Ferrocenyl–Triphenyltin Complexes as Lysosome-Targeted Imaging and Anticancer Agents

Abstract

In this paper, two ferrocenyl–triphenyltin complexes were synthesized and characterized. Complex 2 is constructed as new multifunctional therapeutic platform for lysosome-targeted imaging and displayed much higher cytotoxicity than its analogue 1 by the introduction of a methyl group instead of a hydrogen atom in acylhydrazone. The cyclic voltammograms and reaction with GSH (glutathione) further confirmed that complex 1 has a reversible redox peak and can react with GSH, which indicate that complex 1 might lose its anticancer effect by undergoing reaction with GSH once it enters the cancer cell. Complex 2 could effectively catalyze the oxidation of NADH (the reduced form of nicotinamide adenine dinucleotide) to NAD+ and induce the production of reactive oxygen species (ROS), lead to caspase-dependent apoptosis through damaged mitochondria, simultaneously, accounting for the mitochondrial vacuolization and karyorrhexis. The caspase-3 activation and cytoplasmic vacuolation karyorrhexis induced by complex 2 revealed that the A549 cell lines might undergo cell death primarily mediated by apoptosis and oncosis; however, 1 cannot reproduce this effect. Taken together, these results indicated that complex 2 has more potential for evolution as a new bioimaging and anticancer agent.

Ferrocene-Appended Iridium(III) Complexes: Configuration Regulation, Anticancer Application, and Mechanism Research

“…12 In our previous research, a ferrocene molecule was introduced into triphenyltin compounds. 13 All of these studies indicated that, compared with single metal complexes (ferrocene or other transition-metal complexes), heteronuclear metal complexes all displayed more excellent cytotoxic activity against the cancer cell line.…”

“…Von Poelhsitz et al attempted to combine nitrosylruthenium complexes with ferrocene and indicated that the ferrocene ligand plays a crucial role on the anticancer activity of these complexes. , Rajput et al prepared a series of ferrocenyl compounds containing pyridine ligands and further studied their coordination behavior with platinum, palladium, rhodium, and iridium . In our previous research, a ferrocene molecule was introduced into triphenyltin compounds . All of these studies indicated that, compared with single metal complexes (ferrocene or other transition-metal complexes), heteronuclear metal complexes all displayed more excellent cytotoxic activity against the cancer cell line.…”

Half‐sandwich Ruthenium (II) complexes with triphenylamine modified dipyridine skeleton and application in biology/luminescence imaging

“…Cell function decline was often associated with apoptosis . In this study, flow cytometry was used to determine that by means of A549 cells treated with target Ru II complexes after stained with PI and Annexin V. As shown in Figure and Tables S4‐S5, after incubated with complexes 2 and 4 (0.5 × IC 50 , 1.0 × IC 50 , and 2.0 × IC 50 ) for 24 hr, the values of the early and late apoptotic phase indicate a significant increase in a dose‐dependent manner.…”

Imidazole and Benzimidazole Modified Half-Sandwich IridiumIIIN-Heterocyclic Carbene Complexes: Synthesis, Anticancer Application, and Organelle Targeting

“…Cis-platin exerts good and broad-spectrum anticancer effects (Deubel and Lau, 2006;Romero-Canelón and Sadler, 2013;Muhammad and Guo, 2014), but, when used extensively, platinum-based drugs may promote drug resistance and instability; become insoluble in biological media; and become toxic to blood and gastrointestinal tract (Ma et al, 2014;Liu et al, 2015). Thus, various organometallic anticancer drugs, such as tin, iridium, ruthenium, and osmium anticancer complexes, have been developed (Sun and Che, 2009;Lu et al, 2015;Zeng et al, 2017;Ge et al, 2019;Li et al, 2019).…”