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13992-25-1 Usage

Chemical Properties

WHITE TO BEIGE CRYSTALLINE POWDER

Uses

β-D-Glucopyranosyl Azide 2,3,4,6-Tetraacetate, is an intermediate used for the synthesis of Protein Tyrosine Phosphatase 1B inhibito1. It is used for the preparation of variously coupled conjugates of D-glucose via click chemistry for inhibition of glycogen phosphorylase.

Check Digit Verification of cas no

The CAS Registry Mumber 13992-25-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,9,9 and 2 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 13992-25:
(7*1)+(6*3)+(5*9)+(4*9)+(3*2)+(2*2)+(1*5)=121
121 % 10 = 1
So 13992-25-1 is a valid CAS Registry Number.
InChI:InChI=1/C14H20N3O9/c1-6(18)22-5-10-11(23-7(2)19)12(24-8(3)20)13(25-9(4)21)14(26-10)16-17-15/h10-15H,5H2,1-4H3/q+1

13992-25-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-AZIDO-2,3,4,6-TETRA-O-ACETYL-β-D-GLUCOSE

1.2 Other means of identification

Product number -
Other names 2,3,4,6-Tetra-O-acetyl-D-glucopyranosyl azide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13992-25-1 SDS

13992-25-1Relevant articles and documents

High-Yielding Catalytic Synthesis of Glycosyl Azides from Peracylated Sugars

Matsubara, Koki,Mukaiyama, Teruaki

, p. 247 - 250 (1994)

In the presence of a catalyst generated from SnCl4 and AgClO4, or Yb(OTf)3, various glycosyl azides are synthesized in high yields with complete stereoselectivities from peracylated sugars and trimethylsilyl azide by choosing a suitable solvent such as dichloromethane or nitromethane.

Synthesis of new triazole linked carbohybrids with ROS-mediated toxicity in breast cancer

Kumari, Priti,Dubey, Shraddha,Venkatachalapathy, Sneha,Narayana, Chintam,Gupta, Ashish,Sagar, Ram

, p. 18590 - 18600 (2019)

Carbohybrids are an important class of molecules which exhibit diverse biological activities and are present as structural motifs in many natural products. Two series of new triazole linked N-glycosides of coumarins and quinolones (n = 27) were efficiently synthesized starting from 1-azido-2,3,4,6-tetra-O-acetyl β-d-glucose and 1-azido-2,3,4,6-tetra-O-acetyl β-d-galactose reacting with various 4-O-propargyl coumarins and 4-O-propargyl quinolones in shorter reaction time (30 min) under microwave assisted conditions. Anticancer activity of these newly synthesized triazole linked N-glycosides of coumarins and quinolones was determined in detail through cellular assays against MCF-7 (breast cancer cell line), HepG2 (liver cancer cell line), HCT-116 (colon cancer cell line) and Huh-7.5 cell lines. The selected library member displayed low micromolar (IC50 10.97 μM) and selective toxicity against the breast cancer cell line (MCF-7). Mechanistic studies showed that the anticancer activity of the active compound was because of the generation of reactive oxygen species (ROS).

Application of ball milling technology to carbohydrate reactions-II. Solvent-free mechanochemical synthesis of glycosyl azides

Mugunthan,Kartha, K.P. Ravindranathan

, p. 294 - 299 (2008)

Glycosyl azides have been prepared from a range of readily available glycosyl halides by a solvent-free mechanochemical procedure employing a planetary ball mill in good to excellent yields.

Straightforward synthesis of novel Akt inhibitors based on a glucose scaffold

Cipolla, Laura,Redaelli, Cristina,Granucci, Francesca,Zampella, Giuseppe,Zaza, Antonio,Chisci, Riccardo,Nicotra, Francesco

, p. 1291 - 1298 (2010)

Glucose-based analogues of phosphatidylinositol 3-phosphate were straightforwardly synthesised from 2,3,4,6-tetra-O-acetyl-D-glucosyl bromide as protein kinase B (PKB/Akt) inhibitors. β-D-Glucuronyl diethyl phosphoramidate was identified as a promising hit through biological screening in two different cellular systems. In addition, RNA interference experiments (siRNA) provide evidence of the ability of the compound to exert biological effects specifically through Akt signalling.

