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Drug Release by Direct Jump from Poly(ethylene-glycol-b-ε-caprolactone) Nano-Vector to Cell Membrane.

ABSTRACT: Drug delivery by nanovectors involves numerous processes, one of the most important being its release from the carrier. This point still remains unclear. The current work focuses on this point using poly(ethyleneglycol-b-ε-caprolactone) micelles containing either pheophorbide-a (Pheo-a) as a fluorescent probe and a phototoxic agent or fluorescent copolymers. This study showed that the cellular uptake and the phototoxicity of loaded Pheo-a are ten times higher than those of the free drug and revealed a very low cellular penetration of the fluorescence-labeled micelles. Neither loaded nor free Pheo-a displayed the same cellular localization as the labeled micelles. These results imply that the drug entered the cells without its carrier and probably without a disruption, as suggested by their stability in cell culture medium. These data allowed us to propose that Pheo-a directly migrates from the micelle to the cell without disruption of the vector. This mechanism will be discussed.

SUBMITTER: Till U

PROVIDER: S-EPMC6273951 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Amphiphilic Polymer Conetwork Gel Films Based on Tetra-Poly(ethylene Glycol) and Tetra-Poly(ε-Caprolactone).

Project description:The preparation and investigation of gel films from a model amphiphilic polymer conetwork (ACN) grant a deeper control and understanding of the structure-property relationship in the bulk phase and at the interface of materials with promising applications. In order to allow the simultaneous transport of hydrophilic and hydrophobic substances, polymeric networks with finely distributed hydrophilic and hydrophobic components are very suitable. When designing new soft materials such as coatings, in addition to the structure in the bulk phase, the structure at the interface plays a critical role. In this study, two alternating tetra-arm star polymers poly(ε-caprolactone) (tetra-PCL-Ox) and amino-terminated poly(ethylene glycol) (tetra-PEG-NH2) form an amphiphilic polymer conetwork. The correlation between different synthesis strategies for gel films of this ACN model system and their resulting properties will be described. Through various spin coating techniques, control over film thickness and roughness is achievable and highlights differences to macroscopic gel samples. Atomic force microscopy (AFM) measurements reveal the effect of solvents of different polarities on the swelling ability and surface structure. This correlates with AFM investigations of the mechanical properties on ACN gel films, demonstrating a strong effect on the resulting elastic modulus E, depending on the presence or absence of a good solvent during synthesis. Furthermore, a higher E modulus is obtained in the presence of the selective solvent water, compared to the non-selective solvent toluene. This observation is explained through selective swelling of the tetra-arm star polymers displaying a different hydrophobicity.

| S-EPMC9269314 | biostudies-literature

Mannosylated brush copolymers based on poly(ethylene glycol) and poly(ε-caprolactone) as multivalent lectin-binding nanomaterials.

Project description:A class of linear and four-arm mannosylated brush copolymers based on poly(ethylene glycol) and poly(ε-caprolactone) is presented here. The synthesis through ring-opening and atom transfer radical polymerizations provided high control over molecular weight and functionality. A post-polymerization azide-alkyne cycloaddition allowed for the formation of glycopolymers with different mannose valencies (1, 2, 4, and 8). In aqueous media, these macromolecules formed nanoparticles that were able to bind lectins, as investigated by concanavalin A binding assay. The results indicate that carbohydrate-lectin interactions can be tuned by the macromolecular architecture and functionality, hence the importance of these macromolecular properties in the design of targeted anti-pathogenic nanomaterials.

| S-EPMC6880840 | biostudies-literature

π-π-Stacked Poly(ε-caprolactone)-b-poly(ethylene glycol) Micelles Loaded with a Photosensitizer for Photodynamic Therapy.

Project description:To improve the in vivo stability of poly(-caprolactone)-b-poly(ethylene glycol) (PCL-PEG)-based micelles and cargo retention by π-π stacking interactions, pendant aromatic rings were introduced by copolymerization of -caprolactone with benzyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (TMC-Bz). It was shown that the incorporation of aromatic rings yielded smaller micelles (18-30 nm) with better colloidal stability in PBS than micelles without aromatic groups. The circulation time of i.v. injected micelles containing multiple pendant aromatic groups was longer (t½-α: ~0.7 h; t½-β: 2.9 h) than that of micelles with a single terminal aromatic group (t½ < 0.3 h). In addition, the in vitro partitioning of the encapsulated photosensitizer (meta-tetra(hydroxyphenyl)chlorin, mTHPC) between micelles and human plasma was favored towards micelles for those that contained the pendant aromatic groups. However, this was not sufficient to fully retain mTHPC in the micelles in vivo, as indicated by similar biodistribution patterns of micellar mTHPC compared to free mTHPC, and unequal biodistribution patterns of mTHPC and the host micelles. Our study points out that more detailed in vitro methods are necessary to more reliably predict in vivo outcomes. Furthermore, additional measures beyond π-π stacking are needed to stably incorporate mTHPC in micelles in order to benefit from the use of micelles as targeted delivery systems.

| S-EPMC7238042 | biostudies-literature

Thermo-Responsive Polyurethane Hydrogels Based on Poly(ε-caprolactone) Diol and Amphiphilic Polylactide-Poly(Ethylene Glycol) Block Copolymers.

