110660-22-5Relevant academic research and scientific papers
Synthesis and anticancer activity of novel NHC-gold(I)-sugar complexes
Dada, Oyinlola,Sánchez-Sanz, Goar,Tacke, Matthias,Zhu, Xiangming
, p. 2904 - 2908 (2018)
Gold(I) complexes containing stabilising ligands such as phosphines or N-heterocyclic carbenes (NHCs) are known to be inhibitors of the enzyme thioredoxin reductase (TrxR) and therefore act as potential apoptosis-inducing anticancer drug candidates. The conjugation of biomolecules overexpressed in cancer cells to the gold complexes makes them semi-targeted metabolites. Auranofin, an anti-arthritis agent, encompasses this property and exhibits anti-tumour activities. The synthesis, characterization and biological evaluation of four novel N-heterocyclic carbene-gold(I)-thiosugar complexes derived from glucose, lactose and galactose is reported. The reactions of 1,3-dibenzyl-4,5-diphenyl-imidazol-2-ylidene gold(I) chloride (NHC?-Au-Cl) with pre-synthesized glycosyl thiols under mildly basic conditions gave the desired NHC-Au-thiosugar complexes in high to excellent yields (79–91%). The complexes retain the strong and redox-active Au-S bond contained in Auranofin. All complexes showed good solubility in biological media and were tested against the NCI 60 cancer cell panel for cytotoxicity. The synthesized NHC?-Au derivatives showed good activity in the medium to low micromolar region, while complex 2 showed activity in the low micromolar to nanomolar region against the tested cell lines. To provide a theoretical structure of 4, computational calculations were carried out based on the crystal structures of NHC-Au-SCN and NHC-Au-S-C6H4OMe.
S-glycosyl primary sulfonamides - A new structural class for selective inhibition of cancer-associated carbonic anhydrases
Lopez, Marie,Paul, Blessy,Hofmann, Andreas,Morizzi, Julia,Wu, Quoc K.,Charman, Susan A.,Innocenti, Alessio,Vullo, Daniela,Supuran, Claudiu T.,Poulsen, Sally-Ann
, p. 6421 - 6432 (2009)
In this paper, we present a new class of carbonic anhydrase (CA) inhibitor that was designed to selectively target the extracellular domains of the cancer-relevant CA isozymes. The aromatic moiety of the classical zinc binding sulfonamide CA inhibitors is
Synthesis and structure of novel sugar-substituted bipyridine complexes of rhenium and 99m-technetium
Gottschaldt, Michael,Koth, Daniel,Mueller, Dirk,Klette, Ingo,Rau, Sven,Goerls, Helmar,Schaefern, Bernhard,Baum, Richard P.,Yano, Shigenobu
, p. 10273 - 10280 (2007)
Novel ligands have been obtained from the reaction of 4.4′- dibromomethyl-2.2′-bipyridine with 2,3.4.6-tetra-O-acetyl-β-D- glucopyranosylthiol. 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylthiol or 2,3,4,6-tetra-O-acetyl-α-D-thioacetylmannopyranoside in which the sugar residues are thioglycosidically linked to the bipyridinc in the 4,4′-position. Cleavage of the acetyl groups affords hydrophilic symmetric ligands with free hydroxyl groups. Reaction of the new glycoconjugated ligands (L) with [Re(CO)5Cl] yields fluorescent complexes of general formula [Re(L)-(CO)3Cl]. which were characterised by mass spectrometry, elemental analysis and 1H and 11CNMR. IR. UV/Vis and fluorescence spectroscopy. These complexes exhibit excellent solubility and stability in organic solvents or water, depending on the residues of the sugar. One complex, namely tricarbonyl-4,4′-bis[(2.3.4,6-tetra-O-acetyl-β-D- glycopyranosyl)thiomethyl]-2,2′-bipyridinerhe-niumtricarbonylo chloride, has been characterised by X-ray crystallography. A non-symmetric structure of the complexes could be assigned. Radio-labelling of the unprotected ligands with [99mTc(H2O)3(CO)3]+ affords the corresponding water-soluble technetium complexes (in quantitative yields), which were characterised by their HPLC radiation traces. The formed complexes are stable for several hours in the presence of histidine but show partial ligand-exchange after one day.
Improved Synthesis of 1-Glycosyl Thioacetates and Its Application in the Synthesis of Thioglucoside Gliflozin Analogues
Dong, Hai,Feng, Guang-Jing,Luo, tao,Lv, Jian,Wang, Shuang-Shuang,Wu, Yuzhou
, p. 2940 - 2949 (2021)
An improved method to synthesize 1-glycosyl thioacetates was developed, where per-O-acetylated glycoses were allowed to directly react with potassium thioacetate (KSAc) in the presence of BF3 ? Et2O in ethyl acetate under mild conditions. This method not only overcomes the disadvantage of the traditional one-step method, which is that the odorous and toxic thioacetic acid has to be used, but also overcomes the disadvantage of the traditional two-step method, which is that the unstable intermediate, glycosyl halide, has to be synthesized from the per-O-acetylated glycose in advance. Based on this, the per-O-acetylated glucosyl disulfide and the per-O-acetylated glucosyl 1-thiol were efficiently synthesized in high yields (91 % and 90 % respectively) starting from per-O-acetylated glycoses in two-step without the need to isolate intermediate products. Through metal-catalyzed cross-coupling of per-O-acetylated glucosyl 1-thiol with aryl-iodide under very mild conditions, two thioglucoside gliflozin analogues were efficiently synthesized in high yields for the first time. These two thioglucoside gliflozin analogues were further confirmed to be stable to hydrolysis of β-glucosidase.
