Síntese e atividade citotóxica de alguns azido-ciclopaladados estabilizados com ligantes bifosfínicos

Caires, Antonio C. F.; Almeida, Eduardo Tonon de; Mauro, Antônio Eduardo; Hemerly, Jefferson P.; Valentini, Sandro Roberto

doi:10.1590/s0100-40421999000300008

Cited by 58 publications

(38 citation statements)

References 17 publications

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“…26 Cyclopalladated complexes containing thiosemicarbazones ligands have also shown antitumour properties when coordinated to palladium atoms. 27,28 In the MTT assay, 17 the compound [{Pd(N,C-dmba)} 2 (μ-NCS) 2 ] (1) has not shown a considerable activity when compared to the citotoxic behaviour of the complex [Pd(Cdmba)(NCS)(dppp)] (2) as presented in Figure 2. So, we have verified that complex (2) showed lower IC 50 value (5.29±3.89 μmol L -1 ) than those values of cis-DDP (33.77±2.29) and (1) (47.86±4.32).…”

Section: Biological Activitiesmentioning

confidence: 99%

“…Some cyclopalladated complexes 26 of the type [Pd(C-N)(X)(L)], where C-N is an aromatic or aliphatic amine coordinated via C and N atoms to Pd; L=nitrogen ligand; X= chloride or acetate, have shown to be citotoxic towards seven tumour lines 27 , e.g., [Pd(dmba)(Cl)(py)]; dmba = N,N'-dimethylbenzylamine and py = pyridine. 26 Cyclopalladated complexes containing thiosemicarbazones ligands have also shown antitumour properties when coordinated to palladium atoms.…”

Section: Biological Activitiesmentioning

confidence: 99%

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Citotoxicity and immune response induced by organopalladium(II) compounds in mice bearing Ehrlich ascites tumour

Rocha¹,

Santana²,

Ananias³

et al. 2007

J. Braz. Chem. Soc.

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Os ciclometalados de paládio(II) são compostos inorgânicos reativos empregados em vários estudos biológicos devido a seu potencial antitumoral e interação com o sistema imune. Neste estudo, a resposta imune e citotóxica induzida por dois complexos organopaladados: [{Pd(N,C-dmba)} 2 (μ-NCS) 2 ] (1), [Pd(C-dmba)(NCS)(dppp)] (2) [dmba = N,N'-dimetilbenzilamina, dppp = 1,3-bis(difenilfosfino)propano] e cisplatina (cis-DDP), como padrão, foram investigados em camundongos portadores do tumor ascítico de Ehrlich. Os camundongos foram divididos em cinco grupos e inoculados com (1) ou (2) ou cis-DDP ou apenas veículo ou solução salina tamponada de fosfatos (PBS). Diversos parâmetros foram avaliados, tais como a porcentagem de células tumorais presentes no exsudato peritoneal, os níveis de óxido nítrico (NO) e fator de necrose tumoral (TNF-α) séricos e o aumento na expectativa de vida. Os dados obtidos demonstram que o composto (2) apresentou atividade similar à da cis-DDP, como, por exemplo, aumento na expectativa de vida, diminuição dos níveis séricos de TNF-α e aumento da produção de NO.Cyclometallated palladium(II) complexes are reactive inorganic compounds employed in several biological studies because of their antitumour potential and interaction with immune system. In the present study, the immune and citotoxic response induced by two organopalladated complexes: [{Pd(N,C-dmba)} 2 (μ-NCS) 2 ] (1), [Pd(C-dmba)(NCS)(dppp)] (2) [dmba = N,N'-dimethylbenzylamine, dppp = 1,3-bis(diphenylphosphino)propane] and cisplatin (cis-DDP), as standard, were investigated in mice bearing Ehrlich ascites tumour. The mice were divided into five groups and inoculated with the compounds (1) or (2) or cisplatin, or only vehicle or phosphatebuffered saline (PBS). Many parameters were evaluated, such as tumour cell percentage in the peritoneal exsudate, levels of seric nitric oxide (NO) and tumour necrosis factor-alpha (TNF-α) and increase in life span. Analysis of all data revealed, for compound (2), an activity similar to that presented by cisplatin, resulting in increased life span, lower levels of seric TNF-α and increase in NO production.Keywords: palladium(II) complexes, Ehrlich ascites tumour, macrophages, nitric oxide, tumour necrosis factor-alpha. IntroductionCancer is a disease in which unremitting clonal expansion of somatic cells kills by invading, subverting, and eroding normal tissues. 1 Millions of people die every year from the metastatic spread of cancer that occurs through blood and lymphatic vessels or directly into tissues and body cavities. 2 Between the several types of cancer, breast cancer is the most common malignancy in women worldwide. 3 In some cases, immune cells constitute a prominent component of the host response to cancer, but their participation in tumour pathogenesis remains not completely understood. Dense intratumoral lymphocyte cis-Diamminedichloroplatinum(II), 9 a clinically important antitumour drug, acts like a classical alkylating agent in chemotherapy against some types of cancers. It is a potent ...

