34272-03-2Relevant articles and documents
Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions
Dey, Kalyan,Jayaraman, Narayanaswamy
supporting information, p. 2224 - 2227 (2022/02/17)
A site-specific deprotonation followed by alkylations and acylations of sugar hemiacetals to the corresponding alkyl glycosides and acylated sugars in aqueous solutions is disclosed herein. Pyridoneimine as a new base is developed to mediate the deprotonation of readily available sugar hemiacetals and further reactions with alkylation and acylation agents.
BORON CLUSTER-COUPLED COMPOUND
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Paragraph 0169; 0174-0176, (2021/03/05)
To provide a novel boron-containing compound which increases intratumorous accumulation and tumor retention, and is efficiently taken into a tumor cell.SOLUTION: The present invention relates to a compound represented by formula (I) in the figure or a salt thereof. [In the formula, X represents a divalent to pentavalent organic group; Y represents a linker structure; R represents a monovalent group comprising boron clusters; and n represents 2, 3, 4 or 5.SELECTED DRAWING: None
8-hydroxyquinoline glycoconjugates: Modifications in the linker structure and their effect on the cytotoxicity of the obtained compounds
Krawczyk, Monika,Pastuch-Gawo?ek, Gabriela,Pluta, Aleksandra,Erfurt, Karol,Domiński, Adrian,Kurcok, Piotr
, (2019/11/28)
Small molecule nitrogen heterocycles are very important structures, widely used in the design of potential pharmaceuticals. Particularly, derivatives of 8-hydroxyquinoline (8-HQ) are successfully used to design promising anti-cancer agents. Conjugating 8-HQ derivatives with sugar derivatives, molecules with better bioavailability, selectivity, and solubility are obtained. In this study, 8-HQ derivatives were functionalized at the 8-OH position and connected with sugar derivatives (D-glucose or D-galactose) substituted with different groups at the anomeric position, using copper(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC). Glycoconjugates were tested for inhibition of the proliferation of cancer cell lines (HCT 116 and MCF-7) and inhibition of β-1,4-galactosyltransferase activity, which overexpression is associated with cancer progression. All glycoconjugates in protected form have a cytotoxic effect on cancer cells in the tested concentration range. The presence of additional amide groups in the linker structure improves the activity of glycoconjugates, probably due to the ability to chelate metal ions present in many types of cancers. The study of metal complexing properties confirmed that the obtained glycoconjugates are capable of chelating copper ions, which increases their anti-cancer potential.
Synthesis and optical and electrochemical properties of glucose-cored ferrocenyl dendrimers
Kannan, Ayyavoo,Anandhan, Ramasamy,Rajakumar, Perumal
supporting information, p. 541 - 550 (2017/03/15)
Triazole-based ferrocenyl glycoconjugates 1, 2, and 3 were synthesized by regiospecific copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of azidoferrocenyl derivatives with glucose pentaacetylide. Higher generation ferrocenyl glycoconjugates form the stable ferrocenium cation and exhibit increased light harvesting property as revealed from cyclic voltammogram studies and ultraviolet–visible spectrum respectively due to the presence of more ferrocenyl and triazolyl units than the lower generation dendrimer.
NOVEL SOLANIDINE-DERIVED COMPOUNDS
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Paragraph 0067-0078, (2016/06/28)
Novel solanidine-derived compounds, the synthesis method thereof and the uses of same in the fields of phytosanitary protection and health. In particular, the novel compounds have toxic and/or repellent properties in relation to aphids, as well as other properties.
