Translocation of alkali metal cations by lipophilic cyclodextrin derivatives through black lipid membranes

Lipophilic cyclodextrin (CD) derivatives, synthetic ionophores, were prepared to transport alkali metal cations across a black lipid membrane (BLM). The purpose of this study is to develop a new class of an artificial transportation system of alkali metal cations via bilayer lipid membranes, by using CD derivatives as a cation carrier. A lipophilic CD derivative incorporated into a BLM forms a complex with an alkali metal cation at one surface of the membrane. This charged complex migrates to the opposite side of the membrane and then releases the cation into the subphase. CD derivatives have various types of acyl groups as a complexing site and formed a 1:1 complex with the alkali metal cation. The complex formation was interpreted by an induced-fit mechanism. It is found that the ability of CD derivative for forming a complex and/or transporting cations across the BLM depends on the bulkiness of acyl groups. The conductivities of heptakis (2,6-di-O-propyl-3-O-propionyl)-beta-CD were higher than those of valinomycin regardless of sizes of cations. The order of the conductivity in all derivatives is Li+ < Na+ < K+ approximately = Rb+ approximately = Cs+, regardless of the types of acyl groups in the derivatives. The effects of alkali metal cation concentration in the aqueous phase and CD concentration in the membrane on the translocation are also discussed.