Water-soluble siomycin-A derivatives. Preparation, chemical structures and biological properties of half-esters of the peptide antibiotic.
The peptide antibiotic siomycin-A was transformed into half-esters with dicarboxylic acids with the intention of making siomycin-A soluble in water. Sodium salts of the half-esters were also prepared. Some of the salts showed antibacterial activities comparable to siomycin-A against Gram-positive bacteria in vitro and exhibited better therapeutic effects in infected mice than siomycin-A. The chemical structures of siomycin-A hemiadipate-II and -III were elucidated by comparing their 13C and 1H NMR spectra with those of siomycin-A. Their physicochemical properties are described.
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D055598:Chemical Phenomena; D002621:Chemistry; D002627:Chemistry, Physical; D005260:Female; D051379:Mice; D008813:Mice, Inbred ICR; D010455:Peptides / Q000138:chemical synthesis / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D010455:Peptides; C024711:siomycin A