Photoactivated enediynes as targeted antitumoral agents: Efficient routes to antibody and gold nanoparticle conjugates

Efficient syntheses of a series of functionalized aryl enediynes have been developed. The building blocks were used to effect conjugation to carrier PEG templates which allowed subsequent coupling to a cardiac targeted monoclonal antibody. Immunocompetence of the enediyne-Mab conjugates was demonstrated by ELISA, and both parent enediynes and bioconjugates underwent successful photo-Bergman cyclization. Finally, surface modified (Au) nanoparticle conjugates were prepared and size confirmed by TEM analysis. Application as long-circulating photoactivated prodrugs is anticipated.

A readily accessible enediyne building block was transformed into a number of conjugates, and photoactivation of the core via the photo-Bergman cyclization effected. Application in the form of immunoconjugates and nanoparticles is demonstrated.Figure optionsDownload as PowerPoint slide