A novel bidentate ligand containing oxime, hydrazone and indole moieties and its BF₂⁺ bridged transition metal complexes and their efficiency against prostate and breast cancer cells

Abstract

In this study, a novel bidentate ligand containing oxime, hydrazone, and indole moieties and its BF2+‐bridged transition metal complexes [Ni(II), Cu(II), and Co(II)] were synthesized and their cytotoxic activities against prostate and breast cancer cells were investigated. The vic‐dioxime ligand bearing indole–hydrazone side groups was synthesized by reacting antiglyoximehydrazine (GH2) with 3‐methoxy indole. The ligand forms mononuclear complexes with a metal‐to‐ligand ratio of 1:2 with M = Co(II)(H2O)2, Ni(II), and Cu(II). These metal complexes were then reacted with BF3(C2H5)2O to obtain BF2+‐bridged transition metal complexes. The Co(II) complex of the ligand is proposed to be octahedral with water molecules as axial ligands, whereas the Ni(II) and Cu(II) complexes are proposed to be square planar. Spectral studies showed that the ligand bonded to the metal ion in a neutral bidentate fashion through the azomethine nitrogen atom and the imine oxime group. Structural assignments are supported by a combination of 1H nuclear magnetic resonance (NMR), 13C NMR, Fourier‐transform infrared, LC/MS, elemental analyses, and magnetic susceptibility testing. For determining the cytotoxic effects of the novel anticancer products, cancer cells were cultured. The antiproliferative effects were determined using the MCF‐7 breast cancer and PC‐3 prostate cancer cell lines. The antiproliferative effects of the products were analyzed and their apoptotic or necrotic effects were determined with the Hoechst/propidium iodide double staining method in both cancer cell lines. Paclitaxel was used as the positive control (1 μm). The results indicated that the newly synthesized compounds are effective on both cell lines between concentrations of 5 and 40 μm and show their effects by apoptotic mechanisms. Besides, these products were found to be more effective on the MCF‐7 cell line. The cytotoxic efficiency of the newly synthesized products was more than that of paclitaxel (depending on concentration), which is a chemotherapeutic agent used in cancer therapy.

A new hybrid ligand and its metal complexes from a natural plant (Styrax officinalis) bearing egonol, thiosemicarbazone and oxime units, and their anti‐cancer activities

“…The IR spectra of the new ligands [ ET; egonol thiosemicarbazone and ETO; egonol thiosemicarbazone glyoxime, Scheme 1] displayed new expected peaks different from starting materials [ E and EA ], such as ‐NH 2 (3800 and 3745 cm −1 for ET ), –NH (3446 cm −1 for ET and 3468 cm −1 for ETO ), ‐OH (3200 cm 1 for ETO ), ‐C=N (1665 cm −1 for ET and 1667, 1632 cm −1 for ETO ), and –NO (996 cm −1 for ETO ) stretching vibrations. [ 10,11 ] The ‐NH 2 , ‐NH, ‐OH, C=N and ‐NO stretching vibrations comply with the published thiosemicarbazone and vic ‐dioxime derivatives. [ 7,10,11 ]…”

Transition metal complexes derived fromN′‐(4‐fluorobenzylidene)‐2‐(quinolin‐2‐yloxy) acetohydrazide: Synthesis, structural characterization, and biocidal evaluation

“…The derivatives of quinoline and hydrazone constitute significant categories of compounds that have found multiple applications in therapeutic chemistry because of their wide range of pharmacokinetic properties, [ 1–3 ] especially their prominence in drug discovery programs. [ 4,5 ] The derivatives of quinoline and hydrazone and their complexes have been reported to demonstrate a widespread spectrum of biological properties, [ 6–8 ] such as antimicrobial, [ 9–11 ] antibacterial, [ 12–14 ] antifungal, [ 15,16 ] antiviral, [ 17 ] antiplatelet [ 18 ] antimalarial, [ 19 ] antitubercular, antimycobacterial, [ 20,21 ] anticancer, [ 21–24 ] antianalgesic, anticonvulsant, [ 25 ] and antileishmanial, [ 26,27 ] The hydrazones and their metal complexes also have anti‐uropathogenic, [ 28 ] anti‐arthritic, [ 29 ] antiproliferative, [ 30 ] and antioxidant [ 31–33 ] properties and act as inhibitors for COX‐2, [ 22 ] potent antiangiogenic agents in atherosclerosis, [ 31 ] and potent immunomodulatory agents. [ 34 ] They play a role in the treatment of Alzheimer's disease [ 35,36 ] and inhibit the corrosion of mild steel in acidic media.…”

Synthesis, Characterization, PXRD Studies, Theoretical Calculation, and Antitumor Potency Studies of a Novel N,O‐Multidentate Chelating Ligand and Its Zr(IV), V(IV), Ru(III), and Cd(II) Complexes

“…ese applications are signi cant because of the wide range of their pharmacokinetic properties [2][3][4][5], especially their importance in drug detection programs [6,7]. Numerous studies have con rmed that the hydrazone and carbaldehyde derivatives and their complexes have a wide series of biological properties [8][9][10][11], such as anticancer [12][13][14][15], antibacterial [16][17][18], antimicrobial [19][20][21], antifungal [22,23], antimalarial [24], antiviral [25], antimycobacterial [12,26], antileishmanial [25,27], antiplatelet [28], antianalgesic, antitubercular, anticonvulsant [29], antiuropathogenic [30], antiproliferative [31], antiarthritic [32], and antioxidant [33][34][35] properties and are potent immunomodulatory agents [36] and antiangiogenic agents in atherosclerosis [33]. Moreover, they play an important role in treating Alzheimer's disease [37,38].…”