The synthesis of adamantane-terminated polypeptides by N-carboxyanhydride (NCA) polymerization and their use in the template-based self-assembly of redox-responsive nanocontainers is described. Cyclodextrin vesicles (CDV) serve as a supramolecular template to anchor adamantane terminated polypeptides on to the surface of CDV and to form polypeptide shelled vesicles (PPSVss) which are stabilized by crosslinking with cystamin. Polypeptides are characterized by nuclear magnetic resonance, matrix-assisted laser desorption/ionization (MALDI), and gel permeation chromatography, and nanocontainer formation at each step is confirmed by dynamic light scattering (DLS) and zeta potential measurements. MALDI confirms the presence of the adamantane at the end of the polymers, and isothermal titration calomatry (ITC) of the adamantane-terminated polypeptides with β-cyclodextrin proves the capability of adamantane on the polypeptides to form host-guest inclusion complexes even with the longest polypeptides. Encapsulation of a model dye carboxyfluorescein in PPSVss and its redox-responsive release demonstrates the potential use of this novel type of completely biodegradable and biocompatible nanocontainer for the purpose of intracellullar delivery.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/marc.202000049 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Negatively charged polymer-shielded supramolecular nano-micelles with stimuli-responsive property for anticancer drug delivery.
Int J Pharm
November 2022
State Key Laboratory of Applied Organic Chemistry, Institute of Biochemical Engineering & Environmental Technology, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Road, Lanzhou 730000, PR China. Electronic address:
A new kind of negatively charged polymer-shielded supramolecular nano-micelles with dual-responsive property was designed for tumor treatment, which was prepared on the basis of adamantane terminated linear PAsp(DIP) and disulfide-β-cyclodextrin-terminated PAsp(EDA). The supramolecular nano-micelles comprised a 2,3-dimethylmaleic anhydride (DA) protective layer to stabilize the micelles, a pH-responsive core to package hydrophobic model drugs, and a disulfide-crosslinked interlayer to shackle the core against drug leakage under normal physiological conditions. After arriving at the tumor tissue via EPR, the targeting function could be turned on by dislodging DA groups on the surface of micelles, which allowed the drug-loaded nano-micelles to be easily phagocytized by the tumor cells, and then release the drug inside the cells induced by the increased glutathione level and acidic pH.
View Article and Find Full Text PDFGlutathione sensitive vesicles prepared from supramolecular amphiphiles.
Soft Matter
November 2021
Department of Chemistry and Biochemistry, California Polytechnic State University, 1 Grand Avenue, San Luis Obispo, California, 93401, USA.
Glutathione (GSH) sensitive vesicles were prepared by the self-assembly of amphiphilic inclusion complexes. These novel chemically sensitive supramolecular amphiphiles are anticipated to have applications in drug delivery; the nanocarriers can protect the encapsulated cargo and release it triggered degradation in high concentrations of GSH. Additionally, the sensitivity of the vesicles to GSH indicates that the dynamic covalent disulfide bond at the vesicle surface can be used for post-modification of the nanocarrier a thiol-disulfide exchange, a strategy that can be exploited to introduce targeting moieties to increase treatment specificity.
View Article and Find Full Text PDFBiodegradable supramolecular micelles host-guest interaction of cyclodextrin-terminated polypeptides and adamantane-terminated polycaprolactones.
Chem Commun (Camb)
September 2021
Organic Chemistry Institute and Centre for Soft Nanoscience Westfälische Wilhelms-Universität Münster, Corrensstrasse 36, 48149 Münster, Germany.
Biodegradable supramolecular micelles were prepared exploiting the host-guest interaction of cyclodextrin and adamantane. Cyclodextrin-initiated polypeptides acted as the hydrophilic corona, whereas adamantane-terminated polycaprolactones served as the hydrophobic core.
View Article and Find Full Text PDFAdamantane-Terminated Polypeptides: Synthesis by N-Carboxyanhydride Polymerization and Template-Based Self-Assembly of Responsive Nanocontainers via Host-Guest Complexation with β-Cyclodextrin.
Macromol Rapid Commun
September 2020
Organic Chemistry Institute and Centre for Soft Nanoscience, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, Münster, 48149, Germany.
The synthesis of adamantane-terminated polypeptides by N-carboxyanhydride (NCA) polymerization and their use in the template-based self-assembly of redox-responsive nanocontainers is described. Cyclodextrin vesicles (CDV) serve as a supramolecular template to anchor adamantane terminated polypeptides on to the surface of CDV and to form polypeptide shelled vesicles (PPSVss) which are stabilized by crosslinking with cystamin. Polypeptides are characterized by nuclear magnetic resonance, matrix-assisted laser desorption/ionization (MALDI), and gel permeation chromatography, and nanocontainer formation at each step is confirmed by dynamic light scattering (DLS) and zeta potential measurements.
View Article and Find Full Text PDFModulation of stem cell adhesion and morphology via facile control over surface presentation of cell adhesion molecules.
Biomacromolecules
January 2014
Tissue Engineering and Microfluidic Laboratory, Australian Institute for Bioengineering and Nanotechnology, The University of Queensland , Corner of Cooper and College Road, Brisbane, 4072 Queensland, Australia.
To encourage cell adhesion on biomaterial surfaces in a more facile, safe, and low-cost fashion, we have demonstrated a noncovalent approach to spatially conjugate β-cyclodextrin (β-CD) modified peptide sequences onto self-assembled adamantane-terminated polystyrene-b-poly(ethylene oxide) (PS-PEO-Ada) films through inclusion complexing interactions between β-CDs and adamantane. By simply blending various ratios of unmodified PS-PEO with a newly synthesized PS-PEO-Ada, we produced PS polymer films that displayed well-organized adamantine-decorated cylindrical PEO domains with varying average interdomain spacings ranging from 29 to 47 nm. The presence of the adamantane moiety at the terminal end of the PEO chain permitted rapid, and importantly, oriented attachment of β-CD functionalized peptides onto these surfaces.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!