56644-75-8Relevant academic research and scientific papers
Prednisolone succinate-glucosamine conjugate: Synthesis, characterization and in vitro cellular uptake by kidney cell lines
Lin, Yan,Sun, Xun,Gong, Tao,Zhang, Zhi Rong
, p. 25 - 28 (2012)
Prednisolone succinate-glucosamine (PSG) conjugate, a prodrug for prednisolone, was synthesized and confirmed by NMR and MS spectrum. The stabilities of the prodrug in PBS (pH 2.50, 5.00, 7.20, and 7.89) were studied. Cytotoxicity and uptake assay of the prodrug were perfomed on HK-2 and MDCK cell lines. The results showed that compared with prednisolone, the PSG not only did not increase the cytotoxicity but also improved the uptake to 2.2 times of prednisolone by the cells. Thus, it indicated that glucosamine might be a potential carrier for kidney-targeting delivery of prednisolone.
Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34
Ahadi, Somayeh,Awan, Shahid I.,Werz, Daniel B.
supporting information, (2020/05/04)
A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.
PROTECTED TETRASACCHARIDES, THEIR PROCESS OF PREPARATION AND THEIR USE AS TRANSGLUCOSYLASE ACCEPTOR SUBSTRATES IN THE CHEMO-ENZYMATIC SYNTHESIS OF SHIGELLA FLEXNERI SPECIFIC OLIGOSACCHARIDES
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Page/Page column 38, (2019/01/21)
The present invention provides protected tetrasaccharides, their process of preparation and their use in the synthesis of oligosaccharides, in particular fragments of O-antigens from Shigella flexneri, for example of serotype la, lb, 2a, 2b, 3a, X, 4a, 4b
Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens
Wu, Bin,Yang, Xiaojian,Yan, Mingdi
supporting information, p. 7751 - 7768 (2019/09/10)
Auranofin, an FDA-approved arthritis drug, has recently been repurposed as a potential antimicrobial agent; it performed well against many Gram-positive bacteria, including multidrug resistant strains. It is, however, inactive toward Gram-negative bacteria, for which we are in dire need of new therapies. In this work, 40 auranofin analogues were synthesized by varying the structures of the thiol and phosphine ligands, and their activities were tested against ESKAPE pathogens. The study identified compounds that exhibited bacterial inhibition (MIC) and killing (MBC) activities up to 65 folds higher than that of auranofin, making them effective against Gram-negative pathogens. Both thiol and the phosphine structures influence the activities of the analogues. The trimethylphosphine and triethylphosphine ligands gave the highest activities against Gram-negative and Gram-positive bacteria, respectively. Our SAR study revealed that the thiol ligand is also very important, the structure of which can modulate the activities of the AuI complexes for both Gram-negative and Gram-positive bacteria. Moreover, these analogues had mammalian cell toxicities either similar to or lower than that of auranofin.
Total Synthesis of a Densely Functionalized Plesiomonas shigelloides Serotype 51 Aminoglycoside Trisaccharide Antigen
Qin, Chunjun,Schumann, Benjamin,Zou, Xiaopeng,Pereira, Claney L.,Tian, Guangzong,Hu, Jing,Seeberger, Peter H.,Yin, Jian
supporting information, p. 3120 - 3127 (2018/03/08)
Plesiomonas shigelloides, a pathogen responsible for frequent outbreaks of severe travelers' diarrhea, causes grave extraintestinal infections. Sepsis and meningitis due to P. shigelloides are associated with a high mortality rate as antibiotic resistance increases and vaccines are not available. Carbohydrate antigens expressed by pathogens are often structurally unique and are targets for developing vaccines and diagnostics. Here, we report a total synthesis of the highly functionalized trisaccharide repeating unit 2 from P. shigelloides serotype 51 from three monosaccharides. A judicious choice of building blocks and reaction conditions allowed for the four amino groups adorning the sugar rings to be installed with two N-acetyl (Ac) groups, rare acetamidino (Am), and d-3-hydroxybutyryl (Hb) groups. The strategy for the differentiation of amino groups in trisaccharide 2 will serve well for the syntheses of other complex glycans.
Modular automated solid phase synthesis of dermatan sulfate oligosaccharides
Kandasamy, Jeyakumar,Schuhmacher, Frank,Hahm, Heung Sik,Klein, James C.,Seeberger, Peter H.
supporting information, p. 1875 - 1877 (2014/02/14)
Dermatan sulfates are glycosaminoglycan polysaccharides that serve a multitude of biological roles as part of the extracellular matrix. Orthogonally protected d-galactosamine and l-iduronic acid building blocks and a photo-cleavable linker are instrumental for the automated synthesis of dermatan sulfate oligosaccharides. Conjugation-ready oligosaccharides were obtained in good yield.
Glycoconjugates and use thereof as vaccine against Shigella flexneri serotype 3a and X
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Page/Page column 29, (2014/09/03)
The present invention relates to compounds derived from sugars which reproduce the epitopes of Shigella flexneri serotypes 3a and X and to the use thereof for the preparation of vaccine compositions. More specifically, the subject matter of the present in
Synthesis and scalable conversion of L-iduronamides to heparin-related Di- and tetrasaccharides
Hansen, Steen U.,Miller, Gavin J.,Barath, Marek,Broberg, Karl R.,Avizienyte, Egle,Helliwell, Madeleine,Raftery, James,Jayson, Gordon C.,Gardiner, John M.
, p. 7823 - 7843 (2013/01/15)
A diastereomerically pure cyanohydrin, preparable on kilogram scale, is efficiently converted in one step into a novel L-iduronamide. A new regioselective acylation of this iduronamide and a new mild amide hydrolysis method mediated by amyl nitrite enable
Multi-gram synthesis of a hyaluronic acid subunit and synthesis of fully protected oligomers
Virlouvet, Mickael,Gartner, Michael,Koroniak, Katarzyna,Sleeman, Jonathan P.,Braese, Stefan
supporting information; experimental part, p. 2657 - 2662 (2011/01/05)
Fully protected tetra-, hexa- and octasaccharides of hyaluronic acid were synthesized on a scale of several 100 mg up to gram quantities using allyl (methyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)- (1→3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D- glucopyranoside as a key building block. This disaccharide was subjected to deprotection, then glycosylation via the trichloroacetimidate method was employed to achieve the formation of the oligosaccharides.
CARBOHYDRATE BASED TOLL-LIKE RECEPTOR (TLR) ANTAGONISTS
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Page/Page column 21, (2009/09/07)
The invention provides carbohydrate based compounds, methods of preparation, and compositions useful for modulating signaling through Toll-like receptors. The methods involve contacting a TLR-expressing cell with a carbohydrate based compound of the inven
