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Open AccessFeature PaperArticle

Well-Defined Diblock Poly(ethylene glycol)-b-Poly(ε-caprolactone)-Based Polymer-Drug Conjugate Micelles for pH-Responsive Delivery of Doxorubicin

1
Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, NY 14260, USA
2
Department of Biomedical Engineering, University at Buffalo, The State University of New York, Buffalo, NY 14260, USA
3
Chemistry Department, Faculty of Science, Mansoura University, Mansoura, 35516, Egypt
*
Authors to whom correspondence should be addressed.
Materials 2020, 13(7), 1510; https://doi.org/10.3390/ma13071510
Received: 28 January 2020 / Revised: 17 March 2020 / Accepted: 20 March 2020 / Published: 26 March 2020
(This article belongs to the Special Issue Biomaterial Design for Disease Applications)
Nanoparticles have emerged as versatile carriers for various therapeutics and can potentially treat a wide range of diseases in an accurate and disease-specific manner. Polymeric biomaterials have gained tremendous attention over the past decades, owing to their tunable structure and properties. Aliphatic polyesters have appealing attributes, including biodegradability, non-toxicity, and the ability to incorporate functional groups within the polymer backbone. Such distinctive properties have rendered them as a class of highly promising biomaterials for various biomedical applications. In this article, well-defined alkyne-functionalized poly(ethylene glycol)-b-poly(ε-caprolactone) (PEG-b-PCL) diblock copolymer was synthesized and studied for pH-responsive delivery of doxorubicin (DOX). The alkyne-functionalized PEG-b-PCL diblock copolymer was prepared by the synthesis of an alkyne-functionalized ε-caprolactone (CL), followed by ring-opening polymerization (ROP) using PEG as the macroinitiator. The alkyne functionalities of PEG-b-PCL were modified through copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click reaction to graft aldehyde (ALD) groups and obtain PEG-b-PCL-g-ALD. Subsequently, DOX was conjugated on PEG-b-PCL-g-ALD through the Schiff base reaction. The resulting PEG-b-PCL-g-DOX polymer-drug conjugate (PDC) self-assembled into a nano-sized micellar structure with facilitated DOX release in acidic pH due to the pH-responsive linkage. The nanostructures of PDC micelles were characterized using transmission electron microscopy (TEM) and dynamic light scattering (DLS). In vitro studies of the PDC micelles, revealed their improved anticancer efficiency towards MCF-7 cells as compared to free DOX. View Full-Text
Keywords: polymer-drug conjugate; drug delivery; diblock copolymer; doxorubicin; poly(ε-caprolactone); poly(ethylene glycol); ring-opening polymerization; CuAAC click reaction; Schiff base reaction; micelle polymer-drug conjugate; drug delivery; diblock copolymer; doxorubicin; poly(ε-caprolactone); poly(ethylene glycol); ring-opening polymerization; CuAAC click reaction; Schiff base reaction; micelle
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MDPI and ACS Style

Jafari, A.; Yan, L.; Mohamed, M.A.; Wu, Y.; Cheng, C. Well-Defined Diblock Poly(ethylene glycol)-b-Poly(ε-caprolactone)-Based Polymer-Drug Conjugate Micelles for pH-Responsive Delivery of Doxorubicin. Materials 2020, 13, 1510.

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