title: Synthesis of a polymerizable metal-ion-chelating lipid for fluid bilayers.
abstract: Hydrated lipid structures, such as liposomes, that display tethered metal-ion-chelating groups have proven useful in peptide and protein binding, as well as 2D protein crystallization through molecular recognition of accessible histidine sites in proteins and peptides. Polymerizable metal-ion-chelating lipids bearing a reactive diacetylene group have been described. These interesting compounds can be polymerized in the solid-analogous phase. Here we describe the design of the first polymerizable metal-ion-chelating lipid that can be used in the fluid, i.e., liquid analogous, phase of lipid bilayers. The synthesis of 1-palmitoyl-2-[8-[(E,E)-2',4'-hexadienoyloxy]octanoyl]-sn-glycero-3-N-[11-[N',N'-bis[carboxymethyl]imino]-3,6,9-trioxaundecanoyl] phosphatidylethanolamine (1) is described. The chelator moiety, iminodiacetate (IDA), was linked to the polymerizable phosphatidylethanolamine (PE) with a terminal 2,4-hexadienoyl (sorbyl) group through an oligo(ethylene glycol)-based spacer. Lipid 1-Cu complex is designed to be combined with the corresponding polymerizable matrix lipids (bis-SorbPC) to form functionalized liposomes that can be stabilized by various polymerization methods.
authors.affiliation: C. S. Marvel Laboratories, Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
authors.forename: S W
authors.initials: SW
authors.lastname: Jeong
authors.forename: D F
authors.initials: DF
authors.lastname: O'Brien
mesh_terms: D000818:Animals; D002614:Chelating Agents / Q000138:chemical synthesis*; D003300:Copper; D006639:Histidine / Q000378:metabolism; D006801:Humans; D007098:Imino Acids / Q000737:chemistry; D008051:Lipid Bilayers / Q000737:chemistry*; D008055:Lipids / Q000138:chemical synthesis*; D008081:Liposomes; D010714:Phosphatidylethanolamines / Q000138:chemical synthesis; D011108:Polymers; D011485:Protein Binding; D011506:Proteins / Q000378:metabolism
chemical_list: D002614:Chelating Agents; D007098:Imino Acids; D008051:Lipid Bilayers; D008055:Lipids; D008081:Liposomes; D010714:Phosphatidylethanolamines; D011108:Polymers; D011506:Proteins; D006639:Histidine; D003300:Copper; C008109:iminodiacetic acid