, glycodendrimers, delivery, multivalent effect

Oligosaccharides are currently recognised as having functions that influence the entire spectrum of cell activities. However, a distinct disadvantage naturally occurring oligosaccharides is their metabolic instability in biological systems. Therefore, much effort has been spent past two decades on development feasible routes to carbohydrate mimetics which can compete with O -glycosidic counterparts surface adhesion, inhibit processing enzymes, and interfere biosynthesis specific...

α-Mannosidosis (AM) results from deficient lysosomal α-mannosidase (LAMAN) activity and subsequent substrate accumulation in the lysosome, leading to severe pathology. Many of AM-causative mutations compromise enzyme folding could be rescued with purpose-designed pharmacological chaperones (PCs). We found that PCs combining a LAMAN glycone-binding motif based on 5 N,6 O-oxomethylidenemannojirimycin (OMJ) glycomimetic core different aglycones, either mono- or multivalent displays, elicit...

(6AR,6DR)-6A,6D-Di-C-cyano-β-cyclodextrin (1) and 6A,6D-di-C-cyano-α-cyclodextrin (2) were synthesized shown to catalyze hydrolysis of aryl glycosides into glucose phenol with a reaction following Michaelis−Menten kinetics. At pH 8.0 59 °C 4-nitrophenyl α-glucopyranoside was catalyzed by 1 KM = 10.5 ± 1.5 mM, kcat 1.42(±0.09) × 10-4 s-1, kcat/kuncat 7922. Catalysis observed concentration as low 10 μM. Hydrolysis the other containing stereochemical variation in sugar-moiety 4-nitro-,...

In our ongoing program aimed at the design, synthesis, and biological evaluation of novel gem-difluoromethylenated glycosidase inhibitors, gem-4,4-difluoromethylenated iminosugars (5−9) were synthesized. The these synthetic showed that gem-difluoromethylenyl group generally reduced inhibition glycosidases. However, this was not case pH 5.0, where iminosugar 6 a stronger inhibitor than comparable 1 36, suggesting influence is mainly through its effect on amine. It proposed unprotonated...

alpha- and beta-Cyclodextrin 6(A),6(D)-diacids (1 2), beta-cyclodextrin-6-monoacid (14), beta-cyclodextrin 6(A),6(D)-di-O-sulfate (16) beta-cyclodextrin-6-heptasulfate (19) were synthesised. Acids 1, 2 14 made from perbenzylated or beta-cyclodextrin, by diisobutylaluminum hydride (DIBAL)-promoted debenzylation, oxidation deprotection. Addition of molecular sieves was found to improve the debenzylation reaction. Sulfates 16 19 sulfation appropriately partially protected derivatives Catalysis...

Cyclodextrins are ideal scaffolds for the attachment of bioactive molecules such as glycosides (see scheme). We describe herein a study on both inclusion complexation behaviour and lectin binding affinity branched hyperbranched β-cyclodextrins. In order to evaluate ability multivalent based β-cyclodextrin core site-specific molecular carriers, β-cyclodextrins is presented. A series cluster galactosides constructed containing seven 1-thio-β-lactose or β-lactosylamine bound macrocyclic through...

Trehalose-based Janus cyclooligosaccharides undergo DNA-promoted self-assembling.

A novel family of precision-engineered gene vectors with well-defined structures built on trehalose and trehalose-based macrocycles (cyclotrehalans) comprising linear or cyclic polyamine heads have been synthesized through procedures that exploit click chemistry reactions. The strategy was conceived to enable systematic structural variations and, at the same time, ensuring enantiomerically pure are obtained. Notably, changes in molecular architecture translated into topological differences...

The inclusion behavior and concanavalin A binding properties of hepta-antennated newly synthesized tetradeca-antennated C-6-branched mannopyranosyl glucopyrannosyl cyclomaltoheptaose (β-cyclodextrin) derivatives have been evaluated by isothermal titration microcalorimetry enzyme-linked lectin assay (ELLA), respectively. synthesis three first-order dendrimers based on a β-cyclodextrin core containing 14 1-thio-β-d-glucose, 1-thio-β-mannose, 1-thio-β-rhamnose residues was performed following...

Abstract Three new series of potential anthrax toxin inhibitors based on the β‐cyclodextrin (βCD) scaffold were developed by exploiting face‐selective Cu I ‐catalyzed azide–alkyne 1,3‐cycloadditions, amine–isothiocyanate coupling, and allyl group hydroboration–oxidation/hydroxy → amine replacement reactions. The molecular design follows “symmetry–complementarity” concept between homogeneously functionalized polycationic βCD derivatives protective antigen (PA), a component known to form C 7...

A new method for the synthesis of β-cyclodextrin-based cluster mannosides by application Sonogashira cross-coupling reaction is described. The allows persubstitution β-cyclodextrin at either 2- and 3-positions to give two types heptavalent clusters, both 6-positions clusters with 14 mannopyranoside units 2-, 3-, obtain 21 ligands.

Cyclam, known for its potent chelation properties, is explored diverse applications through selective N-functionalization, offering versatile ligands catalysis, medical research, and materials science. The challenges arising from N-alkylation, which could decrease the coordination are addressed by introducing a robust C-functionalization method. facile two-step synthesis proposed here involves click chemistry-based of hydroxyethyl cyclam derivative using Cu(I)-catalyzed alkyne-azide...

Two cyclodextrin derivatives (1 and 2) were prepared in an attempt to create glycosidase mimics with a general acid catalyst nucleophilic carboxylate group. The catalysts 1 2 found catalyse the hydrolysis of 4-nitrophenyl β-D-glucopyranoside at pH 8.0, but rapidly underwent decomposition loss hydrogen cyanide convert cyanohydrin corresponding aldehyde. initial rate catalysis shows that group these molecules functions as good catalyst, has no positive effect. product aldehydes display little...

The synthesis of cyclodextrin-based O-α-manno, O-β-galactopyranoside and O-β-galactofuranoside clusters, having seven sugar residues attached to the core, through ethylene, ethylenoxyethylene ethylene-(dioxyethylene)-ethylene spacer arms is described. involves glycosylation oxyethylene arm attachment O-glycosides onto heptakis(6-deoxy-6-iodo)-β-cyclodextrin derivative by means nucleophilic displacement reaction using cesium carbonate in dimethylformamide.

Cyclam, known for its potent chelation properties, is explored diverse applications through selective N-functionalization, offering versatile ligands catalysis, medical research, and materials science. The challenges arising from N-alkylation, that could decrease the coordination are addressed by introducing a robust C-functionalization method. facile two-step synthesis proposed here involves click chemistry-based C functionalization of hydroxyethyl cyclam derivative using Cu(I)-catalyzed...

We report the synthesis of functionalized beta-cycloaltrins having azido groups at C-3, C-6, and both C-3 C-6 by nucleophilic epoxy ring-opening per-2,3-anhidro-beta-cyclomannin derivatives. The value these compounds as templates for further functionalization is exemplified conversion heptakis(3,6-diazido-3,6-dideoxy)-beta-cycloaltrin into per-3,6-diamino, per-3,6-diacetamido, per-3,6-dichloroacetamido, per[3,6-bis(N'-ethylureido)] derivatives in good yields.

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