Synthesis, characterization and in vitro cytotoxicity of three types of platinum(II) complexes containing 5,7-diethyl-1,2,4-triazolo[1,5-a]pyrimidine

被引:14
|
作者
Lakomska, Iwona [1 ]
Babinska, Magdalena [1 ]
Wojtczak, Andrzej [2 ]
Sitkowski, Jerzy [3 ,4 ]
机构
[1] Nicolaus Copernicus Univ Torun, Fac Chem, Bioinorgan Chem Res Grp, Gagarina 7, PL-87100 Torun, Poland
[2] Nicolaus Copernicus Univ Torun, Fac Chem, Dept Crystallochem & Biocrystallog, Gagarina 7, PL-87100 Torun, Poland
[3] Natl Inst Med, Chelmska 30-34, PL-00725 Warsaw, Poland
[4] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland
关键词
Platinum(II) complex; 5,7-Diethyl-1,2, 4-triazolo[1, 5-a]pyrimidine; Multinuclear NMR; X-ray structure; In vitro cytotoxicity; RAY CRYSTAL-STRUCTURE; ANTITUMOR-ACTIVITY; MAGNETIC-RESONANCE; TRYPANOSOMA-CRUZI; NICKEL-COMPLEXES; DERIVATIVES; SPECTROSCOPY; LEISHMANIA; NMR; MONONUCLEAR;
D O I
10.1016/j.ica.2016.09.010
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Three structurally different mononuclear dichlorido platinum(II) complexes with 5,7-diethyl-1,2,4triazolo[1,5-a]pyrimidine (detp) were synthesized and characterized through multinuclear magnetic resonance (H-1, C-13, N-15, Pt-195) and infrared spectroscopy. The X-ray structure of cis-[PtCl2(detp)(dmso)] (2) was determined using the single-crystal X-ray diffraction technique. The molecular structure of (2) exhibits a square planar geometry surrounding the Pt(II) ion with a unique placement of two chlorido ligands in the cis position in the presence of a S-dmso molecule in the coordination sphere. All NMR data obtained in solution unambiguously confirmed the square planar geometry of Pt(II) with monodentate N3-bonded detp, a monodentate second ligand (detp or NH3 or dmso) and two chlorido ligands in the cis geometry. Cytotoxicity tests using human carcinoma cell lines, specifically the T47D (breast cancer), A549 (non small cell lung carcinoma), and LoVo (colon cancer) cell lines, and the healthy cell line BALB/3T3 (mouse embryonic fibroblast), indicated that only cis-[PtCl2(detp)(2)] (1) possesses similar in vitro cytotoxicity against T47D and sevenfold lower toxicity than cisplatin. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:516 / 521
页数:6
相关论文
共 50 条
  • [1] Hydrophilic platinum(II) complexes containing 5,7-dimethyl-1,2,4-triazolo [1,5-a]pyrimidine: Spectroscopic and in vitro cytotoxic characterization
    Lakomska, Iwona
    Hoffmann, Kamil
    Sitkowski, Jerzy
    POLYHEDRON, 2022, 227
  • [2] Structure-cytotoxicity relationship for different types of mononuclear platinum(II) complexes with 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine
    Lakomska, Iwona
    Fandzloch, Marzena
    Muziol, Tadeusz
    Sitkowski, Jerzy
    Wietrzyk, Joanna
    JOURNAL OF INORGANIC BIOCHEMISTRY, 2012, 115 : 100 - 105
  • [3] 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine
    Odabasoglu, M
    Büyükgüngör, O
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O1310 - O1311
  • [4] Platinum(II) complexes with 5,7-disubstituted-1,2,4-triazolo [1,5-a]pyrimidines: Spectroscopical characterization and cytotoxic activity in vitro
    Lakomska, Iwona
    Fandzloch, Marzena
    Poplawska, Beata
    Sitkowski, Jerzy
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2012, 91 : 126 - 129
  • [6] Copper(II) complexes with 1,2,4-triazolo[1,5-a] pyrimidine and its 5,7-dimethyl derivative
    Maldonado, Carmen R.
    Quiros, Miguel
    Salas, Juan M.
    POLYHEDRON, 2008, 27 (13) : 2779 - 2784
  • [7] Acetate platinum(II) compound with 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine that overcomes cisplatin resistance: structural characterization, in vitro cytotoxicity, and kinetic studies
    Hoffmann, Kamil
    Lakomska, Iwona
    Wisniewska, Joanna
    Kaczmarek-Kedziera, Anna
    Wietrzyk, Joanna
    JOURNAL OF COORDINATION CHEMISTRY, 2015, 68 (17-18) : 3193 - 3208
  • [8] SYNTHESIS WITH 5-HYDRAZINO-1,2,4-TRIAZOLO[1,5-A]PYRIMIDINE, DERIVATIVES - SYNTHESIS WITH 5-HYDROAZINO-1,2,4-TRIAZOLO[1,5-A]PYRIMIDINES
    LIPPMANN, E
    STRAUCH, P
    TENOR, E
    PHARMAZIE, 1991, 46 (03): : 184 - 187
  • [9] Spectroscopic, kinetic and cytotoxic in vitro study of hexafluoroglutarate platinum(II) complex with 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine
    Lakomska, Iwona
    Hoffmann, Kamil
    Topolski, Adrian
    Kloskowski, Tomasz
    Drewa, Tomasz
    INORGANICA CHIMICA ACTA, 2012, 387 : 455 - 459
  • [10] Synthesis and Biological Activity of Diheterocyclic 5,7-Dimethyl-1,2,4-triazolo[1,5-a]pyrimidine Derivatives
    Ma, Zhong-Hua
    Liu, Zu-Ming
    Chen, Qiong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (11) : 1965 - 1970