Hierarchical Organization of Purely Peptidic Amphiphiles into Peptide Beads

Ouboter, Dirk de Bruyn; Schuster, Thomas; Mantion, Alexandre; Meier, Wolfgang

doi:10.1021/jp203048h

Cited by 12 publications

(12 citation statements)

References 50 publications

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“…They showed embedding of hydrophobic and hydrophilic payloads and can form ordered gold nanoparticle superstructures. 39 The multicompartment micellar (MCM) inner structure of the nanoparticles 54 provides similar volume fractions for hydrophilic and hydrophobic payload but lacking sites for nucleic acid condensation and stimuli-triggered release mechanisms.…”

Section: ■ Introductionmentioning

confidence: 99%

Stimuli-Responsive Codelivery of Oligonucleotides and Drugs by Self-Assembled Peptide Nanoparticles

et al. 2016

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Ever more emerging combined treatments exploiting synergistic effects of drug combinations demand smart, responsive codelivery carriers to reveal their full potential. In this study, a multifunctional stimuli-responsive amphiphilic peptide was designed and synthesized to self-assemble into nanoparticles capable of co-bearing and -releasing hydrophobic drugs and antisense oligonucleotides for combined therapies. The rational design was based on a hydrophobic l-tryptophan-d-leucine repeating unit derived from a truncated sequence of gramicidin A (gT), to entrap hydrophobic cargo, which is combined with a hydrophilic moiety of histidines to provide electrostatic affinity to nucleotides. Stimuli-responsiveness was implemented by linking the hydrophobic and hydrophilic sequence through an artificial amino acid bearing a disulfide functional group (H3SSgT). Stimuli-responsive peptides self-assembled in spherical nanoparticles in sizes (100-200 nm) generally considered as preferable for drug delivery applications. Responsive peptide nanoparticles revealed notable nucleotide condensing abilities while maintaining the ability to load hydrophobic cargo. The disulfide cleavage site introduced in the peptide sequence induced responsiveness to physiological concentrations of reducing agent, serving to release the incorporated molecules. Furthermore, the peptide nanoparticles, singly loaded or coloaded with boron-dipyrromethene (BODIPY) and/or antisense oligonucleotides, were efficiently taken up by cells. Such amphiphilic peptides that led to noncytotoxic, reduction-responsive nanoparticles capable of codelivering hydrophobic and nucleic acid payloads simultaneously provide potential toward combined treatment strategies to exploit synergistic effects.

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Section: ■ Introductionmentioning

confidence: 99%

Stimuli-Responsive Codelivery of Oligonucleotides and Drugs by Self-Assembled Peptide Nanoparticles

et al. 2016

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“…68 A common feature of the peptides that form nanoparticles is the presence of aromatic amino acid residues in their sequences, eg, Phe-Tyr, 69 Phe-Phe-Phe, 70 and various Trpbased oligopeptides derived from the truncation of gramicidin A. 71,72 Presumably, self-assembly of the peptides is facilitated …”

Section: Peptide Nanoparticles As Drug Delivery Agents and Bioimagingmentioning

confidence: 99%

“…73,74 Interestingly, the nanoparticles formed by truncated Trp-peptides of gramicidin A are able to further assemble into higher order peptide beads, 71 in a manner analogous to proteins such as β-lactoglobulin 75 and apo-α-lactalbumin/lysozyme. 76 This makes possible the simultaneous delivery of multiple drugs by compartmentalizing different drugs within a peptide bead.…”

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confidence: 99%

“…76 This makes possible the simultaneous delivery of multiple drugs by compartmentalizing different drugs within a peptide bead. 71,72 The following three features of peptide nanoparticles lend themselves well to drug delivery: 1) the small size of nanoparticles (,100 nm) enables them to permeate the target cells of interest, 77 2) the peptides can be designed to interact with the drug but still can self-assemble and encapsulate the drugs within the core of nanoparticles, 78 and 3) the surface of the nanoparticles can be adorned with cell recognition motifs. 79,80 For example, doxorubicin, a nonpolar anticancer drug, has been loaded inside dendrimeric peptide nanoparticles.…”

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confidence: 99%

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Harnessing supramolecular peptide nanotechnology in biomedical applications

Chan

Lee

Zhuo

et al. 2017

IJN

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The harnessing of peptides in biomedical applications is a recent hot topic. This arises mainly from the general biocompatibility of peptides, as well as from the ease of tunability of peptide structure to engineer desired properties. The ease of progression from laboratory testing to clinical trials is evident from the plethora of examples available. In this review, we compare and contrast how three distinct self-assembled peptide nanostructures possess different functions. We have 1) nanofibrils in biomaterials that can interact with cells, 2) nanoparticles that can traverse the bloodstream to deliver its payload and also be bioimaged, and 3) nanotubes that can serve as cross-membrane conduits and as a template for nanowire formation. Through this review, we aim to illustrate how various peptides, in their various self-assembled nanostructures, possess great promise in a wide range of biomedical applications and what more can be expected.

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“…More complex self‐assembly structures, namely multi‐compartment‐micelles (MCMs) can host both hydrophilic and hydrophobic drugs, making them especially versatile candidates for drug delivery. We have recently reported the redox‐responsive amphiphilic peptide H 3 SSgT (of the sequence H 2 N ‐H 3 ‐X‐[W‐ D L] 3 ‐W‐ NH 2 , where X = –NH‐(CH 2 ) 2 ‐S‐S‐(CH 2 ) 2 ‐NH‐CO‐(CH 2 ) 2 ‐CO– and D L = d ‐Leucine; Figure ), that forms such MCMs . They were shown to efficiently entrap the model compound boron‐dipyrromethene (Bodipy) and release it in presence of physiological amounts of reducing agent .…”

Section: Introductionmentioning

confidence: 99%

Delivery of ROS Generating Anthraquinones Using Reduction‐Responsive Peptide‐Based Nanoparticles

Richard

Craciun

Gaitzsch

et al. 2018

Helvetica Chimica Acta

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In order to limit the side effects associated with antitumor drugs such as doxorubicin, nanosized drug‐delivery systems capable of selectively delivering and releasing the drug in the diseased tissue are required. We describe nanoparticles (NPs), self‐assembled from a reduction responsive amphiphilic peptide, capable of entrapping high amounts of a redox active anticancer drug candidate and releasing it in presence of a reducing agent. This system shows a high entrapment efficiency with up to 15 mg drug per gram of peptide (5.8 mol‐%). Treatment of the NPs with reducing agent results in the disassembly of the NPs and release of the drug molecules. A reduction in cell viability is observed at drug concentrations above 250 nm in HEK293T and HeLa cell lines. This drug delivery system has potential for targeting tumor sites via the EPR effect while taking advantage of the increased reduction potential in tumor microenvironment.

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Hierarchical Organization of Purely Peptidic Amphiphiles into Peptide Beads

Cited by 12 publications

References 50 publications

Stimuli-Responsive Codelivery of Oligonucleotides and Drugs by Self-Assembled Peptide Nanoparticles

Stimuli-Responsive Codelivery of Oligonucleotides and Drugs by Self-Assembled Peptide Nanoparticles

Harnessing supramolecular peptide nanotechnology in biomedical applications

Delivery of ROS Generating Anthraquinones Using Reduction‐Responsive Peptide‐Based Nanoparticles

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