106818-92-2Relevant articles and documents
Synthesis and characterization of novel cationic lipids derived from thio galactose
Qiao, Weihong,Zhou, Min,Luo, Limei
, p. 261 - 268 (2014)
Two double chain cationic lipids QAS Cn -2-S (n = 12, 14) derived from thio galactose and carbamate-linkage tertiary amine were synthesized and their structures were confirmed by MS, TOF-MS, 1H NMR and 13C NMR. The QAS C12-2-S revealed superior surface activity compared with QAS C14-2-S with lower CMC and γCMC. Though Lipo C12-2-S displayed large average particle-size with high polydispersity, positive charged Lipo Cn -2-S can be combined with the negative charged DNA, also negatively stained TEM images confirmed the formation of vesicles. All the above prove that the Lipo Cn -2-S is helpful for gene transfection.
A general procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides, thiooligosaccharides and glycosyl thioesters
Ibatullin,Selivanov,Shavva
, p. 419 - 422 (2001)
A simple procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides by promotion with triethylamine is described. The reaction conditions allow the synthesis of glycosyl thioesters and some thioglycosides, which cannot be prepared using the traditional approach. The procedure has been successfully applied for preparation of thiooligosaccharides, shown by syntheses of methyl 4-thio-α-cellobioside and methyl 4-thio-α-lactoside derivatives.
Glycoviruses: Chemical glycosylation retargets adenoviral gene transfer
Pearce, Oliver M. T.,Fisher, Kerry D.,Humphries, Julia,Seymour, Leonard W.,Smith, Alberto,Davis, Benjamin G.
, p. 1057 - 1061 (2005)
A sugar-specific transfection mechanism is introduced by the glycosylation of adenoviruses (AVs, see picture), and manipulation of the glycosylation pattern allows the selective transfection of human macrophages in favor of the usual target. This dramatic retargeting holds promise for the fine-tuning of adenoviruses for applications such as gene therapy.
Synthesis of some N- and S-glycosides of D-galactose bearing hydrazinocarbonyl and diazomethylcarbonyl functions in the aglycon
Dupuis, Gilles,Leclair, Benoit
, p. 2531 - 2536 (1982)
We describe the synthesis of N- and S-glycosides derived from D-galactopyranose in which the aglycon bears certain reactive groups.In a first series, the anomeric carbon is linked to an amino group that is acylated by a functionalized succinic acid chain.The terminal group of the aglycon moiety is a hydrazide function which can be converted by ultraviolet light irradiation into an azide and a nitrene.Altenatively, the terminal group is a diazoketone function which can be converted into a carbene, by ultraviolet light irradiation.A second series comprises glycosides of 1-thio-β-D-galactopyranose.The aglycon consists of a 6-carbon chain with a carboxylic end group.The latter has been converted into a hydrazide and diazoketone function.We show that the diazo group of the diazoketones (compounds 5 and 12) is susceptible to decomposition by ultraviolet irradiation, being nearly quantitatively decomposed after 3 minutes.These compounds add to a growing list of hexose derivatives which can be used in the field of photoaffinity-labeling of the sugar binding sites of certain lectins and of hexose transport systems, or to prepare modified proteins or ligands for affinity chromatography.
Solvent-free synthesis of thioglycosides by ball milling
Ramrao Patil, Premanand,Ravindranathan Kartha
, p. 953 - 956 (2009)
Thioglycosides have been prepared in excellent yields by three different routes from a range of readily available glycosyl halides under solvent-free conditions employing a planetary ball mill.
Efficient diverse approach for quinoxaline-derived glycosylated and morphinylated analogs
Beldi, Razika,Atta, Kamal F.,Aboul-Ela, Sallah,El Ashry, El Sayed H.
, p. 50 - 56 (2011)
Sulfanyl-glycosides have been synthesized by reaction of 2,3-dimercaptoquinoxaline (1) with acetohalo sugars in presence of base to give the thioglycosides-derived quinoxalines 5-7 and 9. Similarly, the acyclic analogs 23-26 were prepared by coupling of 1 with different acyclo-alkylating agents. The preparation of 3-morpholinyl-quinoxalines 10 and 11 allowed the synthesis of 3-glycosylsulfanyl-2-morpholinyl-quinoxalines 12-14 and 17 as well as the acyclic analogs 27-29. Microwave irradiation of the reactants turned out to be preferred over the conventional method for achieving the synthetic goals. This study made an available venue to the synthesis of diverse quinoxaline derivatives.
