- Profiling of: Haemophilus influenzae strain R2866 with carbohydrate-based covalent probes
-
We demonstrate the application of four covalent probes based on anomerically pure d-galactosamine and d-glucosamine scaffolds for the profiling of Haemophilus influenzae strain R2866. The probes have been used successfully for the labelling of target prot
- Metier, Camille,Dow, Jennifer,Wootton, Hayley,Lynham, Steven,Wren, Brendan,Wagner, Gerd K.
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p. 476 - 485
(2021/01/29)
-
- Design, synthesis and antimicrobial evaluation of novel glycosylated-fluoroquinolones derivatives
-
Herein we report the design, synthesis and biological evaluation of structurally modified ciprofloxacin, norfloxacin and moxifloxacin standard drugs, featuring amide functional groups at C-3 of the fluoroquinolone scaffold. In vitro antimicrobial testing against various Gram-positive bacteria, Gram-negative bacteria and fungi revealed potential antibacterial and antifungal activity. Hybrid compounds 9 (MIC 0.2668 ± 0.0001 mM), 10 (MIC 0.1358 ± 00025 mM) and 13 (MIC 0.0898 ± 0.0014 mM) had potential antimicrobial activity against a fluoroquinolone-resistant Escherichia coli clinical isolate, compared to ciprofloxacin (MIC 0.5098 ± 0.0024 mM) and norfloxacin (MIC 0.2937 ± 0.0021 mM) standard drugs. Interestingly, compound 10 also exerted potential antifungal activity against Candida albicans (MIC 0.0056 ± 0.0014 mM) and Penicillium chrysogenum (MIC 0.0453 ± 0.0156 mM). Novel derivatives and standard fluoroquinolone drugs exhibited near-identical cytotoxicity levels against L6 muscle cell-line, when measured using the MTT assay.
- Mohammed, Aya A. M.,Okechukwu, Patrick N.,Shehadeh, Mayadah B.,Suaifan, Ghadeer A. R. Y.
-
-
- GOLD COMPOSITIONS AND METHODS OF USE THEREOF
-
Gold compounds and pharmaceutically acceptable salts thereof are disclosed. Certain compounds and salts are active as antibacterial, antifungal, and/or anti-parasitic agents. The disclosure provides pharmaceutical compositions containing the gold compounds. Methods of using the gold compounds to treat bacterial infections are disclosed.
- -
-
Paragraph 0089; 0090
(2020/03/05)
-
- 1,8-NAPHTHYRIDINE GLUCOSAMINE DERIVATIVES, THEIR USE IN THE TREATMENT OF MICROBIAL INFECTIONS, AND A METHOD FOR PREPARATION
-
The present disclosure provides a compound of Formula (I) or any pharmaceutically acceptable salt thereof for use in treating a microbial infection in a subject, a method for preparing the same, and a pharmaceutical composition thereof: (I) wherein R
- -
-
Paragraph 049-050
(2020/06/10)
-
- GLYCOSYLATED 3-SUBSTITUTED FLUOROQUINOLONE DERIVATIVES, PREPARATION METHODS THEREOF, AND THEIR USE IN THE TREATMENT OF ANTIMICROBIAL INFECTIONS
-
The present disclosure relates to 3-substituted fluoroquinolone derivatives, and more particularly to glycosylated 3-substitutred fluoroquinolone derivatives, methods of preparation thereof, and uses thereof for treating microbial infections.
- -
-
Paragraph 036; 037
(2020/10/20)
-
- Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34
-
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.
- Ahadi, Somayeh,Awan, Shahid I.,Werz, Daniel B.
-
-
- BIVALENT TARGETED CONJUGATES
-
The invention provides conjugates that comprise a bivalent targeting moiety, a nucleic acid, and optional linking groups as well as synthetic intermediates and synthetic methods useful for preparing the conjugates, compositions comprising the bidentate targeting ligands and the conjugates, as well as methods for targeting therapeutic nucleic acids with the bidentate conjugates. The conjugates are useful to target therapeutic nucleic acids.
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-
Page/Page column 38; 39
(2020/05/28)
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- THERAPEUTIC METHODS
-
The invention provides methods and compositions for delivering a nucleic acid to a cell or the cytosol of the target cell. The method includes contacting the cell with, 1) a membrane-destabilizing polymer; and 2) a nucleic acid conjugate. The nucleic acid conjugate includes a targeting ligand bound to an optional linker and a nucleic acid.