Synthesis of Dense and Chiral Dendritic Polyols Using Glyconanosynthon Scaffolds
Shiao, Tze Chieh,Rej, Rabindra,Rose, Mariécka,Pavan, Giovanni M.,Roy, René
, (2016/05/24)
Most classical dendrimers are frequently built-up from identical repeating units of low valency (usually AB2 monomers). This strategy necessitates several generations to achieve a large number of surface functionalities. In addition, these typical monomers are achiral. We propose herein the use of sugar derivatives consisting of several and varied functionalities with their own individual intrinsic chirality as both scaffolds/core as well as repeating units. This approach allows the construction of chiral, dense dendrimers with a large number of surface groups at low dendrimer generations. Perpropargylated β-D-glucopyranoside, serving as an A5 core, together with various derivatives, such as 2-azidoethyl tetra-O-allyl-β-D-glucopyranoside, serving as an AB4 repeating moiety, were utilized to construct chiral dendrimers using "click chemistry" (CuAAC reaction). These were further modified by thiol-ene and thiol-yne click reactions with alcohols to provide dendritic polyols. Molecular dynamic simulation supported the assumption that the resulting polyols have a dense structure
NIR fluorescent DCPO glucose analogues and their application in cancer cell imaging
Chen, Shiguang,Fang, Yanfen,Zhu, Qiwen,Zhang, Wanli,Zhang, Xiongwen,Lu, Wei
, p. 81894 - 81901 (2016/09/09)
Given the increased glucose uptake in cancer cells than normal cells, near-infrared (NIR) fluorescent glucose analogues have been previously synthesized and applied in cancer cell imaging. However, most NIR dyes usually have one or more charge in their structures, which may cause low cell membrane permeability and hamper their application in cell imaging. Here we report the synthesis and characterization of a series of DCPO-conjugated glucose analogues (N0-N4), which have no charge in their structures and have different lengths of the spacer arm. Experiments in different cancer cell lines showed the uptake of N0-N4 was dependent on the protein levels of GLUT-1. The distance between the dyes and glucose was adjusted by the length of PEG. Of these five glucose analogues, the length of the linker in N2 which contains a diethylene glycol was the most appropriate spacer arm, a longer or shorter linker exhibited reduced cellular uptake efficiency. Moreover, the uptake of DCPO-conjugated glucose analogues could be inhibited by phloretin, a GLUT-1 inhibitor or competitively inhibited by unlabeled d-glucose. Therefore, our study has reported a novel type of NIR-conjugated glucose analogues, whose cell permeability ensured the potential application for cancer cell bioimaging in the NIR region. We also demonstrated, for the first time, that the length of the linker between the dyes and glucose was also an important factor that will affect the delivery efficiency of the glucose analogues to cells.
1,2-cis Alkyl glycosides: Straightforward glycosylation from unprotected 1-thioglycosyl donors
Meng, Bo,Zhu, Zhenqian,Baker, David C.
, p. 5182 - 5191 (2014/07/08)
A 1,2-cis-alkyl glycosidation protocol that makes use of unprotected phenyl 1-thioglycosyl donors is reported. Glycosylation of various functionalized alcohols was accomplished in moderate to high yield and selectivity to give the 1,2-cis-glycosides. In order to quickly develop optimum glycosylation conditions, an FIA (flow injection analysis)-ESI-TOF-MS method was developed that enabled rapid and quantitative evaluation of yield on small scale. This methodology, coupled with NMR spectroscopy, allowed for rapid evaluation of the overall reactions.
Recognition of concanavalin a by cationic glucosylated liposomes
Mauceri, Alessandro,Borocci, Stefano,Galantini, Luciano,Giansanti, Luisa,Mancini, Giovanna,Martino, Antonio,Salvati Manni, Livia,Sperduto, Claudio
, p. 11301 - 11306 (2015/02/19)
The specificity of carbohydrate-lectin interaction has been reported as an attractive strategy for drug delivery in cancer therapy because of the high levels of lectins in several human malignancies. A novel cationic glucosylated amphiphile was therefore
Cell internalization of BODIPY-based fluorescent dyes bearing carbohydrate residues
Papalia, Teresa,Siracusano, Gabriel,Colao, Ivana,Barattucci, Anna,Aversa, Maria Chiara,Serroni, Scolastica,Zappalà, Gabriella,Campagna, Sebastiano,Sciortino, Maria Teresa,Puntoriero, Fausto,Bonaccorsi, Paola
, p. 67 - 71 (2014/08/18)
Red-absorbing BODIPY species have been prepared and their photophysical properties have been studied. The high fluorescence quantum yield of such compounds allowed us to study their cell internalization by fluorescence microscopy, using concentration as l