Water stability and cytotoxic activity relationship of a series of ferrocenium derivatives. ESR insights on the radical production during the degradation process
Water stability and cytotoxic activity relationship of a series of ferrocenium derivatives. ESR insights on the radical production during the degradation process(638 views) Tabbì G, Cassino C, Cavigiolio G, Colangelo D, Ghiglia A, Viano I, Osella D
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2002 Dec 19; 45(26): 5786-5796.
Ist. di Biostrutture e Bioimmagini, CNR, Sezione di Catania, viale A. Doria 6, I-95125, Catania, Italy
Dipto. di Sci./Tecnologie Avazante, Univ. Piemonte Orient. A. Avogadro, corso Borsalino 54, I-15100, Alessandria, Italy
Dipartimento di Scienze Mediche, Univ. Piemonte Orient. A. Avogadro, via Solaroli 17, I-28100, Novara, Italy
Istituto di Biostrutture e Bioimmagini, CNR, Sezione di Catania, viale A. Doria 6, I-95125, Catania, Italy.
Dipto. di Sci. /Tecnologie Avazante, Univ. Piemonte Orient. A. Avogadro, corso Borsalino 54, I-15100, Alessandria, Italy
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K pf-Maier, P., Klap tke, T., Tumor inhibition by ferricenium complexes (1989) Arzneim. -Forsch., 39 (1), pp. 369-371
K pf-Maier, P., Tumor inhibition by ferricenium complexes: Systemic effect in vivo and cell growth inhibition in vitro (1985) Z. Naturforsch., C: Biosci., 40, pp. 843-846
De Zwart, L. L., Meerman, J. H. N., Commandeur, J. N. M., Vermeulen, N. P. E., Biomarkers of free radical damage applications in experimental animals and in humans (1999) Free Radical Biol. Med., 26, pp. 202-226
Burger, R. M., Cleavage of nucleic acids by bleomycin (1998) Chem. Rev., 98, pp. 1153-1169
Shon, R. B., Hendrickson, D. N., Gray, H. B., Electronic structure of metallocenes (1971) J. Am. Chem. Soc., 93, pp. 3603-3612
Lauffer, R. B., Paramagnetic metal complexes as water proton relaxation agents for NMR imaging: Theory and design (1987) Chem. Rev., 87, pp. 901-927
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Buettner, G. R., Spin trapping: ESR parameters of spin adducts (1987) Free Radical Biol. Med., 3, pp. 259-303
Dikalov, S. I., Mason, R. P., Spin trapping of polyunsaturated fatty acid-derived peroxyl radicals: Reassignment to alkoxyl radical adducts (2001) Free Radical Biol. Med., 30, pp. 187-197
Buettner, G. R., Oberley, L. W., Considerations in the spin trapping of superoxide and hydroxyl radical in aqueous systems using 5, 5Dimethyl-1-pyrroline-1-oxide (1978) Biochem. Biophys. Res. Commun., 83, pp. 69-74
Davies, A. G., Lusztyk, J., Photolysis of the carbon-hydrogen bond in pentamethylcyclopentadiene. Properties of the pentamethylcyclopentadienyl radical (1981) J. Chem. Soc., Perkin Trans. 2, pp. 692-696
Tabb, G., Fry, S. C., Bonomo, R. P. E. S. R., Study of nonenzymic scission of xyloglucan by an ascorbate-H2O2-copper system: The involvement of the hydroxyl radical and the degradation of ascorbate (2001) J. Inorg. Biochem., 98, pp. 1153-1169
Simpson, J. A., Cheeseman, K. H., Smith, S. E., Dean, R. T., Free radical generation by copper ions and hydrogen peroxide (1988) Biochem. J., 254, pp. 519-523
Thornalley, P. J., The haemolitic reactions of 1-Acetyl-2Phenylhydrazine and hydrazine: A spin trapping study (1984) Chem. -Biol. Interact., 50, pp. 339-349
Robert, C. K., (1995) Comprehensive Organometallic Chemistry II, 7, pp. 185-198. , Abel, E. W., Gordon, F., Stone, A., Wilkinson, G., Eds.
Duling, D. R., Simulation of multiple isotropic spin trap EPR spectra (1994) J. Magn. Reson., B104, pp. 105-110
Lind, M. D., Hoard, J. L., Hamor, M. J., Hamor, T. A., Stereochemistry of ethylenediaminetetraacetato complexes (1964) Inorg. Chem., 3, p. 34
Hall, L. H., Spijkerman, J. J., Lambert, J. L., Preparation and coordination studies of the complex acid, dihydrogen diethylenetriaminepentaacetatoferrate (III) dihydrate, and several of its metal (I) salts (1968) J. Am. Chem. Soc., 90, pp. 2044-2048
V squez-vivar, J., Hogg, N., Pritchard, K. A., Martasek, K. P., Kalyanaraman, B., Superoxide anion formation from luigenin: An electron spin resonance spin-trapping study (1997) FEBS Lett., 403, pp. 127-130
Water stability and cytotoxic activity relationship of a series of ferrocenium derivatives. ESR insights on the radical production during the degradation process
The cytotoxicity of some ferrocenium salts and the lack of activity of the corresponding ferrocenes has been already demonstrated. The cytotoxic activity in different conditions of decamethylferrocenium tetrafluoroborate (DEMFc(+)) in comparison with four other ferrocenium derivatives on MCF-7 cell line is reported. The relative stability in aqueous solutions with different buffering agents is investigated by means of UV-vis spectroscopy and correlated to the cytotoxic properties of the compounds. DEMFc(+), the most stable compound, shows the highest efficiency in inhibiting cell growth (IC(50) 35 microM, for 48 h treatment). Relaxation time measurements point out the involvement of water molecules in the degradation process. ESR results confirm the ability of ferrocenium cations to produce oxygen radical species as a consequence of their degradation in water. Oxygen-dependent formation of both hydroxyl and superoxide radicals is established by the spin-trapping technique. A direct evidence of the DEMFc(+) radical production into the viable cells is obtained by means of fluorescence-activated cell sorter (FACS) analysis that reveals a dose-dependent growth of 8-oxoguanine, the initial product of the guanine oxidation. This DNA oxidative stress justifies the cytotoxic effect of DEMFc(+). Furthermore, the cytotoxic cooperative effect of bleomycin, an iron-dependent antitumor drug, and DEMFc(+) has been tested. We have demonstrated the synergic effect between the two drugs, that is explained by the complementary oxidative damage inflicted to DNA as well as by the increasing of bleomycin activation by the iron(II/III) species available in the cell compartment from ferrocenium degradation.
Water stability and cytotoxic activity relationship of a series of ferrocenium derivatives. ESR insights on the radical production during the degradation process
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Water stability and cytotoxic activity relationship of a series of ferrocenium derivatives. ESR insights on the radical production during the degradation process