Study of the RAFT homopolymerization and copolymerization of N-[3-(dimethylamino)propyl]methacrylamide hydrochloride and evaluation of the cytotoxicity of the resulting homo- and copolymers?

Polymer Chemistry Pub Date: 2017-06-21 DOI: 10.1039/C7PY00837F

Abstract

The reversible addition–fragmentation chain transfer (RAFT) polymerization of N-[3-(dimethylamino)propyl]methacrylamide hydrochloride (DMAPMA·HCl) was studied. A detailed investigation of the effect of the polymerization conditions was carried out. The polymerization was conducted in a solvent mixture of water (acidic pH) and 2-propanol in the ratio of 2?:?1 using 4-cyanopentanoic acid dithiobenzoate (CTP) as the chain transfer agent (CTA), and 4,4′-azobis(4-cyanovaleric acid) (ACVA) as the initiator which was found to be the optimal condition to access well-defined homopolymers. The synthesis in acidic media and purification with precipitation in acetone allowed the good retention of dithioester chain end groups. The p(DMAPMA·HCl)-based macroCTA was prepared and successfully used in the diblock copolymerization of 2-lactobionamidoethyl methacrylamide (LAEMA), 2-aminoethyl methacrylamide hydrochloride (AEMA), N-(3-aminopropyl) morpholine methacrylamide (MPMA), and 2-methacryloyloxyethyl phosphorylcholine (MPC). Statistical DMAPMA·HCl-based copolymers of those monomers were also synthesized. Finally, the in vitro cytotoxicity of the resulting homo and copolymers of DMAPMA·HCl was investigated by the MTT assay in HeLa cells.

Graphical abstract: Study of the RAFT homopolymerization and copolymerization of N-[3-(dimethylamino)propyl]methacrylamide hydrochloride and evaluation of the cytotoxicity of the resulting homo- and copolymers
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