title: Classification of polyene antibiotics according to chemical structure and biological effects.
abstract: Fourteen polyene antibiotics and six of their semisynthetic derivatives were compared for their effects on potassium (K(+)) leakage and lethality or hemolysis of either Saccharomyces cerevisiae or mouse erythrocytes. These polyene antibiotics fell into two groups. Group I antibiotics caused K(+) leakage and cell death or hemolysis at the same concentrations of added polyene. In this group fungistatic and fungicidal levels were indistinguishable. Group I drugs included one triene (trienin); tetraenes (pimaricin and etruscomycin); pentaenes (filipin and chainin); one hexaene (dermostatin); and one polyene antibiotic with unknown chemical structure (lymphosarcin). Group II antibiotics caused considerable K(+) leakage at low concentrations and cell death or hemolysis at high concentrations. The fungistatic levels were clearly separable from fungicidal. This group included the heptaenes (amphotericin B, candicidin, aureofungin A and B, hamycin A and B), and five of their semisynthetic derivatives (amphotericin B methyl ester, N-acetyl-amphotericin B, hamycin A and B methyl esters, and N-acetyl-candicidin). Nystatin, classified as a tetraene, and its derivative, N-acetyl nystatin, also were in this group.
mesh_terms: D000818:Animals; D000935:Antifungal Agents / Q000145:classification* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D004912:Erythrocytes / Q000187:drug effects; D066298:In Vitro Techniques; D051379:Mice; D011090:Polyenes / Q000145:classification / Q000494:pharmacology; D011188:Potassium / Q000378:metabolism; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D011090:Polyenes; D011188:Potassium