Organoruthenium (II) complexes featuring pyrazole‐linked Schiff base ligands: Crystal structure, DNA/BSA interactions, cytotoxicity and molecular docking

Abstract

Half‐sandwiched ruthenium (II) arene complexes with piano stool‐like geometry with the general formula [(p‐cymene)RuClL1] and [(p‐cymene)RuClL2] [where L1 = (Z)‐N′‐((1,3‐diphenyl‐1H‐pyrazol‐4‐yl)methylene)furan‐2‐carbohydrazide and L2 = (Z)‐N′‐((1,3‐diphenyl‐1H‐pyrazol‐4‐yl)methylene)thiophene‐2‐carbohydrazide] were synthesized and characterized. The single crystal X‐ray data revealed that the complexes belong to the same crystal system (monoclinic) with octahedral geometry, where the ruthenium atom is surrounded by hydrazone ligand coordinated through ON atoms, one chloride labile co‐ligand and the remaining three coordination sites covered by an electron cloud of p‐cymene moiety. The interaction between the complexes and DNA/bovine serum albumin (BSA) was evaluated using absorption and emission titration methods showing intercalative modes of interaction. The DNA cleavage ability of the complexes was checked by agarose gel electrophoresis method exhibiting the destruction of DNA duplex arrangement. To understand the interaction between ruthenium complex and DNA/BSA molecule, molecular docking studies were performed. In vitro cytotoxicity of the complexes was examined by the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) assay on human lung cancer cell line, A549, and found that at lower IC50, cell growth inhibition has occurred. Similarly, the IC50 values of the complexes treated with cancerous cell lines have produced a significant amount of lactase dehydrogenase and nitrite content in the culture medium, which were evaluated as apoptosis‐inducing factors, suggesting that the ruthenium (II) arene hydrazone complexes with pyrazole ligands have promising anticancer activities.

Solid-State Emissive Metallo-Supramolecular Assemblies of Quinoline-Based Acyl Hydrazone

“…Several studies have reported hydrazone-based compounds that can bind metal ions. Various metal ions, including Al 3+ , Cu 2+ , Ru 2+ , Pd 2+ , and Pt 2+ , can form a hydrazone-metal complex, and thus, may be applied in photochromic systems [39], molecular motors [40,41], proton transfer systems [42,43], bioactive materials [44][45][46][47], etc. Acyl hydrazone derivatives are an especially popular type of hydrazone derivatives for metal ion binding.…”

Estudo dos mecanismos de morte induzidos pelo complexo de rutênio hmxbato (cis-[RuII((ŋ2-O2CC7H7O2)(dppm)2]PF6) com atividade contra Leishmania (Leishmania) amazonensis e células tumorais de pulmão – A549

“…Finalmente, a interação do complexo com o DNA foi vista através dos estudos de docking molecular os quais revelaram que o modo de interação do complexo com o DNA pode ocorrer por meio de uma ligação de hidrogênio existente entre o átomo de hidrogênio do grupo -OH (hmxbato) e o átomo de oxigênio do grupo fosfato da guanina DG10 presente na estrutura de DNA analisada (CARUSO et al, 2012;K.S. et al, 2019).…”

“…Foram consideradas diferenças significativas quando p<0,1 (*), p<0,01 (**) e mais significativas quando p<0,001 (***) e p<0,0001 (****). (CARUSO et al, 2012;GOPALAKRISHNAN et al, 2017;GUPTA et al, 2013;KARAMI et al, 2018;K.S. et al, 2019).…”

Efeito citotóxico contra células de câncer de pulmão de novos complexos de rutênio(II) contendo ligantes bifosfínicos, tiossemicarbazonas e semicarbazonas

“…Sendo assim, a compreensão das interações com alvos biológicos fundamentais no funcionamento das células tumorais de potenciais agentes antitumorais, como é o caso de complexos de rutênio, é de suma importância para desvendar seus mecanismos de ação e possibilitar um posterior aperfeiçoamento na seletividade desses compostos. Atualmente, estudos teóricos de ancoragem molecular estão sendo uma importante ferramenta para predizer essas interações com biomoléculas, sendo que muitos deles estão coerentes com ensaios experimentais 50,[66][67][68][69]. As fosfinas são ligantes amplamente estudados na Química de coordenação, uma vez que, nas sínteses envolvendo esses ligantes, há a formação de complexos metálicos com estabilidade adicional.…”