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-
Page/Page column 204; 209-210
(2020/05/28)
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- Design, synthesis, and biological evaluation of 1,8-naphthyridine glucosamine conjugates as antimicrobial agents
-
In the quest for discovering potent antimicrobial agents with lower toxicity, we envisioned the design and synthesis of nalidixic acid-D-(+)-glucosamine conjugates. The novel compounds were synthesized and evaluated for their in vitro antimicrobial activi
- Mohammed, Aya A. M.,Suaifan, Ghadeer A. R. Y.,Shehadeh, Mayadah B.,Okechukwu, Patrick N.
-
p. 179 - 186
(2019/01/04)
-
- Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens
-
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.
- Wu, Bin,Yang, Xiaojian,Yan, Mingdi
-
supporting information
p. 7751 - 7768
(2019/09/10)
-
- Design, synthesis and biological evaluation of novel flavone Mannich base derivatives as potential antibacterial agents
-
Abstract: A series of novel Mannich base derivatives of flavone containing benzylamine moiety was synthesized using the Mannich reaction. The results of antifungal activity are not ideal, but its antifungal effect has a certain increase compared to flavonoids. After that, four bacteria were used to test antibacterial experiments of these compounds; compound 5g (MIC = 0.5, 0.125?mg/L) showed significant inhibitory activity against Staphylococcus aureus and Salmonella gallinarum compared with novobiocin (MIC = 2, 0.25?mg/L). Compound 5s exhibited broad spectrum antibacterial activity (MIC = 1, 0.5, 2, 0.05?mg/L) against four bacteria. The selected compounds 5g and 5s exhibit potent inhibition against Topo II and Topo IV with IC50 values (0.25–16?mg/L). Molecular docking model showed that the compounds 5g and 5s can bind well to the target by interacting with amino acid residues. It will provide some valuable information for the commercial antibacterial agents. Graphical Abstract: [Figure not available: see fulltext.].
- Lv, Xian-Hai,Liu, Hao,Ren, Zi-Li,Wang, Wei,Tang, Feng,Cao, Hai-Qun
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p. 299 - 306
(2018/09/20)
-
- Synthesis, Optimization, and Evaluation of Glycosylated Naphthalimide Derivatives as Efficient and Selective Insect β- N-Acetylhexosaminidase OfHex1 Inhibitors
-
Insect chitinolytic β-N-acetylhexosaminidase OfHex1, from the agricultural pest Ostrinia furnacalis (Guenée), is considered as a potential target for green pesticide design. In this study, rational molecular design and optimization led to the synthesis of compounds 15r (Ki = 5.3 μM) and 15y (Ki = 2.7 μM) that had superior activity against OfHex1 than previously reported lead compounds. Both compounds 15r and 15y had high selectivity toward OfHex1 over human β-N-acetylhexosaminidase B (HsHexB) and human O-GlcNAcase (hOGA). In addition, to investigate the basis for the potency of glycosylated naphthalimides against OfHex1, molecular docking and molecular dynamics simulations were performed to study possible binding modes. Furthermore, the in vivo biological activity of target compounds with efficient OfHex1 inhibitory potency was assayed against Myzus persicae, Plutella xylostella, and O. furnacalis. This present work indicates that glycosylated naphthalimides can be further developed as potential pest control and management agents targeting OfHex1.
- Shen, Shengqiang,Dong, Lili,Chen, Wei,Wu, Renjie,Lu, Huizhe,Yang, Qing,Zhang, Jianjun
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p. 6387 - 6396
(2019/06/07)
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- Total Synthesis of a Densely Functionalized Plesiomonas shigelloides Serotype 51 Aminoglycoside Trisaccharide Antigen
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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.
