Phthalimido–ferrocidiphenol cyclodextrin complexes: Characterization and anticancer activity

Anticancer properties of lipid and poly(ε-caprolactone) nanocapsules loaded with ferrocenyl-tamoxifen derivatives

“…Reagents, molecules and chemical reactions are described in the Supplementary Material . The synthesis of PhtFerr and compound X have been previously described …”

“…The synthesis of PhtFerr and compound X have been previously described. [9] The complete chemical synthesis is detailed in S1. Measurements of the octanol/water partition coefficient (log Po/w) were made using high-performance liquid chromatography (HPLC) according to a method described previously.…”

“…Among this series, some compounds with modification at the ethyl group, that is also inherited from hydroxytamoxifen, had better activity, in particular when a polar group was fixed at the end of the alkyl chain . Thus, the introduction of a polar imide group gave rise to ferrocidiphenol (Ferr) compounds, namely phthalimido‐ferrocidiphenol (PhtFerr) (C 35 H 29 FeNO 4 ) and succinimido‐ferrocidiphenol (SuccFerr) (C 31 H 29 FeNO 4 ), that were found to be very effective on breast cancer cells (MDA‐MB‐231) and, more surprisingly, on human glioblastoma cancer cells (U87) . The mechanism underlying the Ferr cytotoxicity is only partly understood.…”

“…[7,8] Thus, the introduction of a polar imide group gave rise to ferrocidiphenol (Ferr) compounds, namely phthalimido-ferrocidiphenol (PhtFerr) (C 35 H 29 FeNO 4 ) and succinimidoferrocidiphenol (SuccFerr) (C 31 H 29 FeNO 4 ), that were found to be very effective on breast cancer cells (MDA-MB-231) and, more surprisingly, on human glioblastoma cancer cells (U87). [9] The mechanism underlying the Ferr cytotoxicity is only partly understood. Previous in vitro studies demonstrated that at least some Ferr metabolites produced in the cell are electrophilic quinonemethides that can induce growth arrest with senescence and apoptosis phenomena.…”

A New Series of Succinimido-ferrociphenols and Related Heterocyclic Species Induce Strong Antiproliferative Effects, Especially against Ovarian Cancer Cells Resistant to Cisplatin

“…Subsequent reaction with an imide (succinimide, glutarimide or phthalimide) in a basic medium (potassium carbonate in DMF) at 80 °C gave the novel mono-heterocyclic ferrociphenols 3, 7 and 8, in yields of 54, 22 and 58%, respectively, and the known phthalimide, 4, in 83% yield. 44 The new complexes were characterized spectroscopically and, in the case of the succinimido derivative, 3, by X-ray crystallography (Figure 1). To better assess the effect of attaching an imide at the end of the chain, we compared the cytotoxicity of each of these species with that of the reference compound 1a, which has no such attachment.…”