Glycopolymers have showed their potentials as probes to investigate carbohydrate-lectin interaction and bacteria/cell binding [1, 2]. However, the use of biodegradable glycopolymer as an active targeting and drug delivery system remains to be explored and developed. In this study, carbohydrate-conjugated mono-functionalized PLLA (poly(L-lactic acid))/PEG-PLLA as well as multivalent PDLLA (poly(D,L-lactic acid)) were synthesized by Cu(I)-catalyzed cycloaddition of alkyne-polymer and carbohydrate-azide. The coupling efficiency ranged from 13% to 90% depending on the carbohydrate size and functionalization density. Ciprofloxacin, a widely used antibiotic, was covalently conjugated to PDLLA using newly-developed coupling chemistry [3]. Two different types of carbohydrate micelles were prepared by double emulsion with free ciprofloxacin and solvent evaporation with drug-conjugated polymer. Both the releasing kinetics and antimicrobial activities of the differently formulated micelles will be presented. [1] Eissa, A.; Cameron, N. Glycopolymer Conjugates. In Bio-synthetic Polymer Conjugates; Schlaad, H., Ed.; Springer: Berlin Heidelberg, Germany, 2013, pp 71-114. [2] Mahon, E.; Aastrup, T.; Barboiu, M. Multivalent Recognition of Lectins by Glyconanoparticle Systems. Chem. Comm. 2010, 46, 5491-5493. [3] Xie, S.; Lopez, S. A.; Ramström, O.; Yan, M.; Houk, K. N. 1,3-Dipolar Cycloaddition Reactivities of Perfluorinated Aryl Azides with Enamines and Strained Dipolarophiles. J. Am. Chem. Soc. 2015, 137, 2958-2966.

Synthesis of biodegradable glycopolymers and their uses in antibiotic formulation

250th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.