Project description:Waterborne polyurethane (PU) based on poly(ε-caprolactone) (PCL) diol and an amphiphilic polylactide-poly(ethylene glycol) (PLA-PEG) diblock copolymer was synthesized. The molar ratio of PCL/PLA-PEG was 9:1 with different PLA chain lengths. The PU nanoparticles were characterized by dynamic light scattering (DLS), small angle X-ray scattering (SAXS) and rheological analysis. The water contact angle measurement, infrared spectroscopy, wide angle X-ray scattering (WAXS), thermal and mechanical analyses were conducted on PU films. Significant changes in physio-chemical properties were observed for PUs containing 10 mol % of amphiphilic blocks. The water contact angle was reduced to 12°⁻13°, and the degree of crystallinity was 5%⁻10%. The PU dispersions underwent sol-gel transition upon the temperature rise to 37 °C. The gelation time increased as the PLA chain length increased. In addition, the fractal dimension of each gel was close to that of a percolation cluster. Moreover, PU4 with a solid content of 26% could support the proliferation of human mesenchymal stem cells (hMSCs). Therefore, thermo-responsive hydrogels with tunable properties are promising injectable materials for cell or drug delivery.

| S-EPMC6432218 | biostudies-literature

Chitosan grafted methoxy poly(ethylene glycol)-poly(ε-caprolactone) nanosuspension for ocular delivery of hydrophobic diclofenac.

Project description:This study aimed to develop a cationic nanosuspension of chitosan (CS) and methoxy poly(ethylene glycol)-poly(ε-caprolactone) (MPEG-PCL) for ocular delivery of diclofenac (DIC). MPEG-PCL-CS block polymer was synthesized by covalent coupling of MPEG-PCL with CS. The critical micelle concentration of the MPEG-PCL-CS block polymer was 0.000692 g/L. DIC/MPEG-PCL-CS nanosuspension (mean particle size = 105 nm, zeta potential = 8 mV) was prepared and characterized by Fourier transform infrared spectroscopy, X-ray diffraction, and differential scanning calorimetry. The nanosuspension was very stable without apparent physical property changes after storage at 4 °C or 25 °C for 20 days, but it was unstable in the aqueous humor solution after 24 h incubation. Sustained release of the encapsulated DIC from the nanosuspension occurred over 8 h. Neither a blank MPEG-PCL-CS nanosuspension nor a 0.1% (mass fraction) DIC/MPEG-PCL-CS nanosuspension caused ocular irritation after 24 h of instillation. Enhanced penetration and retention in corneal tissue was achieved with a Nile red/MPEG-PCL-CS nanosuspension compared with a Nile red aqueous solution. In vivo pharmacokinetics studies showed enhanced pre-corneal retention and penetration of the DIC/MPEG-PCL-CS nanosuspension, which resulted in a higher concentration of DIC (Cmax) in the aqueous humor and better bioavailability compared with commercial DIC eye drops (P < 0.01).

| S-EPMC4464308 | biostudies-other

2,1,3-Benzothiadiazole (BTD)-moiety-containing red emitter conjugated amphiphilic poly(ethylene glycol)-block-poly(epsilon-caprolactone) copolymers for bioimaging.

Project description:2,1,3-Benzothiadiazole (BTD)-containing red emitter was chemically conjugated onto amphiphilic poly(ethylene glycol)-block-poly(epsilon-caprolactone) (PEG-b-PCL) copolymers to form two new fluorophore-conjugated block copolymers (P5 and P7). P5 is a cationic amino group-containing polymer, whereas, P7 is a neutral polymer. The polymers formed micelles in aqueous solution with average diameters of 45 nm (P7) and 78 nm (P5), which were characterized using dynamic light scattering (DLS) and atomic force microscopy (AFM). Cell internalization of the micelles using mouse macrophage RAW 264.7 was investigated. The micelles formed from P5 were endocytosed into the cell's cytoplasm through a non-specific endocytosis process, which was affected by temperature and calcium ions. Micelles formed from P7 could not be endocytosed. The dramatic difference of cell uptake between P5 and P7 indicated the cationic amino groups had a strong influence on the cell internalization to enhance the endocytosis pathway. 3-(4,5-Dimethyl thiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) viability assay was used to evaluate the cytotoxicity of the P5 micelle and no significant toxicity was observed. This study is the first report regarding the synthesis of BTD-conjugated block copolymers and the application of the biomacromolecules for bioimaging.

| S-EPMC2865149 | biostudies-literature

Protein delivery nanosystem of six-arm copolymer poly(?-caprolactone)-poly(ethylene glycol) for long-term sustained release.

