Search results for "CLICK CHEMISTRY"

Orthogonal Click Conjugation to the Liposomal Surface Reveals the Stability of the Lipid Anchorage as Crucial for Targeting

2016

Synthetic access to multiple surface decorations are a bottleneck in the development of liposomes for receptor mediated targeting. This opens a complex multiparameter space, exploration of which is severely limited in terms of sample numbers and turnaround times. Here, we unlock this technological barrier by a combination of a milligram-scale liposome formulation using dual centrifugation and orthogonal click chemistry on the liposomal surface. Application of these techniques to conceptually new amphiphilic compounds, which feature norbornene and alkyne groups at the apex of sterically stabilizing, hyperbranched polyglycerol moieties, revealed a particular influence of the membrane anchor o…

A fully synthetic glycopeptide antitumor vaccine based on multiple antigen presentation on a hyperbranched polymer.

2014

For antitumor vaccines both the selected tumor-associated antigen, as well as the mode of its presentation, affect the immune response. According to the principle of multiple antigen presentation, a tumor-associated MUC1 glycopeptide combined with the immunostimulating T-cell epitope P2 from tetanus toxoid was coupled to a multi-functionalized hyperbranched polyglycerol by "click chemistry". This globular polymeric carrier has a flexible dendrimer-like structure, which allows optimal antigen presentation to the immune system. The resulting fully synthetic vaccine induced strong immune responses in mice and IgG antibodies recognizing human breast-cancer cells.

Polymethacrylate monoliths with immobilized poly-3-mercaptopropyl methylsiloxane film for high-coverage surface functionalization by thiol-ene click …

2014

In this work, new polythiol-functionalized macroporous monolithic polymethacrylate-polysiloxane composite materials are presented which can be useful substrates for highly efficient immobilization of (chiral) catalysts, chromatographic ligands, and other functional moieties by thiol-ene click reaction. Poly(glycidyl methacrylate-co-ethylene dimethacrylate) (poly(GMA-co-EDMA)) monoliths were coated with a poly-3-mercaptopropyl methylsiloxane (PMPMS) film and subsequently the polymer was covalently immobilized by formation of crosslinks via nucleophilic substitution reaction with pendent 2,3-epoxypropyl groups on the monolith surface. This monolith, though, showed similar levels of surface co…

The conjugation strategy affects antibody orientation and targeting properties of nanocarriers.

2021

Antibody-modified drug delivery systems in the nano-range have the ability to overcome current challenges for treating diseases due to their high specificity towards the targeted body region. However, no antibody-bound nanocarrier has been clinically approved to date. This missing clinical approval may be a result of the conjugation strategy that influences the spatial orientation of the attached antibody on the nanocarriers' surface. What is not missing, however, is a diverse selection of antibody to nanocarrier conjugation strategies that determine the success of an antibody functionalized drug delivery system. In this paper, two antibody conjugation strategies were compared by conjugatin…

12-MC-4 metallacrowns as versatile tools for SMM research

2015

Abstract The outstanding chemical and structural features of 12-MC-4 metallacrowns allow for versatile applications in magneto-chemical research. Herein, we present three novel approaches. The heterometallic, or magnetic director approach, provides a targeted way to attain unusual high-spin ground states in 12-MC-4 complexes. Further, the first cobalt metallacrowns of salicylhydroxamic acid have been established. They comprise a diamagnetic scaffold which facilitates an engineering of the magnetism of the central guest ion and thus three novel SMMs based on single Co(II) ions have been established. Finally, click chemistry has been utilized to realize a linkage of an azide-functionalized mo…

A Click‐Functionalized Single‐Molecule Magnet Based on Cobalt(II) and Its Analogous Manganese(II) and Zinc(II) Compounds

2014

A mononuclear CoII single-molecule magnet suitable for click chemistry was investigated. [M(oda)(aterpy)] complexes (oda2– = oxodiacetate, aterpy = 4′-azido-2,2′:6′,2″-terpyridine) with M = MnII, ZnII, and CoII were synthesized as azide-functionalized building blocks for the copper-catalyzed azide–alkyne cycloaddition reaction. The required structural integrity of the complexes in solution was proven in great detail by using ESI-MS and NMR spectroscopy. For the six-coordinate [Co(oda)(aterpy)] complex, single-molecule magnet behavior was confirmed with an effective energy barrier of 4.2 cm–1.

Slow and Fast Singlet Energy Transfers in BODIPY-gallium(III)corrole Dyads Linked by Flexible Chains

2014

Red (no styryl), green (monostyryl), and blue (distyryl) BODIPY-gallium(III) (BODIPY = boron-dipyrromethene) corrole dyads have been prepared in high yields using click chemistry, and their photophysical properties are reported. An original and efficient control of the direction of the singlet energy transfers is reported, going either from BODIPY to the gallium-corrole units or from gallium-corroles to BODIPY, depending upon the nature of the substitution on BODIPY. In one case (green), both directions are possible. The mechanism for the energy transfers is interpreted by means of through-space Förster resonance energy transfer (FRET).

A reusable polymer-supported copper(I) catalyst for triazole click reaction on water: An experimental and computational study

2019

Rapid and Complete Surface Modification with Strain-Promoted Oxidation-Controlled Cyclooctyne-1,2-Quinone Cycloaddition (SPOCQ)

2017

Abstract Strain‐promoted oxidation‐controlled cyclooctyne‐1,2‐quinone cycloaddition (SPOCQ) between functionalized bicyclo[6.1.0]non‐4‐yne (BCN) and surface‐bound quinones revealed an unprecedented 100 % conjugation efficiency. In addition, monitoring by direct analysis in real time mass spectrometry (DART‐MS) revealed the underlying kinetics and activation parameters of this immobilization process in dependence on its microenvironment.

Strain-Promoted Cycloaddition of Cyclopropenes with o-Quinones : A Rapid Click Reaction

2018

Abstract Novel click reactions are of continued interest in fields as diverse as bio‐conjugation, polymer science and surface chemistry. Qualification as a proper “click” reaction requires stringent criteria, including fast kinetics and high conversion, to be met. Herein, we report a novel strain‐promoted cycloaddition between cyclopropenes and o‐quinones in solution and on a surface. We demonstrate the “click character” of the reaction in solution and on surfaces for both monolayer and polymer brush functionalization.