1155417-73-4Relevant academic research and scientific papers
Ferrocenyl amphiphilic Janus dendrimers as redox-responsive micellar carriers
Mu, Shengdong,Liu, Wentao,Ling, Qiangjun,Liu, Xiong,Gu, Haibin
, (2019)
Amphiphilic Janus dendrimers have attracted increasing attention due to their asymmetric structures and various functional properties compared to the conventional symmetric macromolecules. Herein, a novel ferrocenyl-terminated amphiphilic Janus dendrimer containing nine hydrophilic triethylene glycol branches was synthesized by two synthetic routes, namely the typical chemo selective coupling method and the mixed modular approach. Chemical redox triggers, namely Fe2(SO4)3 as oxidant and ascorbic acid as reductant, could regulate the self-assembly behavior of the Janus dendrimer in water through the redox-switching between ferrocene and ferricinium cations, and the change of micelles formed were investigated and confirmed through scanning electron microscopy and dynamic light scattering. The cargo-loading property of the micelles self-assembled by the Janus dendrimer was further proved by the successful fabrication of Rhodamine B (RhB)-loaded micelles, and the oxidation-triggered release behavior of the encapsulated RhB could be mediated by changing the concentration of oxidants. This work provides an effective approach to prepare ferrocenyl-terminated amphiphilic Janus dendrimers and the self-assembled micelles might be used as a promising molecular carrier in areas such as drug delivery and catalysis.
Conjugation of multivalent ligands to gold nanoshells and designing a dual modality imaging probe
Bdard, Mathieu,Avti, Pramod K.,Lam, Tina,Rouleau, Lonie,Tardif, Jean-Claude,Rhaume, ric,Lesage, Frdric,Kakkar, Ashok
, p. 1788 - 1800 (2015)
Design and synthesis of branched tetraethylene glycol (TEG) based ligands for subsequent conjugation to gold nanoshells are reported. TEG enhances the aqueous solubility of hollow gold nanoshells (HAuNShs), and the branched architecture provides stability
Synthesis of cholesterol-based neoglycoconjugates and their use in the preparation of liposomes for active liver targeting
e Silva, Aline Teixeira Maciel,Maia, Ana Luiza Chaves,de Oliveira Silva, Juliana,de Barros, André Luis Branco,Soares, Daniel Crístian Ferreira,de Magalh?es, Mariana Torquato Quezado,José Alves, Ricardo,Ramaldes, Gilson Andrade
, p. 52 - 57 (2018)
Carbohydrate receptors on liver represent attractive targets for receptor-mediated delivery of nanostructured therapeutics. In this study, two new cholesterol-based glycoconjugates derived from D-galactose and N-acetylglucosamine were synthesized and inco
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.
Dinuclear Copper(I) Thiodiacetate Complex-Mediated Expeditious Synthesis of the Chlorine-Containing Cyclen-Cored 36-Glucose-Coated Glycodendrimer
Agrahari, Anand K.,Kumar, Sunil,Sharma, Anindra,Tiwari, Vinod K.
, (2021/11/17)
High-sugar-tethered glycodendrimers are a remarkable tool in glycobiology for the investigation of carbohydrate-protein interaction using its multivalency property. An enthralling double-stage convergent synthetic approach was selected to build a novel class of chlorine-containing glucose-coated dendrimers using an efficient click catalyst 'dinuclear copper(I) thiodiacetate complex.' In this context, cyclen core was developed through a divergent approach, while the glucodendron was developed via a convergent approach independently. Both azide-alkyne partners were coupled through a modular copper azide-alkyne cycloaddition (CuAAC) strategy to afford a high yield of the desired 36-glucose-coated glycodendrimer. The synthesized glycodendrimer has been elucidated by NMR, gel permeation chromatography (GPC), and IR spectral analysis.
An expeditious click approach towards the synthesis of galactose coated novel glyco-dendrimers and dentromers utilizing a double stage convergent method
Agrahari, Anand K.,Mukherjee, Rishav,Singh., Anoop S.,Tiwari, Vinod K.
