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Thermodynamics of solution, interaction with calf thymus DNA and anticancer activity of phenylhydrazone derivatives

Abstract:

The solubilities in water (W) and in 3 mol·L-1 aqueous acetonitrile at 298.15 K of thiophene-2-, furan-2- and pyrrole-2-carboxaldehyde phenylhydrazone along with their nitro and 2,4-dinitro derivatives, referred to as PCT, PCF, PCP, NPCT, NPCF, NPCP, DPCT, DPCF and DPCP, respectively, are reported. The standard Gibbs energy of transfer from W to solvent mixtures (ΔG<inf>W-mix</inf>transf) was estimated for each solute. The results indicate that the transfer process for all systems is a spontaneous process. Calculations under the scaled-particle theory suggest that the work of cavity creation (ΔΔG<inf>c</inf>), which is associated with the transfer of the phenylhydrazone from W to mix, dominates the magnitude of ΔG<inf>W-mix</inf>transf. UV spectroscopic measurements suggest that these compounds bind calf thymus(CT)-DNA via intercalation mode in a buffer-3 mol·L-1 acetonitrile solution. The binding constant (K<inf>b</inf>) depends on the nitro-substitution on the phenyl moiety and the electronegativity of the heteroatom in the heterocyclic ring. The corresponding Gibbs energy of binding (ΔG<inf>DNA-B</inf>0) of phenylhydrazone derivatives to CT-DNA shows a marked dependence with ΔΔG<inf>c</inf>. The anticancer activity on human breast cancer cell lines MDA-231, MDA-435 and HT-29 human colon adenocarcinoma cell line was evaluated for the compounds NPCT, NPCF, DPCT and PCT. © Springer Science+Business Media, LLC 2010.