Abstract: Two amphiphilic block copolymers using hydrophobic poly(ε-caprolactone) (PCL) and hydrophilic poly(ethylene glycol) (PEG) were successfully synthesized. One of them is an (A-b-B)4 type star polymer [(PCL-b-PEG)4] and the other one is a Y-shaped PEG–(PCL)2. A star-shaped polymer (PCL-b-PEG)4 was prepared by ring-opening polymerization (ROP) of ε-caprolactone continued by click reaction of (PCL-azide)4 and PEG-alkyne. The synthesis of Y-shaped PEG–(PCL)2 block copolymer was carried out via Diels-Alder click reaction of a furan protected maleimide end-functionalized PEG (PEG-MI) with an anthracene end-functionalized PCL following the ROP of ε-caprolactone. The characterization of micelles is carried out using both materials in aqueous media as drug delivery vehicles, which showed satisfying results and enhanced the cytotoxic effect of the anti-cancer drug vinorelbine (VLB). However, micelles consisted of Y-shaped unimers were found to be more convenient for delivery of hydrophobic drugs such as VLB because they formed in lower concentration, carrying a higher amount of drugs and owing a monomodal distribution. We concluded that the free tails of hydrophobic chains in Y-shaped block copolymer facilitate the assembly of amphiphilic material in water to form micelles.
Keywords: polymeric drug delivery systems; micelle; nano formulation; targeted cancer therapy; vinorelbine; amphiphilic block copolymer; star-shaped polymer; Y-shaped polymer
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Bahadori, F.; Dag, A.; Durmaz, H.; Cakir, N.; Onyuksel, H.; Tunca, U.; Topcu, G.; Hizal, G. Synthesis and Characterization of Biodegradable Amphiphilic Star and Y-Shaped Block Copolymers as Potential Carriers for Vinorelbine. Polymers 2014, 6, 214-242.
Bahadori F, Dag A, Durmaz H, Cakir N, Onyuksel H, Tunca U, Topcu G, Hizal G. Synthesis and Characterization of Biodegradable Amphiphilic Star and Y-Shaped Block Copolymers as Potential Carriers for Vinorelbine. Polymers. 2014; 6(1):214-242.
Bahadori, Fatemeh; Dag, Aydan; Durmaz, Hakan; Cakir, Nese; Onyuksel, Hayat; Tunca, Umit; Topcu, Gulacti; Hizal, Gurkan. 2014. "Synthesis and Characterization of Biodegradable Amphiphilic Star and Y-Shaped Block Copolymers as Potential Carriers for Vinorelbine." Polymers 6, no. 1: 214-242.