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Molecules 2015, 20(2), 2857-2867; doi:10.3390/molecules20022857

Ring-Opening Polymerization of ε-Caprolactone Initiated by Ganciclovir (GCV) for the Preparation of GCV-Tagged Polymeric Micelles

Department of Chemical Engineering, Michigan Technological University, Houghton, MI 49931, USA
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Author to whom correspondence should be addressed.
Academic Editor: Atsushi Sudo
Received: 13 December 2014 / Accepted: 3 February 2015 / Published: 10 February 2015
(This article belongs to the Special Issue Ring-Opening Polymerization)
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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. View Full-Text
Keywords: chitosan; ganciclovir; poly(caprolactone); ring-opening polymerization chitosan; ganciclovir; poly(caprolactone); ring-opening polymerization
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Sawdon, A.J.; Peng, C.-A. Ring-Opening Polymerization of ε-Caprolactone Initiated by Ganciclovir (GCV) for the Preparation of GCV-Tagged Polymeric Micelles. Molecules 2015, 20, 2857-2867.

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