16977-78-9Relevant academic research and scientific papers
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.
Surface plasmon resonance imaging studies of protein-carbohydrate interactions
Smith, Emily A.,Thomas, William D.,Kiessling, Laura L.,Corn, Robert M.
, p. 6140 - 6148 (2003)
Carbohydrate arrays fabricated on gold films were used to study carbohydrate-protein interactions with surface plasmon resonance (SPR) imaging. An immobilization scheme consisting of the formation of a surface disulfide bond was used to attach thiol-modified carbohydrates onto gold films and to fabricate carbohydrate arrays. The carbohydrate attachment steps were characterized using polarization modulation Fourier transform infrared reflection absorption spectroscopy; and poly(dimethylsiloxane) microchannels were used to immobilize probe compounds at discrete locations on a gold film. The binding of the carbohydrate-binding proteins concanavalin A (ConA) and jacalin to arrays composed of the monosaccharides mannose and galactose was monitored with SPR imaging. SPR imaging measurements were employed to accomplish the following: (i) construct adsorption isotherms for the interactions of ConA and jacalin to the carbohydrate surfaces, (ii) monitor protein binding to surfaces presenting different compositions of the immobilized carbohydrates, and (iii) measure the solution equilibrium dissociation constants for ConA and jacalin toward mannose and galactose, respectively. Adsorption coefficients (KADS) of 2.2 ± 0.8 × 107 M-1 and 5.6 ± 1.7 × 106 M-1 were obtained for jacalin adsorbing to a galactose surface and ConA adsorbing to a mannose surface, respectively. The solution equilibrium dissociation (KD) constant for the interaction of jacalin and galactose was found to be 16 ± 5 μM, and for ConA and mannose was found to be 200 ± 50 μM.
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 of β-Cyclodextin, Per-O-glycosylated through an Ethylene Glycol Spacer Arm
Garcia-Barrientos, Africa,Garcia-Lopez, Juan J.,Isac-Garcia, Joaquin,Ortega-Caballero, Fernando,Uriel, Clara,Vargas-Berenguel, Antonio,Santoyo-Gonzalez, Francisco
, p. 1057 - 1064 (2001)
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, ethyleneoxyethylene and ethylene-(dioxyethylene)-ethylene spacer arms is described. The synthesis involves the glycosylation of the oxyethylene arm and the attachment of the O-glycosides onto the heptakis(6-deoxy-6-iodo)-β-cyclodextrin derivative by means of nucleophilic displacement reaction using cesium carbonate in dimethylformamide.
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.
An Aromatic Micelle-Based Saccharide Cluster with Changeable Fluorescent Color and its Protein Interactions
Catti, Lorenzo,Narita, Haruna,Yoshizawa, Michito
, p. 12791 - 12795 (2021)
To develop a new type of synthetic saccharide clusters with changeable fluorescent colors, we herein designed a multisaccharide-coated aromatic micelle. The new cluster forms in water through the quantitative assembly of bent polyaromatic amphiphiles bearing three mannose groups. The spherical assembly, with a 2 nm-sized polyaromatic core and ca. 18 saccharide pendants, is stable even under high dilution conditions (up to 0.02 mM). The emission intensity and color of the saccharide cluster can be altered from moderate blue (ΦF=19 %) to strong red, orange, and green (ΦF up to 67 %) upon encapsulation of hydrophobic fluorescent dyes in water. Moreover, the present fluorescent clusters, both with and without the dyes, display selective interactions with mannose-binding proteins in vitro.
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).
Positional isomers of mannose-quinoline conjugates and their copper complexes: Exploring the biological activity
Oliveri, Valentina,Bentivegna, Federica,Caputo, Leonardo,Quintieri, Laura,Viale, Maurizio,Maric, Irena,Lentini, Giovanni,Vecchio, Graziella
, p. 8882 - 8890 (2018)
8-Hydroxyquinolines show a wide range of pharmacological activities, and some are marketed as therapeutic agents. Despite the significant number of biologically active hydroxyquinolines proposed, there is a continued interest in the development of new active derivatives to overcome the drawbacks associated with their use. Herein, we report the synthesis and characterization of a set of positional isomers of hydroxyquinoline-mannose conjugates. Since in many cases the complexation ability of 8-hydroxyquinolines seems to be responsible for their pharmacological activities, we investigated the capacity of these systems to complex copper(ii) ions. We also examined diverse biological activities (antiproliferative, antimicrobial and antioxidant) of the new derivatives and their copper(ii) complex and compared them to those of their parent compounds and an analogous glucose-quinoline conjugate. All compounds show antioxidant activity that depends on the regioisomer. Moreover, specific isomers show significant antibacterial activity against P. aeruginosa and S. aureus. Furthermore only a regioisomer shows a pharmacologically relevant antiproliferative activity against human tumor cells, in the presence of copper(ii) ions.
Thiosugar naphthalene diimide conjugates: G-quadruplex ligands with antiparasitic and anticancer activity
Belmonte-Reche, Efres,Benassi, Alessandra,Cucchiarini, Anne,Doria, Filippo,Freccero, Mauro,Gabelica, Valerie,Mergny, Jean Louis,Morales, Juan Carlos,Guédin, Aurore,Pe?alver, Pablo,Rosu, Frèdèric
, (2022/02/17)
Glycosyl conjugation to drugs is a strategy being used to take advantage of glucose transporters (GLUT) overexpression in cancer cells in comparison with non-cancerous cells. Its extension to the conjugation of drugs to thiosugars tries to exploit their higher biostability when compared to O-glycosides. Here, we have synthesized a series of thiosugar naphthalene diimide conjugates as G-quadruplex ligands and have explored modifications of the amino sidechain comparing dimethyl amino and morpholino groups. Then, we studied their antiproliferative activity in colon cancer cells, and their antiparasitic activity in T. brucei and L. major parasites, together with their ability to bind quadruplexes and their cellular uptake and location. We observed higher toxicity for the sugar-NDI-NMe2 derivatives than for the sugar-NDI-morph compounds, both in mammalian cells and in parasites. Our experiments indicate that a less efficient binding to quadruplexes and a worse cellular uptake of the carb-NDI-morph derivatives could be the reasons for these differences. We found small variations in cytotoxicity between O-carb-NDIs and S-carb-NDIs, except against non-cancerous human fibroblasts MRC-5, where thiosugar-NDIs tend to be less toxic. This leads to a notable selectivity for β-thiomaltosyl-NDI-NMe2 12 (9.8 fold), with an IC50 of 0.3 μM against HT-29 cells. Finally, the antiparasitic activity observed for the carb-NDI-NMe2 derivatives against T. brucei was in the nanomolar range with a good selectivity index in the range of 30- to 69- fold.
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
, (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.
