86651-32-3

Upstream product

• 540-51-2 2-bromoethanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 604-69-3 β-D-glucose pentaacetate 
• 50-99-7 D-glucose 
• 108-24-7 acetic anhydride 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 125412-02-4 (2-bromoethyl)-D-glucopyranoside 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 2280-44-6 D-Glucose 
• 604-68-2 α-D-glucopyranose peracetylate 
• 35023-69-9 2-hydroxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 

Downstream Products

• 382607-84-3 2-(8-aza-O⁶-benzylguan-9-yl)ethyl-β-D-tetra-O-acetylglucoside 
• 382607-69-4 2-(O⁶-benzylguan-9-yl)ethyl-β-D-tetra-O-acetylglucoside 
• 140428-81-5 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 1207987-60-7 2-[2,6-bis(4-pyridylethynyl)phenoxy]ethyl β-D-glucopyranoside 
• 1207987-61-8 2-[2,6-bis(4(4-pyridyl)phenylethynyl)phenoxy]ethyl β-D-glucopyranoside 
• 1207987-64-1 2-[2,6-bis(4-(4-pyridyl)phenylethynyl)phenoxy]ethyl 2,3,4,6-tetra-O-acetyl-D-glucopyranoside 
• 1207987-63-0 2-[2,6-bis(4-pyridylethynyl)phenoxy]ethyl 2,3,4,6-tetra-O-acetyl-D-glucopyranoside 
• 1207987-62-9 2-(2,6-dibromophenoxy)ethyl 2,3,4,6-tetra-O-acetyl-D-glucopyranoside 
• 85193-62-0 2-(p-nitrophenylthio)ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 87019-20-3 2-(p-aminophenylthio)ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 139888-80-5 2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 89266-13-7 2-bromoethyl 4,6-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranoside 
• 89983-41-5 2-bromoethyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 140428-83-7 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Synthesis of a novel sugar cyclotriveratrylene by introduction of O- glycosyl groups

Introduction of sugar moieties to the periphery of the cyclotriveratrylene skeleton is described.

Thiosugar naphthalene diimide conjugates: G-quadruplex ligands with antiparasitic and anticancer activity

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.

Neutral Re(I) Complex Platform for Live Intracellular Imaging

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.

Overcoming hypoxia-induced chemoresistance in cancer using a novel glycoconjugate of methotrexate

The oxygen and nutrient-deprived tumor microenvironment is considered a key mechanism responsible for cancer resistance to chemotherapy. Methotrexate (MTX) is a widely incorporated chemotherapeutic agent employed in the treatment of several malignancies. However, drug resistance and systemic toxicity limit the curative effect in most cases. The present work aimed to design, synthesize, and biologically evaluate a novel glucose-methotrexate conjugate (Glu-MTX). Our study showed that Glu-MTX exerts an increased cytotoxic effect on cancer cells in comparison to MTX in hypoxia (1% O2 ) and glucose starvation conditions. Furthermore, Glu-MTX was found to inhibit the proliferation and migration of cancer cells more effectively than MTX does. Our results demonstrate that the conjugation of MTX to glucose led to an increase in potency against malignant cells under oxygen and nutrient stress. The observations shed light on a potential therapeutic approach to overcome chemoresistance in cancer.

An Aromatic Micelle-Based Saccharide Cluster with Changeable Fluorescent Color and its Protein Interactions

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.

1,6-heptadiynes based cyclopolymerization functionalized with mannose by post polymer modification for protein interaction

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.

Glucose compound, medicinal composition and application thereof

The invention discloses a glucose compound, a medicinal composition and application thereof. The glucose compound or pharmaceutically acceptable salt thereof as shown in a formula I almost has no activity of inhibiting cancer cell proliferation in vitro, but has excellent anti-cancer effect and excellent inhibition effect on tumor metastasis in an in-vivo activity test, and has an excellent marketapplication prospect.

Prophylactic Antiviral Activity of Sulfated Glycomimetic Oligomers and Polymers

In this work, we investigate the potential of highly sulfated synthetic glycomimetics to act as inhibitors of viral binding/infection. Our results indicate that both long-chain glycopolymers and short-chain glycooligomers are capable of preventing viral infection. Notably, glycopolymers efficiently inhibit Human Papillomavirus (HPV16) infection in vitro and maintain their antiviral activity in vivo, while the glycooligomers exert their inhibitory function post attachment of viruses to cells. Moreover, when we tested the potential for broader activity against several other human pathogenic viruses, we observed broad-spectrum antiviral activity of these compounds beyond our initial assumptions. While the compounds tested displayed a range of antiviral efficacies, viruses with rather diverse glycan specificities such as Herpes Simplex Virus (HSV), Influenza A Virus (IAV), and Merkel Cell Polyomavirus (MCPyV) could be targeted. This opens new opportunities to develop broadly active glycomimetic inhibitors of viral entry and infection.

Carbohydrate-functionalized N-heterocyclic carbene Ru(ii) complexes: Synthesis, characterization and catalytic transfer hydrogenation activity

Three Ru complexes containing carbohydrate/N-heterocyclic carbene hybrid ligands were synthesized that were comprised of a triazolylidene coordination site and a directly linked per-acetylated glucosyl (5Glc) or galactosyl unit (5Gal), or a glycosyl unit linked through an ethylene spacer (6). Electrochemical and UV-vis analysis indicate only minor perturbation of the electronic configuration of the metal center upon carbohydrate installation. Deprotection of the carbohydrate was accomplished under basic conditions to afford complexes that were stable in solution over several hours, but decomposed in the solid state. Complexes 5 and 6 were used as pre-catalysts for transfer hydrogenation of ketones under basic conditions, i.e. conditions that lead to in situ deprotection of the carbohydrate entity. The carbohydrate directly influences the catalytic activity of the metal center. Remotely linked carbohydrates (complex 6) induce significantly lower catalytic activity than directly linked carbohydrates (complexes 5Glc, 5Gal), while unfunctionalized triazolylidenes are an order of magnitude more active. These observations and substrate variations strongly suggest that substrate bonding is rate-limiting for transfer hydrogenation in these hybrid carbohydrate/triazolylidene systems.

8-hydroxyquinoline glycoconjugates: Modifications in the linker structure and their effect on the cytotoxicity of the obtained compounds

Small molecule nitrogen heterocycles are very important structures, widely used in the design of potential pharmaceuticals. Particularly, derivatives of 8-hydroxyquinoline (8-HQ) are successfully used to design promising anti-cancer agents. Conjugating 8-HQ derivatives with sugar derivatives, molecules with better bioavailability, selectivity, and solubility are obtained. In this study, 8-HQ derivatives were functionalized at the 8-OH position and connected with sugar derivatives (D-glucose or D-galactose) substituted with different groups at the anomeric position, using copper(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC). Glycoconjugates were tested for inhibition of the proliferation of cancer cell lines (HCT 116 and MCF-7) and inhibition of β-1,4-galactosyltransferase activity, which overexpression is associated with cancer progression. All glycoconjugates in protected form have a cytotoxic effect on cancer cells in the tested concentration range. The presence of additional amide groups in the linker structure improves the activity of glycoconjugates, probably due to the ability to chelate metal ions present in many types of cancers. The study of metal complexing properties confirmed that the obtained glycoconjugates are capable of chelating copper ions, which increases their anti-cancer potential.