Enantioselectivity in the Interaction of Calf Thymus DNA with Acridine Derivatives Having an Amino Ester or Amino Alcohol Substituent

Article abstract of DOI:10.1246/bcsj.65.2050

Unless a bulky aromatic side chain is involved, acridine derivatives 1 and 2 having an amino ester or amino alcohol substituent bind to calf thymus DNA via intercalation.The binding constants evaluated by the Scatchard analysis of the hypochromicity data indicate that (1) the substituents introduced are rather inhibitory of the binding and (2) L-enantiomers are preferred than the D-enantiomers by a factor of K_L/K_D=1.1-1.4, except for the case of aspartic and glutamic esters where the optical selectivity is very low or even reversed.The present enantioselectivity is discussed in terms of a local C₂ chirality of the intercalation site, steric effects of the amino ester or amino alcohol substituents, and a possible conformation-controlling effect of the CO2CH3 or CH2OH group.