On the mechanism of the antitumor activity of ferrocenium derivatives

Osella, Domenico; Ferrali, Marco; Zanello, Piero; Laschi, Franco; Fontani, Marco; Nervi, Carlo; Cavigiolio, Giorgio

doi:10.1016/s0020-1693(00)00147-x

Cited by 246 publications

(162 citation statements)

References 32 publications

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“…Furthermore, some ferrocenyl complexes have also been investigated for their anti-cancer activity, and exhibited promising cytotoxic activities [12][13]. The starting point in the development of new ferrocenyl derivatives as anticancer agents could be traced back to the discovery of the ferrocenium cation as an anticancer agent [14][15][16]. However literature reviews show conflicting conclusions about the important features in ferrocenyl compounds which could be responsible for their cytotoxic activities [12][13].…”

Section: Introducmentioning

confidence: 99%

Bis(ferrocenylimine)palladium(II) and platinum(II) complexes: Synthesis, molecular structures and evaluation as antitumor agents

Motswainyana¹,

Onani²,

Madiehe³

2012

Polyhedron

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Section: Introducmentioning

confidence: 99%

Bis(ferrocenylimine)palladium(II) and platinum(II) complexes: Synthesis, molecular structures and evaluation as antitumor agents

Motswainyana¹,

Onani²,

Madiehe³

2012

Polyhedron

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“…[2][3][4]6,7 The mechanisms of the cytotoxicity of ferrocene derivatives have been investigated. 8 Osella et al 9 proposed that the cytotoxic activity of ferrocenium salts is due to their ability to generate oxygen active species that induce oxidative DNA damage. Kondapi et al 10,11 have shown that ferrocene derivatives inhibit topoisomerase II, a major molecular target for a number of DNA-binding anticancer drugs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of ferrocenyl oxindole compounds with potential anticancer activity

Silva¹,

Ribeiro²,

Pinto³

et al. 2008

J. Braz. Chem. Soc.

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Compostos oxindol-ferrocenos com potencial atividade anticâncer foram preparados a partir de reações de oxindóis substituídos e carboxaldeído-ferroceno na presença de KOH como catalisador. Os produtos foram caracterizados por dados espectroscópicos incluindo RMN de 1 H e 13 C, infravermelho e espectrometria de massas. As configurações E e Z foram estabelecidas por experimentos de nOe ou NOESY.A series of ferrocenyl oxindoles with potential anticancer activity were prepared from the reactions of substituted oxindoles and ferrocenylcarboxyaldehyde in the presence of KOH as catalyst. The products were characterized by spectral data including 1 H and 13 C NMR, IR and mass spectrometry. The E and Z configurations were established by nOe or NOESY experiments. Keywords: ferrocenyl oxindoles, oxindoles, ferrocenecarboxyaldehyde IntroductionThe ferrocenyl (Fc) group has been incorporated to the structure of a number of biologically active molecules resulting in increased anticancer 1,2 and antimalarial [3][4][5] activity, amongst others. Addition, alkylation, acylation, condensation-dehydration, coupling and nucleophilic substitution reactions have been employed to link this group to a variety of compounds. [2][3][4]6,7 The mechanisms of the cytotoxicity of ferrocene derivatives have been investigated.8 Osella et al. 9 proposed that the cytotoxic activity of ferrocenium salts is due to their ability to generate oxygen active species that induce oxidative DNA damage. Kondapi et al. 10,11 have shown that ferrocene derivatives inhibit topoisomerase II, a major molecular target for a number of DNA-binding anticancer drugs.Indolin-2-ones have been shown to exhibit antitumor activity by inhibiting receptor tyrosine kinases VEGF-R, PDGF-R or CDK.12 The indolin-2-one 1 (sunitinib) has been approved by the U.S. We describe herein the condensation reactions of several oxindole derivatives with FcC(O)H in the presence of KOH in EtOH from which good to excellent yields of the products with E and Z configurations were obtained (Scheme 1). 16The products were characterized by mass spectrometry and infrared, 1 H and 13 C NMR spectroscopies, including nOe and NOESY experiments for the determination of the double-bond geometry. 1245 Vol. 19, No. 7, 2008 Preliminary studies of the reaction of oxindole with FcC(O)H (Table 1) were carried out to assess the catalytic potential of various bases. Except for Et 3 N, all the bases employed led to good conversions. However, formation of products with both E and Z configurations depend on the base employed. The use of KOH in EtOH gave the best yield and selectivity for the E-isomer 2a (entry 1). In the presence of piperidine (entry 3) we were able to isolate the E-isomer 2a in 67% yield together with a 30% isolated yield for the corresponding Z-isomer 2b. The geometries of isomers 2a and 2b were determined by nOe experiments and NOESY interactions. The NOESY experiment for 2a shows a correlation between H4 and H2' of the cyclopentadienyl ring, thus revealing an (E)-configuration for this isom...

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“…The oxidation of ferrocenes to ferrocenium ion 1 is very important for biological applications. 2 For example, this can be applied to the antitumor activity 3,4 and the synthesis of bio-related compounds. [5][6][7][8][9] Ferrocene is very stable in air, so that the oxidation from Fe(II) to Fe(III) is difficult.…”

Section: Introductionmentioning

confidence: 99%

The interaction between (o-acetylphenyl)ferrocene and metal ions

Yamamoto¹,

Okada²

2017

Org. Commun.

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Abstract:The oxidation reaction of ferrocene derivatives is important because of its biological applications. The reactivity is affected by metal ions. However, it is not clear how to interact the metal ions with the ferrocenes. In this paper, the oxidation reactivity of (o-acetylphenyl)ferrocene was investigated in the view of solvent effect and the addition effect of salicylic acid. Furthermore, the measurement of the relaxation time was carried out. As a result, Al 3+ would strongly interact with (o-acetylphenyl)ferrocene so that prevent the mobility of the acetyl group.

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On the mechanism of the antitumor activity of ferrocenium derivatives

Cited by 246 publications

References 32 publications

Bis(ferrocenylimine)palladium(II) and platinum(II) complexes: Synthesis, molecular structures and evaluation as antitumor agents

Bis(ferrocenylimine)palladium(II) and platinum(II) complexes: Synthesis, molecular structures and evaluation as antitumor agents

Synthesis of ferrocenyl oxindole compounds with potential anticancer activity

The interaction between (o-acetylphenyl)ferrocene and metal ions

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