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

Abstract

A novel hybrid ligand, a vic‐dioxime ligand (ETO), containing thiosemicarbazone and egonol moieties from a natural plant (Styrax officinalis) and its trinuclear [Ni(II), Cu(II), Co(II), and Fe(II)] and mononuclear [Pd(II) and Zn(II)] complexes have been synthesized and characterized. The ligand, complexes, and natural components were characterized by conventional spectroscopic techniques (IR, NMR, and MS) and evaluated against two human cancer cell lines (MCF‐7 and PC‐3) to determine their antiproliferative and apoptotic properties. Apoptotic or necrotic effects were detected in both cancer cell lines using the Hoechst/propidium iodide double‐staining method. Paclitaxel was used as a positive control (1 μM). The results displayed that the compounds obtained in this study were effective in the concentration range of 5–40 μM in prostate and breast cancer cell lines. It can be said that the compounds (egonol, its derivatives, hybrid ligand, and its metal complexes) are mostly more effective in PC‐3 migration lines. Consequently, the cytotoxic efficiencies of [Cu3(ETO)2·4Cl], 5.27 μM for MCF‐7 and 13.44 μM for PC‐3 and [Zn (ETO)·2Cl] 11.73 μM for MCF‐7 and 9.32 μM for PC‐3 were observed to be close to paclitaxel (a drug used as a cancer chemotherapeutic agent). [Cu3(ETO)2·4Cl] were more effective on the MCF‐7 cell line. Besides this result, [Zn (ETO)·2Cl] was more effective on the PC‐3 cell lines and was more effective by triggering apoptosis in the cells.

Structural variety of Cu (II), Ni (II), and Co (II) complexes of a hydrazone based on 5‐acetyl‐4‐hydroxy‐2H‐1,3‐thiazine‐2,6(3H)‐dione: Synthesis, spectroscopic, density functional theory, antitumor, and docking studies

“…[13,14] The synthesis and characterization of several transition metal complexes of oxygen, nitrogen and sulfurcontaining ligands have greatly enriched coordination chemistry over the past few years. [15] These ligands, as well as their metal complexes, possess antibacterial, [16] antifungal, [17] and antitumour activities. [18] Thiazines are very useful units in the fields of medicinal and pharmaceutical chemistry due to their antimicrobial, [19] anticancer, [20] potential antiinflammatory agents, [21] and antiproliferative activities.…”

“…The synthesis and characterization of several transition metal complexes of oxygen, nitrogen and sulfur‐containing ligands have greatly enriched coordination chemistry over the past few years. [ 15 ] These ligands, as well as their metal complexes, possess antibacterial, [ 16 ] antifungal, [ 17 ] and antitumour activities. [ 18 ]…”

Design, Synthesis and Biological Evaluation of Novel Gypsogenin Derivatives as Potential Anticancer and Antimicrobial Agents

“…Many semi‐synthesized compounds showed remarkable activity for their cytotoxic activities against various human cancer cell lines [36–40] . In the current work, we reported a different method for the semi‐synthesis of new gypsogenin compounds using new amine compounds.…”

“…[28][29][30][31][32][33][34][35] Many semi-synthesized compounds showed remarkable activity for their cytotoxic activities against various human cancer cell lines. [36][37][38][39][40] In the current work, we reported a different method for the semi-synthesis of new gypsogenin compounds using new amine compounds. Then, we evaluated these derivatives for their anticancer and antimicrobial effects and further mechanistic mode of the anticancer activity.…”

Recent Advances in Bioconjugated Transition Metal Complexes for Cancer Therapy

“…It should be remembered that with the term "natural", we can consider all molecules that derive from living organisms present in nature. In this context, the most interesting bioconjugated metallodrugs contain plant derivatives such as coumarins and xanthines (e.g., caffeine) [35][36][37][38][39][40][41], food derivatives (e.g., polyphenols) [39,42] and classical biomolecules of life. Within this context, in 2019, Leung and Ma assembled a review dealing with metal complexes conjugated to natural products for cancer therapy [43].…”