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 49 条
[1]  
[Anonymous], NMR NEWLY ACCESSIBLE
[2]  
[Anonymous], 2014, LEISHMANIASIS TRENDS
[3]  
[Anonymous], CRYSALIS CCD171 RED1
[4]   Synthesis and biological evaluation of thieno [2′,3′:4,5]pyrimido[1,2-b][1,2,4]triazines and thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidines as anti-inflammatory and analgesic agents [J].
Ashour, Hayam M. ;
Shaaban, Omaima G. ;
Rizk, Ola H. ;
El-Ashmawy, Ibrahim M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 62 :341-351
[5]   Coordination chemistry of substituted [1,2,4]triazolo[1,5-a]pyrimidines with first-row transition-metal ions: Synthesis, spectroscopy and single-crystal structure [J].
Balkaran, Jeral M. ;
van Bezouw, Stein C. P. ;
van Bruchem, John ;
Verasdonck, Joeri ;
Verkerk, Peter C. ;
Volbeda, Anne Geert ;
Mutikainen, Ilpo ;
Turpeinen, Urho ;
van Albada, Gerard A. ;
Gamez, Patrick ;
Haasnoot, Jaap G. ;
Reedijk, Jan .
INORGANICA CHIMICA ACTA, 2009, 362 (03) :861-868
[6]  
Billow C., 1909, BERICHTE, V42, P4638
[7]  
Boutaleb-Charki Samira, 2009, Drug Metab Lett, V3, P35
[8]   In vitro and in vivo antiparasital activity against Trypanosoma cruzi of three novel 5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one-based complexes [J].
Caballero, Ana B. ;
Marin, Clotilde ;
Rodriguez-Dieguez, Antonio ;
Ramirez-Macias, Inmaculada ;
Barea, Elisa ;
Sanchez-Moreno, Manuel ;
Salas, Juan M. .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2011, 105 (06) :770-776
[9]   Synthesis, antifungal activity and CoMFA analysis of novel l,2,4-triazolo[1,5-a]pyrimidine derivatives [J].
Chen, Qiong ;
Zhu, Xiao-Lei ;
Jiang, Li-Li ;
Liu, Zu-Ming ;
Yang, Guang-Fu .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (03) :595-603
[10]   Synthesis, characterization and X-ray crystal structure determination of platinum(II)-diaminoalkane complexes [J].
Clement, O ;
Roszak, AW ;
Buncel, E .
INORGANICA CHIMICA ACTA, 1996, 253 (01) :53-63