102339-89-9Relevant academic research and scientific papers
The synthesis of rare earth metal-doped upconversion nanoparticles coated with d-glucose or 2-deoxy-d-glucose and their evaluation for diagnosis and therapy in cancer
Sharma, K. Shitaljit,Thoh, Maikho,Dubey, Akhil K.,Phadnis, Prasad P.,Sharma, Deepak,Sandur, Santosh K.,Vatsa, Rajesh K.
, p. 13834 - 13842 (2020)
Rare earth metal-doped upconversion nanoparticles (UCNPs) are emerging as a new class of biomedical imaging materials due to their higher energy anti-Stokes shift, high optical penetration depth and long term repetitive imaging. In the present study, upconversion nanoparticles based on NaYF4 doped with thulium (Tm) and ytterbium (Yb) were prepared via a thermolysis method using oleic acid as a capping agent and 1-octadecene as a solvent. The X-ray diffraction pattern of the synthesized nanoparticles was found to match the standard hexagonal phase. The nanoparticles were coated with silica using tetraethyl orthosilicate (TEOS) and in order to avoid agglomeration, IGEPAL CO-520 was used as the surfactant. The coatings of SiO2 over NaYF4 were confirmed by the TEM image and XRD pattern. NaYF4@SiO2 was further functionalized by the addition of (3-aminopropyl)trimethoxysilane (APTMS) followed by either d-glucose or 2-deoxy-d-glucose (2-DG). UCNPs-d-glucose and UNCPs-2DG were examined for cell viability (MCF-7 cells) by MTT assay. The cellular uptake of UCNPs in MCF-7 cells was seen in terms of emission of a blue light. Furthermore, the uptake rate of UCNPs coated with 2-deoxy-d-glucose was found to be much faster than that of UCNPs alone under d-glucose starved conditions. The functionalization of UCNPs with 2-deoxy-d-glucose (2-DG) not only increased the uptake of nanoparticles, but also blocked the glycolysis pathway resulting in the inhibition of tumor growth as 2-deoxy-d-glucose (2-DG) is mimicking the d-glucose. The results are indicative that these upconversion nanoparticles may find applications in bio-imaging, removal of tumor by precision surgery, therapy and targeted drug delivery. This journal is
Directed interactions of block copolypept(o) ides with mannose-binding receptors: Peptomicelles targeted to cells of the innate immune system
Heller, Philipp,Mohr, Nicole,Birke, Alexander,Weber, Benjamin,Reske-Kunz, Angelika,Bros, Matthias,Barz, Matthias
, p. 63 - 73 (2015)
Core-shell structures based on polypept(o)ides combine stealth-like properties of the corona material polysarcosine with adjustable functionalities of the polypeptidic core. Mannose-bearing block copolypept(o)ides (PSar-block-PGlu(OBn)) have been synthesized using 11-amino-3,6,9-trioxa-undecyl-2,3,4,6-tetra-O-acetyl-O-α-D-mannopyranoside as initiator in the sequential ring-opening polymerization of α-amino acid N-carboxyanhydrides. These amphiphilic block copolypept(o)ides self-assemble into multivalent PeptoMicelles and bind to mannose-binding receptors as expressed by dendritic cells. Mannosylated micelles showed enhanced cell uptake in DC 2.4 cells and in bone marrow-derived dendritic cells (BMDCs) and therefore appear to be a suitable platform for immune modulation.
Synthesis of C3-Neoglycosides of digoxigenin and their anticancer activities
Li, Xiao-san,Ren, Yi-chang,Bao, Yu-zhou,Liu, Jie,Zhang, Xiao-kun,Zhang, You-wei,Sun, Xue-Long,Yao, Xin-sheng,Tang, Jin-Shan
, p. 252 - 262 (2018)
Cardiac glycosides exhibit significant anticancer effects and the glycosyl substitution at C3 position of digoxigenin is pivotal for their biological activity. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and explore more potent anticancer agents, a series of C3-O-neoglycosides and C3-MeON-neoglycosides of digoxigenin were synthesized by the Koenigs-Knorr and neoglycosylation method, respectively. In addition, digoxigenin bisdigitoxoside and monodigitoxoside were prepared from digoxin by sodium periodate (NaIO4) oxidation and 6-aminocaproic acid hydrolysis. The SAR analysis revealed that C3-O-neoglycosides of digoxigenin exhibited stronger cytotoxicity and induction of Nur77 expression of tumor cells than C3-MeON-neoglycosides. Also, 3β-O-glycosides exhibited stronger anticancer effects than 3α-O-glycosides. Among them, 3β-O-(β-L-fucopyranosyl)-digoxigenin (3i) showed the highest activity on induction of Nur77 expression and translocation from the nucleus to cytoplasm, leading to cancer cell apoptosis.
High-yielding microwave-assisted synthesis of triazole-linked glycodendrimers by copper-catalyzed [3+2] cycloaddition
Joosten, John A. F.,Tholen, Niels T. H.,Ait El Maate, Fatna,Brouwer, Arwin J.,Wilma Van Esse,Rijkers, Dirk T. S.,Liskamp, Rob M. J.,Pieters, Roland J.
