Interactions of some novel amide-linked bis(acridines) with deoxyribonucleic acid.
A novel series of bis(acridines) has been synthesized in which the two potential intercalating chromophores are separated by symmetrical amide-linked chains varying in both length and conformational flexibility. By comparison to a monointercalating adduct, mono- vs. bis-intercalative behavior has been established for the bis(acridines). Spectrophotometric (visible, circular dichroism, and fluorescence) and viscometric (linear sonicated and closed circular superhelical DNA) experiments indicate that a highly rigid 8.8 A separated bis(acridine) monointercalates, whereas the longer and more flexible bis(acridines) are capable of bis-intercalation. In addition, spectrophotometric studies suggest a correlation between the tendency of intramolecular association and the ability to bis-intercalate. The results are in agreement with predictions based on the neighbor-exclusion principle and indicate that connecting chain rigidity is capable of playing a determining role in the mono- vs. bis-intercalation mechanism.
D000166:Acridines / Q000138:chemical synthesis; D000818:Animals; D003086:Bacteriocin Plasmids; D001665:Binding Sites; D002417:Cattle; D055598:Chemical Phenomena; D002621:Chemistry; D002942:Circular Dichroism; D004247:DNA; D004278:DNA, Superhelical; D007364:Intercalating Agents / Q000138:chemical synthesis; D013950:Thymus Gland; D014783:Viscosity
D000166:Acridines; D004278:DNA, Superhelical; D007364:Intercalating Agents; D004247:DNA