Synthesis of tweezer- or non-tweezer-type Ag+ ionophores containing dithiocarbamoyl moieties on steroid backbone and their applications

ORGN 357

Byeong Hyo Kim, Hun Pyo Hong, Kui Tae Cho, Jeung Hoon On, In Seok Jeong, Geun Sig Cha, Young Moo Jun, and Hakhyun Nam. Department of Chemistry, Kwangwoon University, 447-1 Nowon-ku Wolgye-dong, Seoul, 139-701, South Korea
The concept of molecular tweezer-type neutral carriers based on a cholic acid backbone (CAB) has been successfully utilized by us to yield highly selective ionophores for carbonate, calcium, copper and silver. The CAB-based carriers may be as versatile as calix[n]arenes for developing selective ionophores. Based on our initial success in several CAB-based neutral carriers, we design new silver ion-selective ionophores with the same frame. Six tweezer-type and six non-tweezer-type ionophores containing dithiocarbamoyl groups on a 7-deoxycholic amide or cholane derivative were designed and synthesized. Potentiometric evaluation of the PVC membranes containing those deoxycholic amides/cholanes bearing tweezer-type dithiocarbamoyl moieties with a short linkage showed excellent affinity and selectivity to silver(I) ion over alkali, alkaline earth and other transition metal cations. However, deoxycholic amides/cholanes substituted with one dithiocarbamoyl group, i.e. non-tweezer-type ionophores result in relatively poor potentiometric responses.