113(P48) イオノフォア抗生物質Monensinの化学修飾とイオン輸送活性(ポスター発表の部)

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Antibiotic monensin (1), isolated from Streptomyces cinnamonensis, selectively transports Na^+ ion in particular across the lipophilic biological membrane. This ability results in a variety of biological activities. Since the diameter of Na^+ ion is close to that of Ca^<2+> ion, the modification of monensin (1) to the divalent molecules should lead to the Ca^<2+> ionophores. In our previous work, monensin (1) was transformed to 25-carboxylmonensin (3), and 3 indicated Ca^<2+> ion transport activity in 70% the value of that of lasalocid A. Here, we present the chemical modification of monensin to two different types of Ca^<2+> ionophores, 7-O-alkyl-25-carboxylmonensins (4) and 26-O-(ω-carboxylacyl)monensins (5). 7-O-alkyl-25-carboxylmonensins (4) were expected to become more potent Ca^<2+> ionophores than 3, because 7-O-alkylmonensins (2) were more potent Na^+ ionophore than monensin (1). Compounds 4a-c were obtained as indicated in Scheme 2. Ca^<2+> ion transport activity of 4a-c evaluated by the liquid membrane method, was larger than 3 and lasalocid A, as we expected. We also synthesized 25-OMe derivatives, which are more stable than 25-OH derivatives (4). 26-O-(ω-carboxylacyl)monensins (5) were easily prepared from monensin (1) by protection of carboxyl group followed by treatment with corresponding acid anhydrides and deprotection. Although 5a-f were less lipophilic than 3, 5a-f also showed the larger Ca^<2+> ion transport activity. We are going to confirm the ion transport activity of the derivatives (4 and 5) across the biological membrane.
天然有機化合物討論会の論文
1998-08-31

113(P48) イオノフォア抗生物質Monensinの化学修飾とイオン輸送活性(ポスター発表の部)

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