- Qin, Chunjun,Schumann, Benjamin,Zou, Xiaopeng,Pereira, Claney L.,Tian, Guangzong,Hu, Jing,Seeberger, Peter H.,Yin, Jian
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supporting information
p. 3120 - 3127
(2018/03/08)
-
- 4-Hydroxy-3-nitro-5-ureido-benzenesulfonamides Selectively Target the Tumor-Associated Carbonic Anhydrase Isoforms IX and XII Showing Hypoxia-Enhanced Antiproliferative Profiles
-
Human carbonic anhydrases (CA, EC, 4.2.1.1) IX and XII are overexpressed in cancer cells as adaptive response to hypoxia and acidic conditions characteristic of many tumors. In addition, hypoxia facilitates the activity of specific oxido-reductases that may be exploited to selectively activate bioreductive prodrugs. Here, new selective CA IX/XII inhibitors, as analogues of the antitumor phase II drug SLC-0111 are described, namely ureido-substituted benzenesulfonamides appended with a nitro-aromatic moiety to yield an antiproliferative action increased by hypoxia. These compounds were screened for the inhibition of the ubiquitous hCA I/II and the target hCA IX/XII. Six X-ray crystallographies with CA II and IX/mimic allowed for the rationalization of the compounds inhibitory activity. The effects of some such compounds on the viability of HT-29, MDA-MB-231, and PC-3 human cancer cell lines in both normoxic and hypoxic conditions were examined, providing the initiation toward the development of hypoxia-activated antitumor CAIs.
- Nocentini, Alessio,Trallori, Elena,Singh, Srishti,Lomelino, Carrie L.,Bartolucci, Gianluca,Di Cesare Mannelli, Lorenzo,Ghelardini, Carla,McKenna, Robert,Gratteri, Paola,Supuran, Claudiu T.
-
supporting information
p. 10860 - 10874
(2019/01/03)
-
- Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters
-
A series of peracylated glycosamine-derived thioureas have been synthesized and their behavior as bifunctional organocatalysts has been tested in the enantioselective nucleophilic addition of formaldehyde tert-butyl hydrazone to aliphatic α-keto esters fo
- Carmona, José A.,Gonzalo, Gonzalo de,Serrano, Inmaculada,Crespo-Pe?a, Ana M.,?imek, Michal,Monge, David,Fernández, Rosario,Lassaletta, José M.
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p. 2993 - 3005
(2017/04/10)
-
- Synthesis of antimicrobial glucosamides as bacterial quorum sensing mechanism inhibitors
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Bacteria communicate with one another and regulate their pathogenicity through a phenomenon known as quorum sensing (QS). When the bacterial colony reaches a threshold density, the QS system induces the production of virulence factors and the formation of biofilms, a powerful defence system against the host's immune responses. The glucosamine monomer has been shown to disrupt the bacterial QS system by inhibiting autoinducer (AI) signalling molecules such as the acyl-homoserine lactones (AHLs). In this study, the synthesis of acetoxy-glucosamides 8, hydroxy-glucosamides 9 and 3-oxo-glucosamides 12 was performed via the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) and N,N′-dicyclohexylcarbodiimide (DCC) coupling methods. All of the synthesized compounds were tested against two bacterial strains, P. aeruginosa MH602 (LasI/R-type QS) and E. coli MT102 (LuxI/R-type QS), for QS inhibitory activity. The most active compound 9b showed 79.1% QS inhibition against P. aeruginosa MH602 and 98.4% against E. coli MT102, while compound 12b showed 64.5% inhibition against P. aeruginosa MH602 and 88.1% against E. coli MT102 strain at 2?mM concentration. The ability of the compounds to inhibit the production of the virulence factor pyocyanin and biofilm formation in the P. aeruginosa (PA14) strain was also examined. Finally, computational docking studies were performed with the LasR receptor protein.
- Biswas, Nripendra N.,Yu, Tsz Tin,Kimyon, ?nder,Nizalapur, Shashidhar,Gardner, Christopher R.,Manefield, Mike,Griffith, Renate,Black, David StC.,Kumar, Naresh
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p. 1183 - 1194
(2017/02/18)
-
- Glucosamide compound and preparation and application thereof
-
The invention relates to a glucosamide compound and a preparation method thereof. The glucosamide compound has a structure as shown in the formula (I). In the formula (I), R is methoxy group, nitro group, amino-group, hydroxyl group, C1-4 alkyl group or halogen, n is the number of substituent groups, and n is 1 or 2. The glucosamide compound is simple to prepare, has excellent plant induced resistance activity, and can be used as a plant induced resistance agent for controlling cucumber bacterial angular leaf spot, cucumber target leaf spot and tomato late blight. The invention also relates to a plant induced resistant agent containing the compound.
