Water stability and cytotoxic activity relationship of a series of ferrocenium derivatives. ESR insights on the radical production during the degradation process (638 views)
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2002 Dec 19; 45(26): 5786-5796.
Export to BibTeX Export to EndNote
Paper type: Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 4.566, 5-year impact factor: 5.504
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0037137615&partnerID=40&md5=38ade24ffa8485fb569d70f95d767ace
Keywords: 8 Hydroxyguanine, Bleomycin, Ferrocene, Ferrocenium Derivative, Hydroxyl Radical, Oxygen Radical, Superoxide, Unclassified Drug, Antineoplastic Activity, Aqueous Solution, Article, Cell Compartmentalization, Cell Growth, Cell Viability, Controlled Study, Cytotoxicity, Dna Damage, Dose Response, Electron Spin Resonance, Fluorescence Activated Cell Sorting, Growth Inhibition, Human, Human Cell, Oxidative Stress, Ultraviolet Spectroscopy, Antineoplastic Agents, Drug Screening Assays, Antitumor, Drug Stability, Drug Synergism, Electron Spin Resonance Spectroscopy, Ferrous Compounds, Free Radicals, Oxidation-Reduction, Spectrophotometry, Spin Trapping, Tumor Cells, Cultured, Water, Antineoplastic Agents Chemical Synthesis Chemistry Metabolism, Bleomycin Pharmacology, Ferrous Compounds Chemical Synthesis Chemistry Pharmacology, Free Radicals Metabolism, Japna, Polymers, Degradation, Polyvinyl Chloride,
Affiliations:
*** IBB - CNR ***
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
References:
Köpf-Maier, P., Köpf, H., Non-platinum-group metal antitumor agents: History, current status, and perspectives (1987) Chem. Rev., 87, pp. 1137-115
Motohashi, N., Meyer, R., Gollapudi, S.R., Bhattiprolu, K.R., Synthesis and activity of potential antitumor ferrocenes (1990) J. Organomet. Chem., 398, pp. 205-217
Neuse, E.W., Kanzawa, F., Evaluation of the activity of some water-soluble ferrocene and ferricenium compounds. Against carcinoma of the lung by the human tumor clonogenic assay (1990) Appl. Organomet. Chem., 4, pp. 19-26
Osella, D., Ferrali, M., Zanello, P., Laschi, F., Fontani, M., Nervi, C., Cavigiolio, G., On the mechanism of the antitumor activity of ferrocenium derivatives (2000) Inorg. Chim. Acta, 306, pp. 42-48
Köpf-Maier, P., Klapötke, T., Tumor inhibition by ferricenium complexes (1989) Arzneim.-Forsch., 39 (1), pp. 369-371
Köpf-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
Houlton, A., Roberts, R.M.G., Silver, J., Studies on the antitumour activity of some iron sandwich compounds (1991) J. Organomet. Chem., 418, pp. 107-112
Wenzel, M., Wu, Y., Liss, E., Nuse, E.W., Stability of ferricinium and its cytostatic effect (1988) Z. Naturforsch., C: Biosci., 43 C, pp. 963-966
Tamura, H., Miwa, M., DNA cleaving activity cytotoxic activity of ferrocenium cations (1997) Chem. Lett., pp. 1177-1178
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
Prins, R., Korswagen, A.R., Kortbeek, A.G.T.G., Decomposition of the ferricenium cation by nucleophilic reagents (1972) J. Organomet. Chem., 39, pp. 335-344
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
Hait, W.N., Gesmonde, J.F., Lazo, J.S., Effect of anticalmodulin drugs on the growth and sensitivity of C6 rat glyoma cells to bleomycin (1994) Anticancer Res., 14, pp. 1711-1721
Chou, T.C., Talalay, P., Quantitative analyis of dose-effect relationships: The combined effects of multiple drugs or enzyme inhibitors (1984) Adv. Enzyme Regul., 22, pp. 27-55