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Section: Biological Activitiesmentioning

confidence: 99%

Section: Biological Activitiesmentioning

confidence: 99%

Citotoxicity and immune response induced by organopalladium(II) compounds in mice bearing Ehrlich ascites tumour

Rocha¹,

Santana²,

Ananias³

et al. 2007

J. Braz. Chem. Soc.

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“…Nevertheless, a recent breakthrough from Caires et al [18] has shown that a number of C,N-palladacycles were non-cytotoxic anticancer activity, and have notable cathepsin B inhibitory activity with the potential to treat metastatic cancer [19,20]. However, palladacycles are more stable, and, most important, less toxic, suggesting they could have a more specific antitumor activity in vivo [1,[21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Palladacycles Inhibitors of the Cathepsin B Activity and Antitumoral Agents

Elgazwy

Shehata²,

Zaki³

et al. 2013

Med chem (Los Angeles)

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The reaction of 2-bromo-3,4,5-trimethoxybenzaldehyde 1 with Pd(dba) 2 ; dba=dibenzylideneacetone) in the presence of a stoichiometric amount of nitrogen donor ligands, such as N,N,N',, 2,2'-bipyridine (bpy) 4,4'-dimethyl-2,2'-bipyridine (dmbpy) and an 1,10-phenanthroline (Phen), should be added to with equimolar ratio in degassed acetone under nitrogen to give mononuclear σ-aryl palladium (II) complexes cis-[2-Pd{C 6 H(CHO)-6-(OMe) 3 -3,4,5}BrL 2 ] 3a-d, where L 2 =TMEDA (3a); L 2 =bpy (3b); L 2 =dmbpy (3c); L 2 =Phen (3d) in good yields 48-65%. The reaction of the synthesized five-membered C,N-palladacycle cis-[2-Pd{C 6 H(CHO)-6-(OMe) 3 -3,4,5} BrL 2 ] 3a-d, where L 2 =TMEDA (3a); L=bpy (3b); L 2 =dmbpy (3c); L 2 =Phen (3d), with an1-naphthylisocyanates (C 10 H 7 -NCO) and an 1-naphthylisothiocyanates (C 10 H 7 -NCS), leads to the formation of novel palladacycle 4a-d and 5a-d, which was characterized in solution by 1 H NMR spectroscopy. The solid products were characterized by satisfactory elemental analysis and spectra studies. All the resulting complexes 3a-d, 4a-d and 5a-d were tested in vitro against a number of cell lines. For example, it inhibited K562 leukaemia cells with an IC 50 value in the range of (3.00 -4.3) µM (1 h exposure) and displayed cathepsin B inhibitory action with an IC 50 value in the range of (0.045-0.055 µM). .

