Synthesis of 7-deoxycholic amides or cholanes containing distinctive ion-recognizing groups at C3 and C12 and evaluation for ion-selective ionophores

Tweezer-type ionophores containing C3-bipyridyl and C12-dithiocarbamoyl groups, or C3-bithiophenyl with C12-dithiocarbamoyl groups on a 7-deoxycholic amide or cholane derivatives were designed and synthesized. Potentiometric evaluation of the PVC membranes containing those deoxycholic amides/cholanes linked with unsymmetrically substituted tweezer-type bipyridyl or bithiophenyl with dithiocarbamoyl moieties proved their good affinity and selectivity for silver(I) ion. Especially, ionophores with bithiophenyl moiety on the 3α-position and diphenylaminothioxomethylthioacetyloxy group on 12α-position of cholan-24-amide or cholane reveal the most excellent result with a theoretical slope value of 59 mV/decade.