Ring-Opening Polymerization of ε-Caprolactone initiated by Ganciclovir (GCV) for the preparation of GCV-tagged polymeric micelles

Authors

Alicia J. Sawdon, Michigan Technological University
Ching-An Peng, Michigan Technological University

Document Type

Article

Publication Date

2-10-2015

Department

Department of Chemical Engineering

Abstract

Ganciclovir (GCV) is a nucleoside analogue with antiviral activity against herpes viral infections, and the most widely used antiviral to treat cytomegalovirus infections. However, the low bioavailability and short half-life of GCV necessitate the development of a carrier for sustained delivery. In this study, guanosine-based GCV was used as the initiator directly in ring-opening polymerization of ε-caprolactone (ε-CL) to form hydrophobic GCV-poly(caprolactone) (GCV-PCL) which was then grafted with hydrophilic chitosan to form amphiphilic copolymers for the preparation of stable micellar nanoparticles. Successful synthesis of GCV-PCL and GCV-PCL-chitosan were verified by ¹H-NMR analysis. Self-assembled micellar nanoparticles were characterized by dynamic light scattering and zetasizer with an average size of 117 nm and a positive charge of 24.2 mV. The drug release kinetics of GCV was investigated and cytotoxicity assay demonstrated that GCV-tagged polymeric micelles were non-toxic. Our results showed that GCV could be used directly in the initiation of ring-opening polymerization of ε-CL and non-toxic polymeric micelles for GCV delivery can be formed.

Publisher's Statement

© 2015 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/). Publisher’s version of record: https://doi.org/10.3390/molecules20022857

Publication Title

Molecules

Recommended Citation

Sawdon, A. J., & Peng, C. (2015). Ring-Opening Polymerization of ε-Caprolactone initiated by Ganciclovir (GCV) for the preparation of GCV-tagged polymeric micelles. Molecules, 20(2), 2857-2867. http://doi.org/10.3390/molecules20022857
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/1975

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Version

Publisher's PDF