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-
-
- 2-Isocyano glucose used in Ugi four-component reaction: An approach to enhance inhibitory effect against DNA oxidation
-
The Ugi four-component-reaction (Ugi 4CR) allowed synthesizing bisamide from carboxylic acid, aldehyde, amine, and isocyanide in one-pot operation. However, introducing 2-isocyano glucose into the Ugi 4CR and investigating the inhibitory effects of Ugi adducts against radical-induced oxidation of DNA remained technical challenges. We herein applied 2-isocyano glucose (acetylation of hydroxy groups) to perform a catalyst-free Ugi 4CR at room temperature. The gallic, ferulic, caffeic, or p-hydroxybenzoic acids, aniline (or benzylamine and p-aminophenol), and formaldehyde acted as reagents. In the case of inhibiting DNA oxidations induced by 2,2’-azobis(2-amidinopropane hydrochloride) (AAPH), hydroxy radical, and Cu2+/glutathione, the Ugi adduct containing glucose moiety exhibited higher antioxidative activities than the structural analog without glucose moiety involved. It was also proved that high antioxidative property was owing to hydroxy groups in glucose moiety. Therefore, sugar-appended Ugi adducts might hold promising inhibitors for DNA oxidation.
- Zhao, Peng-Fei,Liu, Zai-Qun
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p. 458 - 466
(2017/05/05)
-
- Method for preparing 2-deoxy-D-glucose
-
The invention discloses a method for preparing 2-deoxy-D-glucose. According to the method, D-glucosamine which is low in price and easy to obtain serves as a starting material, p-anisaldehyde is used for protecting amino, pyridine serves as a solvent unde
- -
-
Paragraph 0024-0027
(2017/08/28)
-
- Chemical Synthesis of Modified Hyaluronic Acid Disaccharides
-
Herein we report a chemical synthesis towards new modified hyaluronic acid oligomers by using only commercially available d-glucose and d-glucosamine hydrochloride. The various protected hyaluronic acid disaccharides were synthesized bearing new functional groups at C-6 of the β-d-glucuronic acid moiety with a view to structure-related biological activity tests. The orthogonal protecting group pattern allows ready access to the corresponding higher oligomers. Also, 1H NMR studies of the new derivatives demonstrated the effect of the various functional groups on the intramolecular electronic environment.
- Mende, Marco,Nieger, Martin,Br?se, Stefan
-
supporting information
p. 12283 - 12296
(2017/09/14)
-
- Acetyl glucosamine imidazolemethanol -2, 4, 5-Trion synthetic method of use with bacteriostatic
-
The invention discloses acetylglucosamine imidazol-2,4,5-trione, and further discloses a synthetic method of the acetylglucosamine imidazol-2,4,5-trione and antimicrobial application. The synthetic method is quick, efficient and high in productivity, and
- -
-
Paragraph 0030; 0031
(2017/02/23)
-
- LANTHANIDE CLUSTERS AND METHODS OF USE THEREOF
-
The present invention is directed to multinuclear lanthanides chiral clusters, based on phenyl-oxazoline-amide (POxA) ligands, and to methods of use thereof. The chiral clusters of this invention are highly fluorescent with high stability.
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-
-
- Design, synthesis and in vivo evaluation of novel glycosylated sulfonylureas as antihyperglycemic agents
-
Sulphonylurea compounds have versatile activities such as antidiabetic, diuretic, herbicide, oncolytic, antimalarial, antifungal and anticancer. The present study describes the design, synthesis and in vivo testing of novel glycosylated aryl sulfonylurea compounds as antihyperglycaemic agents in streptozocine-induced diabetic mice. The rational for the introduction of the glucosamine moiety is to enhance selective drug uptake by pancreatic β-cells in order to decrease the cardiotoxic side effect commonly associated with sulfonylurea agents. 2-Deoxy-2-(4-chlorophenylsulfonylurea)-D-glucopyranose was found to be the most potent antihyperglycaemic agents among the synthesized compounds in diabetic mice. This investigation indicates the importance of this novel class as potential antihyperglycaemic agents.
- Suaifan, Ghadeer A. R. Y.,Shehadeh, Mayadah B.,Darwish, Rula M.,Al-Ijel, Hebah,Abbate, Vincenzo
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p. 20063 - 20078
(2015/12/23)
-
- Synthesis of NAG-thiazoline-derived inhibitors for β-N-acetyl-d-hexosaminidases
-
Abstract β-N-Acetyl-d-hexosaminidases are responsible for the metabolism of glycoconjugates in diverse physiological processes that are important targets for medicine and pesticide development. Fourteen new NAG-thiazoline derivatives were synthesized by cyclization and click reaction using d-glucosamine hydrochloride as the starting material. All the compounds created were characterized by NMR and HRMS spectra. A preliminary bioassay, using four enzymes from two β-N-acetyl-d-hexosaminidase families, showed that most of the compounds synthesized exhibit selective inhibition of GH84 β-N-acetyl-d-hexosaminidase. Among the compounds tested, compounds 5a (IC50=12.6 μM, hOGA) and 5e (IC50=12.5 μM, OfOGA) proved to be a highly selective and potent inhibitor.
