Single-triggered AB₆ self-immolative dendritic amplifiers

Self-immolative dendrimers are a unique class of molecules that are able to disassemble upon undergoing a specific triggering reaction through domino-like fragmentations. We have designed and synthesized a novel AB₆ self-immolative dendritic adaptor that amplifies a single cleavage event into the release of six reporter units. The disassembly mechanism is based on a specifically triggered cleavage event followed by elimination of a cyclic urea derivative and six consecutive quinone methide eliminations. The system was disassembled under both organic and aqueous conditions by either chemical or enzymatic triggering. Various reporter molecules and triggering groups were introduced onto the dendritic adaptor to obtaining sensor molecules with enhanced properties for diagnostics and imaging.