Frejaville, C., Karoui, H., Tuccio, B., Le Moigne, F., Culcasi, M., Pietri, S., Lauricella, R., Tordo, P., 5-(Diethoxyphosphoryl)-5methyl-1-pyrroline N-oxide: A new efficient phosphorylated nitrone for the in vitro and in vivo spin trapping of oxygencentered radicals (1995) J. Med. Chem., 38, pp. 258-265
Barker, P.J., Stobart, S.R., West, P.R., Spin trapping of cyclopentadienyl radicals using nitroso compounds and nitrones (1986) J. Chem. Soc., Perkin Trans. 2, pp. 127-130
Bernofsky, C., Bandara, B.M., Spin trapping endogenous radicals in MC-1010 Cells: Evidence for hydroxyl radical and carbon-centered ascorbyl radical adducts (1995) Mol. Cell. Biochem., 148, pp. 155-164
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
Minotti, G., Aust, S.D., The requirements for the iron(III) in the initiation of the lipid peroxidation by iron(II) and hydrogen peroxide (1987) J. Biol. Chem., 262, pp. 1098-1104
Goldstein, G., Meyerstein, D., Czapski, G., The fenton reagents (1993) Free Radic. Biol. Med., 15, pp. 435-445
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
Bielski, B., Cabelli, D.E., Highlights of current research involving superoxide and perhydroxyl radicals in aqueous solutions (1991) Int. J. Radiat. Biol., 59, pp. 291-319
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
Tabbì, 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
Kirsch, M., Lomonosova, E.E., Korth, H.-G., Sustmann, R., De Groot, H., Hydrogen peroxide formation by peroxynitrite with HEPES and related tertiary amines (1998) J. Biol. Chem., 273, pp. 12716-12724
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.
Pergamon: Oxford, Chapter 2.8
Bradley, S., McGowan, P.C., Oughton, K.A., Thornton-Pett, M., Walsh, M.E., Facile synthesis of amino-functionalised ferrocenes and vanadocenes (1999) Chem. Commun., pp. 77-78
Bradley, S., Camm, K.D., Liu, X., McGowan, P.C., Mumtaz, R., Oughton, K.A., Podesta, T.J., Thornton-Pett, M., Synthesis and structural studies of 1,1′-Bis-amino-functionalized ferrocenes, ferrocene salts, and ferrocenium salts (2002) Inorg. Chem., 41, pp. 715-726
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
Bloch, J., Navon, G., A nuclear magnetic resonance relaxation study of iron(III) EDTA in aqueous solution (1980) J. Inorg. Nucl. Chem., 42, pp. 693-699
Oakes, J., Van Karlingen, C.G., Spectroscopic studies of transition-metal ion complexes of diethylenetriaminepenta-acetic acid and diethylenetriamine-penta-methylphosphonic acid (1984) J. Chem. Soc., Dalton Trans., pp. 1133-1137
Vásquez-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
K pf-Maier, P., K pf, H., Non-platinum-group metal antitumor agents: History, current status, and perspectives (1987) Chem. Rev., 87, pp. 1137-115
Neuse, E. W., Kanzawa, F., Evaluation of the activity of some water-soluble ferrocene and ferricenium compounds. Against carcinoma of the lung by the human tumor clonogenic assay (1990) Appl. Organomet. Chem., 4, pp. 19-26
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
Hait, W. N., Gesmonde, J. F., Lazo, J. S., Effect of anticalmodulin drugs on the growth and sensitivity of C6 rat glyoma cells to bleomycin (1994) Anticancer Res., 14, pp. 1711-1721
Chou, T. C., Talalay, P., Quantitative analyis of dose-effect relationships: The combined effects of multiple drugs or enzyme inhibitors (1984) Adv. Enzyme Regul., 22, pp. 27-55
Barker, P. J., Stobart, S. R., West, P. R., Spin trapping of cyclopentadienyl radicals using nitroso compounds and nitrones (1986) J. Chem. Soc., Perkin Trans. 2, pp. 127-130
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
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2002 Dec 19; 45(26): 5786-5796.
