Syntheses, Crystal Structures, and Antitumor Activities of Copper(II) and Nickel(II) Complexes with 2-((2-(Pyridin-2-yl)hydrazono)methyl)quinolin-8-ol

Abstract

Two transition metal complexes with 2-((2-(pyridin-2-yl)hydrazono)methyl)quinolin-8-ol (L), [Cu(L)Cl2]2 (1) and [Ni(L)Cl2]·CH2Cl2 (2), were synthesized and fully characterized. Complex 1 exhibited high in vitro antitumor activity against SK-OV-3, MGC80-3 and HeLa cells with IC50 values of 3.69 ± 0.16, 2.60 ± 0.17, and 3.62 ± 0.12 μM, respectively. In addition, complex 1 caused cell arrest in the S phase, which led to the down-regulation of Cdc25 A, Cyclin B, Cyclin A, and CDK2, and the up-regulation of p27, p21, and p53 proteins in MGC80-3 cells. Complex 1 induced MGC80-3 cell apoptosis via a mitochondrial dysfunction pathway, as shown by the significantly decreased level of bcl-2 protein and the loss of Δψ, as well as increased levels of reactive oxygen species (ROS), intracellular Ca2+, cytochrome C, apaf-1, caspase-3, and caspase-9 proteins in MGC80-3 cells.

Self-Assembly by Tridentate or Bidentate Ligand: Synthesis and Vapor Adsorption Properties of Cu(II), Zn(II), Hg(II) and Cd(II) Complexes Derived from a Bis(pyridylhydrazone) Compound

“…So far, hydrazone-based metal complexes have received considerable attention from chemists in many applications such as chromogenic reagents in the spectrophotometric determination of transition-metal ions, metal extracts and biologically active compounds [ 9 ]. They have also been demonstrated to possess diverse pharmacological properties [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 ], catalytic properties [ 18 , 19 ], adsorption properties [ 20 , 21 ], electrochemical properties [ 22 ], luminescent properties [ 23 , 24 ], etc.…”

Diastereomeric Separation of Chiral fac-Tricarbonyl(iminopyridine) Rhenium(I) Complexes and Their Cytotoxicity Studies: Approach toward an Action Mechanism against Glioblastoma

“…Some groups demonstrated that copper complexes cause elevation of DNA damage-indicating proteins. 57 In the context of cancer therapy, the quantification of γH2AX is a useful biomarker for evaluating the DNA damage caused by diverse compounds. Previously we showed by CD that both coordination complexes modified the DNA structure.…”

Metal Coordination and Biological Screening of a Schiff Base Derived from 8-Hydroxyquinoline and Benzothiazole

“…Overall, it is well-known the variety of alternative mechanisms of action by which metal complexes may exert their biological or pharmacological activity, besides impacting cell cycle [4,8,67]. Various nickel complexes have shown to act through the formation of ROS species and inducing mitochondrial-mediated apoptosis [56,74,81,82] or by activating the tyrosine kinase proapoptotic pathway [58]. In addition, other ruthenium complexes have also demonstrated to exert activity through the apoptotic pathway via cleaved PARP, caspase-3 and caspase-9 [64,83]; lysosome-mediated apoptosis [62]; necrosis [60]; and possibly inhibiting DNA replication by binding to DNA strands [59].…”