Synthesis, spectroscopic characterization and antiproliferative activity of two platinum(II) complexes containing N-donor heterocycles

被引:20
作者
Rubino, S. [1 ]
Di Stefano, V. [1 ]
Attanzio, A. [1 ]
Tesoriere, L. [1 ]
Girasolo, M. A. [1 ]
Nicolo, F. [2 ]
Bruno, G. [2 ]
Orecchio, S. [1 ]
Stocco, G. C. [1 ]
机构
[1] Univ Palermo, Dipartimento Sci & Tecnol Biol Chim & Farmaceut S, I-90128 Palermo, Italy
[2] Univ Messina, Dipartimento Chim Inorgan Chim Analit & Chim Fis, I-98166 Messina, Italy
关键词
Mononuclear platinum complexes; Heterocyclic nitrogen; Dimethylsulfoxide; Antitumor activity; X-RAY-STRUCTURE; METAL-COMPLEXES; PALLADIUM(II) COMPLEXES; MOLECULAR-STRUCTURES; SULFOXIDE COMPLEXES; DIMETHYL-SULFOXIDE; ANTITUMOR-ACTIVITY; IN-VITRO; LIGANDS; CRYSTAL;
D O I
10.1016/j.ica.2014.03.028
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Novel mononuclear complexes of Pt(II), cis-[PtCl2(DMSO) HL]center dot 2DMSO (1), where HL = 7-amino-2-(methylthio)[1,2,4]triazolo[1,5-a] pyrimidine-6-carboxylic acid and Pt(bdt)Cl-2 (2), where bdt = [2,4-bis(5,6-diphenyl-1,2,4-triazin-3yl)-pyridine] have been synthesized and characterized by elemental analysis, IR and H-1 NMR spectroscopy and X-ray crystallography diffraction analyses. The molecular structure of (1) shows that Pt(II) ion has a square planar geometry with N(3) bonded heterocycle ligand, two cis chloride anions and S-bonded dimethylsulfoxide. The antiproliferative activity of complexes (1) and (2) has been tested in vitro against HepG2 human hepatoma cells and non-malignant human-derived hepatic cells (Chang). Complex (1), cis-[PtCl2(DMSO) HL]center dot 2DMSO, was effective inducer of apoptotic death on HepG2 cells and its cytotoxic activity was higher than that exerted by cisplatin. Apoptosis effect was associated with externalization of plasma membrane phosphatidylserine. (C) 2014 Elsevier B. V. All rights reserved.
引用
收藏
页码:112 / 118
页数:7
相关论文
共 44 条
  • [1] Novel N-sulfonamide trans-platinum complexes: synthesis, reactivity and in vitro evaluation
    Aleman, Jose
    del Solar, Virginia
    Alvarez-Valdes, Amparo
    Rios-Luci, Carla
    Padron, Jose M.
    Navarro-Ranninger, Carmen
    [J]. MEDCHEMCOMM, 2011, 2 (08) : 789 - 793
  • [2] Push-Pull Nitrile Ligands Exhibit Specific Hydration Patterns
    Anisimova, Tatyana B.
    Bokach, Nadezhda A.
    Luzyanin, Konstantin V.
    Haukka, Matti
    Kukushkin, Vadim Yu.
    [J]. DALTON TRANSACTIONS, 2010, 39 (44) : 10790 - 10798
  • [3] [Anonymous], 1999, SMART (Version 5.060) and SAINT (Version 6.02)
  • [4] [Anonymous], 1998, SHELXTLNT VERS 5 10
  • [5] Coordination studies of 5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine towards Zn2+ cation.: Synthesis and characterization by X-ray diffraction and spectroscopic methods
    Béreau, V
    Marrot, J
    [J]. COMPTES RENDUS CHIMIE, 2005, 8 (6-7) : 1087 - 1092
  • [6] Replacement of chlorides with dicarboxylate ligands in anticancer active Ru(II)-DMSO compounds: A new strategy that might lead to improved activity
    Bratsos, Ioannis
    Serli, Barbara
    Zangrando, Ennio
    Katsaros, Nikos
    Alessio, Enzo
    [J]. INORGANIC CHEMISTRY, 2007, 46 (03) : 975 - 992
  • [7] BRATTON DL, 1992, J IMMUNOL, V148, P514
  • [8] SIR2004:: an improved tool for crystal structure determination and refinement
    Burla, MC
    Caliandro, R
    Camalli, M
    Carrozzini, B
    Cascarano, GL
    De Caro, L
    Giacovazzo, C
    Polidori, G
    Spagna, R
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2005, 38 : 381 - 388
  • [9] Synthesis, characterization and X-ray crystal structure determination of platinum(II)-diaminoalkane complexes
    Clement, O
    Roszak, AW
    Buncel, E
    [J]. INORGANICA CHIMICA ACTA, 1996, 253 (01) : 53 - 63
  • [10] SULFOXIDES AS LIGANDS .2. THE INFRARED SPECTRA OF SOME DIMETHYL SULFOXIDE COMPLEXES
    COTTON, FA
    FRANCIS, R
    HORROCKS, WD
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1960, 64 (10) : 1534 - 1536