Export to BibTeX Export to EndNote
Paper type: Journal Article, Research Support, Non-U. S. Gov'T,
Impact factor: 4.566, 5-year impact factor: 5.504
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-0037137615&partnerID=40&md5=38ade24ffa8485fb569d70f95d767ace
Keywords: 8 Hydroxyguanine, Bleomycin, Ferrocene, Ferrocenium Derivative, Hydroxyl Radical, Oxygen Radical, Superoxide, Unclassified Drug, Antineoplastic Activity, Aqueous Solution, Article, Cell Compartmentalization, Cell Growth, Cell Viability, Controlled Study, Cytotoxicity, Dna Damage, Dose Response, Electron Spin Resonance, Fluorescence Activated Cell Sorting, Growth Inhibition, Human, Human Cell, Oxidative Stress, Ultraviolet Spectroscopy, Antineoplastic Agents, Drug Screening Assays, Antitumor, Drug Stability, Drug Synergism, Electron Spin Resonance Spectroscopy, Ferrous Compounds, Free Radicals, Oxidation-Reduction, Spectrophotometry, Spin Trapping, Tumor Cells, Cultured, Water, Antineoplastic Agents Chemical Synthesis Chemistry Metabolism, Bleomycin Pharmacology, Ferrous Compounds Chemical Synthesis Chemistry Pharmacology, Free Radicals Metabolism, Japna, Polymers, Degradation, Polyvinyl Chloride,
Affiliations:
*** IBB - CNR ***
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
References:
Köpf-Maier, P., Köpf, H., Non-platinum-group metal antitumor agents: History, current status, and perspectives (1987) Chem. Rev., 87, pp. 1137-115
Motohashi, N., Meyer, R., Gollapudi, S.R., Bhattiprolu, K.R., Synthesis and activity of potential antitumor ferrocenes (1990) J. Organomet. Chem., 398, pp. 205-217
Neuse, E.W., Kanzawa, F., Evaluation of the activity of some water-soluble ferrocene and ferricenium compounds. Against carcinoma of the lung by the human tumor clonogenic assay (1990) Appl. Organomet. Chem., 4, pp. 19-26
Osella, D., Ferrali, M., Zanello, P., Laschi, F., Fontani, M., Nervi, C., Cavigiolio, G., On the mechanism of the antitumor activity of ferrocenium derivatives (2000) Inorg. Chim. Acta, 306, pp. 42-48
Köpf-Maier, P., Klapötke, T., Tumor inhibition by ferricenium complexes (1989) Arzneim.-Forsch., 39 (1), pp. 369-371
Köpf-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
Houlton, A., Roberts, R.M.G., Silver, J., Studies on the antitumour activity of some iron sandwich compounds (1991) J. Organomet. Chem., 418, pp. 107-112
Wenzel, M., Wu, Y., Liss, E., Nuse, E.W., Stability of ferricinium and its cytostatic effect (1988) Z. Naturforsch., C: Biosci., 43 C, pp. 963-966
Tamura, H., Miwa, M., DNA cleaving activity cytotoxic activity of ferrocenium cations (1997) Chem. Lett., pp. 1177-1178
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
Prins, R., Korswagen, A.R., Kortbeek, A.G.T.G., Decomposition of the ferricenium cation by nucleophilic reagents (1972) J. Organomet. Chem., 39, pp. 335-344
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
Hait, W.N., Gesmonde, J.F., Lazo, J.S., Effect of anticalmodulin drugs on the growth and sensitivity of C6 rat glyoma cells to bleomycin (1994) Anticancer Res., 14, pp. 1711-1721
Chou, T.C., Talalay, P., Quantitative analyis of dose-effect relationships: The combined effects of multiple drugs or enzyme inhibitors (1984) Adv. Enzyme Regul., 22, pp. 27-55
Frejaville, C., Karoui, H., Tuccio, B., Le Moigne, F., Culcasi, M., Pietri, S., Lauricella, R., Tordo, P., 5-(Diethoxyphosphoryl)-5methyl-1-pyrroline N-oxide: A new efficient phosphorylated nitrone for the in vitro and in vivo spin trapping of oxygencentered radicals (1995) J. Med. Chem., 38, pp. 258-265
Barker, P.J., Stobart, S.R., West, P.R., Spin trapping of cyclopentadienyl radicals using nitroso compounds and nitrones (1986) J. Chem. Soc., Perkin Trans. 2, pp. 127-130
Bernofsky, C., Bandara, B.M., Spin trapping endogenous radicals in MC-1010 Cells: Evidence for hydroxyl radical and carbon-centered ascorbyl radical adducts (1995) Mol. Cell. Biochem., 148, pp. 155-164
