The synthesis, chemical and biological properties of dichlorido(azpy)gold(III) chloride (azpy= 2-(phenylazo)pyridine) and the gold-induced conversion of the azpy ligand to the chloride of the novel tricyclic pyrido[2,1-c][1,2,4]benzotriazin-11-ium cation
| Autor: | Anthony L. Spek, Huub Kooijman, Hans den Dulk, Ariadna Garza-Ortiz, Jan Reedijk, Jaap Brouwer |
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| Přispěvatelé: | Kristal- en structuurchemie, R¿ntgenparticipatieprogramma, Dep Scheikunde |
| Rok vydání: | 2007 |
| Předmět: |
Spectrometry
Mass Electrospray Ionization Magnetic Resonance Spectroscopy Spectrophotometry Infrared Cell Survival Pyridines Inorganic chemistry Antineoplastic Agents Biochemistry Chloride Medicinal chemistry Coordination complex Gold(III) chloride Inorganic Chemistry Inhibitory Concentration 50 chemistry.chemical_compound Cell Line Tumor Pyridine medicine Animals Humans Reactivity (chemistry) Cell Proliferation chemistry.chemical_classification Molecular Structure Ligand chemistry Cyclization Drug Resistance Neoplasm Spectrophotometry Ultraviolet Chemical stability Gold Cisplatin Organogold Compounds Derivative (chemistry) medicine.drug |
| Zdroj: | Journal of Inorganic Biochemistry. 101:1922-1930 |
| ISSN: | 0162-0134 |
| DOI: | 10.1016/j.jinorgbio.2007.05.008 |
| Popis: | A new Au(III) coordination compound with the ligand 2-(phenylazo)pyridine has been synthesized and fully characterized by means of elemental analysis, IR, UV–visible, conductivity measurements, NMR, electrospray ionization (ESI-MS) and inductively coupled plasma optical emission spectrometry (ICP-OES). The chemical stability of the cation in this compound, [Au(azpy)Cl2]+ (abbreviated: Au-azpy), was analyzed by means of several physicochemical methods. While stable in the solid state, stability studies performed with the gold compound in solution showed an unexpected and unprecedented reactivity. A cationic organic derivative of 2-(phenylazo)pyridine, (abbreviated: pyrium), was produced from the solution and has been isolated as its chloride salt and characterized by crystal structure determination, elemental analysis, NMR, ESI-MS and conductivity studies in solution. This cyclization reaction is reported for the first time in the case of gold coordination compounds. The Au adduct and the pyrium cation were investigated as potential cytotoxic and anticancer agents, and both show moderate to high cytotoxic properties in cisplatin-sensitive and cisplatin-resistant ovarian carcinoma cell lines, A2780; and cisplatin-sensitive and cisplatin-resistant murine lymphocytic leukemia cell lines, L1210. Significant anticancer activity against the cisplatin resistant cell lines was found for the pyrium salt, ruling out the occurrence of cross resistance phenomena. |
| Databáze: | OpenAIRE |
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