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Polymers 2014, 6(1), 214-242; doi:10.3390/polym6010214

Synthesis and Characterization of Biodegradable Amphiphilic Star and Y-Shaped Block Copolymers as Potential Carriers for Vinorelbine

1
Department of Chemistry, Faculty of Science and Letters, Istanbul Technical University, Maslak, Istanbul 34469, Turkey
2
Department of Biopharmaceutical Sciences, University of Illinois at Chicago, Chicago, IL 60612-7231, USA
3
Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Bezmialem Vakif University, Fatih, Istanbul 34093, Turkey
4
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 / Revised: 13 January 2014 / Accepted: 14 January 2014 / Published: 17 January 2014
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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 polymeric drug delivery systems; micelle; nano formulation; targeted cancer therapy; vinorelbine; amphiphilic block copolymer; star-shaped polymer; Y-shaped polymer
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

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.

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