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
Minotti, G., Aust, S.D., The requirements for the iron(III) in the initiation of the lipid peroxidation by iron(II) and hydrogen peroxide (1987) J. Biol. Chem., 262, pp. 1098-1104
Goldstein, G., Meyerstein, D., Czapski, G., The fenton reagents (1993) Free Radic. Biol. Med., 15, pp. 435-445
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
Bielski, B., Cabelli, D.E., Highlights of current research involving superoxide and perhydroxyl radicals in aqueous solutions (1991) Int. J. Radiat. Biol., 59, pp. 291-319
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
Tabbì, 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
Kirsch, M., Lomonosova, E.E., Korth, H.-G., Sustmann, R., De Groot, H., Hydrogen peroxide formation by peroxynitrite with HEPES and related tertiary amines (1998) J. Biol. Chem., 273, pp. 12716-12724
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.
Pergamon: Oxford, Chapter 2.8
Bradley, S., McGowan, P.C., Oughton, K.A., Thornton-Pett, M., Walsh, M.E., Facile synthesis of amino-functionalised ferrocenes and vanadocenes (1999) Chem. Commun., pp. 77-78
Bradley, S., Camm, K.D., Liu, X., McGowan, P.C., Mumtaz, R., Oughton, K.A., Podesta, T.J., Thornton-Pett, M., Synthesis and structural studies of 1,1′-Bis-amino-functionalized ferrocenes, ferrocene salts, and ferrocenium salts (2002) Inorg. Chem., 41, pp. 715-726
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
Bloch, J., Navon, G., A nuclear magnetic resonance relaxation study of iron(III) EDTA in aqueous solution (1980) J. Inorg. Nucl. Chem., 42, pp. 693-699
Oakes, J., Van Karlingen, C.G., Spectroscopic studies of transition-metal ion complexes of diethylenetriaminepenta-acetic acid and diethylenetriamine-penta-methylphosphonic acid (1984) J. Chem. Soc., Dalton Trans., pp. 1133-1137
Vásquez-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
K pf-Maier, P., K pf, H., Non-platinum-group metal antitumor agents: History, current status, and perspectives (1987) Chem. Rev., 87, pp. 1137-115
Neuse, E. W., Kanzawa, F., Evaluation of the activity of some water-soluble ferrocene and ferricenium compounds. Against carcinoma of the lung by the human tumor clonogenic assay (1990) Appl. Organomet. Chem., 4, pp. 19-26
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
Hait, W. N., Gesmonde, J. F., Lazo, J. S., Effect of anticalmodulin drugs on the growth and sensitivity of C6 rat glyoma cells to bleomycin (1994) Anticancer Res., 14, pp. 1711-1721
Chou, T. C., Talalay, P., Quantitative analyis of dose-effect relationships: The combined effects of multiple drugs or enzyme inhibitors (1984) Adv. Enzyme Regul., 22, pp. 27-55
Barker, P. J., Stobart, S. R., West, P. R., Spin trapping of cyclopentadienyl radicals using nitroso compounds and nitrones (1986) J. Chem. Soc., Perkin Trans. 2, pp. 127-130
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
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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
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.
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
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Zaiss M, Anemone A, Goerke S, Longo DL, Herz K, Pohmann R, Aime S, Rivlin M, Navon G, Golay X, Scheffler K
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Perrino C, Feliciello A, Schiattarella GG, Esposito G, Guerriero R, Zaccaro L, Del Gatto A, Saviano M, Garbi C, Carangi R, Di Lorenzo E, Donato G, Indolfi C, Avvedimento VE, Chiariello M
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New conjugates of superoxide dismutase/catalase mimetics with cyclodestrins (196 views)
Journal Of Inorganic Biochemistry, 2009; 103(3): 381-388.
