Poly(ethylene oxide)‐<i>block</i>‐poly(α‐cinnamyl‐ε‐caprolactone‐<i>co</i>‐ε‐caprolactone) diblock copolymer nanocarriers for enhanced solubilization of caffeic acid phenethyl ester

Atanasova, Mariya‐Desislava; Grancharov, Georgy; Petrov, Petar

doi:10.1002/pol.20200706

Cited by 3 publications

(8 citation statements)

References 30 publications

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“…The organic solvent was evaporated under vacuum to afford transparent micellar solutions of concentration 1 gL −1 . The copolymer concentration was approximately an order of magnitude higher than the critical micelle concentrations (CMC) of PEO-b-P(CyCL-co-CL) and PEO-b-PCL, as determined in our previous study [24]. Next, the micelles were loaded with CBD at an initial copolymer/drug mass ratio of 10:1, 7:1, and 5:1.…”

Section: Preparation Of Cannabidiol-loaded Polymeric Micellesmentioning

confidence: 85%

“…In this study, two types of carriers from cinnamyl-modified and unmodified copolymers were tested for solubilization and release of CBD. Well-defined micellar nanocarriers were prepared by the solvent evaporation method [24]. Since the used copolymers were not directly soluble in water, they were first dissolved in acetone, which is a common solvent for PEO and PCL, and the copolymer solution was slowly added to distilled water.…”

Section: Preparation Of Cannabidiol-loaded Polymeric Micellesmentioning

confidence: 99%

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In Situ Gelling Hydroxypropyl Cellulose Formulation Comprising Cannabidiol-Loaded Block Copolymer Micelles for Sustained Drug Delivery

Kamenova,

Momekova,

Grancharov

et al. 2023

IJMS

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Cannabidiol (CBD) is a natural terpenophenolic compound with known pharmacological activities, but the poor solubility of CBD in water limits its widespread use in medicine and pharmacy. Polymeric (nano)carriers demonstrated high potential for enhancing the solubility and therapeutic activity of lipophilic drugs such as CBD. Here, we report the elaboration of a novel hydroxypropyl cellulose (HPC)-based in situ gelling formulation for controlled delivery of CBD. In the first stage, nanosized polymeric micelles from poly(ethylene oxide)-block-poly(α-cinnamyl-ε-caprolactone-co-ε-caprolactone) (PEO-b-P(CyCL-co-CL) diblock copolymers) were used to increase the solubility of CBD in water. Different copolymers were assessed, and the carrier with the highest encapsulation efficiency (EE) and drug loading capacity (DLC) was selected for further elaboration of nanocomposite in situ gel formulations. Next, the sol-to-gel transition behavior of HPC as a function of K2SO4 concentration in the aqueous solution was investigated by microcalorimetry and dynamic oscillatory rheology, and the optimal formulation capable of forming a physical gel under physiological conditions was determined. Finally, injectable nanocomposite hydrogels comprising cannabidiol were fabricated, and their drug release profile and cytotoxicity against human tumor cell lines were evaluated. The in situ gels exhibited prolonged drug release over 12 h, controlled by gel erosion, and the cytotoxicity of formulated cannabidiol was comparable with that of a free drug.

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Section: Preparation Of Cannabidiol-loaded Polymeric Micellesmentioning

confidence: 85%

Section: Preparation Of Cannabidiol-loaded Polymeric Micellesmentioning

confidence: 99%

In Situ Gelling Hydroxypropyl Cellulose Formulation Comprising Cannabidiol-Loaded Block Copolymer Micelles for Sustained Drug Delivery

Kamenova,

Momekova,

Grancharov

et al. 2023

IJMS

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“…The efficiency of this reaction and the structural stability of the carrier, respectively, were confirmed using DLS analysis. The reason to present the DLS data as number-weighted plots is the light-scattering phenomenon discussed in detail in our early works [ 26 , 27 ]. In summary, we found that the micelles comprising PCL, constructed from either single copolymer or a copolymers blend, exhibited a bimodal particle size distribution in the intensity-weighted plot.…”

Section: Discussionmentioning

confidence: 99%

“…This is the main obstacle for in vivo administration of CAPE and its use in emerging areas, such as tumor therapy. Recently, a few studies have reported the positive effects of micellar core–shell nanocarriers towards enhancing the solubility of CAPE in aqueous media [ 23 , 24 , 25 , 26 ]. The systems exhibited sustained release profiles, with or without burst release, depending on the nature of the core-forming polymers.…”

