Synthesis, characterization and antitumor activity of palladium(II) complexes of monoethyl 8-quinolylmethylphosphonate

The complex-forming properties of monoethyl 8-quinolylmethylphosphonate (8-Hmqmp) towards palladium(II) ion have been investigated by reactions of the hydrochloride, 8-Hmqmp · HCl · H2O, and sodium salt, Na(8-mqmp) · 2H2O, of this monoester with palladium(II) halide compounds in aqueous solution over a wide pH range. Depending on pH and initial quinolinium and palladium salts, four types of complexes have been formed. Under acidic solution the ion-pair salt complexes [8-H2mqmp]2[PdX4] (1 and 2, pH < 3) and [8-H2mqmp]2[Pd2X6] (3 and 4, pH ∼ 3), with protonated quinoline ligand as cation and tetrahalopalladate or hexahalodipalladate complex as anion (X = Cl, Br), were isolated. By heating in methanol the chloro complexes 1 and 3 as well as bromo complexes 2 and 4 were converted into the quinolinium salt complexes, [8-H2mqmp][Pd(8-Hmqmp)X3], 5 and 6, respectively, containing as anion the quinoliniummethylphosphonatetrihalopalladate complex with palladium bonded at the phosphonic acid moiety. The chelate complex 7, [Pd(8-mqmp)2], with ligand bonded through the quinoline nitrogen and the deprotonated phosphonic acid oxygen and forming two seven-membered {N,O} chelate rings, was obtained in neutral and basic media. The complexes were identified and characterized by elemental analysis, magnetic and conductance measurements, spectroscopic studies (IR, 1H NMR, UV–Vis, positive/negative ion FAB MS) and thermal analysis (TG, DTA). As a preliminary screening for their biological activity, complexes were investigated for their ability to inhibit the cancer growth in vitro in the human KB and murine L1210 cell lines. The results obtained were compared with those obtained for the complexes of diethyl 8-quinolylmethylphosphonate (8-dqmp) and monoethyl 2-quinolylmethylphosphonate (2-Hmqmp), and structural factors that determine the complex activity were discussed.

Monoethyl 8-quinolylmethylphosphonate (8-Hmqmp) depending on pH and initial quinolinium and palladium salts forms four types of palladium(II) complexes. The complexes [8-H2mqmp]2[PdX4], [8-H2mqmp]2[Pd2X6], [8-H2mqmp][Pd(8-Hmqmp)X3] (X = Cl, Br) and [Pd(8-mqmp)2] · 2H2O were characterized by spectroscopic (IR, UV–Vis, 1H NMR, FAB MS) and thermal (TG, DTA) studies. The antitumor activity in vitro of complexes was investigated against the human and murine cell lines.Figure optionsDownload as PowerPoint slide