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Vecchio G, Lanza V
Synthesis of Superoxide Dismutase (SOD) enzyme mimetics: A bioinorganic laboratory experiment (325 views)
Journal Of Chemical Education, 2009; 86(12): 1419-1421.
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Tabbì G, Fry SC, Bonomo RP
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Tabbì G, Nauser T, Koppenol WH, Reedijk J
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Wink DA, Cook JA, Kim SY, Vodovotz Y, Pacelli R, Krishna MC, Russo A, Mitchell JB, Jourd'heuil D, Miles AM, Grisham MB
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Tabbì G, Driessen WL, Reedijk J, Bonomo RP, Veldman N, Spek AL
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Wink DA, Cook JA, Pacelli R, Liebmann J, Krishna MC, Mitchell JB
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Pacelli R, Wink DA, Cook JA, Krishna MC, DeGraff W, Friedman N, Tsokos M, Samuni A, Mitchell JB
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Bonomo RP, Conte E, Marchelli R, Santoro AM, Tabbì G
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Costanzo LL, De Guidi G, Giuffrida S, Rizzarelli E, Vecchio G
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* Quantification of hydroxyl exchange of D-Glucose at physiological conditions for optimization of glucoCEST MRI at 3, 7 and 9. 4 Tesla (142 views)
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Impact Factor: 2.983
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Dell'Acqua S, Bacchella C, Monzani E, Nicolis S, Di Natale G, Rizzarelli E, Casella L
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Impact Factor: 4.7
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Zhang Y, Dood J, Beckstead AA, Li X-B, Nguyen KV, Burrows CJ, Improta R, Kohler B
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Impact Factor: 9.674
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Merlino A, Russo Krauss I, Castellano I, Ruocco MR, Capasso A, De Vendittis E, Rossi B, Sica F
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Impact Factor: 4.882
View Export to BibTeX Export to EndNote
Grasso GI, Arena G, Bellia F, Rizzarelli E, Vecchio G
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J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2014 Feb; 131: 56-63.
Impact Factor: 3.444
View Export to BibTeX Export to EndNote
Merlino A, Russo Krauss I, Rossi B, De Vendittis A, Marco S, De Vendittis E, Vergara A, Sica F
* Identification of an active dimeric intermediate populated during the unfolding process of the cambialistic superoxide dismutase from Streptococcus mutans (352 views)
Biochimie (ISSN: 0300-9084, 1638-6183, 1638-6183electronic), 2012 Mar; 94(3): 768-775.
Impact Factor: 3.142
View Export to BibTeX Export to EndNote
Merlino A, Russo Krauss I, Castellano I, De Vendittis E, Rossi B, Conte M, Vergara A, Sica F
* Structure and flexibility in cold-adapted iron superoxide dismutases: The case of the enzyme isolated from Pseudoalteromonas haloplanktis (497 views)
J Struct Biol (ISSN: 1047-8477, 1047-8477linking), 2010 Dec; 172(3): 343-352.
Impact Factor: 3.5
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Perrino C, Feliciello A, Schiattarella GG, Esposito G, Guerriero R, Zaccaro L, Del Gatto A, Saviano M, Garbi C, Carangi R, Di Lorenzo E, Donato G, Indolfi C, Avvedimento VE, Chiariello M
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Cardiovascular Research (ISSN: 0008-6363), 2010 Oct; 88(1): 101-110.
Impact Factor: 6.051
View Export to BibTeX Export to EndNote
Milardi D, Pappalardo M, Grasso DM, La Rosa C
* Unveiling the unfolding pathway of FALS associated G37R SOD1 mutant: A computational study (337 views)
Mol Biosyst (ISSN: 1742-206x), 2010; 6(6): 1032-1039.