The first synthesis of the N-glucosyl analogue of the antitumor agent etoposide

Allevi, Pietro,Anastasia, Mario,Ciuffreda, Pierangela

, p. 7313 - 7316 (1993)

The first synthesis of 1-aminoglucose analogue of the antitumor agent etoposide is accomplished by condensation of 4,6-tO-ethylidene-2,3-di-tO-trimethylsilyl-β-D-glucopyranosylamine with 4-bromo-4-deoxy-4′-demethylepipodophyllotoxin in the presence of Hg(

Phase transfer catalysis as a general and stereoselective entry into glycosyl azides from glycosyl halides

Tropper,Andersson,Braun,Roy

, p. 618 - 620 (1992)

Peracetylated glycosyl- and glycobiosyl bromides and chlorides 1-5 including acetochloroneuraminic acid 6 were converted to their corresponding glycosyl azides 7-12 in 93-98% yields under phase transfer catalyzed conditions. The stereoselective reactions occurred with complete inversion at the anomeric centers to provide a general, high-yielding entry into 1,2-trans-glycosyl azides together with α-sialic acid azide.

Glycoconjugated Metallohelices have Improved Nuclear Delivery and Suppress Tumour Growth In Vivo

Allison, Simon J.,Brabec, Viktor,Bridgewater, Hannah E.,Kasparkova, Jana,Kostrhunova, Hana,Novohradsky, Vojtech,Phillips, Roger M.,Pracharova, Jitka,Rogers, Nicola J.,Scott, Peter,Shepherd, Samantha L.,Song, Hualong

, p. 14677 - 14685 (2020)

Monosaccharides are added to the hydrophilic face of a self-assembled asymmetric FeII metallohelix, using CuAAC chemistry. The sixteen resulting architectures are water-stable and optically pure, and exhibit improved antiproliferative selectivity against colon cancer cells (HCT116 p53+/+) with respect to the non-cancerous ARPE-19 cell line. While the most selective compound is a glucose-appended enantiomer, its cellular entry is not mainly glucose transporter-mediated. Glucose conjugation nevertheless increases nuclear delivery ca 2.5-fold, and a non-destructive interaction with DNA is indicated. Addition of the glucose units affects the binding orientation of the metallohelix to naked DNA, but does not substantially alter the overall affinity. In a mouse model, the glucose conjugated compound was far better tolerated, and tumour growth delays for the parent compound (2.6 d) were improved to 4.3 d; performance as good as cisplatin but with the advantage of no weight loss in the subjects.

Effective synthesis of novel C(2)-propargyl derivatives of betulinic and ursolic acids and their conjugation with β-d-glucopyranoside azides via click chemistry

Spivak, Anna Yu.,Gubaidullin, Rinat R.,Galimshina, Zulfiya R.,Nedopekina, Darya A.,Odinokov, Victor N.

, p. 1249 - 1256 (2016)

A new synthetic approach to the incorporation of an alkynyl group into pentacyclic triterpenoids was developed and utilized to prepare C(2)-propargyl derivatives of lupane- and ursane-type triterpenoic acids. Novel triterpenoid derivatives with a propynyl group at the C(2) atom were successfully used for click chemistry bioconjugation with glucopyranoside azides.

Tetramethylguanidinium azide as a new reagent for the stereoselective synthesis of glycosyl azides

Li,Arasappan,Fuchs

, p. 3535 - 3538 (1993)

Tetramethylguanidium azide was used in the quantitative conversion of glycosyl halides 1 - 6 to the corresponding glycosyl azides 7 - 12. The stereoselective reactions occurred with complete inversion at the anomeric centers.

Synthesis and Antifungal Activities of Glycosylated Derivatives of the Cyclic Peptide Fungicide Caspofungin

Guo, Junxiang,Hu, Honggang,Zhao, Qingjie,Wang, Ting,Zou, Yan,Yu, Shichong,Wu, Qiuye,Guo, Zhongwu

, p. 1496 - 1503 (2012)

Diseases caused by systemic fungal infections have become a significant clinical problem in recent decades. A series of glycosyl derivatives of the approved cyclic peptide antifungal drug caspofungin conjugated with β-D-glucopyranose, β-D-galactopyranose, β-D-xylopyranose, β-L-rhamnopyranose, β-maltose and β-lactose units were designed, synthesized, and evaluated as new potential antifungal drugs. The compounds were obtained by coupling the corresponding glycosyl amines to the free primary amino groups of caspofungin through a bifunctional glutaryl linker. In contrast to caspofungin, these glycosylated derivatives are soluble in water, but are not hygroscopic and moreover, are more stable than caspofungin under high humidity and temperature. CD studies showed that glycosylation has very little impact on the conformation of the cyclic peptide of caspofungin. Invitro antifungal tests against seven human pathogenic fungi revealed that the caspofungin-monosaccharide conjugates, but not the disaccharide conjugates, have increased antifungal activities against the majority of tested fungus species relative to caspofungin. The β-D-glucopyranosyl derivative 2a showed the strongest and broadest antifungal activity, providing a lead for further studies.

