Polymeric micelles made from functionalized poly (e-caprolactone) (PCL) diblock copolymers were investigated in an attempt to generate improved drug delivery systems. This report presents the synthesis of ?-substituted e-caprolactone monomers with varying substituents and polymerization to generate diblock copolymers which can self-assemble into micellar drug delivery vehicles. The functionalized ?-2-[2-(2-methoxyethoxy)ethoxy]ethoxy-e-caprolactone was synthesized in a multi-step synthesis and used as the hydrophilic block in the diblock copolymers that contain either unsubstituted e-caprolactone or a cholesterol ?-substituted e-caprolactone as the hydrophobic block. The polymers were prepared via a ring-opening polymerization (ROP) using tin(II) 2-ethylhexanoate as the catalyst and benzyl alcohol as the initiator. The polymers were synthesized with varying block lengths achieved by using differing ratios of the two monomers to determine the effect of composition on the properties. The composition and the molecular weight of the polymers were determined using size exclusion chromatography (SEC) and 1HNMR. The properties of the various diblock copolymer micelles were investigated by the determination of the critical micellar concentration (CMC) using fluorescence measurements with pyrene as a probe as well as the determination of the size of the hydrodynamic diameter by dynamic light scattering (DLS) measurements.

?-Substituted e-caprolactone monomers for the synthesis of diblock copolymers for micellar drug delivery applications

247th National Meeting (2014)

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