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
  • [41] Synthesis and Herbicidal Activites of Novel 1,2,4-Triazolo[1,5-a]pyrimidine Containing Oxime Ether Moiety
    Jiang, Lili
    Chen, Chaonan
    Zhou, Yanfei
    Chen, Qiong
    Yang, Guangfu
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (09) : 1392 - 1404
  • [42] Mono- and dinuclear platinum(II) compounds with 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine. Structure, cytotoxic activity and reaction with 5′-GMP
    Lakomska, Iwona
    Kooijman, Huub
    Spek, Anthony L.
    Shen, Wei-Zheng
    Reedijk, Jan
    DALTON TRANSACTIONS, 2009, (48) : 10736 - 10741
  • [43] 5-Methyl-1,2,4-triazolo[1,5-a]pyrimidine-6-carbonitrile
    Lokaj, J
    Kettmann, V
    Katuscák, S
    Cernuchová, P
    Milata, V
    Gregán, F
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2006, 62 : O1252 - O1253
  • [44] SYNTHESIS AND REACTIONS OF 7-METHYL-1,2,4-TRIAZOLO (1,5-A)PYRIMIDINE-5-CARBALDEHYDE
    LIPPMANN, E
    BECKER, V
    ZEITSCHRIFT FUR CHEMIE, 1973, 13 (08): : 293 - 294
  • [45] Design and synthesis of novel anthranilic diamides containing 5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine
    Dong, Wei-li
    Liu, Xing-hai
    Xu, Jun-ying
    Li, Zheng-ming
    JOURNAL OF CHEMICAL RESEARCH, 2008, (09) : 530 - 533
  • [46] Synthesis and antimicrobial activity of certain new 1,2,4-triazolo[1,5-a]pyrimidine derivatives
    Yaser A. -H. Mostafa
    Mostafa A. Hussein
    Awwad A. Radwan
    Abd El-Hamid N. Kfafy
    Archives of Pharmacal Research, 2008, 31
  • [47] MECHANISM OF ACTION OF 1,2,4-TRIAZOLO[1,5-A]PYRIMIDINE SULFONAMIDE HERBICIDES
    SUBRAMANIAN, MV
    LONEY, V
    PAO, L
    PROSPECTS FOR AMINO ACID BIOSYNTHESIS INHIBITORS IN CROP PROTECTION AND PHARMACEUTICAL CHEMISTRY, 1989, 42 : 97 - 100
  • [48] Synthesis and characterization of the energetic 5,7-diamino-2-nitro-1,2,4-triazolo[1,5-a]-1,3,5-triazine
    Roux, Maxwell A.
    Zeller, Matthias
    Byrd, Edward F. C.
    Piercey, Davin G.
    PROPELLANTS EXPLOSIVES PYROTECHNICS, 2023, 48 (10)
  • [49] Factors Affecting the Stability of Platinum(II) Complexes with 1,2,4-Triazolo[1,5-a]pyrimidine Derivatives and Tetrahydrothiophene-1-Oxide or Diphenyl Sulfoxide
    Jakubowski, Mateusz
    Lakomska, Iwona
    Kaszuba, Adriana
    Wojtczak, Andrzej
    Sitkowski, Jerzy
    Jarzecki, Andrzej A.
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2022, 23 (07)
  • [50] 5,7-Diphenyl[1,2,4]triazolo[1,5-a]pyrimidine at 122 K
    Department of Chemistry, Nicholas Copernicus University, Gagarina 7, 87-100 Toruń, Poland
    不详
    Acta Crystallogr Sect C Cryst Struct Commun, 8 (1337-1339):