Non-mesogenic crystal structure of a synthetic 1-D-glucosamide bolaamphiphile

Masuda, Mitsutoshi,Shimizu, Toshimi

, p. 139 - 147 (1997)

The crystal structure of the synthetic l-glucosamide bolaamphiphile, N,N'-bis(β-D-glucopyranosyl)undecane-1,11-dicarboxamide (I) was determined by single-crystal X-ray analysis. The space group is P21 with cell dimensions: a = 6.220(1), b = 48.25(1), c = 4.922(2) A, β = 105.67(2)°, and Z = 2. The glucopyranosyl ring is in a 4C1 chair conformation. The bolaamphiphile molecules are arranged in a layered structure with the alkylene chains packed antiparallel in a pleated sheet. The glucosamine moieties are linked by a three-dimensional intermolecular hydrogen-bonding network. The n-alkylene chain has an all-trans zigzag conformation with a small left-handed twist.

Synthesis and preliminary evaluation of a 99mTc labelled deoxyglucose complex {[99mTc]DTPA-bis(DG)} as a potential SPECT based probe for tumor imaging

Singh, Shivani,Singh, Sweta,Sharma, Rakesh K.,Kaul, Ankur,Mathur, Rashi,Tomar, Sarika,Varshney, Raunak,Mishra, Anil K.

, p. 3062 - 3071 (2020)

Carbohydrate based radiotracers have been in routine use as a potential PET imaging agent for tumor targeting, worldwide. The aim of our study was to develop a cost effective and more accessible SPECT based tumor targeted molecular imaging probe. A 1-d-deoxyglucose conjugate was proposed and evaluated as a tumor imaging agent. DTPA-bis(DG) was synthesized by conjugating two molecules of glucose employing a click chemistry approach. It involved a facile methodology, characterization and subsequent radiolabelling with 99mTc with high radiochemical purity and specific activity (187 ± 17 MBq μmol-1) followed by in vitro and in vivo evaluation to prove its potency as an imaging agent. In vitro cytotoxicity studies in the A549 and HEK cell lines showed no substantial toxicity. A cell uptake study revealed that the transportation of [99mTc]DTPA-bis(DG) was GLUT1 independent. In vivo blood kinetic studies in New Zealand rabbits showed fast clearance with a Td1/2 of 28.12 ± 0.63 min and Te1/2 = 101.25 ± 0.34. A significant tumor uptake of 3.88 ± 0.05% ID per g was observed in A549 tumor bearing mice at 4 h p.i. The tumor-to-muscle and tumor-to-blood ratios at 4 h p.i. were 20.46 ± 0.07 and 3.59 ± 0.03 respectively. No significant persistence in any other organs was observed. The tumor (A549) grafted in athymic mice was clearly distinguishable in the gamma-scintigraphy image. The results suggested that this [99mTc]glycoconjugate would be a promising candidate for cancer targeted imaging.

'Click' assembly of glycoclusters and discovery of a trehalose analogue that retards Aβ40 aggregation and inhibits Aβ40-induced neurotoxicity

Rajaram, Hemalatha,Palanivelu, Manoj Kumar,Arumugam, Thiruma V.,Rao, Venkatesan M.,Shaw, P. Nicholas,McGeary, Ross P.,Ross, Benjamin P.

, p. 4523 - 4528 (2014)

Osmolytes have been proposed as treatments for neurodegenerative proteinopathies including Alzheimer's disease. However, for osmolytes to reach the clinic their efficacy must be improved. In this work, copper(I)-catalyzed azide-alkyne cycloaddition chemistry was used to synthesize glycoclusters bearing six copies of trehalose, lactose, galactose or glucose, with the aim of improving the potency of these osmolytes via multivalency. A trehalose glycocluster was found to be superior to monomeric trehalose in its ability to retard the formation of amyloid-beta peptide 40 (Aβ40) fibrils and protect neurons from Aβ40-induced cell death.

