[Spectroscopic research on the interaction of 2-(4-dimethylaminophenyl)-5-fluoro-6-(morpholin-4-yl)-1H-benzimidazole and calf thymus DNA].

UV-Vis spectra of the aqueous solutions of 2-(4-dimethylaminophenyl)-5-fluoro-6-(morpholin-4-yl)-1H-benzimidazole (1) at different pH values revealed that compound 1 is a tertiary base, which can combine three protons. Through the non-linear least square method, the logarithm of the three accumulative protonation constants of compound 1, namely, lgbeta1, lgbeta2 and lgbeta3, were determined to be 4.96 +/- 0.03, 5.72 +/- 0.07 and 7.95 +/- 0.10, respectively. UV-Vis and the steady-state fluorescence spectra indicated that a special interaction occurs between compound 1 and calf thymus DNA at the pH value of 3.40, of which thebinding constant, Kb, is (2.30 +/- 0.10) x 10(4) mol(-1) x L. Compound 1 in the concentration range of 10(-8) to 1.2 x 10(-6) mol x L(-1) has a potential application to the quantitative determination of DNA.

[Synthesis of 2-(4-dimethylaminophenyl)-5-fluoro-6-(morpholin-4-yl)-1H-benzimidazole and its spectroscopic research].

A new potential pharmaceutical compound, 2-(4-dimethylaminophenyl)-5-fluoro-6-(morpholin-4-yl)-1H-benzimidazole (4) was synthesized. The effect of the pH value of aqueous solution on the absorption spectrum of compound 4 and its interaction with beta-cyclodextrin (beta-CD) were investigated by UV-Vis spectrum, steady-state fluorescence and time-resolved spectroscopic measurements. The results indicate that compound 4 mainly exists in neutral molecular state when pH value of the aqueous phase is above 7.0. In the pH range from 7.0 to 3.8 the neutral molecular state and protonated univalent cationic form coexist. As the pH value decreases, the content of univalent cationic form increases. When 2.76 < pH < 3.8, the protonated univalent cationic form is the predominant species. With further decrease of the pH value, the univalent cation is protonated by another H+ to form a bivalent cation, and both univalent and bivalent cations coexist in the solution. The steady-state fluorescence and time-resolved spectroscopic measurements revealed that compound 4 is a sensitive molecular probe. The interaction of compound 4 and beta-CD is very strong. The guest:host ratio of inclusion complex between compound 4 and beta-CD formed in the aqueous solution (pH = 9.50) is 1:1, and the association constant was determined to be (1.02 +/- 0.04) x 10(3) mol x L(-1).