Impact Factor: 3.825
View Export to BibTeX Export to EndNote
Merlino A, Vitagliano L, Howes BD, Verde C, Di Prisco G, Smulevich G, Sica F, Vergara A
* Combined Crystallographic and Spectroscopic Analysis of Trematomus bernacchii Hemoglobin Highlights Analogies and Differences in the Peculiar Oxidation Pathway of Antarctic Fish Hemoglobins (413 views)
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2009 Dec; 91(12): 1117-1125.
Impact Factor: 2.605
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La Mendola D, Bonomo RP, Caminati S, Di Natale G, Emmi SS, Hansson O, Maccarrone G, Pappalardo G, Pietropaolo A, Rizzarelli E
* Copper(II) complexes with an avian prion N-terminal region and their potential SOD-like activity (393 views)
J Chem Res (ISSN: 1873-3344, 0162-0134, 0162-0134print), 2009 Feb; 103(2): 195-204.
Impact Factor: 3.252
View Export to BibTeX Export to EndNote
Lanza V, Vecchio G
New conjugates of superoxide dismutase/catalase mimetics with cyclodestrins (196 views)
Journal Of Inorganic Biochemistry, 2009; 103(3): 381-388.
Impact Factor: 0
View Export to BibTeX Export to EndNote
Vecchio G, Lanza V
Synthesis of Superoxide Dismutase (SOD) enzyme mimetics: A bioinorganic laboratory experiment (325 views)
Journal Of Chemical Education, 2009; 86(12): 1419-1421.
Impact Factor: 0
View Export to BibTeX Export to EndNote
La Mendola D, Pietropaolo A, Pappalardo G, Zannoni C, Rizzarelli E
* Prion proteins leading to neurodegeneration (420 views)
Current Alzheimer Research (ISSN: 1567-2050), 2008 Dec; 5(6): 579-590.
Impact Factor: 4.132
View Export to BibTeX Export to EndNote
Esposito L, Seydel A, Aiello R, Sorrentino G, Cendron L, Zanotti G, Zagari
* The crystal structure of the superoxide dismutase from Helicobacter pylori reveals a structured C-terminal extension (380 views)
Bba-Gen Subjects (ISSN: 1570-9639, 0006-3002, 0925-4439), 2008 Nov; 1784(11): 1601-1606.
Impact Factor: 2.233
View Export to BibTeX Export to EndNote
Bonomo RP, D'Alessandro F, Grasso G, Impellizzeri G, Pappalardo G, Rizzarelli E, Tabbì G
* Carcinine-beta-cyclodextrin derivatives as scavenger entities of (OH) radicals and SOD-like properties of their copper(II) complexes (284 views)
Inorg Chim Acta (ISSN: 0020-1693), 2008 May 5; 361(6): 1705-1714.
Impact Factor: 1.94
View Export to BibTeX Export to EndNote
Merlino A, Russo Krauss I, Castellano I, De Vendittis E, Vergara A, Sica F
* Crystallization and preliminary x-ray diffraction studies of a psychrophilic iron superoxide dismutase from Pseudoalteromonas haloplanktis (369 views)
Protein Pept Lett (ISSN: 0929-8665, 1875-5305), 2008; 15(4): 415-418.
Impact Factor: 1.281
View Export to BibTeX Export to EndNote
Salvatore A, Cigliano L, Bucci EM, Corpillo D, Velasco S, Carlucci A, Pedone C, Abrescia P
* Haptoglobin binding to apolipoprotein A-I prevents damage from hydroxyl radicals on its stimulatory activity of the enzyme lecithin-cholesterol acyl-transferase (407 views)
Biochemistry (ISSN: 0006-2960, 1520-4995, 1520-4995electronic), 2007 Oct 2; 46(39): 11158-11168.
Impact Factor: 3.368
View Export to BibTeX Export to EndNote
D'Agata R, Grasso G, Iacono G, Spoto G, Vecchio G
* Lectin recognition of a new SOD mimic bioconjugate studied with surface plasmon resonance imaging (303 views)
Org Biomol Chem (ISSN: 1477-0520, 1477-0539, 1477-0539electronic), 2006 Feb 21; 4(4): 610-612.
