- Novel targeted anti-tumor nanoparticles developed from folic acid-modified 2-deoxyglucose
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The glucose analog, 2-deoxyglucose (2-DG), specifically inhibits glycolysis of cancer cells and interferes with the growth of cancer cells. However, the excellent water solubility of 2-DG makes it difficult to be concentrated in tumor cells. In this study, a targeted nano-pharmacosome was developed with folic acid-modified 2-DG (FA-2-DG) by using amino ethanol as a cleavable linker. FA-2-DG was able to self-assemble, forming nano-particles with diameters of 10–30 nm. The biological effects were evaluated with cell viability assays and flow cytometry analysis. Compared with a physical mixture of folic acid and 2-DG, FA-2-DG clearly reduced cell viability and resulted in cell cycle arrest. A computational study involving docking simulation suggested that FA-2-DG can dock into the same receptor as folic acid, thus confirming that the structural modification did not affect the targeting performance. The results indicated that the nano-pharmacosome consisting of FA-2-DG can be used for targeting in a nano-drug delivery system.
- Jin, Shaoming,Du, Zhongyao,Ren, Fazheng,Wang, Pengjie,Guo, Huiyuan,Zhang, Hao
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Read Online
- General Strategy for the Synthesis of Rare Sugars via Ru(II)-Catalyzed and Boron-Mediated Selective Epimerization of 1,2- trans-Diols to 1,2- cis-Diols
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Human glycans are primarily composed of nine common sugar building blocks. On the other hand, several hundred monosaccharides have been discovered in bacteria and most of them are not readily available. The ability to access these rare sugars and the corresponding glycoconjugates can facilitate the studies of various fundamentally important biological processes in bacteria, including interactions between microbiota and the human host. Many rare sugars also exist in a variety of natural products and pharmaceutical reagents with significant biological activities. Although several methods have been developed for the synthesis of rare monosaccharides, most of them involve lengthy steps. Herein, we report an efficient and general strategy that can provide access to rare sugars from commercially available common monosaccharides via a one-step Ru(II)-catalyzed and boron-mediated selective epimerization of 1,2-trans-diols to 1,2-cis-diols. The formation of boronate esters drives the equilibrium toward 1,2-cis-diol products, which can be immediately used for further selective functionalization and glycosylation. The utility of this strategy was demonstrated by the efficient construction of glycoside skeletons in natural products or bioactive compounds.
- Li, Xiaolei,Tang, Weiping,Wu, Jicheng
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supporting information
p. 3727 - 3736
(2022/03/02)
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- 3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL
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The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.
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Page/Page column 38
(2021/08/20)
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- Photolabile Protecting Group-Mediated Synthesis of 2-Deoxy-Glycosides
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A green and efficient photolabile protecting group (PPG)-mediated glycosidation approach for the synthesis of 2-deoxy-glycosides is reported. By employing ortho-nitrobenzyl carbonate (oNBC) as PPG, N,N-dimethylformamide (DMF)-modulated SPhosAuNTf2/s
- Li, Xiaoqian,Ma, Zhi,Liu, Rongkun,Hurevich, Mattan,Yang, You
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supporting information
p. 3309 - 3314
(2021/10/14)
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- 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
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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
- Sharma, K. Shitaljit,Thoh, Maikho,Dubey, Akhil K.,Phadnis, Prasad P.,Sharma, Deepak,Sandur, Santosh K.,Vatsa, Rajesh K.
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p. 13834 - 13842
(2020/09/07)
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- Substituted pyrazole compound, preparation method, pharmaceutical composition and applications thereof
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The invention discloses a substituted pyrazole compound represented by a formula I, and a preparation method, a pharmaceutical composition and applications thereof, wherein the compound has characteristics of good stability, excellent solubility, low cytotoxicity and remarkable neuroprotective effect, can effectively prevent and treat nerve cell injury, and is an ideal medicinal compound for preventing or treating cerebral stroke, cerebral embolism, cerebral stroke sequelae, cerebral stroke dyskinesia, mitochondrial encephalomyopathy and amyotrophic lateral sclerosis of spinal cord.
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Paragraph 0331-0334
(2020/03/12)
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- Method for preparing 2-deoxy-D-glucose
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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
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Paragraph 0024-0027
(2017/08/28)
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- Iterative α-glycosylation strategy for 2-deoxy- and 2,6-dideoxysugars: Application to the one-pot synthesis of deoxysugar-containing oligosaccharides
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This paper describes the development of an iterative and α-selective glycosylation method for 2-deoxyglycosyl and 2,6-dideoxythioglycoside donors based on the DMF modulation concept. We used NMR spectroscopy to probe the 2-deoxyglycosyl imidinium intermediate and elucidated the conditions to decrease the formation of glycal and thus to increase the reaction yields. Further elaboration of the glycosylation method opened the gate for an iterative one-pot synthesis of 2-deoxy- and 2,6-dideoxyglycoside-containing oligosaccharides
- Chen, Jiun-Han,Ruei, Jyh-Herng,Mong, Kwok-Kong Tony
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supporting information
p. 1827 - 1831
(2014/04/03)
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- Iterative α-Glycosylation Strategy for 2-Deoxy- and 2,6-Dideoxysugars: Application to the One-Pot Synthesis of Deoxysugar-Containing Oligosaccharides
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This paper describes the development of an iterative and α-selective glycosylation method for 2-deoxyglycosyl and 2,6-dideoxythioglycoside donors based on the DMF modulation concept. We used NMR spectroscopy to probe the 2-deoxyglycosyl imidinium intermediate and elucidated the conditions to decrease the formation of glycal and thus to increase the reaction yields. Further elaboration of the glycosylation method opened the gate for an iterative one-pot synthesis of 2-deoxy- and 2,6-dideoxyglycoside-containing oligosaccharides. An iterative glycosylation method is established for highly reactive 2-deoxyglycosyl donors on the basis of the DMF modulation concept. This method is effective for 2-deoxy- and 2,6-dideoxythioglycosyl donors, and it opens the gate for the one-pot synthesis of deoxysugar-containing oligosaccharides; NIS = N-iodosuccinimide. Tf = trifluoromethylsulfonyl, NAP = 2-naphthylmethyl, STol = p-tolylthio, Bz = benzoyl.
