New heteroleptic palladium(II) dithiocarbamates: synthesis, characterization, packing and anticancer activity against five different cancer cell lines

被引:42
作者
Khan, Shahan Zeb [1 ,2 ]
Amir, Muhammad Kashif [1 ]
Ullah, Imdad [1 ]
Aamir, Asma [1 ]
Pezzuto, John M. [3 ,4 ]
Kondratyuk, Tamara [3 ]
Belanger-Gariepy, Francine [5 ]
Ali, Akbar [1 ]
Khan, Sajid [2 ]
Zia-ur-Rehman [1 ]
机构
[1] Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan
[2] Univ Sci & Technol, Dept Chem, Bannu 28100, Kpk, Pakistan
[3] Univ Hawaii, Coll Pharm, 34 Rainbow Dr, Hilo, HI 96720 USA
[4] Long Isl Univ, Arnold & Marie Schwartz Coll Pharm, Brooklyn, NY 11201 USA
[5] Univ Montreal, Dept Chim, CP 6128, Montreal, PQ H3C 3J7, Canada
关键词
palladium(II) dithiocarbamate; supramolecular; anticancer; DNA binding; DFT; DNA-BINDING; PLATINUM COMPLEXES; LIGAND; CYTOTOXICITY; ANTITUMOR; AGENTS; DRUGS;
D O I
10.1002/aoc.3445
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Two new heteroleptic palladium(II) complexes have been synthesized by reacting equimolar quantities of palladium(II) chloride, sodium 4-(2-methoxyphenyl)piperazine-1-carbodithioate and diphenyl-p-tolylphosphine (1) or tri-p-tolylphosphine (2). Complexes 1 and 2 have been characterized using elemental analysis, Fourier transform infrared spectroscopy, multinuclear NMR (H-1, C-13 and P-31) spectroscopy and single-crystal X-ray analysis. The latter technique confirms a pseudo square-planar geometry in which two adjacent positions are occupied by bidentate dithiocarbamate while chloro and substituted triphenylphosphine are present at the remaining two positions. The anticancer activity of both complexes against five different cancer cell lines (LU - human lung carcinoma, established at UIC, Department of Surgical Oncology; MCF7 - human breast adenocarcinoma, ATCC number HTB-22 (TM); MDA-MB-231 - human breast adenocarcinoma, ATCC number HTB-26 (TM); Hepa-1c1c7 - mouse liver hepatoma, ATCC number CRL-2026 (TM); PC-3 - human prostate adenocarcinoma, ATCC number CRL-1435 (TM)) was determined by MTT assay, revealing 2 has higher activity than 1. A drug-calf thymus DNA binding study with UV-visible spectroscopy reveals a higher DNA binding affinity of 2 (3.511 x 10(4) M-1) than 1 (4.213 x 10(3) M-1). Density functional theory studies confirm the relatively more stable nature of 2 than 1. Copyright (C) 2016 John Wiley & Sons, Ltd.
引用
收藏
页码:392 / 398
页数:7
相关论文
共 53 条
  • [1] Synthesis, Characterization, and Antibacterial Studies of Pd(II) and Pt(II) Complexes of Some Diaminopyrimidine Derivatives
    Ajibade, Peter A.
    Idemudia, Omoruyi G.
    [J]. BIOINORGANIC CHEMISTRY AND APPLICATIONS, 2013, 2013
  • [2] Characterization studies and cytotoxicity assays of Pt(II) and Pd(II) dithiocarbamate complexes by means of FT-IR, NMR spectroscopy and mass spectrometry
    Alverdi, V
    Giovagnini, L
    Marzano, C
    Seraglia, R
    Bettio, F
    Sitran, S
    Graziani, R
    Fregona, D
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2004, 98 (06) : 1117 - 1128
  • [3] [Anonymous], SPECTROCHIM ACTA A
  • [4] Exploration of the medical periodic table: towards new targets
    Barry, Nicolas P. E.
    Sadler, Peter J.
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (45) : 5106 - 5131
  • [5] A SPECTROPHOTOMETRIC INVESTIGATION OF THE INTERACTION OF IODINE WITH AROMATIC HYDROCARBONS
    BENESI, HA
    HILDEBRAND, JH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) : 2703 - 2707
  • [6] Syntheses, crystal structures and photoluminescent properties of new homoleptic and heteroleptic zinc(II) dithiocarbamato complexes
    Bharti, A.
    Bharati, Pooja
    Chaudhari, U. K.
    Singh, A.
    Kushawaha, S. K.
    Singh, N. K.
    Bharty, M. K.
    [J]. POLYHEDRON, 2015, 85 : 712 - 719
  • [7] Boulikas T, 2003, ONCOL REP, V10, P1663
  • [8] OLEX2: a complete structure solution, refinement and analysis program
    Dolomanov, Oleg V.
    Bourhis, Luc J.
    Gildea, Richard J.
    Howard, Judith A. K.
    Puschmann, Horst
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 : 339 - 341
  • [9] Recent developments in the field of tumor-inhibiting metal complexes
    Galanski, M
    Arion, VB
    Jakupec, MA
    Keppler, BK
    [J]. CURRENT PHARMACEUTICAL DESIGN, 2003, 9 (25) : 2078 - 2089
  • [10] Ghani N. T. A., 2012, J COORD CHEM, V65, P763