Synthesis and characterization of biodegradable amphiphilic star and Y-shaped block copolymers as potential carriers for vinorelbine

Fatemeh Bahadori; Aydan Dag; Hakan Durmaz; Nese Cakir; Hayat Onyuksel; Umit Tunca; Gulacti Topcu; Gurkan Hizal

doi:10.3390/polym6010214

Synthesis and characterization of biodegradable amphiphilic star and Y-shaped block copolymers as potential carriers for vinorelbine

Fatemeh Bahadori, Aydan Dag, Hakan Durmaz, Nese Cakir, Hayat Onyuksel, Umit Tunca, Gulacti Topcu^*, Gurkan Hizal

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

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.

Original language	English
Pages (from-to)	214-242
Number of pages	29
Journal	Polymers
Volume	6
Issue number	1
DOIs	https://doi.org/10.3390/polym6010214
Publication status	Published - 2014

Keywords

Amphiphilic block copolymer
Micelle
Nano formulation
Polymeric drug delivery systems
Star-shaped polymer
Targeted cancer therapy
Vinorelbine
Y-shaped polymer

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/polym6010214

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title = "Synthesis and characterization of biodegradable amphiphilic star and Y-shaped block copolymers as potential carriers for vinorelbine",

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 = "Amphiphilic block copolymer, Micelle, Nano formulation, Polymeric drug delivery systems, Star-shaped polymer, Targeted cancer therapy, Vinorelbine, Y-shaped polymer",

author = "Fatemeh Bahadori and Aydan Dag and Hakan Durmaz and Nese Cakir and Hayat Onyuksel and Umit Tunca and Gulacti Topcu and Gurkan Hizal",

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pages = "214--242",

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T1 - Synthesis and characterization of biodegradable amphiphilic star and Y-shaped block copolymers as potential carriers for vinorelbine

AU - Bahadori, Fatemeh

AU - Dag, Aydan

AU - Durmaz, Hakan

AU - Cakir, Nese

AU - Onyuksel, Hayat

AU - Tunca, Umit

AU - Topcu, Gulacti

AU - Hizal, Gurkan

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

KW - Amphiphilic block copolymer

KW - Micelle

KW - Nano formulation

KW - Polymeric drug delivery systems

KW - Star-shaped polymer

KW - Targeted cancer therapy

KW - Vinorelbine

KW - Y-shaped polymer

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DO - 10.3390/polym6010214

M3 - Article

AN - SCOPUS:84894042002

SN - 2073-4360

VL - 6

SP - 214

EP - 242

JO - Polymers

JF - Polymers

IS - 1

ER -

Synthesis and characterization of biodegradable amphiphilic star and Y-shaped block copolymers as potential carriers for vinorelbine

Abstract

Keywords

UN SDGs

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