Cyto- and genotoxic effects of novel aromatic nitroxide radicals in vitro

Free Radical Biology and Medicine

Volumn 28, Issue 3, 2000, Pages 330-336

  Damiani, Elisabetta ^a   Greci, Lucedio ^a   Hrelia, Patrizia ^b  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Aliphatic and aromatic nitroxides; Ames test; Antioxidants; CHO AS52 cells; Cytotoxicity; Free radical; Mutagenicity

Indexed keywords

ALIPHATIC COMPOUND; ANTIOXIDANT; AROMATIC COMPOUND; BUTYLCRESOL; FREE RADICAL; INDOLINONIC NITROXIDE; NITROXIDE; PIPERIDINIC NITROXIDE; PYRROLIDINIC NITROXIDE; QUINOLINIC NITROXIDE; QUINONEIMINE N OXIDE; UNCLASSIFIED DRUG;

AMES TEST; ANIMAL CELL; ARTICLE; CHO CELL; COLONY FORMATION; CONTROLLED STUDY; CYTOTOXICITY; GENOTOXICITY; MUTAGENICITY; NONHUMAN; PRIORITY JOURNAL; SALMONELLA TYPHIMURIUM;

ANIMALS; CELL SURVIVAL; CHO CELLS; COLONY-FORMING UNITS ASSAY; CRICETINAE; FREE RADICALS; MUTAGENICITY TESTS; MUTAGENS; NITROGEN OXIDES; SALMONELLA TYPHIMURIUM;

CELL FUSING AGENT VIRUS; CRICETINAE; CRICETULUS GRISEUS; SALMONELLA TYPHIMURIUM; TYPHIMURIUM;

EID: 0033952204     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(99)00245-2     Document Type: Article

References (52)

