title: 8-Acyloxy-1,3-benzoxazine-2,4-diones as siderophore components for antibiotics.
abstract: 8-Acyloxy-1,3-benzoxazine-2,4-diones as masked catechol derivatives represent a novel type of siderophore components, whose growth promoting activity is low or not existing if tested alone. But after conjugation with beta-lactam antibiotics the resulting conjugates show a significantly increased antibacterial activity against Gram-negative bacteria compared with their parent antibiotics. Investigations using a set of penetration and iron transport mutants demonstrated that the conjugates use iron transport systems to penetrate the bacterial outer membrane. Title compounds were synthesized from (2,3-dimethoxycarbonyloxy)-benzoic acid and different amino compounds. Conjugates with penicillins and cephalosporins were prepared.
authors.affiliation: Department of Biostructure Chemistry, Hans-Knöll-Institute for Natural Product Research, Jena, Germany.
authors.forename: S
authors.initials: S
authors.lastname: Wittmann
authors.forename: I
authors.initials: I
authors.lastname: Scherlitz-Hofmann
authors.forename: U
authors.initials: U
authors.lastname: Möllmann
authors.forename: D
authors.initials: D
authors.lastname: Ankel-Fuchs
authors.forename: L
authors.initials: L
authors.lastname: Heinisch
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002463:Cell Membrane Permeability / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D007094:Imides / Q000138:chemical synthesis* / Q000494:pharmacology; D007769:Lactams; D008826:Microbial Sensitivity Tests; D010078:Oxazines / Q000138:chemical synthesis* / Q000494:pharmacology; D021281:Quantitative Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D007094:Imides; D007769:Lactams; D010078:Oxazines