Abstract
AbstractWe have developed a facile method for preparation of ionic copolypeptide vesicles that requires no protecting groups or expensive components. We prepared amphiphilic copolypeptides containing segments of water‐soluble methionine sulfonium residues. These were derived by aqueous phase, direct alkylation of a fully hydrophobic precursor diblock copolypeptide, poly(L‐methionine)65‐block‐poly(L‐leucine0.5‐stat‐L‐phenylalanine0.5)20 (M65[L0.5/F0.5]20), with simple alkylating reagents. Methylation of M65(L0.5/F0.5)20 gave the cationic methyl‐methionine sulfonium derivative MM65(L0.5/F0.5)20, and carboxymethylation gave the zwitterionic carboxymethyl‐methionine sulfonium derivative MC65(L0.5/F0.5)20. Assembly of MM65(L0.5/F0.5)20 or MC65(L0.5/F0.5)20 in water gave rise to vesicles with average diameters of a few microns, which could then be extruded to nanoscale diameters. While the cationic MM‐based vesicles were found to be cytotoxic, the zwitterionic MC‐based vesicles were found to possess minimal cytotoxicity.
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