Iron(III) chloride as an efficient catalyst for stereoselective synthesis of glycosyl azides and a cocatalyst with Cu(0) for the subsequent click chemistry

Salunke, Santosh B.,Babu, N. Seshu,Chen, Chien-Tien

, p. 10440 - 10442 (2011)

A highly efficient and mild method for azido glycosylation of glycosyl β-peracetates to 1,2-trans glycosyl azides was developed by using inexpensive FeCl3 as the catalyst. In addition, we demonstrated, for the first time, that FeCl3 in combination with copper powder can promote 1,3-dipolar cycloaddition (click chemistry) of azido glycosides with terminal alkynes. Good to excellent yields were obtained with exclusive formation of a single isomer in both glycosyl azidation and subsequent cycloaddition processes.

Synthesis of Homoleptic and Heteroleptic Ruthenium Complexes Appended with Glucosyl Ligand by the Click-to-Chelate Approach

Xiao,Cheng,Zhu,Cheng,Wu,Yu,Wang

, p. 3036 - 3042 (2017)

Homoleptic and heteroleptic complexes of Ru(TAGP-tapy)3Cl2 {TAGP-tapy is 2-[1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl]-pyridine} bearing a clustered glucose-derived ligand and Ru(bpy)2(TAGP-tapy)Cl2 (bpy is 2,2'-bipyridine) have been synthesized by the chelating reaction of RuCl3·3H2O with TAGP-tapy and cis-Ru(bpy)2Cl2 with TAGP-tapy, respectively. The bidentate 1,2,3-triazolelinked glucose-derived ligand TAGP-tapy was prepared by copper-catalyzed coupling (click reaction) of 2-ethynylpyridine with acetyl protected glucosyl azide, 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide (TAGP-N3). TAGP-N3 was prepared by nucleophilic substitution reaction of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (TAGP-Br) with NaN3. These ruthenium complexes were purified by column chromatography or HPLC. Structures of the intermediates and ruthenium complexes were confirmed by HPLC, 1H and 13C NMR, FT-IR, and ESI-MS spectroscopies. UV-Vis and fluorescence spectroscopic methods were used to study optical properties of the ligand TAGP-tapy and ruthenium complexes. TAGP-tapy exhibited interesting solvent-polarity dependent fluorescence properties and a significant red-shift in emissions. Both complexes demonstrated distinctive fluorescence emission band in the visible region.

2,3,4,6-Tetra-O-acetyl-α- d-gluco-pyranosyl azide

Dedola, Simone,Nepogodiev, Sergey A.,Hughes, David L.,Field, Robert A.

, p. o445-o446 (2008)

The CuI-catalysed 1,3-dipolar cyclo-addition of an azide and a terminal alkyne is becoming an increasingly popular tool for synthetic chemists. This is the most representative of the so-called click reactions and it is used to generate 1,4-di-substituted triazoles in high yield. During studies on such cyclo-addition reactions, a reduced reactivity of an -glucosyl azide with respect to the corresponding Β-anomer was observed. With the aim of understanding this phenomenon, the structure of the title compound, C14H19N3O9, has been determined at 140 K. The glucopyranosyl ring appears in a regular 4 C 1 chair conformation with all the substituents in equatorial positions, except for the anomeric azide group, which adopts an axial orientation. The observed bond lengths are consistent with a strong anomeric effect, which is reflected in a change in dipolar character and hence reduced reactivity of the -glucosyl azide.

A simple and convenient synthesis of glycosyl azides

Ibatullin, Farid M.,Shabalin, Konstantin A.

, p. 2819 - 2823 (2000)

Treatment of glycosyl halides with NaN3 in aqueous acetone or acetonitrile is a convenient method for the stereoselective synthesis of 1,2- transper-O-acetyl-glycosyl azides.

tert-Alcohol-functionalized imidazolium ionic liquid: catalyst for mild nucleophilic substitution reactions at room temperature

Shinde, Sandip S.,Chi, Hyung Min,Lee, Byoung Se,Chi, Dae Yoon

, p. 6654 - 6657 (2009)

Encouraged by a synergistic effect on nucleophilic fluorination, an imidazolium mesylate salt (1a) possessing two different solvent properties in one molecule-tert-alcohol and ionic liquid was utilized in various nucleophilic substitution reactions. By a

Binding of Fe(ii)-complex of phenanthroline appended glycoconjugate with DNA, plasmid and an agglutinin protein

Dinda, Subrata Kumar,Polepalli, Sirilata,Rao, Chebrolu Pulla

, p. 11727 - 11738 (2020)

