A Synthetic Bioinspired Carbohydrate Polymer with Mucoadhesive Properties
Abstract
Mucoadhesive polymers are of significant interest to the pharmaceutical, medical device, and cosmetic industries. Polysaccharides possessing charged functional groups, such as chitosan, are known for mucoadhesive properties but suffer from poor chemical definition and solubility, while the chemical synthesis of polysaccharides is challenging with few reported examples of synthetic carbohydrate polymers with engineered‐in ionic functionality. We report the design, synthesis, and evaluation of a synthetic, cationic, enantiopure carbohydrate polymer inspired by the structure of chitosan. These water‐soluble, cytocompatible polymers are prepared via an anionic ring‐opening polymerization of a bicyclic β‐lactam sugar monomer. The synthetic method provides control over the site of amine functionalization and the length of the polymer while providing narrow dispersities. These well‐defined polymers are mucoadhesive as documented in single‐molecule scale (AFM), bulk solution phase (FRAP), and ex vivo tissue experiments. Polymer length and functionality affects bioactivity as long, charged polymers display higher mucoadhesivity than long, neutral polymers or short, charged polymers.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Nov 27, 2019
- Source ID
- 10.1002/ange.201911720
Entities
People
- Anant S. Balijepalli
- Béla Suki
- Mark W Grinstaff
- Mingfu Chen
- Robert C. Sabatelle
Organizations
- Boston University
- United States Department of Defense