Effect of different reaction conditions on the structural diversity of zinc(II) complexes with 9-deazahypoxanthine

Gáliková, Jana; Trávníček, Zdeněk

doi:10.1016/j.poly.2014.05.008

Cited by 6 publications

(4 citation statements)

References 38 publications

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“…Despite the above-mentioned biological potential of 9-deazahypoxanthine derivatives in clinical applications, its coordination chemistry is still quite new. To date, only one work has been published in connection with the study of coordination compounds incorporating the molecule of 9-deazahypoxanthine [46] .…”

Section: Introductionmentioning

confidence: 99%

Gold(I) Complexes of 9-Deazahypoxanthine as Selective Antitumor and Anti-Inflammatory Agents

et al. 2014

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The gold(I) mixed-ligand complexes involving O-substituted derivatives of 9-deazahypoxanthine (HLn) and triphenylphosphine (PPh3) with the general formula [Au(Ln)(PPh3)] (1–5) were prepared and thoroughly characterized by elemental analysis, FT-IR and multinuclear NMR spectroscopy, ESI+ mass spectrometry, single crystal X-ray (HL5 and complex 2) and TG/DTA analyses. Complexes 1–5 were evaluated for their in vitro antitumor activity against nine human cancer lines, i.e. MCF7 (breast carcinoma), HOS (osteosarcoma), A549 (adenocarcinoma), G361 (melanoma), HeLa (cervical cancer), A2780 (ovarian carcinoma), A2780R (ovarian carcinoma resistant to cisplatin), 22Rv1 (prostate cancer) and THP-1 (monocytic leukaemia), for their in vitro anti-inflammatory activity using a model of LPS-activated macrophages, and for their in vivo antiedematous activity by λ-carrageenan-induced hind paw edema model on rats. The results showed that the complexes 1–5 exhibit selective in vitro cytotoxicity against MCF7, HOS, 22Rv1, A2780 and A2780R, with submicromolar IC50 values for 2 against the MCF7 (0.6 µM) and HOS (0.9 µM). The results of in vitro cytotoxicity screening on primary culture of human hepatocytes (HEP220) revealed up to 30-times lower toxicity of compounds against healthy cells as compared with cancer cells. Additionally, the complexes 1–5 significantly influence the secretion and expression of pro-inflammatory cytokines TNF-α and IL-1β by a similar manner as a commercially used anti-arthritic drug Auranofin. The tested complexes also significantly influence the rate and overall volume of the edema, caused by the intraplantar application of λ-carrageenan polysaccharide to rats. Based on these promising results, the presented compounds could qualify to become feasible candidates for advanced testing as potential antitumor and anti-inflammatory drug-like compounds.

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Section: Introductionmentioning

confidence: 99%

Gold(I) Complexes of 9-Deazahypoxanthine as Selective Antitumor and Anti-Inflammatory Agents

et al. 2014

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“…In the case of the Zn-Cl bond lengths in 1b, the ZnCl1 length [2.2207(6)] fell within the interval of 2.21-2.24 Å found in CSD, while the Zn-Cl2 [2.2622(6) Å] length was slightly longer. Further, the Zn-N bond lengths in the complex 1b were compared with those in the previously reported polynuclear and dinuclear zinc(II) complexes involving 6-oxo-9-deazapurine (9dhx), namely, [Zn(9dhx)Cl 2 ] n and [{Zn(9dhx)(H 2 O) 3 } 2 (l-SO 4 ) 2 ] [19]. As results show, the determined Zn-N bond lengths in 1b were significantly different in comparison with the lengths in the polymeric and dimeric complexes, i.e.…”

Section: Methodsmentioning

confidence: 99%

“…, also involving the 6-oxo-9-deazapurine-based N-donor ligand (9dhx), was performed against malignant melanoma (G361) and prostate epithelial (22Rv1) human cancer cell lines, showing moderate cytotoxicity [19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray crystal structure and biological evaluation of zinc(II)-dichlorido complexes with 9-deazahypoxathine derivatives

Gáliková

Hošek

Trávníček

2015

Inorganica Chimica Acta

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“…Furthermore, the first screening of biological activity of zinc(II) compound with 6-oxo-9-deazapurine, i.e. , [{Zn(9dhx)(H 2 O) 3 } 2 (μ-SO 4 ) 2 ], brought promising results of in vitro cytotoxicity against the malignant melanoma (G361) cancer cell line (IC 50 ≈ 21 μM) [ 21 ]. Other coordination compounds, i.e.…”

Section: Introductionmentioning

confidence: 99%

Structural Diversity of Copper(II) Complexes with 9-Deazahypoxanthine and Their in Vitro SOD-Like Activity

Gáliková

Trávníček

2015

IJMS

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Two structurally different copper(II) complexes of the compositions [{Cu(9dhx)(H2O)3}2(µ-SO4)2] (1) and [Cu(9dhx)2(H2O)2(NO3)2]·H2O (2), involving 9-deazahypoxanthine (9dhx; 6-oxo-9-deazapurine; 9-deazahypoxanthine), have been prepared and characterized by elemental analysis, infrared and electronic spectroscopy, electrospray ionisation (ESI) mass spectrometry, thermogravimetric (TG) and differential thermal (DTA) analyses, and cyclic voltammetry. The X-ray structures of complexes 1 and [Cu(9dhx)2(H2O)2(NO3)2] (2a) revealed the distorted octahedral geometry in the vicinity of the copper(II) atoms, with the NO5 and N2O4 donor set, respectively. In the dimeric compound 1, the {Cu(9dhx)(H2O)3}2 units are bridged by sulfate groups with the Cu···Cu separation being 5.3446(2) Å. In both structures the 9dhx ligands are coordinated through the N3 atoms of the pyrimidine moieties. The SOD-like activity of complexes 1 and 2 was evaluated in vitro showing moderate effect, with the IC50 values equal to 18.20, and 53.33 μM, respectively.

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Effect of different reaction conditions on the structural diversity of zinc(II) complexes with 9-deazahypoxanthine

Cited by 6 publications

References 38 publications

Gold(I) Complexes of 9-Deazahypoxanthine as Selective Antitumor and Anti-Inflammatory Agents

Gold(I) Complexes of 9-Deazahypoxanthine as Selective Antitumor and Anti-Inflammatory Agents

Synthesis, X-ray crystal structure and biological evaluation of zinc(II)-dichlorido complexes with 9-deazahypoxathine derivatives

Structural Diversity of Copper(II) Complexes with 9-Deazahypoxanthine and Their in Vitro SOD-Like Activity

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