Syntheses, Structural Snapshots, Solution Redox Properties, and Cytotoxic Performances of Designated Ferrocene Scaffolds Appended with Organostannyl(IV) benzoates en Route for Human Hepatic Carcinoma

Abstract

Although several strategies have been established to circumvent the limitations of platinum-based chemotherapy, the basic problems still persist. For this purpose, the new series of heterobimetallic formulations [FcL n SnPh 3 ] (1, 3, and 9)], [FcL n SnBu 3 ] n (2, 4 and 8), [FcL 3 SnCy 3 ] (10), and [FcL 3 SnR 3 (MeOH)] (R = Me (5), Et (6), or Pr (7)), where FcL n (n = 1−3) refers to the isomeric 2-/3-/4-ferrocenylbenzoates, was synthesized which can target cancer cells and successively support functional iron deficiencies during chemotherapy. Compounds 1−10 have been characterized by elemental analysis, and their spectroscopic properties were investigated using IR, NMR, electronic, and fluorescence techniques. The molecular structures of metallo proligands FcL 1 H and FcL 3 H and the six heterobimetallic compounds 2, 3, 5−7, and 10 have been determined by X-ray crystallography. The redox properties of FcL n H and their compounds 1−10 were also investigated by cyclic voltammetry. In vitro cytotoxic activities of compounds 1−4, 8, and 9 were assessed by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against human hepatic carcinoma (HepG2) cells, with IC 50 values revealing high activity better than that of doxorubicin. More importantly, compound 2 demonstrated maximum inhibition in HepG2 cells (IC 50 = 0.10 μM) among other studied cell lines of human origin, e.g. embryonic kidney (HEK-293T), breast (MDA-MB-231), and lung (A-549) cancer cells, with negligible effect on human peripheral blood mononuclear cells (PBMC). Compound 2 effectively inhibited cell viability, and the apoptosis proceeded via activation of caspases and cleavages of caspase-dependent proteins, as revealed from a PARP cleavage assay. Membrane microviscosity results point toward changes in fluidity that are sufficient to stop biological activities mediated by growth factors.

High Proton Conduction in Three Highly Water-Stable Hydrogen-Bonded Ferrocene-Based Phenyl Carboxylate Frameworks

“…Since crystal structures of 2 and 3 have been described previously, , they are briefly summarized in this paper for the convenience of discussing proton conduction. Both 2 and 3 indicate similar structures, except that the position of the carboxyl group on the benzene ring is different, with one in the interposition and the other in the counter position.…”

“…After 2 was synthesized in accordance with the literature approach. 45 Different from the literature reports, we used a similar method as 1 to obtain dark-red crystals of 2. Anal.…”

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

“…Organotin complexes play important roles in biological activities and human health, and a large number of organotin complexes have shown anticancer activity higher than that of the widely used anticancer drug cisplatin in vitro. − It is well-known that the biochemical activity of organotin complexes is influenced greatly by the type of groups in the organotin moiety and the number of Sn–C bonds . By tackling these factors, the toxic side effects of organotin complexes could be decreased.…”