Impact Factor: 2.874
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Calabrese V, Colombrita C, Guagliano E, Sapienza M, Ravagna A, Cardile V, Scapagnini G, Santoro AM, Mangiameli A, Butterfield DA, Giuffrida Stella AM, Rizzarelli E
* Protective effect of carnosine during nitrosative stress in astroglial cell cultures (379 views)
Neurochemical Research (ISSN: 0364-3190, 1573-6903), 2005 Jun; 30(6-7): 797-807.
Impact Factor: 2.187
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Pedone E, Bartolucci S, Fiorentino G
* Sensing and adapting to environmental stress: The Archaeal tactic (327 views)
Frontiers In Bioscience (ISSN: 1093-9946, 1093-4715), 2004 Sep 1; 9: 2909-2926.
Impact Factor: 3.226
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Puglisi A, Tabbì G, Vecchio G
* Bioconjugates of cyclodextrins of manganese salen-type ligand with superoxide dismutase activity (401 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2004 Jun; 98(6): 969-976.
Impact Factor: 2.225
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Bonomo RP, Impellizzeri G, La Mendola D, Maccarone G, Pappalardo G, Santoro A, Tabbì G, Vecchio G, Rizzarelli E
* Functional Mimics Of Cu, Zn-Superoxide Dismutase Enzymes, In Metal-Ligand Interactions In Nano-, Micro-, And Macro-Systems In Complex Environments (235 views)
In Complex Environmentsmetal Ligand Interactions (ISSN: 1568-2609, 1568-8260), 2003 Jan; 116: 41-63.
Impact Factor: 5.664
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Bonomo RP, Impellizzeri G, La Mendola D, Maccarone G, Pappalardo G, Santoro A, Tabbì G, Vecchio G, Rizzarelli E
* Functional mimics of Cu, Zn-superoxide dismutase enzymes (234 views)
In Complex Environmentsmetal Ligand Interactions (ISSN: 1568-2609, 1568-8260), 2003; 116: 41-63.
Impact Factor: 5.664
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Bonomo RP, Bruno V, Conte E, De Guidi G, La Mendola D, Maccarrone G, Nicoletti F, Rizzarelli E, Sortino S, Vecchio G
* Potentiometric, spectroscopic and antioxidant activity studies of SOD mimics containing carnosine (385 views)
Dalton T (ISSN: 1477-9226, 1477-9234, 1477-9234electronic), 2003; (23): 4406-4415.
Impact Factor: 2.908
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La Mendola D, Sortino S, Rizzarelli E, Vecchiog
* Synthesis Of New Carnosine Derivatives Of R-Cyclodextrin And Their Hydroxyl Radical Scavanger Ability (320 views)
Helvetica Chimica Acta, 2002; 85: 1633-1643.
Impact Factor: 1.394
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Tabbì G, Fry SC, Bonomo RP
ESR study of the non-enzymic scission of xyloglucan by an ascorbate-H2O2-copper system: The involvement of the hydroxyl radical and the degradation of ascorbate (311 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 2001 Apr; 84(3-4): 179-187.
Impact Factor: 1.729
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Tabbì G, Nauser T, Koppenol WH, Reedijk J
A Pulse Radiolysis Study of an Imidazolato-Bridged Asymmetric Dicopper(II) Complex: A Structural and Functional Mimic of Superoxide Dismutase (269 views)
Eur J Inorg Chem (ISSN: 1434-1948, 1099-0682e), 1998; (12): 1939-1943.
Impact Factor: 2.222
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Bonomo RP, Impellizzeri G, Pappalardo G, Purrello R, Rizzarelli E, Tabbì G
Co-ordinating properties of cyclopeptides. Thermodynamic and spectroscopic study on the formation of copper(II) complexes with cyclo(Gly-His)4 and cyclo(Gly-His-Gly)2 and their superoxide dismutase-like activity (452 views)
Journal Of The Chemical Society Dalton Transactions (ISSN: 0300-9246), 1998; (22): 3851-3857.
