Analogs of Monensin with a Modified C25-C26 Moiety: Na+/k+ Selectivity and Biological Activity

Abstract

C25-C26 chemical derivatives of monensin (1) were prepared: 25-dehydroxymethyl, 25-oxo (2); 25, 26-isopropyliden (3); 25-O-methyl (4); 26-O-acyl (5); 26-O-[N-chlorophenyl]carbamoyl (6); and 26-O-[N-chIorophenyl, N-methyl]carbamoyl (7). Measurements of Na+ and K+ extractions in a water/toluene-butanol (70:30) system by these analogs showed the key role of the C[26]H2-OH arm for the stability and selectivity of 1:1 complexes formed by monensin. The antibiotic activity and toxicity in mice were determined in relation to the Na+/K+ cationic affinity. © 1990, Japan Society for Bioscience, Biotechnology, and Agrochemistry. All rights reserved.