Enantiomeric dynemicin analogs, preparation and use thereof

Abstract

An enantiomer of a fused ring system compound is disclosed that contains an epoxide group on one side of the fused rings and an enediyne macrocyclic ring on the other side of the fused rings. The enantiomeric compounds have DNA-cleaving, antimicrobial and tumor growth-inhibiting properties that are enhanced over their racemates. Chimeric compounds having the enantiomeric fused ring system compound as an aglycone bonded to (i) a sugar moiety as the oligosaccharide portion or (ii) a monoclonal antibody or antibody combining site portion thereof that immunoreacts with target tumor cells are also disclosed. Compositions containing an enatiomeric compound or an enantiomeric chimer are disclosed, as are methods of preparing an enantiomeric compound.