- Kong, Hanchu,Chen, Wei,Lu, Huizhe,Yang, Qing,Dong, Yanhong,Wang, Daoquan,Zhang, Jianjun
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p. 135 - 144
(2015/07/07)
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- Synthesis and characterization of N-acyl-tetra-O-acyl glucosamine derivatives
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Novel 1,3,4,6-tetra-O-acyl-N-acyl-d-glucosamine derivatives were synthesized from glucosamine hydrochloride (GlcN·HCl) by the acylation with pyridine as a catalyst. A derivative of tetra-O-acetyl glucosamine contained ketoprofen, a non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic effects, was first synthesized. In analysis of the NMR spectra, the ratio of α:β-anomer showed that penta-acyl-d- glucosamine derivatives and N-acetylated glucosamines containing O-acyl groups have been only the α-anomer. Meanwhile, both the intermediates and the glucoconjugate compound of ketoprofen have only the β-anomer.
- Dang, Chi-Hien,Nguyen, Cong-Hao,Nguyen, Thanh-Danh,Im, Chan
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p. 6239 - 6245
(2014/01/23)
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- Glycoconjugates and use thereof as vaccine against Shigella flexneri serotype 3a and X
-
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
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Page/Page column 27-28
(2014/09/03)
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- Synthesis of unnatural N-glycosyl α-amino acids via Petasis reaction
-
A convenient and efficient protocol for the synthesis of unnatural N-glycosyl α-amino acids was developed. Condensation of 1,3,4,6-tetra-O-actyl-β-d-glucosamine hydrochloride, alkenyl boronic acid, and glyoxylic acid was achieved in CH2Cl2
- Tao, Chuan-Zhou,Zhang, Zhong-Tang,Wu, Jian-Wei,Li, Rong-Hua,Cao, Zhi-Ling
-
supporting information
p. 532 - 534
(2014/05/06)
-
- Synthesis and characterisation of glucosamine-NSAID bioconjugates
-
Strategies to couple non-steroidal anti-inflammatory drugs (NSAIDs) to a glucosamine hydrochloride salt via an amino acid linker are investigated and a series of novel NSAID-glucosamine bioconjugates have been prepared. This journal is
- Jones, Rachel A.,Thillier, Yann,Panda, Siva S.,Rivera Rosario, Nicole,Hall, C. Dennis,Katritzky, Alan R.
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p. 8325 - 8335
(2015/01/08)
-
- Diazo group as a new chemical reporter for bioorthogonal labelling of biomolecules
-
Diazoacetyl groups have been shown to undergo spontaneous cycloaddition reactions with strained alkenes and alkynes. The rates of reaction are similar to the equivalent reactions of azide groups. This allows diazo groups to be used as bioorthogonal reporter groups. This is demonstrated by fluorescent labelling of a diazoacetylated protein and of cell-surface glycans via metabolic incorporation of a diazoacetylated sugar. This journal is
- Josa-Culler, Laia,Wainman, Yelena A.,Brindle, Kevin M.,Leeper, Finian J.
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p. 52241 - 52244
(2015/01/09)
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- Study on synthesis of 2-(substituted benzylidene)amino-2-deoxy-1,3,4,6- tetra-O-acetyl-β-D-glucopyranoses from D-glucosamine
-
The conditions in catalysts and in reaction time for the reaction of protected β-D-glucosamine hydrochloride with different substituted benzaldehydes have been investigated in the presence of various inorganic and organic bases. Based on obtained results,
- Thanh, Nguyen Dinh,Quoc, Nguyen Van
-
-
- PERMEABLE GLYCOSIDASE INHIBITORS AND USES THEREOF
-
Disclosed are compounds of Formula (I), wherein each substituent of Formula (I) is defined as in the specification, pharmaceutical formulations comprising these compounds which are useful as 0-linked N-acetylglucosaminidase (O-GlcNAcase) inhibitors, and thus are useful for the treatment of certain disorders such as Alzheimer' s disease including reducing NFTs and/or hyperphosphorylated tau. Also disclosed is the use of the compounds as O-GlcNAcase imaging agents.