Project description:BackgroundTo address the issue of delivery of proteins, a six-arm copolymer, six-arm poly (?-caprolactone)-poly(ethylene glycol) (6S-PCL-PEG), was synthesized by a simple two-step reaction. Thereafter, the application of 6S-PCL-PEG as a protein carrier was evaluated.Materials and methodsA six-arm copolymer, six-arm poly(?-caprolactone) (6S-PCL), was synthesized by ring-opening polymerization, with stannous octoate as a catalyst and inositol as an initiator. Then, poly(ethylene glycol) (PEG) was linked with 6S-PCL by oxalyl chloride to obtain 6S-PCL-PEG. Hydrogen-1 nuclear magnetic resonance spectrum, Fourier-transform infrared spectroscopy, and gel-permeation chromatography were conducted to identify the structure of 6S-PCL-PEG. The biocompatibility of the 6S-PCL-PEG was evaluated by a cell counting kit-8 assay. Polymeric nanoparticles (NPs) were prepared by a water-in-oil-in-water double emulsion (W1/O/W2) solvent evaporation method. The size distribution and zeta potential of NPs were determined by dynamic light scattering. Transmission electron microscopy was used to observe the morphology of NPs. Drug-loading capacity, encapsulation efficiency, and the release behavior of ovalbumin (OVA)-loading NPs were tested by the bicinchoninic acid assay kit. The stability and activity of OVA released from NPs were detected and the uptake of NPs was evaluated by NIH-3T3 cells.ResultsAll results indicated the successful synthesis of amphiphilic copolymer 6S-PCL-PEG, which possessed excellent biocompatibility and could formulate NPs easily. High drug-loading capacity and encapsulation efficiency of protein NPs were observed. In vitro, OVA was released slowly and the bioactivity of OVA was maintained for over 28 days.Conclusion6S-PCL-PEG NPs prepared in this study show promising potential for use as a protein carrier.

| S-EPMC5951147 | biostudies-literature

Interfacial properties and micellization of triblock poly(ethylene glycol)-poly(?-caprolactone)-polyethyleneimine copolymers.

Project description:Graphical abstractThis paper found the correlation between molecular arrangement and self-assembly and inspired us to tune block compositions to achieve desired nanostructure and drug loading.Image 1

| S-EPMC7332608 | biostudies-literature

Crystallization of Poly(ε-caprolactone) in Poly(vinylidene fluoride)/Poly(ε-caprolactone) Blend.

Project description:The crystallization behavior of poly(ε-caprolactone) (PCL) in a poly(vinylidene fluoride) (PVDF)/PCL blend as well as on a highly orientated PVDF substrate was studied by means of POM, DSC and TEM. The results show that the miscibility of the PVDF/PCL blend and the spherulitic morphology of PVDF varies with the blend ratio. For all the compositions, the pre-existing PVDF crystals accelerated the crystallization of PCL because the PVDF exhibits very strong nucleation ability toward PCL as reflected by the occurrence of heteroepitaxy and the transcrystallization of PBA on the PVDF substrate. This is associated with the perfect lattice matching between the PBA and PVDF crystals.

| S-EPMC6432374 | biostudies-literature

Fibrous Materials Made of Poly(ε-caprolactone)/Poly(ethylene oxide)-b-Poly(ε-caprolactone) Blends Support Neural Stem Cells Differentiation.

Project description:In this work, we design and produce micron-sized fiber mats by blending poly(ε-caprolactone) (PCL) with small amounts of block copolymers poly(ethylene oxide)m-block-poly(ε-caprolactone)n (PEOm-b-PCLn) using electrospinning. Three different PEOm-b-PCLn block copolymers, with different molecular weights of PEO and PCL, were synthesized by ring opening polymerization of ε-caprolactone using PEO as initiator and stannous octoate as catalyst. The polymer blends were prepared by homogenous solvent mixing using dichloromethane for further electrospinning procedures. After electrospinning, it was found that the addition to PCL of the different block copolymers produced micron-fibers with smaller width, equal or higher hydrophilicity, lower Young modulus, and rougher surfaces, as compared with micron-fibers obtained only with PCL. Neural stem progenitor cells (NSPC), isolated from rat brains and grown as neurospheres, were cultured on the fibrous materials. Immunofluorescence assays showed that the NSPC are able to survive and even differentiate into astrocytes and neurons on the synthetic fibrous materials without any growth factor and using the fibers as guidance. Disassembling of the cells from the NSPC and acquisition of cell specific molecular markers and morphology progressed faster in the presence of the block copolymers, which suggests the role of the hydrophilic character and porous topology of the fiber mats.

| S-EPMC6835932 | biostudies-literature

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