8-Hydroxyquinoline glycoconjugates containing sulfur at the sugar anomeric position—synthesis and preliminary evaluation of their cytotoxicity
Erfurt, Karol,Hadasik, Agnieszka,Krawczyk, Monika,Pastuch-Gawo?ek, Gabriela
, (2020)
One of the main factors limiting the effectiveness of many drugs is the difficulty of their delivery to their target site in the cell and achieving the desired therapeutic dose. Moreover, the accumulation of the drug in healthy tissue can lead to serious side effects. The way to improve the selectivity of a drug to the cancer cells seems to be its conjugation with a sugar molecule, which should facilitate its selective transport through GLUT transporters (glucose transporters), whose overexpression is seen in some types of cancer. This was the idea behind the synthesis of 8-hydroxyquinoline (8-HQ) derivative glycoconjugates, for which 1-thiosugar derivatives were used as sugar moiety donors. It was expected that the introduction of a sulfur atom instead of an oxygen atom into the anomeric position of the sugar would increase the stability of the obtained glycoconjugates against untimely hydrolytic cleavage. The anticancer activity of new compounds was determined based on the results of the MTT cytotoxicity tests. Because of the assumption that the activity of this type of compounds was based on metal ion chelation, the effect of the addition of copper ions on cell proliferation was tested for some of them. It turned out that cancer cells treated with glycoconjugates in the presence of Cu2+ had a much slower growth rate compared to cells treated with free glycoconjugates in the absence of copper. The highest cytotoxic activity of the compounds was observed against the MCF-7 cell line.
Synthesis of interglycosidically S-linked 1-thio-oligosaccharides under microwave irradiation
El Ashry, El Sayed H.,Awad, Laila F.,Hamid, H. M. Abdel,Atta, Atta I.
, p. 745 - 753 (2005)
Microwave irradiation (MWI) has accelerated the synthesis of S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiouronium bromide (2a), whose reaction with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (1a) in the presence of Et3N afforded stereoselectively the acetylated β,β-1-thiotrehalose 4a. Similarly, the respective D-galactopyranosyl 4b and 2-acetylamino-2-deoxy-D-glucopyranosyl 4c analog as well as 4,4′-di-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) 4d and 4,4′-di-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl) 4e derivatives of 2,2′,3,3′,6,6′-hexa-O-acetyl β,β-1-thiotrehalose were prepared. Copyright Taylor & Francis, Inc.
POLYMER FOR DELIVERY OF BIOLOGICALLY ACTIVE MATERIALS
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Page/Page column 14; 15, (2019/01/17)
The present invention mainly relates to a polymer for delivery of biologically active materials, a complex and a method of synthesis thereof. The polymer comprises a poly(ethylene imine) and at least one monomer, each monomer comprising a modified sugar moiety, preferably galactose, comprising a sulphur atom or a nitrogen atom and a chemical moiety comprising a terminal epoxide for linking the polyethylene imine to the monomer, wherein the sulphur atom or the nitrogen atom links the modified sugar moiety to the chemical moiety. The biologically active material is preferably a gene, siRNA, mRNA, or plasmid DNA. Further disclosed is the medical use of said complex in treating a disease caused by a genetic disorder, for example cancer.
Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics
Brink?, Anne,Risinger, Christian,Lambert, Annie,Blixt, Ola,Grandjean, Cyrille,Jensen, Henrik H.
supporting information, p. 7544 - 7548 (2019/10/08)
Here, we report on the first combined one-pot use of the two so-called "click reactions": The thiol-ene coupling and the copper-catalyzed alkyne-azide cycloaddition. These reactions were employed in an alternating and one-pot fashion to combine appropriately functionalized monomeric carbohydrate building blocks to create mimics of trisaccharides and tetrasaccharides as single anomers, with only minimal purification necessary. The deprotected oligosaccharide mimics were found to bind both plant lectins and human galectin-3.
