30854-62-7Relevant academic research and scientific papers
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).
Catalyst-proximity protein chemical labelling on affinity beads targeting endogenous lectins
Tsushima, Michihiko,Sato, Shinichi,Niwa, Tatsuya,Taguchi, Hideki,Nakamura, Hiroyuki
, p. 13275 - 13278 (2019)
Magnetic affinity beads functionalized with lactose and ruthenium/dcbpy complexes were developed. Using MAUra, a catalyst-proximity labelling reagent, the catalytic labeling of lactose-binding proteins was achieved with high selectivity on the beads. The first unbiased identification of cellular endogenous lectins bound to lactose (galectin-1 and galectin-3) was achieved with chemical labelling on the affinity beads.
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.
Delivery of a lactose derivative of endomorphin 1 to the brain via the olfactory epithelial pathway
Cros, Cécile D.,Toth, Istvan,Blanchfield, Joanne T.
, p. 1373 - 1375 (2014)
The rapid and direct delivery of a neuroactive endomorphin 1 derivative to the brain via nasal delivery is reported. A synthetic derivative of the native opioid peptide, endomorphin 1 bearing a lactose unit on the N-terminus of the peptide has been previously reported to exhibit antinoceceptive activity similar to morphine after both intravenous and oral administration. This compound has been administered nasally to rats and appeared in the olfactory bulb within 10 min of administration with negligible levels appearing in the circulating blood or in the rest of the brain. These results indicate that the peptide is absorbed into the brain via the olfactory epithelial pathway suggesting nasal delivery may be a viable alternative route of delivery in clinical applications.
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.
Semisynthesis and in vitro photodynamic activity evaluations of halogenated and glycosylated derivatives of pheophorbide a
Cieckiewicz, Ewa,Mathieu, Véronique,Angenot, Luc,Gras, Thierry,Dejaegher, Bieke,de Tullio, Pascal,Pirotte, Bernard,Frédérich, Michel
, p. 6061 - 6074 (2015)
The present work focuses on the semisynthesis of halogenated and glycosylated derivatives of pheophorbide a (Pha). Because of the low reaction yields enocuntered en route to halogenated derivatives, we then focused only on the semisynthesis of glycosylated derivatives of Pha with the aim at enhancing the Pha specificity for cancer cells by introducing β-galactose moieties expected to bind gal-1. We applied LC-SPE-NMR/MS, to facilitate the direct identification of glycosylated derivatives. The transposition of these analytical methods to a preparative scale facilitated the isolation of glycosylated compounds in quantities sufficient to evaluate in vitro photodynamic efficacies. The in vitro growth inhibi-tory activity of semisynthesized compounds was then evaluated using the MTT colorimetric assay in the presence and absence of light. However, this pharmacological evaluation method seems to be unable to efficiently yield information about carbohydrate effects in relation to possible compound specificities for gal-1 overexpressed by B16F10 cancer cells.
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.
α1,4-Galactosyltransferase-catalyzed glycosylation of sugar and lipid modified Leu-enkephalins
Simerska, Pavla,Christie, Michelle P.,Goodwin, Daryn,Jen, Freda E.-C.,Jennings, Michael P.,Toth, Istvan
, p. 196 - 202 (2013)
Glycosylation of therapeutic peptides has been reported to improve delivery and targeting of various vaccines and drugs to specific cells/tissues. However, chemical synthesis of complex oligosaccharide derivatives via conventional methods can be challengi
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
Synthesis and gelation property of a series of disaccharide triazole derivatives
Okafor, Ifeanyi S.,Wang, Guijun
, p. 81 - 94 (2017)
Low molecular weight gelators are important for the study of supramolecular chemistry and have useful applications for biomaterials. Glycomimetics that are easily accessible and have useful gelation properties are especially interesting molecules. In this
