Cinnamyl modified polymer micelles as efficient carriers of caffeic acid phenethyl ester

Kalinova, Radostina; Yordanov, Yordan; Tzankov, Borislav; Tzankova, Virginia; Yoncheva, Krassimira; Dimitrov, Ivaylo

doi:10.1016/j.reactfunctpolym.2020.104763

Cited by 5 publications

(5 citation statements)

References 50 publications

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“…The purpose to minimize the number of cinnamyl groups into one PCL block was to avoid the possible π‐π stacking interactions between closely situated aromatic rings 28 . Such interactions could make the micellar core more compact and to decrease the loading efficiency as reported for PEO‐b‐PLA (polylactide) copolymers bearing cinnamyl groups 29 …”

Section: Resultsmentioning

confidence: 99%

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

Atanasova

Grancharov

Petrov

2020

Journal of Polymer Science

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We report novel micellar carriers, comprising pendant cinnamyl moieties in the core-forming block, designed to increase the solubilization of caffeic acid phenethyl ester (CAPE) in aqueous media. Amphiphilic poly(ethylene oxide)block-poly(α-cinnamyl-ε-caprolactone-co-ε-caprolactone) (PEO-b-P(CyCL-co-CL) diblock copolymers were synthesized by ring-opening copolymerization of α-propargyl-ε-caprolactone and ε-caprolactone from a monofunctional PEO macroinitiator and subsequent attachment of cinnamyl groups via click reaction. In addition, a linear PEO-b-PCL diblock copolymer was synthesized and used in this study for comparison. Next, nanosized micelles from PEO-b-P (CyCL-co-CL) and PEO-b-PCL were formed via the solvent evaporation method and then loaded with CAPE. Dynamic and electrophoretic light scattering, and transmission electron microscopy were used to characterize both blank and loaded carriers. The potential of the micelles comprising pendant cinnamyl group to solubilize CAPE in water was evaluated in a comparative fashion to that of nonmodified PEO-b-PCL diblock copolymer.

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Section: Resultsmentioning

confidence: 99%

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

Atanasova

Grancharov

Petrov

2020

Journal of Polymer Science

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“…Amphiphilic block copolymers of various architectures containing carbonate units in their hydrophobic segments have been synthesized and evaluated as drug-delivery systems [ 28 , 29 ]. The introduction of various functionalities along the hydrophobic polycarbonate segments of the amphiphilic block copolymers gives an additional option to tune the micelles’ core properties either via enhancing drug solubilization or external stimuli-triggered core disintegration and subsequent drug release [ 30 , 31 , 32 ].…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis and the Evaluation of a Functional Amphiphilic Block Copolymer as a Micellar Curcumin Delivery System

Kalinova

Grancharov

Doumanov

et al. 2023

IJMS

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Polymer micelles represent one of the most attractive drug delivery systems due to their design flexibility based on a variety of macromolecular synthetic methods. The environmentally safe chemistry in which the use or generation of hazardous materials is minimized has an increasing impact on polymer-based drug delivery nanosystems. In this work, a solvent-free green synthetic procedure was applied for the preparation of an amphiphilic diblock copolymer consisting of biodegradable hydrophobic poly(acetylene-functional carbonate) and biocompatible hydrophilic polyethylene glycol (PEG) blocks. The cyclic functional carbonate monomer 5-methyl-5-propargyloxycarbonyl-1,3-dioxane-2-one (MPC) was polymerized in bulk using methoxy PEG-5K as a macroinitiator by applying the metal-free organocatalyzed controlled ring-opening polymerization at a relatively low temperature of 60 °C. The functional amphiphilic block copolymer self-associated in aqueous media into stable micelles with an average diameter of 44 nm. The copolymer micelles were physico-chemically characterized and loaded with the plant-derived anticancer drug curcumin. Preliminary in vitro evaluations indicate that the functional copolymer micelles are non-toxic and promising candidates for further investigation as nanocarriers for biomedical applications.

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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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Cinnamyl modified polymer micelles as efficient carriers of caffeic acid phenethyl ester

Cited by 5 publications

References 50 publications

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

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

Green Synthesis and the Evaluation of a Functional Amphiphilic Block Copolymer as a Micellar Curcumin Delivery System

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

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