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Synthesis and Characterization of Biodegradable Amphiphilic Star and Y-Shaped Block Copolymers as Potential Carriers for Vinorelbine
Department of Chemistry, Faculty of Science and Letters, Istanbul Technical University, Maslak, Istanbul 34469, Turkey
Department of Biopharmaceutical Sciences, University of Illinois at Chicago, Chicago, IL 60612-7231, USA
Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Bezmialem Vakif University, Fatih, Istanbul 34093, Turkey
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Bezmialem Vakif University, Fatih, Istanbul 34093, Turkey
* Authors to whom correspondence should be addressed.
Received: 18 November 2013; in revised form: 13 January 2014 / Accepted: 14 January 2014 / Published: 17 January 2014
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.