Synthesis and characterization of a novel inhibitor of an aminoglycoside-inactivating enzyme.

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Abstract
A novel low-MW inhibitor of an aminoglycoside-inactivating enzyme, initially isolated from fermentation broths of Streptomyces neyagawaensis, was determined to be 7-hydroxytropolone. Its structure was confirmed by synthesis. In vitro synergy was demonstrated between 7-hydroxytropolone and certain aminoglycosides against bacteria which were resistant to those aminoglycosides by virtue of a 2''''-O-adenyltransferase. The synthesis and characterization of some analogs of 7-hydroxytropolone is also described.