DNA-binding compounds--synthesis and intercalating properties of a peptide-diamino diacridine

A novel diacridine has been prepared in which two acridines are linked by a flexible peptide chain composed of gamma-aminobutyric acid, tyrosine, lysine and glycine. Synthesis of N-[9-acridinyl)-4-aminobutanoyl-tyrosyl-lysyl-lysyl-glycyl)-N'-(9- acridinyl)-1, 3-diaminopropane (VII) was achieved in 8% overall yield by a solution phase stepwise procedure. This compound binds to DNA by intercalation of both chromophores with at least a 140-fold enhancement of affinity compared to 9-aminoacridine.