Low-dimensional compounds containing bioactive ligands. V: Synthesis and characterization of novel anticancer Pd(II) ionic compounds with quinolin-8-ol halogen derivatives.
Three novel palladium(II) complexes, NH2(CH3)2[PdCl2(CQ)] (1) (CQ=5-chloro-7-iodo-quinolin-8-ol), NH2(CH3)2[PdCl2(dClQ)] (2) (dClQ=5,7-dichloro-quinolin-8-ol) and NH2(CH3)2[PdCl2(dBrQ)] (3) (dBrQ=5,7-dibromo-quinolin-8-ol) have been prepared and characterized. Their structures contain square-planar [PdCl2(XQ)](-) complex anions in which deprotonated XQ ligands are coordinated to the Pd atoms via the pyridine nitrogen and the phenolato oxygen atoms, other two cis-positions are occupied by two chlorido ligands. Negative charges of these anions are balanced by uncoordinated dimethylammonium cations. Coordination of the XQ ligands to Pd(II) atom was confirmed by the differences in the stretching ν(OH) and ν(CN) vibrations in the IR spectra of ligands and prepared complexes while bands of aliphatic CH and NH stretching vibrations observed in the spectra of 1-3 confirm the presence of dimethylammonium cations in the complexes. The binding of complexes 1-3 to calf thymus DNA was investigated using UV-visible and fluorescence emission spectrophotometry. The fluorescence spectral results indicate that the complexes can bind to DNA through an intercalative mode. The Stern-Volmer quenching constants obtained from the linear quenching plot are in the 1.04 × 10(4) to 4.35 × 10(4) M(-1) range. The complexes exhibit significant anticancer activity tested on A2780 cells and cisplatin resistant cell line A2780/CP.
Department of Inorganic Chemistry, Institute of Chemistry, P. J. Šafárik University, Moyzesova 11, SK-04154 Košice, Slovak Republic.
Peter
P
Vranec
Department of Inorganic Chemistry, Institute of Chemistry, P. J. Šafárik University, Moyzesova 11, SK-04154 Košice, Slovak Republic. Electronic address: ivan.potocnak@upjs.sk.
Ivan
I
Potočňák
Department of Biochemistry, Institute of Chemistry, P. J. Šafárik University, Moyzesova 11, SK-04154 Košice, Slovak Republic.
Danica
D
Sabolová
Department of Biochemistry, Institute of Chemistry, P. J. Šafárik University, Moyzesova 11, SK-04154 Košice, Slovak Republic.
Veronika
V
Farkasová
Department of Biochemistry and Microbiology, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, SK-81237 Bratislava, Slovak Republic.
Zuzana
Z
Ipóthová
Department of Biochemistry and Microbiology, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, SK-81237 Bratislava, Slovak Republic.
Jana
J
Pisarčíková
Department of Biochemistry and Microbiology, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, SK-81237 Bratislava, Slovak Republic.
Helena
H
Paulíková
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D045744:Cell Line, Tumor / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D002945:Cisplatin / Q000494:pharmacology; D004247:DNA / Q000378:metabolism; D019008:Drug Resistance, Neoplasm; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D006219:Halogens / Q000737:chemistry; D006801:Humans; D006860:Hydrogen Bonding; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D006219:Halogens; D008024:Ligands; D011804:Quinolines; D010165:Palladium; D004247:DNA; C427203:calf thymus DNA; C037219:quinoline; D002945:Cisplatin
Crystal structure; Cytotoxicity; DNA binding; Palladium(II) complexes; Quinolin-8-ol halogen derivatives