140428-81-5Relevant articles and documents
Synthesis of Dense and Chiral Dendritic Polyols Using Glyconanosynthon Scaffolds
Shiao, Tze Chieh,Rej, Rabindra,Rose, Mariécka,Pavan, Giovanni M.,Roy, René
, (2016)
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
Synthesis, click reaction, molecular structure, spectroscopic and DFT computational studies on 3-(2,6-bis(trifluoromethyl)phenoxy)-6-(prop-2-yn-1-yloxy)phthalonitrile
Hasan, Muhammad,Shalaby, Mona
, p. 88 - 98 (2016)
The compound 3-(2,6-bis(trifluoromethyl)phenoxy)-6-(prop-2-yn-1-yloxy)phthalonitrile has been synthesized and confirmed by different characterization techniques such as elemental analysis, IR, UV-vis spectroscopy, and X-ray single-crystal determination. The molecular geometry from X-ray determination of this compound in the ground state has been compared using the Hartree-Fock (HF) and density functional theory (DFT) with the 6-31G(d) basis set. This compound reacted with sugar azide via click reaction to form triazol ring. The synergy between carbohydrate molecule and fluorinated organic compound achieved novel synthetic pathways, properties, and applications in chemistry science.
Derivatization of glucose and 2-deoxyglucose for transition metal complexation: Substitution reactions with organometallic 99mTc and re precursors and fundamental NMR investigations
Petrig, Jeannine,Schibli, Roger,Dumas, Cecile,Alberto, Roger,Schubiger
, p. 1868 - 1873 (2001)
Synthetic strategies for the bifunctionalization of glucose and 2-deoxyglucose at position C-1 for transition metal coordination are reported. In particular organometallic technetium and rhenium complexes for potential use in diagnostic nuclear medicine w
Synthesis and biodistribution of novel 99mTcN complexes of glucose dithiocarbamate as potential probes for tumor imaging
Liu, Teli,Gan, Qianqian,Zhang, Junbo,Jin, Zhonghui,Zhang, Weifang,Zhang, Yanyan
, p. 1381 - 1386 (2016)
In this study, two novel glucose dithiocarbamates (3a and 3b) were successfully synthesized via a "click chemistry" route and then radiolabeled with a [99mTcN]2+ core to prepare the corresponding 99mTcN complexes in high yields. Both of them were hydrophilic and had good in vitro stability. The in vivo biodistribution studies in mice bearing S180 tumor showed that the complexes accumulated in the tumor with high uptake and good retention. Through comparison, 99mTcN-3b had the advantages of higher tumor uptake, tumor/blood and tumor/muscle ratios at 2 h post-injection. The single-photon emission computed tomography (SPECT) image studies of 99mTcN-3b showed obvious radioactive uptake in the tumor region and the tumor-to-non-target ratio was high, suggesting that it could be regarded as a promising tumor imaging agent.
The synthesis of new fluorinated or nonfluorinated sugar phosphonates and phosphoramidates as building blocks in the synthesis of modified hyaluronic acid subunits
Koroniak-Szejn, Katarzyna,Tomaszewska, Joanna,Koroniak, Henryk
, p. 683 - 694 (2017)
The synthesis of several new fluorinated or nonfluorinated sugar phosphonates and phosphoramidates as building blocks for the synthesis of modified hyaluronic acid subunits is described. These compounds were prepared from d-glucose and d-glucosamine hydro
Neutral Re(I) Complex Platform for Live Intracellular Imaging
Bader, Christie A.,Brooks, Doug A.,Brooks, Robert D.,Caporale, Chiara,Gillam, Todd A.,Hickey, Shane M.,Massi, Massimiliano,Morrison, Janna L.,Plush, Sally E.,Sorvina, Alexandra,Stagni, Stefano,Werrett, Melissa V.,Wright, Phillip J.,Zacchini, Stefano
, p. 10173 - 10185 (2021/07/26)
Luminescent metal complexes are a valuable platform for the generation of cell imaging agents. However, many metal complexes are cationic, a factor that can dominate the intracellular accumulation to specific organelles. Neutral Re(I) complexes offer a more attractive platform for the development of bioconjugated imaging agents, where charge cannot influence their intracellular distribution. Herein, we report the synthesis of a neutral complex (ReAlkyne), which was used as a platform for the generation of four carbohydrate-conjugated imaging agents via Cu(I)-catalyzed azide-alkyne cycloaddition. A comprehensive evaluation of the physical and optical properties of each complex is provided, together with a determination of their utility as live cell imaging agents in H9c2 cardiomyoblasts. Unlike their cationic counterparts, many of which localize within mitochondria, these neutral complexes have localized within the endosomal/lysosomal network, a result consistent with examples of dinuclear carbohydrate-appended neutral Re(I) complexes that have been reported. This further demonstrates the utility of these neutral Re(I) complex imaging platforms as viable imaging platforms for the development of bioconjugated cell imaging agents.
Synthesis of a novel resorcin[4]arene-glucose conjugate and its catalysis of the CuAAC reaction for the synthesis of 1,4-disubstituted 1,2,3-triazoles in water
Husain, Ali A.,Bisht, Kirpal S.
, p. 10109 - 10116 (2019/04/10)
The Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) in aqueous media using resorcin[4]arene glycoconjugate (RG) is reported. The eight β-d-glucopyranoside moieties constructed on the resorcin[4]arene upper rim provide a pseudo-saccharide cavity that offers a suitable host environment for water-insoluble hydrophobic azido and/or alkyne substrates in water. The utility of RG was established as an efficient inverse phase transfer catalyst for the CuAAC in water as a green approach for the synthesis of 1,4-disubstituted 1,2,3-triazole species. The catalytic utility of RG (1 mol%) was demonstrated in a multicomponent one-pot CuAAC for various azido/alkyne substrates. The RG acts as a molecular host and a micro-reactor resulting in the 1,4-disubstituted 1,2,3-triazoles in excellent yield.