30854-62-7Relevant articles and documents
Supramolecular hydrogels based on glycoamphiphiles: Effect of the disaccharide polar head
Clemente, Maria J.,Romero, Pilar,Oriol, Luis,Fitremann, Juliette,Serrano, Jose L.
, p. 3847 - 3858,12 (2012)
Supramolecular hydrogelators based on amphiphilic glycolipids have been prepared by clicking different sugar polar heads to a hydrophobic linear chain by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. The influence of the sugar polar head on the gelation properties in water has been studied, and the liquid crystalline properties of the amphiphilic materials have also been characterized. Stable hydrogels at room temperature have been obtained and the fibrillar supramolecular structures formed by the self-assembly have been studied by different microscopic techniques on the dried gel (xerogel) and hydrated conditions in order to characterize the micro- and nanostructures. Self-assembly gives rise to supramolecular ribbons with a torsion that is related to a chiral supramolecular arrangement of amphiphiles. The formation of an opposite helical arrangement of the ribbons has been found to depend on the sugar polar head. This fact was confirmed by circular dichroism (CD).
Phase diagrams of monoacylated amide-linked disaccharide glycolipids
Gerber,Wulf,Milkereit,Vill,Howe,Roessle,Garidel,Gutsmann,Brandenburg
, p. 118 - 130 (2009)
A series of monoacylated glycolipids with even-numbered acyl chain lengths ranging from saturated C11 to C15 and an unsaturated C17:1 fatty acid connected by an amide in linkage to the disaccharide head groups maltose, melibiose and lactose were synthesized. The structural polymorphism of the glycolipids was investigated using Fourier-transform infrared spectroscopy and differential scanning calorimetry for the detection of the gel to liquid-crystalline acyl chain melting behaviour and small-angle X-ray scattering for the elucidation of the physical structure of the lipid aggregates. Also, the phase morphology was studied by polarizing microscopy in contact preparations. The data clearly show the existence of uni- and multilamellar structures. Although only one acyl chain is present, there is no evidence for the existence of micelles - of spherical or of cylindrical (HI) type - or of interdigitated phases. The preference for lamellar phases seems to be correlated with the intrinsic high conformational order of the amide linkage of these compounds which inhibits the formation of highly curved structures.
Ruthenium-centred btp glycoclusters as inhibitors for: Pseudomonas aeruginosa biofilm formation
O'Reilly, Ciaran,Blasco, Salvador,Parekh, Bina,Collins, Helen,Cooke, Gordon,Gunnlaugsson, Thorfinnur,Byrne, Joseph P.
, p. 16318 - 16325 (2021)
Carbohydrate-decorated clusters (glycoclusters) centred on a Ru(ii) ion were synthesised and tested for their activity against Pseudomonas aeruginosa biofilm formation. These clusters were designed by conjugating a range of carbohydrate motifs (galactose, glucose, mannose and lactose, as well as galactose with a triethylene glycol spacer) to a btp (2,6-bis(1,2,3-triazol-4-yl)pyridine) scaffold. This scaffold, which possesses a C2 symmetry, is an excellent ligand for d-metal ions, and thus the formation of the Ru(ii)-centred glycoclusters 7 and 8Gal was achieved from 5 and 6Gal; each possessing four deprotected carbohydrates. Glycocluster 8Gal, which has a flexible spacer between the btp and galactose moieties, showed significant inhibition of P. aeruginosa bacterial biofilm formation. By contrast, glycocluster 7, which lacked the flexible linker, didn't show significant antimicrobial effects and neither does the ligand 6Gal alone. These results are proposed to arise from carbohydrate-lectin interactions with LecA, which are possible for the flexible metal-centred multivalent glycocluster. Metal-centred glycoclusters present a structurally versatile class of antimicrobial agent for P. aeruginosa, of which this is, to the best of our knowledge, the first example.
