Structural studies and cytotoxic activity of a new dinuclear coordination compound of palladium(II)-2,2:6,2-terpyridine with rigid dianionic 1,2,4-triazole-3-sulfonate linker

被引:14
作者
Buyukeksi, Sebile Isik [1 ]
Erkisa, Merve [2 ]
Sengul, Abdurrahman [1 ]
Ulukaya, Engin [2 ]
Oral, Arzu Yilmaztepe [3 ]
机构
[1] Bulent Ecevit Univ, Fac Arts & Sci, Dept Chem, TR-67100 Zonguldak, Turkey
[2] Istinye Univ, Dept Clin Biochem, Med Sch, TR-34010 Istanbul, Turkey
[3] Uludag Univ, Med Sch, Dept Med Biochem, TR-16059 Gorukle, Bursa, Turkey
关键词
cytotoxicity; dinuclear; palladium; terpyridine; triazole; CRYSTAL-STRUCTURE; MOLECULAR-STRUCTURE; PLATINUM COMPLEXES; BENZENE SULFONATE; FT-IR; PALLADIUM(II); TERPYRIDINE; DESIGN; RAMAN; DNA;
D O I
10.1002/aoc.4406
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A new dinuclear coordination compound of palladium(II), [Pd-2(terpy)(2)(-tas-N-1,N-4)]SO(4)11H(2)O (1), was synthesized by tethering a doubly deprotonated 1,2,4-triazole-3-sulfonate (tas) linker generated in situ via oxidation of 1,2,4-triazole-3-thione (tat) under the synthetic conditions. X-ray diffraction analysis reveals that tat molecules adopt the thione form in the solid state, and are combined in infinite chains by symmetrically related classical intermolecular hydrogen bonds N1H1S1, N3H3N2 to give rise to R-2(2)(7) pattern in one-dimensional chains along the b-axis propagating along the a-axis. Further short contacts through lone pairs of N2S1 on the rings between the adjacent chains along the a-axis lead to a two-dimensional network structure. Compound 1 was characterized using infrared, H-1 NMR and UV-visible spectroscopies, electrospray ionization mass spectrometry and X-ray crystallography. The crystal structure determination of 1 reveals that the Pd(II) ions are coordinated with four nitrogen atoms: three from terpy and one from tas acting as an end-to-end (-1,4) bridging ligand. The Pd(II) ions in 1 adopt a distorted square planar geometry. The anti-growth effect of 1 was tested on colorectal cancer (HCT-15), non-small-cell lung cancer (A549), prostate cancer (PC-3) and cervical cancer (HeLa) cell lines using sulforhodamine B viability assay. The cytotoxic effect was further confirmed using adenosine triphosphate viability assay. Compound 1 shows a promising cytotoxic activity in the diverse cancer cell models in vitro (p <0.0001).
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页数:11
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共 63 条
[1]   Biochemical and Proteomic Analysis of a Potential Anticancer Agent: Palladium(II) Saccharinate Complex of Terpyridine Acting through Double Strand Break Formation [J].
Adiguzel, Zelal ;
Baykal, Ahmet Tarik ;
Kacar, Omer ;
Yilmaz, Veysel T. ;
Ulukaya, Engin ;
Acilan, Ceyda .
JOURNAL OF PROTEOME RESEARCH, 2014, 13 (11) :5240-5249
[2]   Artificial molecular double-stranded helices [J].
Albrecht, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (40) :6448-6451
[3]   Resonance-induced hydrogen bonding at sulfur acceptors in R1R2C=C and R1CS2- systems [J].
Allen, FH ;
Bird, CM ;
Rowland, RS ;
Raithby, PR .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1997, 53 :680-695
[4]  
ANDREOTTI PE, 1995, CANCER RES, V55, P5276
[5]  
[Anonymous], 2017, J MOL STRUCT
[6]   PATTERNS IN HYDROGEN BONDING - FUNCTIONALITY AND GRAPH SET ANALYSIS IN CRYSTALS [J].
BERNSTEIN, J ;
DAVIS, RE ;
SHIMONI, L ;
CHANG, NL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (15) :1555-1573
[7]   TRIAZOLES .11. SYNTHESIS OF 1,2,4-TRIAZOLE-3-SULPHONIC ACIDS BY OXIDATION OF 1,2,4-TRIAZOLINE-3-THIONES [J].
BLACKMAN, AJ ;
POLYA, JB .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (17) :2403-&
[8]   TRIAZOLES .8. 1,2,4-TRIAZOLE-3-SULPHONIC ACIDS [J].
BLACKMAN, AJ ;
BROWNE, EJ ;
POLYA, JB .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (08) :661-&
[9]   Tautomerism of azacycles:: III.: Molecular and crystal structures of 3H- and 2-phenyl-1H,4H-4,5-dihydro-1,2,4-triazole-5-thiones [J].
Buzykin, B. I. ;
Mironova, E. V. ;
Gubaidullin, A. T. ;
Litvinov, I. A. ;
Nabiullin, V. N. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (04) :634-648
[10]  
CARMICHAEL J, 1987, CANCER RES, V47, P936