The phenanthroline appended glycoconjugate (L) and its Fe(ii)-complex were synthesized and characterized using analytical and spectral methods. The complexation of Fe2+ with L has been shown using absorption and fluorescence spectral studies. 1H NMR titration of L with Fe2+ supports that the phenanthroline moiety acts as the metal binding core. The interaction and binding of the Fe-complex with calf thymus DNA (ct-DNA) were studied using spectral techniques, such as UV-Vis absorption, circular dichroism (CD) and DNA melting temperatures. The corresponding data supported the minor groove binding of ct-DNA by the Fe-complex along with electrostatic interactions. The gel electrophoresis studies carried out using pBR322 plasmid showed a tight binding of the iron complex with the plasmid and this resulted in the condensation of the pBR322 plasmid as revealed by the blob-like structures observed in the atomic force microscopy data. The binding of the Fe-complex by WGA was demonstrated by absorption, fluorescence and CD spectra, and the microstructures were observed via scanning electron microscopy (SEM). Star-like nanostructures observed via SEM support that the octahedral iron complex connects the protein molecules in three dimensions through their carbohydrate terminal moieties. Thus, a new Fe-complex possessing a biocompatible glucosyl moiety interacts and binds to biomolecules, such as DNA and protein, and the resulting species are of importance in biological applications.

Stereoselective Ethynylation and Propargylation of Chiral Cyclic Nitrones: Application to the Synthesis of Glycomimetics

García-Vi?uales, Sara,Delso, Ignacio,Merino, Pedro,Tejero, Tomás

, p. 3339 - 3351 (2016)

Ethynylation and propargylation of chiral nonracemic polyhydroxylated cyclic nitrones with Grignard reagents are efficient methods for preparing building blocks containing an alkyne moiety to be used in copper-catalyzed azide alkyne cycloaddition click chemistry. Whereas ethynylation takes place with excellent diastereoselectivity, propargylation afforded mixtures of diastereomers in some cases. The use of (trimethylsilyl)propargyl bromide as precursor of the Grignard reagent is necessary to avoid the formation of undesired allene derivatives. DFT calculations explain, within the experimental error, the observed behavior. Cycloaddition of the obtained pyrrolidinyl alkynes with sugar azides derived from β-(1,3)-glucans provides glycomimetics suitable to be used against fungal transglycosylases.

Long chain alkyl and fluoroalkyl glucose and glucosamine derivatives as hyaluronic acid subunits—Scaffolds for drug delivery

Koroniak-Szejn, Katarzyna,Tomaszewska, Joanna,Grajewski, Jakub,Koroniak, Henryk

, p. 98 - 105 (2019)

Synthesis of hyaluronic acid components modified with long alkyl or fluorinated alkyl chain has been described as potential scaffold for drug delivery systems. The strategy of introducing fluorinated motifs in sugar anomeric position via “click” reaction has been studied showing various reactivity when position 2 was substituted with trichloro- and trifluoroamide unit. To determine the conformations of model 1,2,3-triazole substituted derivatives of acylated glucose or glucosamine, CD spectra were recorded and conformational analysis was supported by molecular modeling.

Multi-mannosides based on a carbohydrate scaffold: Synthesis, force field development, molecular dynamics studies, and binding affinities for lectin con A

Gouin, Sebastien G.,Vanquelef, Enguerran,Fernandez, Jose Manuel Garcia,Mellet, Carmen Ortiz,Dupradeau, Francois-Yves,Kovensky, Jose

, p. 9032 - 9045 (2007)

(Chemical Equation Presented) A short and efficient strategy for the synthesis of multi-valent mannosides based on a selectively functionalized carbohydrate scaffold was reported involving (i) direct regioselective azidation of unprotected commercial saccharides, (ii) acetylation, (iii) grafting of the mannosyl ligands by click chemistry, and (iv) deacetylation. New glycoclusters with a valency ranging from 1 to 4 and different spatial arrangements of the epitopes were obtained. Binding affinities of the new glycoclusters toward concanavalin A (Con A) lectin were investigated by an enzyme-linked lectin essay (ELLA). The synthetic multi-valent compounds exhibited a remarkable cluster effect with a relative potency per mannoside residue ranging from 8.1 to 9.1 depending on the structures. ELLA experiments were in agreement with the establishment of favorable interactions between triazole ring and Con A, increasing the binding affinity. A new force field topology database was developed in agreement with the GLYCAM 2004 force field. Molecular dynamics performed on representative glyco-conjugates revealed interesting structural features such as rigidity of the scaffold for a well-defined presentation of the ligands and highly flexible mannose counterparts. The new glycoconjugates reported may be promising tools as probes or effectors of biological processes involving lectins.

