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Preparation of stable single compartment vesicles with cationic and zwitterionic amphiphiles involving amino acid residues

, : Preparation of stable single compartment vesicles with cationic and zwitterionic amphiphiles involving amino acid residues. Journal of Organic Chemistry 47(11): 2137-2144

Cationic and zwitterionic amphiphiles involving amino acid residues were synthesized as modifications of the phospholipids. Their aggregated structures in both dilute aqueous dispersion and solution were investigated by EM. Amphiphiles involving an alanine residue or a sarcosine residue, N,N-didodecyl-N.alpha.-[6-(trimethylammonio)hexanoyl]-L-alaninamide bromide, N,N-didodecyl-N.alpha.-[6-[dimethyl(2-carboxyethyl)ammonio]hexanoyl]-L-alaninamide bromide, N,N-didodecyl-N.alpha.-[6-(trimethylammonio)hexanoyl]sarcosinamide bromide, and N,N-didodecyl-N.alpha.-[6-[dimethyl(2-carboxyethyl)ammonio]hexanoyl]sarcosinamide bromide, readily form well-developed multiwalled bilayer assemblies (lamellae and vesicles) and stable single-walled vesicles without any additives in dilute aqueous dispersion and sonicated aqueous solution, respectively. On the other hand, those involving 1 or 3 leucine residues, N,N-didodecyl-N.alpha.-[6-(trimethylammonio)hexanoyl]-L-leucinamide bromide, N,N-didodecyl-N.alpha.-[6-[dimethyl(2-carboxyethyl)ammonio]hexanoyl]-L-leucinamide bromide, and N,N-didodecyl-N.alpha.-[N.alpha.'[-N.alpha.''-[6-(trimetylammonio)hexanoyl]-L-leucyl]-L-leucyl]-L-leucinamide bromide, form partly developed multiwalled bilayer assembles in aqueous dispersion while stable single- or double-walled vesicles are observable in sonicated aqueous solution. The significance of the tripartite structure in amphiphile assemblies for the formation of stable single-walled bilayer vesicles has been discussed.

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