, p. 31553 - 31562 (2020/09/21)
The primary motive behind this article is to bring to the forefront a unique kind of dendrimer which has remained a dark horse since its discovery, namely dentromer. We herein report the synthesis of glycodendrimers and glycodentromers crowned with galactose units by harnessing an expeditious synthesis of dendrimer core 18 and dentromer core 19, divergently with branching directionality (1 → 2) and (1 → 3), respectively. A competent, double stage convergent synthetic path was chosen to facilitate ease of refining and spectroscopic elucidations. By exploiting a Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction strategy, we successfully developed a new series of galactosylated dendrimers 20, 21, 22, and 24 containing 6, 12, 18, and 18 peripheral galactose units, respectively. We are first to report the practical synthesis of 9-peripheral galactose coated glycodentromer 23 (0th generation) and 27-peripheral galactose coated glycodentromer 25 (1st generation). These synthesized scaffolds were characterized by spectral studies such as 1H, 13C NMR, FT-IR, MALDI-TOF MS, HRMS and SEC analysis. Additionally, gel permeation chromatography depicted the regular progression in size from 6 to 27-peripheral galactose coated glycodendrimers along with glycodentromers, with their high monodispersity. Also, the glyco-dendrimers and dentromers synthesized from two different hypercore units i.e. dendrimers core (18) and dentromer core (19), have been supported by their UV-visible absorbance and emission spectroscopy. This journal is
Ferrocenyl Janus mixed-dendron stars and their stabilization of Au and Ag nanoparticles
Liu, Yue,Mu, Shengdong,Liu, Xiong,Ling, Qiangjun,Hang, Chaodong,Ruiz, Jaime,Astruc, Didier,Gu, Haibin
supporting information, p. 4777 - 4789 (2018/07/31)
Janus molecular architectures have recently attracted attention due to their structures and properties that differ from those of traditional symmetric structures. Herein, two new small redox-reversible mixed-dendron star-shape molecules containing three ferrocenyl groups have been synthesized by linking two distinct dendrons using an esterification reaction. These organometallic nano structures were characterized by 1H and 13C NMR, MS, IR and UV–vis. spectroscopies and cyclic voltammetry confirming the number of ferrocenyl groups and AFM and DLS showing micellar assemblies. Au and Ag nanoparticles were stabilized in the presence of a mixed-dendron structure having amidoferrocene termini upon reaction of the nanoparticle metal precursor with NaBH4. Compared reactions of the two star-molecules with HAuCl4 showed a slow redox reaction leading to Au nanoparticles only with the star-molecule terminated with triazolyferrocene termini, which is taken into account by the difference of their redox potentials.
Dendritic ionic liquids based on imidazolium-modified poly(aryl ether) dendrimers
Qin, Tianyi,Li, Xuying,Chen, Jinping,Zeng, Yi,Yu, Tianjun,Yang, Guoqiang,Li, Yi
, p. 3641 - 3649 (2015/01/16)
A series of dendritic ionic liquids (DILs) based on imidazoliummodified poly(aryl ether) dendrimers IL-Br-Gn (n=0-3) were synthesized by a modified convergent approach and "click" chemistry. The resulting DILs exhibited high thermal resistance with decomposition temperatures up to 270 °C and low glass transition temperatures in the range of approximately -5-0 °C. All IL-Br-Gn were found to be miscible with water at any ratio and could encapsulate hydrophobic molecules. The reversible phase transfer of the DILs between the aqueous and organic phases was accomplished by simple anion exchange between the hydrophilic Br- anion and the hydrophobic bis(trifluoromethylsulfonyl)amide anion (NTf2-). IL-Br-Gn could be used as transporters to shuttle hydrophobic molecules between the organic and aqueous phases efficiently. The present work provides a new kind of transporting materials with potential applications in substance separation, drug delivery, and biomolecule transport.
Click chemistry inspired synthesis of glycoporphyrin dendrimers
Kushwaha, Divya,Tiwari, Vinod K.
, p. 8184 - 8190 (2013/09/12)
A series of porphyrin-cored glycodendrimers containing 8, 12, 16, and 24 β-d-glucopyranose units at the periphery, have been synthesized by convergent methodology using click chemistry. The structure of developed dendrimers is established by 1H
"Click" chemistry-mediated phenylene-cored carborane dendrimers
Dash, Barada Prasanna,Satapathy, Rashmirekha,Bode, Barrie P.,Reidl, Cory T.,Sawicki, James W.,Mason, Allen J.,Maguire, John A.,Hosmane, Narayan S.
experimental part, p. 2931 - 2935 (2012/06/15)
Phenylene-cored small dendrimers containing three to nine peripheral o-carborane clusters were synthesized via Cu(I)-catalyzed Huisgen-type azide alkyne cycloaddition reactions. The resulting dendrimers have been characterized by IR and NMR spectroscopy a
