ChemInform Abstract: Synthesis, Characterization and Cytotoxic Properties of the First “ Metallocenonucleosides”.

Meunier, Philippe; Ouattara, Issa Napoléon; Gautheron, B.; Tirouflet, J.; Camboli, D.; Besançon, J.

doi:10.1002/chin.199132251

Cited by 2 publications

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“…The first “metallocenonucleosides” were synthesized and characterized by Meunier and co-workers in 1991 [ 42 ]. The term “metallocenonucleosides” was derived from nucleosides containing a metallocene moiety and these compounds were prepared in order to study their chemical as well as cytotoxic properties ( Scheme 28 ).…”

Section: Reviewmentioning

confidence: 99%

Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

Brulíková¹,

Hlaváč²

2011

Beilstein J. Org. Chem.

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Section: Reviewmentioning

confidence: 99%

Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

Brulíková¹,

Hlaváč²

2011

Beilstein J. Org. Chem.

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“…Accordingly, the Fc molecule has been suitably modified with a multitude of organic functionalities, accomplished by electrophilic substitution at the cyclopentadienyl rings and single-electron oxidation . Notably, the ferrocenyl unit was conjugated with known compounds possessing chemotherapeutic properties, e.g., adenine, , peptides, , nucleosides and nucleobases, , vitamins, , and phenols including taxoids (paclitaxel and docetaxel, antineoplastic agents), in order to have built-in efficacy. Thus, Fc as an effective bioisostere has provided a potential platform for drug design by virtue of its aforementioned properties and three-dimensional metallocene unit, which may lead to some alterations in selectivity toward biological targets, in comparison with phenyl or alkyl groups. , …”

Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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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.

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ChemInform Abstract: Synthesis, Characterization and Cytotoxic Properties of the First “ Metallocenonucleosides”.

Cited by 2 publications

References 1 publication

Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

Synthesis, reactivity and biological activity of 5-alkoxymethyluracil analogues

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

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