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

Abstract

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.

Polycarbonate-Based Copolymer Micelles as Biodegradable Carriers of Anticancer Podophyllotoxin or Juniper Extracts

“…The amphiphilic block copolymer MPEG- b -PC was synthesized according to a previously reported procedure [ 25 ]. Briefly, the ring-opening polymerization of an alkyne-functional cyclic monomer was initiated by a methoxy-poly(ethylene glycol) (MPEG) macroinitiator using 4-(dimethylamino)pyridine as a catalyst and was performed in bulk at 60 °C.…”

“…A biocompatible and biodegradable amphiphilic block copolymer MPEG-b-PC [methoxy poly(ethylene glycol)-block-polycarbonate] (Figure 2) was obtained recently by green polymer synthesis and its curcumin-loaded micelles were formed by co-association in aqueous media [25]. The present study was aimed at determination of the physico-chemical characteristics, bioactive component loading properties and antiproliferative activity of poly(ethylene glycol)-block-polycarbonate (MPEG-b-PC) based micelles loaded with PPT or cytotoxic Juniperus virginiana (JV) or Juniperus sabina var.…”

“…A biocompatible and biodegradable amphiphilic block copolymer MPEG- b -PC [methoxy poly(ethylene glycol)- block- polycarbonate] ( Figure 2 ) was obtained recently by green polymer synthesis and its curcumin-loaded micelles were formed by co-association in aqueous media [ 25 ].…”

Investigation of morphology and structure of drug‐loaded PLA‐b‐PEO‐b‐PLA polymeric micelle: A dissipative particle dynamics simulations study

“…The utilization of a drug carrier with the ability to moderate drug release kinetics represents a promising therapeutic strategy, as it can effectively reduce the likelihood and severity of drug‐associated side effects while concurrently enhancing the overall efficacy of treatment. The self‐assembly of amphiphilic block copolymers into micellar structures has garnered increasing attention from the scientific community as a highly promising drug delivery platform with controlled release capabilities 5–9 . In aqueous environments, the amphiphilic copolymers self‐assembly into core‐shell micellar structure.…”

Poly(2-(dimethylamino)ethyl methacrylate)-Grafted Amphiphilic Block Copolymer Micelles Co-Loaded with Quercetin and DNA

“…Initially, well-defined α,ω-heterobifunctional PDMAEMA was synthesized via atom transfer radical polymerization (ATRP). In the next step, a previously synthesized multifunctional amphiphilic diblock copolymer [ 43 ] was used as a modular platform for the PDMAEMA grafts attachment by applying the highly efficient azide–alkyne “click” reaction. The copolymer is self-associated in aqueous media with the formation of colloidally stable nanosized micelles.…”