Multivalent effect of glycopolypeptide based nanoparticles for galectin binding
Bonduelle, Colin,Oliveira, Hugo,Gauche, Cony,Huang, Jin,Heise, Andreas,Lecommandoux, Sébastien
, p. 11251 - 11254 (2016)
Synthetic glycopolypeptides are versatile glycopolymers used to conceive bioinspired nanoassemblies. In this work, novel amphiphilic glycopolypeptides were designed to incorporate lactose or galactan in order to prepare polymeric nanoassemblies with sizes below 50 nm. The bioactivity of the two different outer surface sugar units was evaluated by defining glycan relative binding affinities to human galectins 1 and 3. A specific multivalent effect was found only for polymeric nanoparticles displaying galactan with a significant increase of the binding activity as compared to free glycan in solution. Such synthetic designs present great potential as therapeutic tools to address galectin related pathologies.
Teaming up synthetic chemistry and histochemistry for activity screening in galectin-directed inhibitor design
Roy, René,Cao, Yihong,Kaltner, Herbert,Kottari, Naresh,Shiao, Tze Chieh,Belkhadem, Karima,André, Sabine,Manning, Joachim C.,Murphy, Paul V.,Gabius, Hans-Joachim
, p. 285 - 301 (2017)
A hallmark of endogenous lectins is their ability to select a few distinct glycoconjugates as counterreceptors for functional pairing from the natural abundance of cellular glycoproteins and glycolipids. As a consequence, assays to assess inhibition of le
Single step syntheses of lactosylated clusters by telomerizations
Aravind, Sivasubramanian,Park, William K. C.,Brochu, Stephane,Roy, Rene
, p. 7739 - 7742 (1994)
N-acryloylated lactoside derivatives containing spacer arms of different length were polymerized in the presence of thiols acting as radical scavengers to provide small oligomeric clusters (telomers) in a single step. t-Butyl mercaptan and methyl 3-mercap
CuAAC mediated synthesis of cyclen cored glycodendrimers of high sugar tethers at low generation
Agrahari, Anand K.,Jaiswal, Manoj K.,Yadav, Mangal S.,Tiwari, Vinod K.
, (2021/07/30)
Glycodendrimers are receiving considerable attention to mimic a number of imperative features of cell surface glycoconjugate and acquired excellent relevance to a wide domain of investigations including medicine, pharmaceutics, catalysis, nanotechnology, carbohydrate-protein interaction, and moreover in drug delivery systems. Toward this end, an expeditious, modular, and regioselective triazole-forming CuAAC click approach along with double stage convergent synthetic method was chosen to develop a variety of novel chlorine-containing cyclen cored glycodendrimers of high sugar tethers at low generation of promising therapeutic potential. We developed a novel chlorine-containing hypercore unit with 12 alkynyl functionality originated from cyclen scaffold which was confirmed by its single crystal X-ray data analysis. Further, the modular CuAAC technique was utilized to produce a variety of novel 12–sugar coated (G0) glycodendrimers 12-15 adorn with β-Glc-, β-Man-, β-Gal-, β-Lac, along with 36-galactose coated (G1) glycodendrimer 18 in good-to-high yield. The structures of the developed glycodendrimer architectures have been well elucidated by extensive spectral analysis including NMR (1H & 13CNMR), HRMS, MALDI-TOF MS, UV–Vis, IR, and SEC (Size Exclusion Chromatogram) data.
Convenient synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter-solvent: Readily access to non-ionic triazolylglycoside surfactants for evaluation of cytotoxic activity
Ketsomboon, Nutthanicha,Saeeng, Rungnapha,Srisook, Klaokwan,Sirion, Uthaiwan
, (2021/08/26)
A convenient method for the one-pot synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter and solvent is described via a sequential one-pot two-step glycosidation-CuAAc click reaction. The reaction was carried out using commercially available substrates, including glycosyl bromides, sodium azide and various long alkyl-chain alkynes to achieve the corresponding products in moderate to high yields. Furthermore, this approach was successfully applied for the preparation of non-ionic monocatenary triazolylglycoside surfactants in excellent yields through simple deacetylation. Subsequently, these surfactants were further evaluated for their cytotoxic activity.
