Smart tools and orthogonal click-like reactions onto small unilamellar vesicles

Salomé, Christophe; Spanedda, Maria Vittoria; Hilbold, Benoît; Berner, Etienne; Heurtault, Béatrice; Fournel, Sylvie; Frisch, Benoı̂t; Bourel-Bonnet, Line

doi:10.1016/j.chemphyslip.2015.03.004

Cited by 10 publications

(9 citation statements)

References 58 publications

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“…The entries are organized by number of carbon atoms of the phosphane (and then grouped by publication), and it will cover examples up to beginning of 2020 (for not or only partly covered examples, see refs − ).…”

Section: Mechanism and Stereochemistrymentioning

confidence: 99%

The Staudinger Ligation

et al. 2020

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While the Staudinger reaction has first been described a hundred years ago in 1919, the ligation reaction became one of the most important and efficient bioconjugation techniques in the 1990s and this century. It holds the crucial characteristics for bioorthogonal chemistry: biocompatibility, selectivity, and a rapid and high-yielding turnover for a wide variety of applications. In the past years, it has been used especially in chemical biology for peptide/protein synthesis, posttranslational modifications, and DNA labeling. Furthermore, it can be used for cell-surface engineering, development of microarrays, and drug delivery systems. However, it is also possible to use the reaction in synthetic chemistry for general formation of amide bonds. In this review, the three major types, traceless and nontraceless Staudinger Ligation as well as the Staudinger phosphite reaction, are described in detail. We will further illustrate each reaction mechanism and describe characteristic substrates, intermediates, and products. In addition, not only its advantages but also stereochemical aspects, scope, and limitations, in particular side reactions, are discussed. Finally, the method is compared to other bioorthogonal labeling methods.

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Section: Mechanism and Stereochemistrymentioning

confidence: 99%

The Staudinger Ligation

et al. 2020

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“…In contrast to post‐insertion approaches that often rely on potentially incompatible, elevated temperatures, we prepared liposomal nanoparticles that allow for a post‐preparational, orthogonal surface derivatization. While this concept has been described only in a single work to date for the use of SPAAC, we add CuAAC and IEDDA reactions to this repertoire, thereby only relying biocompatible conjugation sites.…”

Section: Figurementioning

confidence: 99%

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

Fritz

Voigt

Worm

et al. 2016

Chemistry A European J

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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 of functional amphiphiles. Folic acid residues clicked to cholesterol-based amphiphiles were inefficient in folate-mediated cell targeting, while dialkyl-anchored amphiphiles remained stable in the liposomal membrane and imparted efficient targeting properties. These findings are of specific importance considering the popularity of cholesterol as a lipophilic anchor.

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“…Bioconjugation of targeting moieties to lipids or to liposomes is typically carried out via the reaction of thiol-functionalised targeting moieties to malemide-derivatised lipids, using click chemistry, or amide bond formation, 29,44 although hydrazone linkages 45 and Staudiger ligations 44 have also been reported. The majority of peptide-targeted liposomes to date have relied on the post-formulation bioconjugation of thiol-functionalised targeting moieties to liposomes containing DSPE-PEG2000-Mal, 29,30,41 although other maleimide-containing lipids with shorter or no PEG linkages have been reported.…”

Section: Design Of Lipopolyplexes: Peptide Targeting and Lipopolyplmentioning

confidence: 99%

Development of lipopolyplexes for gene delivery: A comparison of the effects of differing modes of targeting peptide display on the structure and transfection activities of lipopolyplexes

Bofinger

Thin

Mitchell

et al. 2018

Journal of Peptide Science

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The design, synthesis and formulation of non‐viral gene delivery vectors is an area of renewed research interest. Amongst the most efficient non‐viral gene delivery systems are lipopolyplexes, in which cationic peptides are co‐formulated with plasmid DNA and lipids. One advantage of lipopolyplex vectors is that they have the potential to be targeted to specific cell types by attaching peptide targeting ligands on the surface, thus increasing both the transfection efficiency and selectivity for disease targets such as cancer cells. In this paper, we have investigated two different modes of displaying cell‐specific peptide targeting ligands at the surface of lipopolyplexes. Lipopolyplexes formulated with bimodal peptides, with both receptor binding and DNA condensing sequences, were compared with lipopolyplexes with the peptide targeting ligand directly conjugated to one of the lipids. Three EGFR targeting peptide sequences were studied, together with a range of lipid formulations and maleimide lipid structures. The biophysical properties of the lipopolyplexes and their transfection efficiencies in a basal‐like breast cancer cell line were investigated using plasmid DNA bearing genes for the expression of firefly luciferase and green fluorescent protein. Fluorescence quenching experiments were also used to probe the macromolecular organisation of the peptide and pDNA components of the lipopolyplexes. We demonstrated that both approaches to lipopolyplex targeting give reasonable transfection efficiencies, and the transfection efficiency of each lipopolyplex formulation is highly dependent on the sequence of the targeting peptide. To achieve maximum therapeutic efficiency, different peptide targeting sequences and lipopolyplex architectures should be investigated for each target cell type.

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Smart tools and orthogonal click-like reactions onto small unilamellar vesicles

Cited by 10 publications

References 58 publications

The Staudinger Ligation

The Staudinger Ligation

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

Development of lipopolyplexes for gene delivery: A comparison of the effects of differing modes of targeting peptide display on the structure and transfection activities of lipopolyplexes

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