Self-immolative polymers are a class of materials that degrade by an end-to-end depolymerization mechanism in response to a stimulus-mediated cleavage of a stabilizing end-cap from the polymer terminus (1, 2). Relative to conventional stimuli-responsive or biodegradable polymers, they exhibit several unique properties including a degradation time dependent on the degree of polymerization and the ability to change their responsiveness to stimuli by simply changing the end-cap. These aspects make them of increasing interest for a wide variety of applications including sensors and controlled drug release. This presentation will describe our group’s progress toward the development of self-immolative polyglyoxylates (Figure 1) (3). End-capping strategies that enable these polymers to depolymerize in response to an array of different stimuli while at the same time providing linkers for the synthesis of block copolymers will be described. The self-assembly of such block copolymers in aqueous solution enables the development of stimuli-responsive assemblies such as micelles and vesicles that can encapsulate and release drugs in a controlled manner. Furthermore, the incorporation of glyoxylate monomers with functional groups will allow the conjugation of molecules to the polymer backbone to introduce new functions and properties. Polyglyoxylates are particularly attractive for applications as they depolymerize to afford glyoxylic acid hydrate, a metabolic intermediate in the glyoxylic acid cycle, which has been demonstrated to be non-toxic in mammalian models and in the environment (4). 1. Wong, A. D.; DeWit, M. A.; Gillies, E. R. Adv. Drug Delivery Rev. 2012, 64, 1031. 2. Phillips, S. T.; DiLauro, A. M. ACS Macro Lett. 2014, 3, 298. 3. Fan, B.; Trant, J. F.; Wong, A. D.; Gillies, E. R. J. Am. Chem. Soc. 2014, 136, 10116. 4. Belloncle, B.; Bunel, C.; Menu-Bouaouiche, L.; Lesouhaitier, O.; Burel, F. J. Polym. Environ. 2012, 20, 726.

Self-immolative polyglyoxylates: Towards functional backbones and assemblies

251st National Meeting (2016)

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