Amphiphilic and Hydrophilic Block Copolymers from Aliphatic N‑Substituted 8‑Membered Cyclic Carbonates: A Versatile Macromolecular Platform for Biomedical Applications

• Published in: Biomacromolecules 2017-01, Vol.18 (1), p.178-188
• Main Authors: Venkataraman, Shrinivas, Tan, Jeremy P. K, Ng, Victor W. L, Tan, Eddy W. P, Hedrick, James L, Yang, Yi Yan
• Format: Article
• Language: English
• Subjects: Anti-Inflammatory Agents, Non-Steroidal - chemistry; Anti-Inflammatory Agents, Non-Steroidal - metabolism; Antibiotics, Antineoplastic - chemistry; Antibiotics, Antineoplastic - metabolism; Biocompatible Materials - chemistry; Carbonates - chemistry; Diclofenac - chemistry; Diclofenac - metabolism; Doxorubicin - chemistry; Doxorubicin - metabolism; Drug Delivery Systems; Humans; Hydrophobic and Hydrophilic Interactions; Macromolecular Substances - chemistry; Polyethylene Glycols - chemistry; Polymers - chemistry
• ISSN: 1525-7797; 1526-4602
• DOI: 10.1021/acs.biomac.6b01463

Introduction of hydrophilic components, particularly amines and zwitterions, onto a degradable polymer platform, while maintaining precise control over the polymer composition, has been a challenge. Recognizing the importance of these hydrophilic residues in multiple aspects of the nanobiomedicine field, herein, a straightforward synthetic route to access well-defined amphiphilic and hydrophilic degradable block copolymers from diethanolamine-derived functional eight-membered N-substituted aliphatic cyclic carbonates is reported. By this route, tertiary amine, secondary amine, and zwitterion residues can be incorporated across the polymer backbone. Demonstration of pH-responsiveness of these hydrophilic residues and their utility in the development of drug-delivery vehicles, catered for the specific requirements of respective model drugs (doxorubicin and diclofenac sodium salt) are shown. As hydrophilic components in degradable polymers play crucial roles in the biological interactions, these materials offers opportunities to expand the scope and applicability of aliphatic cyclic carbonates. Our approach to these functional polycarbonates will expand the range of biocompatible and biodegradable synthetic materials available for nanobiomedicine, including drug and gene delivery, antimicrobials, and hydrophilic polymers as poly­(ethylene glycol) (PEG) alternatives.