Impact Factor: 2.507
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Wink DA, Cook JA, Kim SY, Vodovotz Y, Pacelli R, Krishna MC, Russo A, Mitchell JB, Jourd'heuil D, Miles AM, Grisham MB
Superoxide modulates the oxidation and nitrosation of thiols by nitric oxide-derived reactive intermediates (336 views)
Jbc Papers (ISSN: 0021-9258, 1083-351x, 0021-9258linking), 1997 Apr 25; 272(17): 11147-11151.
Impact Factor: 6.963
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Tabbì G, Driessen WL, Reedijk J, Bonomo RP, Veldman N, Spek AL
High Superoxide Dismutase Activity Of A Novel, Intramolecularly Imidazolato-Bridged Asymmetric Dicopper(ii) Species; Design, Synthesis, Structure And Magnetism Of Cu(ii) Complexes With A Mixed Pyrazole-Imidazole Donor Set (321 views)
Inorg Chem (ISSN: 0020-1669, 1520-510x, 1520-510xelectronic), 1997; 36(6): 1168-1175.
Impact Factor: 2.736
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Wink DA, Cook JA, Pacelli R, Liebmann J, Krishna MC, Mitchell JB
Nitric oxide (NO) protects against cellular damage by reactive oxygen species (517 views)
Toxicology Letters (ISSN: 0378-4274), 1995 Dec; 82-3: 221-226.
Impact Factor: 1.128
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Pacelli R, Wink DA, Cook JA, Krishna MC, DeGraff W, Friedman N, Tsokos M, Samuni A, Mitchell JB
NITRIC-OXIDE POTENTIATES HYDROGEN PEROXIDE-INDUCED KILLING OF ESCHERICHIA-COLI (428 views)
Journal Of Experimental Medicine (ISSN: 0022-1007), 1995 Nov 1; 182(5): 1469-1479.
Impact Factor: 14.384
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Miles AM, Gibson MF, Kirshina M, Cook JC, Pacelli R, Wink D, Grisham MB
Effects of superoxide on nitric oxide-dependent n-nitrosation reactions (292 views)
Free Radic Res Free Radical Research (ISSN: 1071-5762), 1995 Oct; 23(4): 379-390.
Impact Factor: 2.361
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Vinci C, Caltabiano V, Santoro AM, Rabuazzo AM, Buscema M, Purrello R, Rizzarelli E, Vigneri R, Purrello F
Copper Addition Prevents The Inhibitory Effects Of Interleukin 1-Beta On Rat Pancreatic Islets (442 views)
Diabetologia, 1995 Jan; 38(1): 39-45.
Impact Factor: 0
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Condorelli G, Costanzo LL, De Guidi G, Giuffrida S, Rizzarelli E, Vecchio G
INHIBITION OF PHOTOHEMOLYSIS BY COPPER(II) COMPLEXES WITH SOD-LIKE ACTIVITY (489 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 1994 Jun; 54(4): 257-265.
Impact Factor: 1.342
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Bonomo RP, Conte E, Marchelli R, Santoro AM, Tabbì G
O2 - scavenger properties of copper(II) complexes with diamino-diamide-type ligands (363 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 1994 Feb 1; 53(2): 127-138.
Impact Factor: 1.342
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Costanzo LL, De Guidi G, Giuffrida S, Rizzarelli E, Vecchio G
Determination of superoxide dismutase-like activity of copper(II) complexes. Relevance of the speciation for the correct interpretation of in vitro O2 - scavenger activity (515 views)
J Chem Res (ISSN: 0162-0134, 1873-3344, 0162-0134print), 1993 Jun; 50(4): 273-281.
Impact Factor: 1.342
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38 Records (38 excluding Abstracts).
Total impact factor: 125.21 (125.21 excluding Abstracts).
Total 5 year impact factor: 140.947 (140.947 excluding Abstracts).
Total impact factor: 125.21 (125.21 excluding Abstracts).
Total 5 year impact factor: 140.947 (140.947 excluding Abstracts).
638 views. Last view on Thursday 16 February 2023, 18:44:19
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