Enhancing the performance of PEG-b-PCL-based nanocarriers for curcumin through its conjugation with lipophilic biomolecules

Abstract

Curcumin is a natural substance extracted from Curcuma longa Linn with beneficial pharmaceutical properties such as anticancer activity against several cellular lines. However, it presents poor bioavailability due to its low solubility in aqueous media and chemical instability. In this research, curcumin was encapsulated in polymer micelles obtained by the self-assembly of a biodegradable poly (ethylene glycol)-block-poly(ɛ-caprolactone) copolymer conjugated with cholesterol or oleic acid. A hydroxyl-terminated poly (ethylene glycol)-block-poly(ɛ-caprolactone) was reacted with cholesteryl chloroformate or oleyl chloride to obtain conjugated copolymers. The resulting polymeric materials were characterised through proton nuclear magnetic resonance, gel permeation chromatography and differential scanning calorimetry, and their critical aggregation concentration was measured through fluorescence spectroscopy. Poly (ethylene glycol)-block-poly(ɛ-caprolactone) conjugated with cholesterol and oleic acid posed an improved capacity of encapsulating curcumin, resulting in the loading capacities of 8.8% and 15.2%, respectively. Cell viability studies confirmed that curcumin loaded in polymer micelles maintained its anticancer activity against MCF-7 human breast cancer cells but presented low cytotoxicity against mouse fibroblasts. Hence, these formulations have good potential for applications in drug delivery systems for breast cancer treatment.

Polymeric Drug Delivery Systems Bearing Cholesterol Moieties: A Review

“…The use of diverse polymers and possibility of their modification allows the encapsulation of almost any substance. Polymeric drug carriers containing cholesterol in their structure are mainly tested for the transport of anti-cancer [16,17,48,[70][71][72], anti-fungal [58,152], antibacterial [117], and anti-inflammatory drugs [44,99,117] as well as antioxidants [15,54,117]. By using cholesterol-containing systems, endocytosis or fusion of siRNA [100] or pDNA [134] is possible.…”

Melt-extruded biocompatible surgical sutures loaded with microspheres designed for wound healing

“…The mixture of PLA/curcumin was soluble in DCM but could not be dissolved in pure water due to the density and polarity differences [46]. Adding PLA or curcumin-containing DCM into the PVA solution under high-speed rotation enabled the formation of a stable emulsion.…”

Co-encapsulation of curcumin and salicylic acid in mucoadhesive polymer nanoparticles

“…m-PEG-b-PCL copolymers were synthesized following previously reported procedures [10,24,25]. with slight modifications to the method.…”

“…The DSC traces obtained during heating (Fig. 3) show that the empty nanoparticles had a broad endothermic peak centered at 59°C, indicating the melting of the PCL crystalline domains and possibly PEG [10]. Because the molecular weight of PEG is low, it is likely miscible with PCL [29].…”

“…The co-encapsulation of Cur and SCA in polymer nanoparticles is challenging because of their different chemical properties. Cur has been successfully encapsulated using various polymeric nanoparticles, liposomes, dendrimers, solid lipid nanoparticles, and nanostructured lipid carriers [10][11][12][13]. In contrast, SCA has been encapsulated in liposomal particles and inorganic structures such as silica and clay [14][15][16].…”