Study of aryl triazoles for absolute configuration determination

Tejera, Sara,Dorta, Rosa L.,Vázquez, Jesús T.

, p. 896 - 909 (2016)

A variety of chiral mono- and di-1,4-disubstituted 1,2,3-triazoles were synthesized by CuAAC ‘click chemistry’ as model compounds and their spectroscopic properties characterized. The UV and CD studies of these compounds showed that 4-substituted aryl tri

Novel pentacyclic triterpenes exhibiting strong neuroprotective activity in SH-SY5Y cells in salsolinol- and glutamate-induced neurodegeneration models

Gonzalez, Gabriel,Hodoň, Ji?í,Kazakova, Anna,D'Acunto, Cosimo Walter,Kaňovsky, Petr,Urban, Milan,Strnad, Miroslav

, (2021)

Novel triterpene derivatives were prepared and evaluated in salsolinol (SAL)- and glutamate (Glu)-induced models of neurodegeneration in neuron-like SH-SY5Y cells. Among the tested compounds, betulin triazole 4 bearing a tetraacetyl-β-D-glucose substituen

Stereochemical effect of even-odd connecting links on supramolecular assemblies made of 1-glucosamide bolaamphiphiles

Shimizu, Toshimi,Masuda, Mitsutoshi

, p. 2812 - 2818 (1997)

Bolaamphiphiles with a 1-glucosamide-head group at each end, N,N'-bis(β-D-glucopyranosyl)alkane-1, n-dicarboxamide [Glc-NC(n)CN-Glc, n = 6, 9, 10, 11, 12, 13, and 14], have been synthesized. Self-assembled supramolecular structures in water strongly depend on whether n is even or odd, which respectively give rise to fibrous assemblies or planar platelets as well as amorphous solids. In connection with this even-odd effect of the hydrocarbon links, internal molecular arrangements of the solid fibers were investigated using FT-IR spectroscopy, X-ray diffraction and crystal analyses, and transmission electron microscopy. The oligomethylene groups of the Glc-NC(12)CN-Glc pack in a monoclinic or an orthorhombic mode in the fiber. We propose a possible self-assembled model based on a monolayer sheet, which is stabilized by hydrogen-bond networks via sugar-head and amide groups.

A glycol nanomedicine via a metal-coordination supramolecular self-assembly strategy for drug release monitoring and chemo-chemodynamic therapy

Li, Jiahui,Pei, Yuxin,Pei, Zhichao,Wang, Yi

, p. 3338 - 3341 (2022/03/31)

A glycol nanomedicine based on a metal-coordination supramolecular self-assembly strategy of GluCC (a copper complex of glucose modified coumarin derivative) and a chemotherapeutic agent of doxorubicin (DOX) was successfully developed. In vitro studies revealed that the nanomedicine achieved drug target delivery and release monitoring. The anti-cancer efficiency could be enhanced through synergistic therapy of chemotherapy (CT) and chemodynamic therapy (CDT). It may gain important applications in drug tracking and CDT-combined cancer therapy.

CuAAC mediated synthesis of cyclen cored glycodendrimers of high sugar tethers at low generation

Agrahari, Anand K.,Jaiswal, Manoj K.,Yadav, Mangal S.,Tiwari, Vinod K.

, (2021/07/30)

Glycodendrimers are receiving considerable attention to mimic a number of imperative features of cell surface glycoconjugate and acquired excellent relevance to a wide domain of investigations including medicine, pharmaceutics, catalysis, nanotechnology, carbohydrate-protein interaction, and moreover in drug delivery systems. Toward this end, an expeditious, modular, and regioselective triazole-forming CuAAC click approach along with double stage convergent synthetic method was chosen to develop a variety of novel chlorine-containing cyclen cored glycodendrimers of high sugar tethers at low generation of promising therapeutic potential. We developed a novel chlorine-containing hypercore unit with 12 alkynyl functionality originated from cyclen scaffold which was confirmed by its single crystal X-ray data analysis. Further, the modular CuAAC technique was utilized to produce a variety of novel 12–sugar coated (G0) glycodendrimers 12-15 adorn with β-Glc-, β-Man-, β-Gal-, β-Lac, along with 36-galactose coated (G1) glycodendrimer 18 in good-to-high yield. The structures of the developed glycodendrimer architectures have been well elucidated by extensive spectral analysis including NMR (1H & 13CNMR), HRMS, MALDI-TOF MS, UV–Vis, IR, and SEC (Size Exclusion Chromatogram) data.

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