Acetyl-[alpha]-d-mannopyranose-based cationic polymer via RAFT polymerization for lectin and nucleic acid bindings

• Published in: Journal of applied polymer science Vol. 134; no. 24
• Main Authors: Ting, S R Simon, Min, Eun Hee, Lau, Benjamin K F, Hutvagner, Gyorgy
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley Subscription Services, Inc 20.06.2017
• Subjects: Materials science; Polymers
• DOI: 10.1002/app.44947
• ISSN: 0021-8995

Functional cationic polymers carrying mannose moieties were synthesized in a facile manner by employing RAFT polymerization. Initially, a protected carbohydrate based monomer, [2-(2,3,4,6-tetra-O-acetyl-[alpha]-d-mannopyranosyloxy)ethyl methacrylate (AcManEMA)], was prepared by the O-glycosylation of 2-hydroxyethyl methacrylate (HEMA). Subsequently, a macroRAFT agent of poly[2-(dimethyl)amino ethyl methacrylate] (PDMAEMA) was generated, and a further chain extension polymerization with AcManEMA was carried out in dioxane to form a acetylated mannose cationic diblock copolymer, PDMAEMA-b-PAcManEMA. It was attained in high yields and displayed low dispersity (Ð). Acetylated mannose moieties on the polymer were deprotected with sodium methoxide and the amines from the DMAEMA block were protonated to yield a cationic diblock glycopolymer, PDMAEMA-b-PManEMA. The cationic property of polymers were characterized by mixing with a negatively charged siRNA duplex and a pDNA, and aggregates of 102 and 233 nm were obtained, respectively. Agarose gel shift assay revealed that the polymers were able to retain the nucleic acids as large polymer complexes. Lectin binding assay proved that the mannose residue on the polymers were only able to bind specifically with ConA. PNA lectin was employed as a control and did not show specific binding. The cationic glycopolymer could be advantageous in targeted nucleic acids delivery in specific cells. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44947.