Journal of Physical Chemistry, Vol.99, No.21, 8927-8935, 1995
Excited-State Proton Transfers in 9-Aminoacridine Carboxamides
Excited-state proton transfers have been investigated for several isomeric and homologous N-((dimethylamino)alkyl)-9-aminoacridine carboxamides in a time-correlated single photon counting fluorescence study. The pH behavior of these DNA intercalators’ steady-state absorption and fluorescence spectra has also been investigated. While the excited-state pK(a)* for removal of a proton from the singly protonated species is close to the ground-state pK(a) in the parent molecule 9-aminoacridine, the presence of the carboxamide substituent renders pK(a)* much lower than pK(a) for the corresponding deprotonation in the present compounds. This fact, along with the presence of an additional deprotonation site at the distal N atom of the side chain, endows these molecules with complex pH dependence in their excited-state kinetics. Triexponential model functions are generally required to fit the experimental fluorescence decays, The pH dependence of the component lifetimes and preexponential factors can be simulated with a kinetic model for sequential deprotonations involving four aminoacridine species in both the ground and fluorescing states. These results provide a baseline study for comparisons with these intercalators’ excited-state kinetics in DNA.
Keywords:POTENTIAL ANTITUMOR AGENTS;DNA-BINDING KINETICS;BIOLOGICAL-ACTIVITY;FLUORESCENCE DECAY;BIS(SUBSTITUTED AMINOALKYLAMINO)ANTHRAQUINONES;DERIVATIVES;ACRIDINE;ANALOGS;CHAIN