title: Synthesis and ionophoric activities of functionalized bis(choloyl) conjugates with a rigid core.
abstract: Three bis(choloyl) conjugates bearing a rigid p-phenylenediamine/p-bis(aminomethyl)benzene linker and amino/acetamido groups were synthesized, and fully characterized on the basis of (1)H NMR, ESI-MS and HRMS. Their ionophoric activities were investigated by means of pH discharge assay. The results indicate that these conjugates exhibit potent ionophoric activities across egg-yolk l-α-phosphatidylcholine (EYPC)-based liposomal membranes, via a cation/proton antiport mechanism. They show moderate ion selectivity among alkali metal ions. Of the three conjugates, the ones having amino groups transport alkali metal ions in the order of Na(+)>Li(+)>K(+)≈Rb(+)≈Cs(+), whereas the one having acetamido groups functions in the order of Li(+)>Na(+)>K(+)≈Rb(+)≈Cs(+).
authors: School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, PR China.
authors: Jia
authors: J
authors: Zhou
authors: Yong-Ming
authors: YM
authors: Lu
authors: Li-Qun
authors: LQ
authors: Deng
authors: Zhong-Zhen
authors: ZZ
authors: Zhou
authors: Wen-Hua
authors: WH
authors: Chen
mesh_terms: D006863:Hydrogen-Ion Concentration; D017136:Ion Transport; D007476:Ionophores / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007477:Ions / Q000737:chemistry; D007700:Kinetics; D008051:Lipid Bilayers / Q000737:chemistry / Q000378:metabolism; D008672:Metals, Alkali / Q000737:chemistry; D010655:Phenylenediamines / Q000737:chemistry
chemical_list: D007476:Ionophores; D007477:Ions; D008051:Lipid Bilayers; D008672:Metals, Alkali; D010655:Phenylenediamines; C029728:4-phenylenediamine