- Chen, Jiun-Han,Ruei, Jyh-Herng,Mong, Kwok-Kong Tony
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supporting information
p. 1827 - 1831
(2015/10/05)
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- HALOGENATED DIDEOXY SUGAR DERIVATES, PREPARATION METHOD AND APPLICATION THEREOF
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A halogenated dideoxy sugar derivative, having the following general structure I wherein X is halogen, R1 and R2 are H or Br; R3 and R4 are OH or OAc. The compounds 1-14 of the current invention has strong inhib
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Page/Page column 6
(2012/11/13)
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- HALOGENATED DIDEOXY SACCHARIDE DERIVATIVES, PREPARATION METHOD AND USE THEREOF
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The current invention is related to a halogenated dideoxy sugar derivative, wherein that the derivative has the following general structure I wherein X is halogen, or R1 and R2 are H or Br; R3 and R4 are OH or O
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Page/Page column 8; 10
(2012/12/13)
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- Synthesis of nonnatural nucleoside diphosphate sugars
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Recently, we reported an efficient chemical method for the synthesis of a variety of naturally occurring nucleoside diphosphate (NDP) sugars. This method, which is based on the cycloSal approach, can also be used, in principle, for the preparation of rare or even nonnatural NDP sugars. Herein, the syntheses of sulfoquinovose-, glucose-6-sulfate-, L-galactose-, and 2-fluoroglycopyranoside- containing NDP sugars are presented, as well as the synthesis of NDP sugars with non-natural nucleosides. The reactions described gavestereoisomerically defined NDP sugars in high yields and short reaction times.
- Wolf, Saskia,Berrio, Rosmirt Molina,Meier, Chris
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scheme or table
p. 6304 - 6313
(2011/12/16)
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- Design of chiral auxiliaries for the allene ether Nazarov cyclization
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A 1,3- or a 1,4-cis axial tert-butyldimethylsilyloxy substituent on the pyranose derived chiral auxiliary for the allene ether Nazarov cyclization leads to products in high optical purity. α-Pyranose and β-pyranose derived auxiliaries lead to enantiomeric products. Copyright
- Banaag, April R.,Tius, Marcus A.
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p. 5328 - 5329
(2008/02/04)
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- Syntheses and biological activities of disaccharide daunorubicins
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Carbohydrate moiety is found in many anticancer nature products. To explore the carbohydrate moiety of daunorubicin in enhancing anticancer efficacy, several daunorubicin derivatives bearing disaccharide (1-8) have been synthesized. Their cytotoxicities w
- Zhang, Guisheng,Fang, Lanyan,Zhu, Lizhi,Aimiuwu, Josephine E.,Shen, Jie,Cheng, Hao,Muller, Mark T.,Lee, Gun Eui,Sun, Duxin,Wang, Peng George
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p. 5269 - 5278
(2007/10/03)
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- PROCESS FOR THE SYNTHESIS OF 2-DEOXY-D-GLUCOSE
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The present invention provides a process for the synthesis of 2-deoxy-D-glucose comprising haloalkoxylation of R-D-Glucal wherein R is selected from H and 3, 4, 6-tri-O-benzyl, to obtain alkyl 2-deoxy-2-halo-R-α/β-D-gluco/mannopyranoside, converting alkyl
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- Efficient Route to 2-Deoxy β-O-Aryl-D-Glycosides via Direct Displacement of Glycosyl Iodides
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(Equation presented) The conversion of glycals to 2-deoxy glycosyl acetates followed by reaction with trimethylsilyl iodide affords the corresponding glycosyl iodides, which readily undergo substitution with aryl alkoxy anions to provide 2-deoxy-β-O-aryl
- Lam, Son N.,Gervay-Hague, Jacquelyn
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p. 4219 - 4222
(2007/10/03)
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- Modified kojibiosides analogues
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Disclosed are novel analogues of kojibiose and pharmaceutical compositions comprising such analogues.
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- Hydrolytic activity of α-mannosidase against deoxy derivatives of p-nitrophenyl α-D-mannopyranoside
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Deoxy derivatives of p-nitrophenyl (PNP) α-D-mannopyranoside, PNP 2-deoxy-α-D-arabino-hexopyranoside, 3-deoxy-α-D-arabino-hexopyranoside, 4-deoxy-α-D-lyxo-hexopyranoside, and α-D-rhamnopyranoside, were synthesized and hydrolytic activities of jack bean an
- Nishio, Toshiyuki,Miyake, Yayoi,Tsujii, Hitomi,Hakamata, Wataru,Kadokura, Kazunari,Oku, Tadatake
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p. 2038 - 2042
(2007/10/03)
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- Synthesis of C-disaccharides via glucal dimerisation
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Treatment of 3-O-acetyl glucal and related species with acetylperchlorate provides good yields of the corresponding C-disaccharides with a high degree of stereocontrol at the new C-C bond. Copyright (C) 1996 Elsevier Science Ltd.
- Byerley, Andrew L. J.,Kenwright, Alan M.,Steel, Patrick G.
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p. 9093 - 9096
(2007/10/03)
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