151168-59-1Relevant articles and documents
Enzymatic Derivatization of Saccharides and Their Chemical Polymerization
Blinkovsky, Alexander M.,Dordick, Jonathan S.
, p. 1221 - 1228 (1993)
The enzymatic synthesis of sugar-based acetylene and ethylene derivatives as precursors to hydrophilic polymers is described.Propargyl and allyl alcohols have been used as glycosyl acceptors in the transglycosylation reactions of glycosidases with various disaccharides including lactose, maltose, and cellobiose.Reaction of propargyl and allyl alcohols with lactose catalyzed by β-galactosidase resulted in the formation of propargyl-β-D-galalactopyranoside and allyl-β-D-galactopyranoside in 42 and 13percent yields, respectively.Polymerization of propargyl-β-D-galactopyranoside with AlBr3 in ethanol resulted in the formation of oligomeric poly(acetylenic) species (Mw = 1,300).Free radical polymerization of allyl-β-D-galactopyranoside in DMF or water resulted in poly(ethylenic) species with Mw > 30,000.The combined enzymatic and chemical reactions inherent in these syntheses provide a unique approach in the preparation of hydrophilic polymers containing sugars and their derivatives.
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)
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
Towards biodegradable elastomers: Green synthesis of carbohydrate functionalized styrene-butadiene-styrene copolymer by click chemistry
Singh, Rakesh,Varma
, p. 348 - 356 (2012)
Random attachment of sugar molecules to synthetic polymers is an important strategy to induce biodegradability in these polymers. The present study successfully employs "click" chemistry to introduce low levels of sugar molecules onto styrene-butadiene-styrene (SBS) copolymer, a widely used commodity polymer which is not biodegradable. Spectral, morphological and thermal studies of the modified polymers were carried out to show the dramatic changes in the properties of these modified polymers. Thermal stability of glucose linked SBS had onset of degradation at 428 °C, down from 478 °C observed for SBS. Morphology studied by WAXRD and SEM showed destructuring of the polymer domains of SBS, which is beneficial for biodegradation of these polymers. Previous studies showed that sugars anchored by hydrolysable ester groups onto polystyrene were biodegradable; current studies show that sugars anchored by unhydrolyzable C-C bonds on the butadiene component of SBS copolymer are also significantly biodegradable.
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.
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.
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.