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“…As ligands, 1,2,4-triazoles are extremely versatile and display the ability to act as monodentate, exobidentate N(1),N (2) and exobidentate N (2),N(4) when neutral or monodentate, exobidentate N (1),N (2), exobidentate N (1), N(4) and N (1),N (2),N(4)-tridentate when deprotonated. 17 In pursuing our interest on chemical and biological aspects of palladium(II) complexes, 14,18,19 we describe in this work the synthesis, spectroscopic characterization and thermal investigation of the two new 1,2,4-triazolylbridged polynuclear complexes [{PdCl 2 (µ-Htrz)} n ] (1) and [{PdBr 2 (µ-Htrz)} n ] (2). We also investigated the immunomodulatory effects of the compounds 1,2,4-triazole (Htrz), 1, 2, and cisplatin by the release of NO and H 2 O 2 in the culture supernatants of treated murine peritoneal cells.…”

Section: Introductionmentioning

confidence: 99%

Immunomodulatory effects of palladium(II) complexes of 1,2,4-triazole on murine peritoneal macrophages

Bego¹,

Frem²,

Netto³

et al. 2009

J. Braz. Chem. Soc.

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Os complexos polinucleares [{PdCl 2 (µ-Htrz)} n ] (1) e [{PdBr 2 (µ-Htrz)} n ] (2) (Htrz = 1,2,4-triazol) foram sintetizados neste trabalho. O composto 1 foi preparado a partir da substituição da acetonitrila do precursor [PdCl 2 (MeCN) 2 ] pelo 1,2,4-triazol. A adição posterior de brometo de potássio ao meio reacional resultou na formação do complexo 2. Os complexos inéditos foram isolados, purificados e caracterizados por análise elementar, espectroscopias vibracional no infravermelho e eletrônica no UV-visível e curvas de análise termogravimétrica (TG). Os resultados experimentais sugerem que, em ambos os casos, a coordenação do 1,2,4-Htrz ocorra via átomos N(2) e N(4), atuando como pontes entre centros de paládio. O poliedro de coordenação quadrado-planar ao redor do paládio(II) é determinado pelos dois átomos de N do heterociclo e por dois ligantes cloro (1) ou bromo (2), em uma provável configuração trans. As curvas TG indicaram que a natureza do ligante aniônico não afeta significativamente a estabilidade térmica de 1 e 2. Os produtos finais de decomposição térmica foram identificados como paládio metálico pela técnica de difratometria de raios X de pó. Testes preliminares envolvendo a avaliação dos efeitos dos compostos 1, 2 e Htrz na produção de H 2 O 2 e NO em culturas de macrófagos peritoneais de camundongos BALB/c foram realizados in vitro.The 1,2,4-triazolyl-bridged polynuclear complexes [{PdCl 2 (µ-Htrz)} n ] (1) and [{PdBr 2 (µ-Htrz)} n ] (2) have been obtained in this work. Compound 1 is prepared by the displacement of acetonitrile from [PdCl 2 (MeCN) 2 ] by 1,2,4-triazole (Htrz). Further addition of potassium bromide to the reaction medium afforded complex 2. The new complexes have been isolated, purified and characterized by means of elemental analysis, IR and UV-visible electronic spectroscopies and thermogravimetric (TG) curves. The experimental data suggested that, in both cases, the coordination of 1,2,4-Htrz takes place through the N(2) and N(4) atoms, bridging the palladium centers. The square-planar coordination polyhedron of palladium(II) is determined by two nitrogen atoms from the triazole ligands, while the other two coordination positions are occupied by the chloro (1) or bromo (2) ligands. TG curves indicated that the nature of the anionic ligand does not affect significantly the thermal stability of 1 and 2. The final products of the thermal decompositions were identified as metallic palladium by X-ray powder diffractometry. Preliminary tests involving the evaluation of the effects of compounds 1, 2 and Htrz on H 2 O 2 and NO production in cultures of peritoneal macrophages from BALB/c mice were carried out in vitro.

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Síntese e atividade citotóxica de alguns azido-ciclopaladados estabilizados com ligantes bifosfínicos

Cited by 58 publications

References 17 publications

Citotoxicity and immune response induced by organopalladium(II) compounds in mice bearing Ehrlich ascites tumour

Citotoxicity and immune response induced by organopalladium(II) compounds in mice bearing Ehrlich ascites tumour

Synthesis of Novel Palladacycles Inhibitors of the Cathepsin B Activity and Antitumoral Agents

Immunomodulatory effects of palladium(II) complexes of 1,2,4-triazole on murine peritoneal macrophages

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