1-palmitoyl-2-oleoylphosphatidylcholine and 4-phenylenediamine

This paper describes the design and synthesis of a family of pore-forming amphiphiles. Two of these amphiphiles, which are derived from cholic acid, lysine, and p-phenylenediamine, can produce pores in lipid bilayers as individual molecules. In sharp contrast, analogous amphiphiles that do not contain a rigid 1,4-phenylenediamide moiety favor the formation of dimer-based pores. Kinetic evidence in support of monomer- and dimer-based pores has been obtained from Na+ transport measurements across bilayers made from 1-palmitoyl-2-oleoyl-2-sn-glycero-3-phosphocholine (POPC). Structure-activity studies that have been carried out with pore-forming, dimer-based amphiphiles have also revealed a significant activity dependence on their overall compactness. The practical potential of pore-forming amphiphiles with controllable supramolecular properties is briefly discussed.

Topics: Carbohydrate Sequence; Cholic Acids; Kinetics; Lysine; Molecular Sequence Data; Molecular Structure; Phenylenediamines; Phosphatidylcholines; Polymers; Sodium; Structure-Activity Relationship; Surface-Active Agents; Time Factors