Novel non-ionic block copolymers tailored for interactions with phospholipids

Amado, Elkin; Blume, Alfred; Kreßler, Jörg

doi:10.1016/j.reactfunctpolym.2008.12.021

Cited by 31 publications

(28 citation statements)

References 52 publications

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“…Furthermore, when a hydrophilic–lipophilic polymer is supplied with a third structural element, it expands the possibilities for the development of self-assembled multi-compartment macromolecules [92,93,94,95,96,97,98,99,100,101,102,103,104]. It often has remarkable effects on the catalytic behavior [92,105,106], the interaction with biological membranes [107,108,109,110], or the transport of active substances [103,109,111,112].…”

Section: From Polymer Amphiphilicity To Polyphilicitymentioning

confidence: 99%

Polyphilicity—An Extension of the Concept of Amphiphilicity in Polymers

2018

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Recent developments in synthetic pathways as simple reversible-deactivation radical polymerization (RDRP) techniques and quantitative post-polymerization reactions, most notoriously ‘click’ reactions, leading to segmented copolymers, have broadened the molecular architectures accessible to polymer chemists as a matter of routine. Segments can be blocks, grafted chains, branchings, telechelic end-groups, covalently attached nanoparticles, nanodomains in networks, even sequences of random copolymers, and so on. In this review, we describe the variety of the segmented synthetic copolymers landscape from the point of view of their chemical affinity, or synonymous philicity, in bulk or with their surroundings, such as solvents, permeant gases, and solid surfaces. We focus on recent contributions, current trends, and perspectives regarding polyphilic copolymers, which have, in addition to hydrophilic and lipophilic segments, other philicities, for example, towards solvents, fluorophilic entities, ions, silicones, metals, nanoparticles, and liquid crystalline moieties.

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Section: From Polymer Amphiphilicity To Polyphilicitymentioning

confidence: 99%

Polyphilicity—An Extension of the Concept of Amphiphilicity in Polymers

2018

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“…To overcome this drawback, it was proposed to substitute the PEO blocks by poly(glycerol monomethacrylate) (PGMA) blocks. 10,11 Due to the high propensity of PGMA to act as hydrogen bond donor and acceptor, the interaction with the lipid headgroups should be markedly increased. Moreover, the bulkiness of the PGMA side chains might increase the membrane disturbing effects, as it was reported for copolymers containing hyperbranched polyglycerols.…”

Section: 9mentioning

confidence: 99%

Binding of amphiphilic and triphilic block copolymers to lipid model membranes: the role of perfluorinated moieties

et al. 2014

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A novel class of symmetric amphi-and triphilic (hydrophilic, lipophilic, fluorophilic) block copolymers has been investigated with respect to their interactions with lipid membranes. The amphiphilic triblock copolymer has the structure PGMA 20 -PPO 34 -PGMA 20 (GP) and it becomes triphilic after attaching perfluoroalkyl moieties (F9) to either end which leads to F 9 -PGMA 20 -PPO 34 -PGMA 20 -F 9 (F-GP). The hydrophobic poly(propylene oxide) (PPO) block is sufficiently long to span a lipid bilayer. The poly(glycerol monomethacrylate) (PGMA) blocks have a high propensity for hydrogen bonding. The hydrophobic and lipophobic perfluoroalkyl moieties have the tendency to phase segregate in aqueous as well as in hydrocarbon environments. We performed differential scanning calorimetry (DSC) measurements on polymer bound lipid vesicles under systematic variation of the bilayer thickness, the nature of the lipid headgroup, and the polymer concentration. The vesicles were composed of phosphatidylcholines (DMPC, DPPC, DAPC, DSPC) or phosphatidylethanolamines (DMPE, DPPE, POPE). We showed that GP as well as F-GP binding have membrane stabilizing and destabilizing components.PPO and F9 blocks insert into the hydrophobic part of the membrane concomitantly with PGMA block adsorption to the lipid headgroup layer. The F9 chains act as additional membrane anchors. The insertion of the PPO blocks of both GP and F-GP could be proven by 2D-NOESY NMR spectroscopy. By fluorescence microscopy we show that F-GP binding increases the porosity of POPC giant unilamellar vesicles (GUVs), allowing the influx of water soluble dyes as well as the translocation of the complete triphilic polymer and its accumulation at the GUV surface. These results open a new route for the rational design of membrane systems with specific properties.

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“…Namely, it has been shown that triphilic polymers bearing bulky and lipophobic perfluorinated blocks do not mix well with the hydrocarbon chains of lipids, explaining their low membrane partition coefficients. [23,24] This is the reason why fluorinated surfactants are non-cytolytic, that is, they are unable to solubilize membranes, as opposed to their hydrogenated counterparts. [25] Herein, we report on the synthesis and antiviral plus antibacterial evaluation of perfluoroalkyl derivatives of vancomycin aglycone and teicoplanin pseudoaglycone.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Antiviral Perfluoroalkyl Derivatives of Teicoplanin and Vancomycin

et al. 2020

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The limited scope of antiviral drugs and increasing problem of antiviral drug resistance represent a global health threat. Glycopeptide antibiotics and their lipophilic derivatives have emerged as relevant inhibitors of diverse viruses. Herein, we describe a new strategy for the synthesis of dual hydrophobic and lipophobic derivatives of glycopeptides to produce selective antiviral agents without membrane‐disrupting activity. Perfluorobutyl and perfluorooctyl moieties were attached through linkers of different length to azido derivatives of vancomycin aglycone and teicoplanin pseudoaglycone, and the new derivatives were evaluated against a diverse panel of viruses. The teicoplanin derivatives displayed strong anti‐influenza virus activity at nontoxic concentrations. Some of the perfluoroalkylated glycopeptides were also active against a few other viruses such as herpes simplex virus or coronavirus. These data encourage further exploration of glycopeptide analogues for broad antiviral application.

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Novel non-ionic block copolymers tailored for interactions with phospholipids

Cited by 31 publications

References 52 publications

Polyphilicity—An Extension of the Concept of Amphiphilicity in Polymers

Polyphilicity—An Extension of the Concept of Amphiphilicity in Polymers

Binding of amphiphilic and triphilic block copolymers to lipid model membranes: the role of perfluorinated moieties

Synthesis of Antiviral Perfluoroalkyl Derivatives of Teicoplanin and Vancomycin

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