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Ruthenium in Medicinal Chemistry
Published in Ajay Kumar Mishra, Lallan Mishra, Ruthenium Chemistry, 2018
Another interesting approach for the development of novel metal-based antimalarials has been the inclusion of a metallocene center into the scaffold of CQ to enhance its pharmacological properties and circumvent P. falciparum resistance. In particular, the ferrocene compound ferroquine (FQ) is being developed by Sanofi-Aventis under phase II clinical trials as the first bioorganometallic drug candidate (Fig. 2.12) (Dive and Biot, 2008; Biot, 2004; Dubar et al., 2008).
Binuclear ruthenium(II) complexes of 4,4′-azopyridine bridging ligand as anticancer agents: synthesis, characterization, and in vitro cytotoxicity studies
Published in Journal of Coordination Chemistry, 2019
Priyanka Khanvilkar, Ramadevi Pulipaka, Kavita Shirsath, Ranjitsinh Devkar, Debjani Chakraborty
Ferrocene, one of the members of the well-known organometallic family “metallocenes”, shows properties appropriate for the design of potential pharmaceutical agents. Its lipophilicity (logP = 2.66) facilitates its derivatives for membrane penetration and bioavailability [10–12]. The rotation of the aromatic cyclopentadienyl ring confers conformational diversity on ferrocene (staggered or eclipsed conformation), which is of advantage for orientating ferrocene-derived ligands into their receptor pockets [13]. An exclusive review [14] focuses on ferrocene’s basic properties, ferrocene-containing ligands, the ferrocene/ferricinium redox couple, the ferricinium/ferrocene redox shuttle in catalysis, ligand-exchange reactions, ferrocene-containing polymers, ferrocenes in supramolecular ensembles, liquid crystals, and nonlinear optical materials, ferrocene-containing dendrons, dendrimers, and nanoparticles (NPs) and their application in redox sensing and catalysis. The review also focuses on the use of ferrocenes in nanomedicine; a few have been exemplified here. The ferrocene/ferricinium redox couple is currently used as a redox mediator for the amperometric detection of glucose in blood [15, 16]. The most used ferrocene-based drug in medicine is the antimalarial drug ferroquine [17]. This organoiron drug has also recently been found to inhibit infection by the hepatitis C virus [18]. Antitumor activities of ferrocenes were first reported in 1978 by Brynes’ group, with derivatives bearing an amine or amido group that were active against lymphocytic leukemia P-388 [19]. Ferrocenyl compounds based on selective estrogen modulators, including ferrocifens, ferrociphenols, and ferrocenophanes [20], as well as ferrocenyl raloxifen, show promising results for breast cancer [21]. Ferrocene-derived ligands coordinated to transition-metal ions including those of Ru, Rh, Ir, Pd, Pt, and Au have also shown excellent anticancer activites [22, 23]. Most recently, ferrocene-related anticancer research is also focusing on ferrocene–chalcogeno-triazole–sugar conjugates [24], membrane interactions of nitroaryl ferrocenes [25], PEGylated ferrocene radiosensitizers of cancer cells [26], tubulin-binding ferrocene-substituted 3,3′-diindolylmethane [27], ferrocene-modified phospholipids [28], ferrocene–iminosugar hybrids [29], ferrocene–N-heterocyclic carbene–gold(I) complexes targeting antioxidant pathways [30] and dendrimer-related strategies [31]. In terms of drug delivery, an elegant approach was reported by Wang’s group with pH-responsive supramolecular vesicles based on water-soluble pillar[6]arene and ferrocene derivatives [32]. Thus, design and development of ferrocene derivatives and their metal complexes could be regarded as an effective approach to discover potential novel pharmaceutical agents.