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Page/Page column 28; 29
(2013/12/03)
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- PERMEABLE GLYCOSIDASE INHIBITORS AND USES THEREOF
-
The present invention is directed to compounds and pharmaceutical formulations comprising these compounds which are useful as O-linked N-acetylglucosaminidase (O-GlcNAcase) inhibitors, and thus may be useful for the treatment of certain disorders such as Alzheimer's disease including reducing NFTs and/or hyperphosphorylated tau. The invention is also directed to use of the compounds as O-GlcNAcase imaging agents.
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Page/Page column 28; 29
(2013/12/03)
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- Inhibition of Mucin-type O-glycosylation through metabolic processing and incorporation of N-thioglycolyl-d-galactosamine peracetate (Ac 5GalNTGc)
-
Mucin-type O-glycans form one of the most abundant and complex post-translational modifications (PTM) on cell surface proteins that govern adhesion, migration, and trafficking of hematopoietic cells. Development of targeted approaches to probe functions o
- Agarwal, Kavita,Kaul, Rachna,Garg, Monika,Shajahan, Asif,Jha, Saroj Kumar,Sampathkumar, Srinivasa-Gopalan
-
supporting information
p. 14189 - 14197
(2013/10/21)
-
- MAGNETIC LABELING OF BACTERIA
-
The present invention provides novel methods of magnetically labeling a bacterial cell by contacting the call with an affinity ligand and subsequently contacting the cell with a magnetic agent, where the affinity ligand and magnetic agent include bioorthogonally reactive groups that can react with each other to form a covalent bond. Compounds, compositions, kits and applications of the method are also described.
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-
-
- SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF
-
The invention is directed to compounds for selectively inhibiting glycosidases, uses of the compounds and pharmaceutical compositions including the compounds, and methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, and/or accumulation or deficiency of O-GlcNAc.
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Page/Page column 35
(2012/05/31)
-
- SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF
-
The invention is directed to compounds for selectively inhibiting glycosidases, uses of the compounds and pharmaceutical compositions including the compounds, and methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, and/or accumulation or deficiency of O-GlcNAc.
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Page/Page column 33
(2012/05/31)
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- PYRANO[3,2-D]THIAZOL DERIVATIVES AND USES THEREOF AS SELECTIVE GLYCOSIDASE INHIBITORS
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Pyrano[3,2-d]thiazol derivatives of formula (I) for selectively inhibiting glycosidases, uses of the compounds and pharmaceutical compositions including the compounds are disclosed. Methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc are also provided.
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Page/Page column 34; 35
(2012/05/31)
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- Chemoenzymatic synthesis of uridine diphosphate-GlcNAc and uridine diphosphate-GalNAc analogs for the preparation of unnatural glycosaminoglycans
-
Eight N-acetylglucosamine-1-phosphate and N-acetylgalactosamine-1-phosphate analogs have been synthesized chemically and were tested for their recognition by the GlmU uridyltransferase enzyme. Among these, only substrates that have an amide linkage to the C-2 nitrogen were transferred by GlmU to afford their corresponding uridine diphosphate(UDP)-sugar nucleotides. Resin-immobilized GlmU showed comparable activity to nonimmobilized GlmU and provides a more facile final step in the synthesis of an unnatural UDP-donor. The synthesized unnatural UDP-donors were tested for their activity as substrates for glycosyltransferases in the preparation of unnatural glycosaminoglycans in vitro. A subset of these analogs was useful as donors, increasing the synthetic repertoire for these medically important polysaccharides.
- Masuko, Sayaka,Bera, Smritilekha,Green, Dixy E.,Weiwer, Michel,Liu, Jian,Deangelis, Paul L.,Linhardt, Robert J.
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p. 1449 - 1456
(2012/03/11)
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- Prednisolone succinate-glucosamine conjugate: Synthesis, characterization and in vitro cellular uptake by kidney cell lines
-
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.
