Convergent Synthesis and Characterization of Dumbbell Type Dendritic Materials by Click Chemistry

Sung, Sae Reum; Han, Seung Choul; Jin, Sung‐Ho; Lee, Jae Woo

doi:10.5012/bkcs.2011.32.11.3933

Cited by 13 publications

(9 citation statements)

References 49 publications

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“…Polystyrene (E) The coupling reaction between polymer (D) and di-propargylamine give a mixture of two polymers (E+E'). The proposed structure for (E) was confirmed by IR spectroscopy (Figure 9), but the structure of (E') was similar to that obtained by Sung et al [17]. The percentage of nitrogen present in (E+E') was 4.409% or 2.9mmol of N.g -1 .…”

Section: [4-(n-propynyl Amino Methyl)triazol-1-yl]methylsupporting

confidence: 83%

Chemical Modification of Polystyrene Merrifield: Extraction of Zinc and Magnesium Located in Wastewater

Dardouri¹,

Elamari²,

Ammari³

et al. 2019

AJPST

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In order to remove metals (Zn & Mg) located in wastewater, a new series of clickable polystyrene Merrifield grafted with azide and alkynes were synthesized and implicated in this domain. In a first step, we transformed the polystyrene Merrifield into the known Azidomethyl polystyrene, in a second step, a coupling reaction between the Azidomethyl polystyrene and dipropargylamine was realized for the synthesis of a new terminated polystyrene alkyne containing one unit of (1,4)-triazole. To increase the length of the chain grafted on the polystyrene Merrifield, several coupling reactions are applied, the main idea of this work was to increase the number of (1,2,3)-triazole units of this grafted chain. The click chemistry based on the Huygens's reaction catalyzed by copper (I) was used in this synthesis, the new polymers containing (1,4)-disubstituted triazole are tested for the extraction of Mg and Zn located in wastewater. The structure of new obtained polymers was confirmed by infrared spectroscopy (ATR-FTIR), UV-visible spectroscopy and elemental analysis for nitrogen. Differential Thermal Analysis (DTA) and Thermo Gravimetric Analysis (TGA) were used to study crosslinking behavior of these polymers. This study shows a low selectivity of studied polymers for the retention of magnesium, while for the Zinc, the percentage removal was average, it's in the order of 30%.

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Section: [4-(n-propynyl Amino Methyl)triazol-1-yl]methylsupporting

confidence: 83%

Chemical Modification of Polystyrene Merrifield: Extraction of Zinc and Magnesium Located in Wastewater

Dardouri¹,

Elamari²,

Ammari³

et al. 2019

AJPST

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“…As previously reported, the reaction of tetraethylene glycol with an equal amount of propargyl bromide in the presence of NaH in THF at room temperature gave the monoalkyne terminated PEG4. 30 Then the Michael addition of the resulting compound to tert -butyl acrylate in the presence of catalytic sodium metal gave compound 7 in 70% yield. 31 Having assembled the important intermediates (compounds 6 and 7 ), the next objective was their CuAAC conjugation assisted by copper iodide.…”

Section: Resultsmentioning

confidence: 99%

Thiodigalactoside–Bovine Serum Albumin Conjugates as High-Potency Inhibitors of Galectin-3: An Outstanding Example of Multivalent Presentation of Small Molecule Inhibitors

et al. 2018

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Galectin inhibitors are urgently needed to understand the mode of action and druggability of different galectins, but potent and selective agents still evade researchers. Small-sized inhibitors based on thiodigalactoside (TDG) have shown their potential while modifications at their C3 position indicated a strategy to improve selectivity and potency. Considering the role of galectins as glycoprotein traffic police, involved in multivalent bridging interactions, we aimed to create multivalent versions of the potent TDG inhibitors. We herein present for the first time the multivalent attachment of a TDG derivative using bovine serum albumin (BSA) as the scaffold. An efficient synthetic method is presented to obtain a novel type of neoglycosylated proteins loaded with different numbers of TDG moieties. A polyethylene glycol (PEG)-spacer is introduced between the TDG and the protein scaffold maintaining appropriate accessibility for an adequate galectin interaction. The novel conjugates were evaluated in galectin binding and inhibition studies in vitro. The conjugate with a moderate density of 19 conjugated TDGs was identified as one of the most potent multivalent Gal-3 inhibitors so far, with a clear demonstration of the benefit of a multivalent ligand presentation. The described method may facilitate the development of specific galectin inhibitors and their application in biomedical research.

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“…The CuAAC reaction has also been applied by other authors in the preparation of LDBCs . However, examples involving other click chemistry reactions to construct hybrid BCs are scarce.…”

Section: Synthetic Strategies For Ldbcs: the Click Coupling Approachmentioning

confidence: 99%

Responsive Linear‐Dendritic Block Copolymers

Blasco

Piñol

Oriol

2014

Macromol. Rapid Commun.

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The combination of dendritic and linear polymeric structures in the same macromolecule opens up new possibilities for the design of block copolymers and for applications of functional polymers that have self‐assembly properties. There are three main strategies for the synthesis of linear‐dendritic block copolymers (LDBCs) and, in particular, the emergence of click chemistry has made the coupling of preformed blocks one of the most efficient ways of obtaining libraries of LDBCs. In these materials, the periphery of the dendron can be precisely functionalised to obtain functional LDBCs with self‐assembly properties of interest in different technological areas. The incorporation of stimuli‐responsive moieties gives rise to smart materials that are generally processed as self‐assemblies of amphiphilic LDBCs with a morphology that can be controlled by an external stimulus. Particular emphasis is placed on light‐responsive LDBCs. Furthermore, a brief review of the biomedical or materials science applications of LDBCs is presented.

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Convergent Synthesis and Characterization of Dumbbell Type Dendritic Materials by Click Chemistry

Cited by 13 publications

References 49 publications

Chemical Modification of Polystyrene Merrifield: Extraction of Zinc and Magnesium Located in Wastewater

Chemical Modification of Polystyrene Merrifield: Extraction of Zinc and Magnesium Located in Wastewater

Thiodigalactoside–Bovine Serum Albumin Conjugates as High-Potency Inhibitors of Galectin-3: An Outstanding Example of Multivalent Presentation of Small Molecule Inhibitors

Responsive Linear‐Dendritic Block Copolymers

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