Guanidinium group: A versatile moiety inducing transport and multicompartmentalization in complementary membranes

Pantos, Alexandros; Tsogas, Ioannis; Paleos, Constantinos M.

doi:10.1016/j.bbamem.2007.12.003

Cited by 105 publications

(78 citation statements)

References 74 publications

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“…The guanidinium groups contained in this SMAMP are also found in polyA C H T U N G T R E N N U N G (arginine) and other cell-penetrating peptides, [85][86][87][88][89] and such cell-penetrating peptides are known to be able to cross membranes, transport cargo into cells, and bind DNA. [85,88,[90][91][92][93][94][95] In the light of this body of literature and the above results, it was postulated that polymer 10 is antibacterially active by first penetrating the cell membrane without causing damage, and then interacting with an intracellular target, potentially the bacteria DNA, which leads to the cells death. [62] Recent studies confirmed the ability of these polymers to traverse membranes and gave further evidence that this mechanism is reasonable, as these guanidinium-rich polymers behaved remarkably similar to polyA C H T U N G T R E N N U N G (arginine).…”

mentioning

confidence: 94%

Synthetic Mimics of Antimicrobial Peptides—A Versatile Ring‐Opening Metathesis Polymerization Based Platform for the Synthesis of Selective Antibacterial and Cell‐Penetrating Polymers

Lienkamp

Tew

2009

Chemistry A European J

147

139

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Natural macromolecules exhibit an extensive arsenal of properties, many of which have proven difficult to recapitulate in simpler synthetic systems. Over the last couple of years, foldamers have emerged as one important step toward increased functionality in synthetic systems. While the great majority of work in this area has focused on folded structures, hence the name, more recent progress has centered on polymers that mimic protein function. These efforts have resulted in the design of relatively simple macromolecules; one example are the synthetic mimics of antimicrobial peptides (SMAMPs) that capture the central physicochemical features of their natural archetypes irrespective of the specific folded form. Here we present our recent efforts to create polymers which display biological activity similar to natural proteins, including antimicrobial and cell-penetrating peptides.

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mentioning

confidence: 94%

Synthetic Mimics of Antimicrobial Peptides—A Versatile Ring‐Opening Metathesis Polymerization Based Platform for the Synthesis of Selective Antibacterial and Cell‐Penetrating Polymers

Lienkamp

Tew

2009

Chemistry A European J

147

139

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“…Very large aggregates (>1000 nm diameter) resulted from the addition of polyarginine to vesicles (100 nm diameter) bearing 5% mol/ mol di(hexadecyl)phosphate, but heating to the bilayer melting temperature (T m ) resulted in partial penetration of the polypeptide into the bilayer. Similarly, guanidylated dendrimers often caused vesicles to fuse rather than aggregate, or form multicompartment "vesosomes" (18). To prevent unwanted vesicle fusion we used the histidine-Cu (iminodiacetate) (His-Cu(IDA)) interaction (Fig.…”

Section: (A) Vesicle Cross-linking By Polymers and Proteinsmentioning

confidence: 99%

Creating Functional Vesicle Assemblies from Vesicles and Nanoparticles

2009

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Vesicles (liposomes) have been shown to be excellent vehicles for drug delivery, yet assemblies of vesicles (vesicle aggregates) have been used infrequently in this context. However vesicle assemblies have useful properties not available to individual vesicles; their size can cause localisation in specific tissues and they can incorporate more functionality than is possible with individual vesicles. This article reviews progress on controlling the properties of vesicle assemblies in vitro, applications of vesicle assemblies in vivo, and our recent creation of magnetic nanoparticle-vesicle assemblies. The latter assemblies contain vesicles crosslinked by coated Fe3O4 nanoparticles and this inclusion of magnetic functionality makes them magnetically responsive, potentially allowing magnetically-induced contents release. This article describes further studies on the in vitro formation of these magnetic nanoparticle-vesicle assemblies, including the effect of changing magnetic nanoparticle concentration, pH, adhesive lipid structure and bilayer composition. These investigations have led to the development of thermally-sensitive magnetic nanoparticle-vesicle assemblies that release encapsulated methotrexate on warming.

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“…In addition, guanidinium groups at appropriate concentration on liposomal surfaces facilitate their transport through cell membranes. [24][25][26] Furthermore, polyethylene glycol chains introduced onto liposomal surfaces, in addition to acting as protecting coatings of liposomes in the biological environment, [27][28][29][30][31] also induce fusion. [32][33][34][35] For these reasons liposomal formulations with enhanced PEG content were also prepared by incorporation of non-guanidinylated PEGylated cholesterol (PEG-CHOL).…”

Section: Introductionmentioning

confidence: 98%

Structural Features of Interacting Complementary Liposomes Promoting Formation of Multicompartment Structures

et al. 2009

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The structural features of complementary liposomes and factors favoring formation of multicompartment systems are investigated. Specifically, liposomal formulations consisting of PEGylated unilamellar liposomes with guanidinium moieties located at the distal end of polyethylene glycol (PEG) chains interact with complementary multilamellar liposomes bearing phosphate moieties. Furthermore, the number of PEG chains attached to the unilamellar interface of the liposomes is enhanced by incorporating PEGylated cholesterol in their bilayer. While molecular recognition of the liposomes is the driving force for initiating multicompartmentalization, it is the enhanced PEGylation at the liposomal interface that synergistically promotes fusion resulting in large and well-formed multicompartment systems. A mechanism is proposed according to which initial adhesion of the liposomes, followed by reorganization of their membrane lipids, leads to giant bilayer aggregates incorporating large liposomes.

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Guanidinium group: A versatile moiety inducing transport and multicompartmentalization in complementary membranes

Cited by 105 publications

References 74 publications

Synthetic Mimics of Antimicrobial Peptides—A Versatile Ring‐Opening Metathesis Polymerization Based Platform for the Synthesis of Selective Antibacterial and Cell‐Penetrating Polymers

Synthetic Mimics of Antimicrobial Peptides—A Versatile Ring‐Opening Metathesis Polymerization Based Platform for the Synthesis of Selective Antibacterial and Cell‐Penetrating Polymers

Creating Functional Vesicle Assemblies from Vesicles and Nanoparticles

Structural Features of Interacting Complementary Liposomes Promoting Formation of Multicompartment Structures

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