1. PEG Analogs Synthesized by Ring-Opening Metathesis Polymerization for Reversible Bioconjugation.
- Author
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Pelegri-O'Day EM, Matsumoto NM, Tamshen K, Raftery ED, Lau UY, and Maynard HD
- Subjects
- Aldehydes chemical synthesis, Amines chemical synthesis, Animals, Chickens, Models, Molecular, Muramidase chemical synthesis, Polyethylene Glycols chemical synthesis, Polymerization, Proteins chemistry, Aldehydes chemistry, Amines chemistry, Muramidase chemistry, Polyethylene Glycols chemistry
- Abstract
Poly(ethylene glycols) (PEGs) with protein-reactive end-groups are widely utilized in bioconjugation reactions. Herein, we describe the use of ring-opening metathesis polymerization (ROMP) to synthesize unsaturated protein-reactive PEG analogs. These ROMP PEGs (rPEGs) contained terminal aldehyde functionality and ranged in molecular weight from 6 to 20 kDa. The polymers were readily conjugated to free amines on the protein hen egg-white lysozyme (Lyz). Biocompatibility of the unsaturated PEGs was assessed in vitro, revealing the polymers to be nontoxic up to concentrations of at least 1 mg/mL in human dermal fibroblasts (HDFs). The resulting unsaturated rPEG-lysozyme conjugates underwent metathesis-based depolymerization, resulting in decreased molecular weight of the conjugate.
- Published
- 2018
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