Poly(choloyl)-based amphiphiles as pore-forming agents: transport-active monomers by design.
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.
Chen
Wen-Hua
WH
Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 18015, USA.
Shao
Xue-Bin
XB
Regen
Steven L
SL
D002240:Carbohydrate Sequence; D002793:Cholic Acids / Q000138:chemical synthesis / Q000737:chemistry; D007700:Kinetics; D008239:Lysine / Q000138:chemical synthesis / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010655:Phenylenediamines / Q000138:chemical synthesis / Q000737:chemistry; D010713:Phosphatidylcholines / Q000737:chemistry / Q000502:physiology; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry; D012964:Sodium / Q000737:chemistry* / Q000502:physiology; D013329:Structure-Activity Relationship; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry; D013997:Time Factors
D002793:Cholic Acids; D010655:Phenylenediamines; D010713:Phosphatidylcholines; D011108:Polymers; D013501:Surface-Active Agents; D012964:Sodium; D008239:Lysine; C028694:1-palmitoyl-2-oleoylphosphatidylcholine; C029728:4-phenylenediamine