16977-78-9Relevant articles and documents
Gas chromatographic investigation of the boron trifluoride etherate-induced formation and anomerization of glucopyranosides
Ellervik, Ulf,Jansson, Karl,Magnusson, Goeran
, p. 777 - 784 (1998)
Boron trifluoride etherate-induced glucosylation of methanol, 1-propanol, 2-propanol, 2-bromoethanol, and 3-bromo-2-(bromomethyl)propan-1-o1, using 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose as donor, gave the corresponding β-glucopyranosides. The α-glucosides and 1,2,3,4,6-penta-O-acetyl-α-D-glucopyranose were formed as byproducts in varying amounts, according to GLC analysis. The propensity of the different glucopyranosides to anomerize was determined in separate experiments.
Alkyl-imidazolium glycosides: Non-ionic - Cationic hybrid surfactants from renewable resources
Salman, Abbas Abdulameer,Tabandeh, Mojtaba,Heidelberg, Thorsten,Hussen, Rusnah Syahila Duali,Ali, Hapipah Mohd
, p. 28 - 33 (2015)
A series of surfactants combining carbohydrate and imidazolium head groups were prepared and investigated on their assembly behavior. The presence of the imidazolium group dominated the interactions of the surfactants, leading to high CMCs and large molecular surface areas, reflected in curved rather than lamellar surfactant assemblies. The carbohydrate, on the other hand, stabilized molecular assemblies slightly and reduced the surface tension of surfactant solutions considerably. A comparative emulsion study discourages the use of pure alkyl imidazolium glycosides owing to reduced assembly stabilities compared with APGs. However, the surfactants are believed to have potential as component in carbohydrate based surfactant mixtures.
Synthesis and in vitro screening of novel heterocyclic β-D-gluco- And β-D-galactoconjugates as butyrylcholinesterase inhibitors
Baumann, Kre?imir,Kordi?, Lorena,Mo?ibob, Marko,?inko, Goran,Tomi?, Sr?anka
, (2019)
The development of selective butyrylcholinesterase (BChE) inhibitors may improve the treatment of Alzheimer’s disease by increasing lower synaptic levels of the neurotransmitter acetylcholine, which is hydrolysed by acetylcholinesterase, as well as by overexpressed BChE. An increase in the synaptic levels of acetylcholine leads to normal cholinergic neurotransmission and improved cognitive functions. A series of 14 novel heterocyclic β-d-gluco- and β-d-galactoconjugates were designed and screened for inhibitory activity against BChE. In the kinetic studies, 4 out of 14 compounds showed an inhibitory effect towards BChE, with benzimidazolium and 1-benzylbenzimidazolium substituted β-d-gluco- and β-d-galacto-derivatives in a 10–50 micromolar range. The analysis performed by molecular modelling indicated key residues of the BChE active site, which contributed to a higher affinity toward the selected compounds. Sugar moiety in the inhibitor should enable better blood–brain barrier permeability, and thus increase bioavailability in the central nervous system of these compounds.
Mononucleoside SATE glucosyl phosphorothiolates as a new series of pronucleotides
Jochum,Schlienger,Gosselin,Imbach,Aubertin,Perigaud
, p. 899 - 901 (2003)
The synthesis and the study of two phosphorothiolate derivatives of 3′-azido-2′,3′-dideoxythymidine (AZT) bearing a S-pivaloyl-2-thioethyl (tBuSATE) group and glucosyl residues associated to the phosphorus atom by a 2-oxyethyl link, are reported. These derivatives could be considered as prototypes of a new series of nucleotide prodrugs (pronucleotides).
A "Smart" Magnetic Resonance Imaging Agent That Reports on Specific Enzymatic Activity
Moats, Rex A.,Fraser, Scott E.,Meade, Thomas J.
, p. 726 - 728 (1997)
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Neutral Re(I) Complex Platform for Live Intracellular Imaging
Bader, Christie A.,Brooks, Doug A.,Brooks, Robert D.,Caporale, Chiara,Gillam, Todd A.,Hickey, Shane M.,Massi, Massimiliano,Morrison, Janna L.,Plush, Sally E.,Sorvina, Alexandra,Stagni, Stefano,Werrett, Melissa V.,Wright, Phillip J.,Zacchini, Stefano
, p. 10173 - 10185 (2021/07/26)
Luminescent metal complexes are a valuable platform for the generation of cell imaging agents. However, many metal complexes are cationic, a factor that can dominate the intracellular accumulation to specific organelles. Neutral Re(I) complexes offer a more attractive platform for the development of bioconjugated imaging agents, where charge cannot influence their intracellular distribution. Herein, we report the synthesis of a neutral complex (ReAlkyne), which was used as a platform for the generation of four carbohydrate-conjugated imaging agents via Cu(I)-catalyzed azide-alkyne cycloaddition. A comprehensive evaluation of the physical and optical properties of each complex is provided, together with a determination of their utility as live cell imaging agents in H9c2 cardiomyoblasts. Unlike their cationic counterparts, many of which localize within mitochondria, these neutral complexes have localized within the endosomal/lysosomal network, a result consistent with examples of dinuclear carbohydrate-appended neutral Re(I) complexes that have been reported. This further demonstrates the utility of these neutral Re(I) complex imaging platforms as viable imaging platforms for the development of bioconjugated cell imaging agents.
1,6-heptadiynes based cyclopolymerization functionalized with mannose by post polymer modification for protein interaction
Das, Rituparna,Dash, Tapan K.,Kanjilal, Pintu,Kumar, Pawan,Le, Trong-Nghia,Mohanan, Manikandan,Mukhopadhyay, Balaram,Rao, N. Vijayakameswara,Shunmugam, Raja
supporting information, (2021/07/22)
Carbohydrate functionalized polymers or Glycopolymers have earned a great deal of interest in recent times for their potential biomedical applications. In the present study, a mannose containing glycopolymer was synthesized by cyclopolymerization of malonic acid derivative using second generation Hoveyda Grubbs′ catalyst. Post-polymerization modification was done to install a propargyl moiety. Finally, functionalization of the propargylated polymer with 2-azidoethyl mannoside using azide-alkyne “click chemistry” furnished the target glycopolymer which was successfully characterized using NMR, FT-IR, mass spectroscopy and advanced polymer chromatography. The glycopolymer was found to self-assemble into capsule and spherical shape in water and DMSO respectively and these morphologies were observed through SEM and TEM. Upon interaction with Con A, the mannose containing glycopolymer showed an increment in aggregation induced fluorescence with increasing concentration of the lectin. In vitro cytotoxicity studies on MCF 7 cell line showed 90% cell viability up to glycopolymer concentration of 500 μg/mL.