Design and fabrication of multivalent Gal-containing quantum dots and study of its interactions with asialoglycoprotein receptor (ASGP-R)
Yang, Yang,Zhao, Yue-Tao,Yan, Ting-Ting,Yu, Min,Sha, Yin-Lin,Zhao, Zhi-Hui,Li, Zhong-Jun
, p. 4182 - 4185 (2010)
Multivalent lactose (Lac-QDs)- and galactose (Gal-QDs)- coated CdSeS-ZnS core-shell quantum dots (QDs) were prepared. The formula of the glyco-QDs was determined by nuclear magnetic resonance (NMR) and inductively coupled plasma-optical emission spectrometry (ICP-OES). The uptake of the Gal-containing glyco-QDs by HepG2 cells was investigated. Flow cytometry (FCM) and fluorescence microscopy analysis indicated that the uptake is receptor mediated and selective. The prepared multivalent glyco-QDs could be used to mimic the oligosaccharides in the study of hepatic endocytosis. Furthermore, this type of glyco-QDs can be used as a useful fluorescent probe in cell imaging and analysis of carbohydrate-protein interactions.
A building block approach to the synthesis of a family of S-linked α-1,6-oligomannosides
Belz, Tyson,Williams, Spencer J.
, p. 38 - 47 (2016)
The syntheses of α-1,6-S-linked methyl di-, tetra- and hexamannosides are reported. The sulfur linkages are generated through coupling of thiolates (derived from anomeric thioacetates or isothiouronium bromides) with 6-deoxy-6-iodo sugars. Two approaches are detailed that involve [2 + 2 + 2] construction from either the reducing end or the non-reducing end. In constructing from the reducing end, coupling of a disaccharide thioacetate with a 6'-iodo reducing end disaccharide, followed by activation of the resulting tetrasaccharide to a 6'''-iodide, and iterative coupling with the same disaccharide thioacetate afforded the S-linked hexasaccharide, as well as the intermediate di- and tetrasaccharides. On the other hand, construction from the non-reducing end involved coupling of the above disaccharide thioacetate with an anomeric S-trityl protected 6'-iodo disaccharide. The resulting S-trityl tetrasaccharide was converted to a tetrasaccharide thioacetate, which was coupled with the same anomeric S-trityl protected 6'-iodo disaccharide to afford the hexasaccharide, which was elaborated to the methyl thioglycoside. The developed methodology may prove useful for the construction of other S-linked oligosaccharides.
Novel synthesis of 1-thioglycopyranoses via thioiminium salts
Fujihira, Takayoshi,Chida, Mitsutaka,Kamijo, Haruo,Takido, Toshio,Seno, Manabu
, p. 287 - 292 (2002)
Methanolysis of a glycosylthioiminium salt, which was prepared from the reaction of acetohalogenosugar with thioacetamide, afforded the corresponding per-O-acetylated 1,2-trans-1-thioglycose in good yield after fractional crystallization. This synthetic method is very convenient in operation and proceeds without loss of acetyl groups, as the reaction is carried out under mild and neutral conditions.
Characterization of some mesogenic alkyl 1-thioglycosides
Henrissat,Hamer,Taylor,Marchessault, Robert
, p. 1162 - 1165 (2002)
A series of dodecyl 1-thio-β-D-glycosides has been synthesized and characterized (DSC, NMR, CP MAS, X-ray diffraction) as possible new marking materials with liquid-crystalline properties. These compounds undergo solid to liquid crystal phase transitions at various temperatures, which depend on the nature of the carbohydrate part of the structure. Their liquid-crystalline phases show extreme shear thinning behaviour.
Bivalent glycoconjugates based on 1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione (“bimane”) as a central scaffold
Szabó, Tamás,Bényei, Attila,Szilágyi, László
, p. 88 - 98 (2019)
The heteroaromatic fused diazabicyclic “bimane” ring system, discovered four decades ago, is endowed with remarkable chemical and photophysical properties. No carbohydrate derivatives of bimanes have, however, been described thus far. Here we report on the syntheses of a range of bimanes decorated with various glycosyl residues. Mono- and disaccharide residues were attached to syn- or anti-bimane central cores via thio-, disulfido- or selenoglycosidic linkages to obtain novel fluorescent or nonfluorescent glycoconjugates. Cu(I)-catalyzed cycloaddition of glycosyl azides to a bimane diethynyl derivative furnished further bivalent glycoconjugates with sugar residues linked to the central bimane core via 1,2,3-triazole rings. We have determined the crystal and molecular structures of several glycosylated and non-glycosylated bimanes and report fluorescence data for the new compounds.
α-S-GalCer: Synthesis and evaluation for iNKT cell stimulation
Blauvelt, Marisa L.,Khalili, Maryam,Jaung, Weonjoo,Paulsen, Janet,Anderson, Amy C.,Brian Wilson,Howell, Amy R.
, p. 6374 - 6376 (2008)
The synthesis and evaluation for iNKT stimulation of α-S-galactosylceramide is reported. Prepared by alkylation of a galactosylthiol, this analog of the potent immunostimulatory agent, KRN7000, did not stimulate iNKT cells either in vitro or in vivo.
