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Maleimide‐Functionalized Poly(2‐Oxazoline)s and Their Conjugation to Elastin‐Like Polypeptides
Authors:Jonas F Nawroth  Ashutosh Chilkoti  Rainer Jordan  Robert Luxenhofer
Institution:1. Department Chemie, Technische Universit?t Dresden, Dresden, Germany;2. Department of Biomedical Engineering, Duke University, Durham, NC, USA
Abstract:The design of drug delivery systems capable of efficiently delivering poorly soluble drugs to target sites still remains a major challenge. Such materials require several different functionalities; typically, these materials should be biodegradable and nontoxic, nonimmunogenic, responsive to their environment, and soluble in aqueous solution while retaining the ability to solubilize hydrophobic drugs. Here, a polypeptide‐polymer hybrid of elastin‐like polypeptides (ELPs) and poly(2‐oxazoline)s (POx) is reported. This paper describes the chemical synthesis, physical characteristics, and drug loading potential of these novel hybrid macromolecules. A novel method is introduced for terminal functionalization of POx with protected maleimide moieties. Following recovery of the maleimide group via a retro Diels–Alder reaction, the consecutive Michael addition of thiol‐functionalized ELPs yields the desired protein‐polymer conjugate. These conjugates form nanoparticles in aqueous solution capable of solubilizing the anti‐cancer drug paclitaxel with up to 8 wt% loading.
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Keywords:bioconjugation  drug delivery systems  elastin‐like polypeptides  paclitaxel  ring‐opening polymerization
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