- Lin, Yan,Sun, Xun,Gong, Tao,Zhang, Zhi Rong
-
-
- Hybrid stereoisomers of a compact molecular probe based on a jasmonic acid glucoside: Syntheses and biological evaluations
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12-O-β-d-glucopyranosyl jasmonic acid (JAG) shows unique biological activities, including leaf-closing of Samanea saman. It is expected that the mode of action for such regulation is distinct from that of other jasmonates. We developed high-performance compact molecular probes (CMPs) based on JAG that can be used for the FLAG-tagging of JAG target. We synthesized four hybrid-type JAG-CMP stereoisomers (7, ent-7, 8, and ent-8), which are composed of (-)-12-OH-JA (2)/d-galactopyranoside, (-)-2/l-galactopyranoside, (+)-ent-2/d-galactopyranoside, and (+)-ent-2/l-galactopyranoside moieties, respectively, and we examined their biological features, such as the stereospecific induction of shrinkage, rate of the cellular response, and dependence on potassium channel activity. These features of the JAG-CMPs were completely consistent with those of the original JAG. These results indicate the biological equivalence of JAG and the JAG-CMPs. During the course of such biological evaluations, it was revealed that the biological activity of the CMPs is greatly dependent on the d/l-stereochemistry of a glycon moiety. To the best of our knowledge, this is the first study suggesting that the d/l-stereochemistry of the glycon moiety significantly affects the biological activity of the associated glycoside.
- Ueda, Minoru,Yang, Gangqiang,Ishimaru, Yasuhiro,Itabashi, Tetsuya,Tamura, Satoru,Kiyota, Hiromasa,Kuwahara, Shigefumi,Inomata, Sho,Shoji, Mitsuru,Sugai, Takeshi
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p. 5832 - 5843
(2012/11/06)
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- DETECTION OF MYCOBACTERIA
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A method for determining the presence of mycobacteria species in an organism or biological sample, the method comprising adding to the organism or biological sample a probe molecule comprising a substrate and a label, which probe molecule can be incorporated into mycobacteria, the presence of mycobacteria being determined by a detector responsive to the presence of the label, optionally after applying a stimulus; suitable probe molecules include compounds comprising a label and a substrate, which label is can be detected by a detector responsive to the presence of the label, optionally after applying a stimulus, characterised by compound being able to engage with the active site of Antigen 85B (Ag85B) such that it can form simultaneous hydrogen bonds with two or more amino acids in the active site selected from Arg 43, Trp 264, Ser126, His 262 and Leu 42, or the corresponding amino acids in Antigen 85A (Ag85A) or Antigen 85C (Ag85C), at least one of which is with Ser126.
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- Steroid and bile acids amide conjugates with D-glucosamine
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New type of amide conjugates of steroid and bile acids with D-glucosamine 1 and 2 were prepared. Title compounds are prepared via acid chloride or using N-[({[(1E)-1-cyano- 2-ethoxy-2-oxoethylidene]amino}oxy)(dimethylamino) methylidene]-N-methylmethanaminium tetrafluoroborate as condensation agent. They were examined for gelation properties with negative results. Per-O-acetylated D-glucosamine hydrochloride was prepared in one step procedure from D-glucosamine hydrochloride by acetylation in a mixture of acetyl chloride and acetic acid.
- Novakova, Zdena,Tomanova, Jana,Sterbova, Lucie,Drasar, Pavel
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experimental part
p. 65 - 74
(2011/09/21)
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- Synthesis of an Fmoc-threonine bearing core-2 glycan: A building block for PSGL-1 via Fmoc-assisted solid-phase peptide synthesis
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Selectins (L, E, and P) are vascular endothelial molecules that play an important role in the recruitment of leukocytes to inflamed tissue. In this regard, P-Selectin glycoprotein-1 (PSGL-1) has been identified as a ligand for P-Selectin. PSGL-1 binds to
- Krishnamurthy, Venkata R.,Dougherty, Ann,Kamat, Medha,Song, Xuezheng,Cummings, Richard D.,Chaikof, Elliot. L.
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experimental part
p. 1541 - 1547
(2010/08/20)
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- Multi-gram synthesis of a hyaluronic acid subunit and synthesis of fully protected oligomers
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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.