, p. 3182 - 3185 (2005)
A facile and high-yielding synthesis of multivalent 1,4-disubstituted 1,2,3-triazole-linked glycodendrimers is described. Azido carbohydrates are linked by a CuI-catalyzed [3+2] cycloaddition reaction to dendritic acetylenes using microwave irradiation. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Control of Stem-Cell Behavior by Fine Tuning the Supramolecular Assemblies of Low-Molecular-Weight Gelators
Latxague, Laurent,Ramin, Michael A.,Appavoo, Ananda,Berto, Pierre,Maisani, Mathieu,Ehret, Camille,Chassande, Olivier,Barthélémy, Philippe
, p. 4517 - 4521 (2015)
Controlling the behavior of stem cells through the supramolecular architecture of the extracellular matrix remains an important challenge in the culture of stem cells. Herein, we report on a new generation of low-molecular-weight gelators (LMWG) for the culture of isolated stem cells. The bola-amphiphile structures derived from nucleolipids feature unique rheological and biological properties suitable for tissue engineering applications. The bola-amphiphile-based hydrogel scaffold exhibits the following essential properties: it is nontoxic, easy to handle, injectable, and features a biocompatible rheology. The reported glycosyl-nucleoside bola-amphiphiles (GNBA) are the first examples of LMWG that allow the culture of isolated stem cells in a gel matrix. The results (TEM observations and rheology) suggest that the supramolecular organizations of the matrix play a role in the behavior of stem cells in 3D environments.
Mild synthesis of disaccharidic 2,3-enopyranosyl cyanides and 2-C-2-deoxy pyranosyl cyanides with Hg(CN)2/HgBr2/TMSCN
Franz, Andreas H.,Wei, YiQiu,Samoshin, Vyacheslav V.,Gross, Paul H.
, p. 7662 - 7669 (2002)
Lewis acid-catalyzed dimerization of mono- and disaccharidic per-O-acetylated glycals gave di- and tetrasaccharidic O-acetylated C-glycosides, respectively. 2,3-Enopyranosyl cyanides were obtained from per-O-acetylated glycals by a new, mild anomeric SN′-acetoxy displacement with Hg(CN)2/HgBr2/TMSCN. Per-O-acetylated 2-C-2-deoxy-pyranoses were converted into pyranosyl cyanides by the same reagent. An unprecedented acetic acid elimination from dimers with D-galacto- and L-fuco-configurations accompanied the SN-displacement under those conditions. A new set of 1H NMR coupling constants for 2,3-enopyranosyl systems was used for configurational assignment of complicated tetrasaccharide mimics.
Determination of the absolute configuration of monosaccharides using (+) or (-) 2-tert-butyl-2-methyl-1,3-benzodioxole-4- carboxylic acid and high-resolution 1H-n.m.r. spectroscopy
Nishida,Kumagai,Kamiyama,Ohrui,Meguro
, p. 63 - 73 (1991)
Reaction of (-) 2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid with per-O-acetyl-D- and L-glucopyranosyl bromides yielded diastereomeric per-O-acetylated glycopyranosyl 2-tert-butyl-2-methyl-1,3-benzodiazole-4-carboxylates. Their 1H-n.m.r. signals, especially the strong singlet peaks of tert-Bu and Me groups in the 1-ester portion were diagnostic for the determination of the D,L-configuration and optical purity of monosaccharides. Reaction of (-)2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid with per-O-acetyl-D-and L-glucopyranosyl bromides yielded diastereomeric per-O-acetylated glycopyranosyl 2-tert-butyl-2-methyl-1, 3-benzodiazole-4-carboxylates. Their H-n.m.r. signals, especially the strong singlet peaks of tert-bu and Me groups in the 1-ester portion were diagnostic for the determination of the D,L-configuration and optical purity of monosaccharides.
A simple protocol for the synthesis of triazole-linked cyclic glycopeptidomimetics: A sequential Ugi-MCR and azide-alkyne cycloaddition approach
Samarasimhareddy,Hemantha, Hosahalli P.,Sureshbabu, Vommina V.
, p. 3104 - 3107 (2012)
Sequential combination of Ugi-MCR and click chemistry has been employed for the synthesis of triazole linked cyclic glycopeptidomimetics. The protocol employs Poc-amino alkyl isonitriles, sugar-1-amines, azido acids, and simple aldehydes as precursors. The dual nature of the propargyloxycarbonyl (Poc) group was explored for amine protection as well as cycloaddition with an azide. All the cyclic glycopeptidomimetics are isolated and characterized.
Thio-sugars. Part 5: From D-glucal to 3-deoxy-(1→2)-2-S-thiodisaccharides through isolevoglucosenone-a simple approach
Witczak, Zbigniew J.,Chen, Hong,Kaplon, Peter
, p. 519 - 532 (2000)
A new synthesis of isolevoglucosenone and its stereoselective functionalization into 3-deoxy-(1-2)-2-S-thiodisaccharides is described. The base-catalyzed conjugate addition of 1-thiosugars to isolevoglucosenone followed by the reduction of the C-4 keto function constitute a new two-step general approach to these classes of biologically important thio-sugars. Copyright (C) 2000 Elsevier Science Ltd.
Phosphatidylinositol 3-phosphate mimics based on a sulfoquinovose scaffold: Synthesis and evaluation as protein kinase B inhibitors
Gabrielli, Luca,Calloni, Ilaria,Donvito, Giulia,Costa, Barbara,Arrighetti, Noemi,Perego, Paola,Colombo, Diego,Ronchetti, Fiamma,Nicotra, Francesco,Cipolla, Laura
, p. 5962 - 5967 (2014)
New sulfoquinovose analogues of phosphatidylinositol 3-phosphate have been synthesised based on a sulfoquinovose scaffold as potential protein kinase B (PKB) inhibitors. The synthetic strategy involved the introduction into glucose of a thioacetate group at the 6-position and of an azide group at the anomeric position as precursors of the sulfonate and phosphoramidate moieties present in the final compounds. The synthesised compounds were tested in vitro on isolated PKB by means of ELISA assays and for their anti-proliferative activity against the human ovarian carcinoma cell line IGROV-1. Sulfoquinovose derivatives 2b and 2c showed inhibitory activity in the low micromolar range.