Section: Introductionmentioning

confidence: 99%

Redox-Responsive Crosslinked Mixed Micelles for Controllable Release of Caffeic Acid Phenethyl Ester

et al. 2022

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We report the elaboration of redox-responsive functional micellar nanocarriers designed for triggered release of caffeic acid phenethyl ester (CAPE) in cancer therapy. Three-layered micelles, comprising a poly(ε-caprolactone) (PCL) core, a middle poly(acrylic acid)/poly(ethylene oxide) (PAA/PEO) layer and a PEO outer corona, were prepared by co-assembly of PEO113-b-PCL35-b-PEO113 and PAA13-b-PCL35-b-PAA13 amphiphilic triblock copolymers in aqueous media. The preformed micelles were loaded with CAPE via hydrophobic interactions between the drug molecules and PCL core, and subsequently crosslinked by reaction of carboxyl groups from PAA and a disulfide crosslinking agent. The reaction of crosslinking took place in the middle layer of the nanocarriers without changing the encapsulation efficiency (EE~90%) of the system. The crosslinked polymeric micelles (CPMs) exhibited superior structural stability and did not release CAPE in phosphate buffer (pH 7.4). However, in weak acidic media and in the presence of 10 mM reducing agent (dithiothreitol, DTT), the payload was released at a high rate from CPMs due to the breakup of disulfide linkages. The physicochemical properties of the nanocarriers were investigated by dynamic and electrophoretic light scattering (DLS and ELS) and atomic force microscopy (AFM). The rapid release of CAPE under intracellular-like conditions and the lack of premature drug release in media resembling the blood stream (neutral pH) make the developed CPMs a promising candidate for controllable drug release in the microenvironment of tumors.

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“…For example, the covalent attachment of different ligands to the hydrophilic corona-forming segments allows for the better internalization of the nanocarrier by the tumor cells, thus eliminating the systemic side effects of antineoplastic drugs and hypersensitization toward multidrug resistance. On the other hand, introducing specific pendant groups or segments into the hydrophobic blocks increases the compatibility between the micellar core and the hydrophobic drugs, resulting in enhanced drug-loading efficiency [ 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Cinnamyl-Modified Polyglycidol/Poly(ε-Caprolactone) Block Copolymer Nanocarriers for Enhanced Encapsulation and Prolonged Release of Cannabidiol

et al. 2023

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The present study describes the development of novel block copolymer nanocarriers of the phytocannabinoid cannabidiol (CBD), designed to enhance the solubility of the drug in water while achieving high encapsulation efficiency and prolonged drug release. Firstly, a well-defined amphiphilic block copolymer consisting of two outer hydrophilic polyglycidol (PG) blocks and a middle hydrophobic block of poly(ε-caprolactone) bearing pendant cinnamyl moieties (P(CyCL-co-CL)) were synthesized by the click coupling reaction of PG-monoalkyne and P(CyCL-co-CL)-diazide functional macroreagents. A non-modified polyglycidol/poly(ε-caprolactone) amphiphilic block copolymer was obtained as a referent system. Micellar carriers based on the two block copolymers were formed via the solvent evaporation method and loaded with CBD following two different protocols—loading during micelle formation and loading into preformed micelles. The key parameters/characteristics of blank and CBD-loaded micelles such as size, size distribution, zeta potential, molar mass, critical micelle concentration, morphology, and encapsulation efficiency were determined by using dynamic and static multiangle and electrophoretic light scattering, transmission electron microscopy, and atomic force microscopy. Embedding CBD into the micellar carriers affected their hydrodynamic radii to some extent, while the spherical morphology of particles was not changed. The nanoformulation based on the copolymer bearing cinnamyl moieties possessed significantly higher encapsulation efficiency and a slower rate of drug release than the non-modified copolymer. The comparative assessment of the antiproliferative effect of micellar CBD vs. the free drug against the acute myeloid leukemia-derived HL-60 cell line and Sezary Syndrome HUT-78 demonstrated that the newly developed systems have pronounced antitumor activity.

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Poly(ethylene oxide)‐block‐poly(α‐cinnamyl‐ε‐caprolactone‐co‐ε‐caprolactone) diblock copolymer nanocarriers for enhanced solubilization of caffeic acid phenethyl ester

Cited by 3 publications

References 30 publications

In Situ Gelling Hydroxypropyl Cellulose Formulation Comprising Cannabidiol-Loaded Block Copolymer Micelles for Sustained Drug Delivery

In Situ Gelling Hydroxypropyl Cellulose Formulation Comprising Cannabidiol-Loaded Block Copolymer Micelles for Sustained Drug Delivery

Redox-Responsive Crosslinked Mixed Micelles for Controllable Release of Caffeic Acid Phenethyl Ester

Cinnamyl-Modified Polyglycidol/Poly(ε-Caprolactone) Block Copolymer Nanocarriers for Enhanced Encapsulation and Prolonged Release of Cannabidiol

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