- Virlouvet, Mickael,Gartner, Michael,Koroniak, Katarzyna,Sleeman, Jonathan P.,Braese, Stefan
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supporting information; experimental part
p. 2657 - 2662
(2011/01/05)
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- Nickel-catalyzed stereoselective glycosylation with C(2)- N-substituted benzylidene d-glucosamine and galactosamine trichloroacetimidates for the formation of 1,2-cis-2-amino glycosides. applications to the synthesis of heparin disaccharides, GPI anchor pseudodisaccharides, and α-GalNAc
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The 1,2-cis-2-amino glycosides are key components found within a variety of biologically important oligosaccharides and glycopeptides. Although there are remarkable advances in the synthesis of 1,2-cis-2-amino glycosides, disadvantages of the current state-of-the-art methods include limited substrate scope, low yields, long reaction times, and anomeric mixtures. We have developed a novel method for the synthesis of 1,2-cis-2-amino glycosides via nickel-catalyzed α-selective glycosylation with C(2)-N-substituted benzylidene d-glucosamine and galactosamine trichloroacetimidates. These glycosyl donors are capable of coupling to a wide variety of alcohols to provide glycoconjugates in high yields with excellent levels of α-selectivity. Additionally, only a substoichiometric amount of nickel (5-10 mol %) is required for the reaction to occur at 25 °C. The current nickel method relies on the nature of the nickel-ligand complex to control the α-selectivity. The reactive sites of the nucleophiles or the nature of the protecting groups have little effect on the α-selectivity. This methodology has also been successfully applied to both disaccharide donors and acceptors to provide the corresponding oligosaccharides in high yields and α-selectivity. The efficacy of the nickel procedure has been further applied toward the preparation of heparin disaccharides, GPI anchor pseudodisaccharides, and α-GluNAc/GalNAc. Mechanistic studies suggest that the presence of the substituted benzylidene functionality at the C(2)-amino position of glycosyl donors is crucial for the high α-selectivity observed in the coupling products. Additionally, the α-orientation of the C(1)-trichloroacetimidate group on glycosyl donors is necessary for the coupling process to occur.
- Mensah, Enoch A.,Yu, Fei,Nguyen, Hien M.
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supporting information; experimental part
p. 14288 - 14302
(2010/12/19)
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- MOENOMYCIN ANALOGS, METHODS OF SYNTHESIS, AND USES THEREOF
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The present invention provides novel moenomycin analogs as well as pharmaceutical compositions thereof, methods of synthesis, and methods of use in treating an infection by administering an inventive compound to a subject in need thereof. The moenomycin a
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- Synthesis of new optically active D-glucosamine-pyrrole derivatives
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From D-glucosamine hydrochloride was synthesized, for the first time, three new optically active derivatives of D-glucosamine-pyrrole with the pyrrole group unsubstituted in the 2- and 5-positions. New N-benzylpyrrole-D-glucosamine derivatives were also prepared from the same substrate. Georg Thieme Verlag Stuttgart.
- Frontana-Uribe, Bernardo A.,Escarcega-Bobadilla, Martha V.,Juarez-Lagunas, Jorge,Toscano, Ruben A.,De La Mora, Gustavo A. Garcia,Salmon, Manuel
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scheme or table
p. 980 - 984
(2009/12/04)
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- An expeditious and efficient synthesis of β-d-galactopyranosyl-(1→3)-d-N-acetylglucosamine (lacto-N-biose) using a glycosynthase from Thermus thermophilus as a catalyst
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Mutant glycosynthases or transglycosidases obtained from a Thermus thermophilus β-d-glycosidase (TtbGly) efficiently catalyzed the synthesis of β-(1→3)-disaccharides. Unfortunately, this regioselectivity was changed to the β-(1→4) one when N-acetylglucosa
- D'Almeida, Ayite,Ionata, Marina,Tran, Vinh,Tellier, Charles,Dion, Michel,Rabiller, Claude
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scheme or table
p. 1243 - 1246
(2009/11/30)
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- A carbohydrate-linked hypericinic photosensitizing agent
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With respect to an enhanced solubility under physiological conditions, a carbohydrate-containing hypericin-based second-generation photosensitizer was prepared. Its photochemical properties were tested by means of the light-sensitized destruction of bilir
- Zuschrader, Joachim,Schoefberger, Wolfgang,Falk, Heinz
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experimental part
p. 1387 - 1390
(2009/12/06)
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- Influence on the enantioselectivity in allylic alkylation of the anomeric position of the phosphine-amide ligands derived from d-glucosamine
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The synthesis of a new series of chiral phosphine amides derived from d-glucosamine is described. The palladium-catalyzed asymmetric allylic alkylations of racemic (E)-1,3-diphenyl-2-propenyl acetate with dimethyl malonate using these ligands have been in
- Glego?a, Katarzyna,Framery, Eric,Goux-Henry, Catherine,Micha? Pietrusiewicz,Sinou, Denis
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p. 7133 - 7141
(2008/02/07)
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