Ferrocene Functionalized Endocrine Modulators as Anticancer Agents

Hillard, Elizabeth A.; Vessières, Anne; Jaouen, Gérard

doi:10.1007/978-3-642-13185-1_4

Cited by 126 publications

(100 citation statements)

References 160 publications

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“…[13][14][15][16][17][18][19][20][21][22][23][24][25][26] This strategy was found very successful with ferroquine (FQ), a ferrocenyl analogue of the antimalarial drug chloroquine (CQ), as FQ is active on CQ-resistant Plasmodium falciparum strains. Furthermore, intensive chemical biology studies have recently allowed unveiling additional modes of action for FQ compared to the parent drug in FQ, which were attributed to the presence of the organometallic unit.…”

Section: Introductionmentioning

confidence: 99%

Ferrocenyl Derivatives of the Anthelmintic Praziquantel: Design, Synthesis, and Biological Evaluation

et al. 2012

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The design, synthesis and biological evaluation of eighteen ferrocenyl derivatives (4A-12A and 4B-12B) of the most-well known drug against schistosomiasis, namely praziquantel (PZQ), are reported.These compounds which have been all isolated as racemates were unambiguously characterized by 1 H and 13 C NMR spectroscopy, mass spectrometry and elemental analysis as well as by X-ray crystallography for 4A, 5A and 7A. Cytotoxicity studies revealed that the complexes were moderately toxic towards a cervical cancer cell line (HeLa) and, importantly, significantly less active towards a noncancerous cell line (MRC-5). The in vitro anthelmintic activity of the eighteen ferrocenyl PZQ derivatives was tested against Schistosoma mansoni and values in the micromolar range (26-68 µM) were determined for the four most active compounds. It was also demonstrated using two compounds of the series as models (8A and 8B) that the complexes were stable when incubated for 24 h at 37°C in human plasma. 3Introduction.

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Section: Introductionmentioning

confidence: 99%

Ferrocenyl Derivatives of the Anthelmintic Praziquantel: Design, Synthesis, and Biological Evaluation

et al. 2012

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“…[16,17] Biomolecules connected to ferrocene include peptides and proteins, [9,[18][19][20] nucleic acids, [9,10] carbohydrates, [9,10] porphyrins, [21] and a number of antitumoral derivatives, in which a ferrocene building block replaces a benzene ring. [22][23][24] Remarkably, the chemistry of ferrocene-alkaloid conjugates has not been explored to a comparable extent. As early as 1974, Kalish and Walser reported 4-ferrocenyl-1,4-benzodiazepin-2-ones.…”

Section: Introductionmentioning

confidence: 98%

Tricyclic Quinazoline Alkaloids Conjugated to Ferrocene: Synthesis, Structure, and Redox Behavior of Ferrocenylmethylene‐Substituted 7H‐Deoxyvasicinones

et al. 2015

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Abstract:The first organometallic derivatives of tricyclic quinazoline derivatives are prepared by condensation of the active C-3 methylene group of 7H-deoxyvasicinones with ferrocenecarbaldehyde. By following this route the conjugated parent alkaloid and derivatives with nitro, amino, as well as some alkanoylamino groups at C-7 were attached at the ferrocene moiety, thereby significantly extending the π system. In addition, the parent compound was subjected to the reaction by treatment with ferrocene-1,1′-dicarbaldehyde, giving rise to the

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“…Using the known properties of tamoxifen as a basis, ferrocifen was evaluated in a hormone-dependent breast cancer MCF-7 cell line. Ferrocifen showed excellent antiproliferative activity on MCF-7, and docking studies on ERα revealed that its activity is due to the antiestrogenic properties it elicits from the receptor [12]. There are more recent precedents of titanocenes and half-titanocenes with enhanced antiproliferative activity on the MCF-7 cell line, particularly some of them with IC 50 values in the micromolar range [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

“…One of the most remarkable organometallic compounds that have encountered application in hormone-dependent breast cancer is ferrocifen, the ferrocene analog of tamoxifen [12]. It is important to point out that tamoxifen is a selective estrogen receptor modulator (SERM) serving as an antagonist, which is commonly used in hormone-dependent breast cancer therapy [13].…”

Section: Introductionmentioning

confidence: 99%

Steroid-Functionalized Titanocenes: Docking Studies with Estrogen Receptor Alpha

et al. 2016

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Estrogen receptor alpha (ERα) is a transcription factor that is activated by hormones, with 17β-estradiol being its most active agonist endogenous ligand. ERα is also activated or inactivated by exogenous ligands. ER is overexpressed in hormone-dependent breast cancer, and one of the treatments for this type of cancer is the use of an ER antagonist to halt cell proliferation. We have previously reported four steroid-functionalized titanocenes: pregnenolone, dehydroepiandrosterone (DHEA), trans-androsterone, and androsterone. These steroids have hormonal activity as well as moderate antiproliferative activity, thus these steroids could act as vectors for the titanocene dichloride to target hormone-dependent cancers. Also, these steroids could increase the antiproliferative activity of the resulting titanocenes based on synergism. In order to elucidate which factors contribute to the enhanced antiproliferative activity of these steroid-functionalized titanocenes, we performed docking studies between ERα and the titanocenes and the steroids. The binding affinities and type of bonding interactions of the steroid-functionalized titanocenes with ERα are herein discussed.

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Ferrocene Functionalized Endocrine Modulators as Anticancer Agents

Cited by 126 publications

References 160 publications

Ferrocenyl Derivatives of the Anthelmintic Praziquantel: Design, Synthesis, and Biological Evaluation

Ferrocenyl Derivatives of the Anthelmintic Praziquantel: Design, Synthesis, and Biological Evaluation

Tricyclic Quinazoline Alkaloids Conjugated to Ferrocene: Synthesis, Structure, and Redox Behavior of Ferrocenylmethylene‐Substituted 7H‐Deoxyvasicinones

Steroid-Functionalized Titanocenes: Docking Studies with Estrogen Receptor Alpha

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