A new class of DNA intercalators based on the 8H-pyridazino[1‘,6‘:1,2]pyrido[4,3-b]indol-5-inium
system in which the cationic nature of the chromophore is provided by a brigdehead quaternary
nitrogen has been obtained. These cations along with 10H-indolo[3,2-c]pyridazino[1,6-a]quinolin-5-inium, 13H-dibenz[f,h]indolo[3‘,2‘:3,4]pyrido[1,2-b]cinnolin-10-inium, and 5H-acenaphtho[1‘,2‘:3‘,4‘]pyridazino[1‘,6‘:1,2]pyrido[4,3-b]indol-8-inium were synthesized by the Westphal reaction of
carbolinium derivatives with various 1,2-dicarbonyl compounds. When these tetra-, penta-, and
heptacyclic heteroaromatic nuclei were evaluated as DNA intercalators using UV−vis spectroscopy,
viscometric determinations, and unwinding angle determinations, we found that only the 8H-pyridazino[1‘,6‘:1,2]pyrido[4,3-b]indol-5-inium cations behaved as DNA intercalators. Molecular
modeling studies allowed the preferred orientation of the intercalating chromophore within a CpG
intercalation site to be explored and will provide help in the rational design of novel bis-intercalators
based on these chromophores.