Due to their excellent biodegradability and biocompatibility, polysaccharides are ideal candidates for a variety of biomedical applications. However, the access of polysaccharides in pure form is limited. Herein, we report for the first time a reverse anomeric effect (RAE)-mediated polymerization to synthesize high molecular weight sugar poly(orthoesters). When RAE-enabled promoters, including 4-dimethylaminopyridine (DMAP), triphenyl phosphine (TPP) and imidazole were employed, sugar poly(orthoesters) with molecular weights up to 18.1 kDa were achieved. In comparison, when a RAE-unenabled catalyst, such as tetrabutylammonium bromide (TBABr) or tetrabutylammonium iodide (TBAI) was used, only a small molecular weight polymer in the range of 3-6 kDa was obtained.The sugar poly(orthoesters) were then subjected to construct nanoparticles by emulsion/evaporation procedure.With the orthoester linkages, the NPs were highly pH-responsive and demonstrated a quick decompose to release of the drug payloads at low pH values. The cell viability studies demonstrated that the drug-loaded NPs exhibit significantly higher killing effect at lower pH values.

Reverse anomeric effect (RAE)-mediated syntheses of sugar poly(orthoesters)

249th National Meeting (2015)

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