1. Kocherginsky N., Swartz H.M. Introduction. Kocherginsky N., Swartz H.M. Nitroxide spin labels, reactions in biology and chemistry. 1995;1-14 CRC Press, Boca Raton.
2. Rozantsev E.G. Free nitroxyl radicals. 1970;Plenum Press, New York.
3. Berliner, L. J.; Reuben, J. Spin labeling I and II, theory and applications. Vols. 1 and 2. New York: Academic Press; 1976-1979.
4. Hamilton C.L., McConnell H.M. Rich A., Davidson N. Structural chemistry and molecular biology. 1968;115-149 W.A. Freeman, San Francisco.
5. Swartz H.M., Feig E. Advances in magnetic resonance imaging. 1988;Ablex Publishing Co, Norwood, NJ.
6. Berliner L.J., Fujii H. Magnetic resonance imaging of biological specimens by electron paramagnetic resonance of nitroxide spin labels. Science. 227:1985;517-519.
7. Sosnovsky G., Li S.W. In the search for new anticancer drugs XII. Synthesis and biological evaluation of spin labeled nitrosoureas. Life Sci. 36:1985;1479-1483.
8. Konovalova N.P., Diatchkovskaya R.R., Volkova L.M., Varfolomeev V.N. Nitroxyl radicals decrease toxicity of cytostatic agents. Anticancer Drugs. 2:1991;591-595.
9. Krishna M.C., Samuni A. Nitroxides as antioxidants. Methods Enzymol. 234:1994;580-589.
10. Samuni A., Krishna M.C. Antioxidant properties of nitroxides and nitroxide SOD mimics. Packer L., Cadenas E. Handbook of synthetic antioxidants. 1997;351-373 Marcel Dekker, New York.
11. Mitchell J.B., Samuni A., Krishna M.C., De Graff W.O., Ahn M.S., Samuni U., Russo A. Biologically active metal-independent superoxide dismutase mimics. Biochemistry. 29:1990;2802-2807.
12. Samuni A., Winkelsberg D., Pinson A., Hahn S.M., Mitchell J.B., Russo A. Nitroxide stable radicals protect beating cardiomyocytes against oxidative damage. J. Clin. Invest. 87:1991;1526-1530.
13. De Graff W.G., Krishna M.C., Kaufman D., Mitchell J.B. Nitroxide-mediated protection against X-ray- and neocarzinostatin-induced DNA damage. Free Radic. Biol. Med. 13:1992;479-487.
14. Miura Y., Utsumi H., Hamada A. Antioxidant activity of nitroxide radicals in lipid peroxidation of rat liver microsomes. Arch. Biochem. Biophys. 300:1993;148-156.
15. Samuni A., Godinger D., Aronovitch J., Russo A., Mitchell J.B. Nitroxides block DNA scission and protect cells from oxidative damage. Biochemistry. 30:1991;555-561.
16. Krishna M.C., Halevy R.F., Zhang R., Gutierrez P.L., Samuni A. Modulation of streptonigrin cytotoxicity by nitroxide SOD mimics. Free Radic. Biol. Med. 17:1994;379-388.
17. Zhang R., Hirsh O., Mohsen M., Samuni A. Effects of nitroxide stable radicals on juglone cytotoxicity. Arch. Biochem. Biophys. 312:1994;385-391.
18. Weil T.J., Van der Veen J., Olcott H.S. Stable nitroxides as lipid antioxidants. Nature. 219:1968;168-169.
19. Bowry V.W., Ingold K.U. Kinetics of nitroxide radical trapping. 2. Structural effects. J. Am. Chem. Soc. 114:1992;4992-4997.
20. Nilsson U.A., Olsson L.I., Carlin G., Bylund F.A. Inhibition of lipid peroxidation by spin labels. Relationship between structure and function. J. Biol. Chem. 264:1989;11131-11135.
21. Stipa P., Carloni P., Greci L., Damiani E. Synthesis and thermal stability of alkoxyamines. Polymer Degradation and Stability. 55:1997;323-327.
22. Carloni P., Greci L., Stipa P., Eberson L. Electron-transfer reactions. Oxidation of Grignard reagents in the presence of an aminoxyl as a radical trapping agent. Journal of Organic Chemistry. 56:1991;4733-4737.
23. Damiani E., Carloni P., Stipa P., Greci L. Reactivity of an indolinonic aminoxyl with superoxide anion and hydroxyl radicals. Free Radic. Res. 31:1999;113-121.
24. Greci L. Homolytic substitution in indolinone nitroxide radicals. Part III. Reactions with terbutoxy and methyl radicals. Tetrahedron. 38:1982;2435-2439.
25. Cardellini L., Carloni P., Greci L., Stipa P., Faucitano A. Homolytic substitution in indolinone nitroxide radicals. Part 5. Reactions with tert-butylperoxy radicals. Gazzetta Chimica Italiana. 119:1989;621-625.
26. Berti C., Colonna M., Greci L., Marchetti L. Homolytic substitutions in indolinone nitroxide radicals 1. Reaction with aroyloxyl radicals. Tetrahedron. 33:1977;3149-3154.
27. Damiani E., Carloni P., Iacussi M., Stipa P., Greci L. Reactivity of sulphur-centered radicals with indolinonic and quinolinic aminoxyls. European Journal of Organic Chemistry. 1999;2405-2412.
28. Alberti A., Greci L., Stipa P., Sgarabotto P., Ugozzoli F. Homolytic substitution in indolinone nitroxide. IV. Reaction with aminyl radicals. Spectroscopic and crystallographic study. Tetrahedron. 43:1987;3031-3040.
29. Antosiewicz J., Bertoli E., Damiani E., Greci L., Popingis J., Przybylski S., Tanfani F., Wozniak M. Indolinonic and quinolinic aminoxyls as protectants against oxidative stress. Free Radic. Biol. Med. 15:1993;203-208.
30. Damiani E., Paganga G., Greci L., Rice-Evans C. Inhibition of copper-mediated low density lipoprotein peroxidation by quinoline and indolinone nitroxide radicals. Biochem. Pharmacol. 48:1994;1155-1161.
31. Antosiewicz J., Popinigis J., Wozniak M., Damiani E., Carloni P., Greci L. Effects of indolinic and quinolinic aminoxyls on protein and lipid peroxidation of rat liver microsomes. Free Radic. Biol. Med. 18:1995;913-917.
32. Antosiewicz J., Damiani E., Jassem W., Wozniak M., Orena M., Greci L. Influence of structure on the antioxidant activity of indolinic nitroxide radicals. Free Radic. Biol. Med. 22:1997;249-255.
33. Tanfani F., Carloni P., Damiani E., Greci L., Wozniak M., Kulawiak D., Jankowski K., Kaczor J., Matuskiewicz A. Quinolinic aminoxyl protects albumin against peroxyl radical mediated damage. Free Radic. Res. 21:1994;309-315.
34. Villarini M., Moretti M., Damiani E., Greci L., Santroni A.M., Fedeli D., Falcioni G. Detection of DNA damage in stressed trout nucleated erythrocytes using the comet assay protection by nitroxide radicals . Free Radic. Biol. Med. 24:1998;1310-1315.
35. Damiani E., Greci L., Parsons R., Knowland J. Nitroxide radicals protect DNA from damage when illuminated in vitro in the presence of dibenzoylmethane and a common sunscreen ingredient. Free Radic. Biol. Med. 26:1999;809-816.
36. Gabbianelli R., Falcioni G., Santroni A., Caulini G., Greci L., Damiani E. Effect of aromatic nitroxides on hemolysis of human erythrocytes entrapped with isolated hemoglobin chains. Free Radic. Biol. Med. 23:1997;278-284.
37. Falcioni G., Gabbianelli R., Damiani E., Santroni A.M., Fedeli D., Wozniak M., Greci L. The effect of indolinic and quinolinic nitroxide radicals on trout erythrocytes exposed to oxidative stress. Free Radic. Res. 28:1998;507-516.
38. Kocherginsky N., Swartz H.M., Sentjurc M. Toxicity and the use of nitroxides as drugs. Kocherginsky N., Swartz H.M. Nitroxide spin labels, reactions in biology and chemistry. 1995;175-198 CRC Press, Boca Raton.
39. Ankel E.G., Lai C.-S., Hopwood L.E., Zivkovic Z. Cytotoxicity of commonly used nitroxide radical spin probes. Life Sci. 40:1987;495-498.
40. Sosnovsky G. A critical evaluation of the present status of toxicity of aminoxyl radicals. J. Pharm. Sci. 81:1992;496-499.
41. Sies H., Mehlhorn R. Mutagenicity of nitroxide-free radicals. Arch. Biochem. Biophys. 251:1986;393-396.
42. Aruoma O.I., Halliwell B. Free radicals and food additives. 1991;Taylor and Francis, London.
43. Colonna M., Greci L., Berti C., Marchetti L. Stable nitroxide radicals from phenyl-isatogen and arylimino derivatives with organometallic compounds. Tetrahedron. 31:1975;1745-1753.
44. Berti C., Colonna M., Greci L., Marchetti L. Nitroxide radicals from 2-substituted quinoline-N-oxides with organometallic compounds. Tetrahedron. 32:1976;2147-2151.
45. Rozantsev E.G., Krinitskaya L.A. Free iminoxyl radicals in the hydrogenated pyrrole series. Tetrahedron. 21:1965;491-499.
46. Maron D.M., Ames B.N. Revised methods for the Salmonella mutagenicity test. Mutat. Res. 113:1983;173-215.
47. Hrelia P., Vigagni F., Maffei F., Fimognari C., Lamartina L., Spinelli D., Juric P., Guerra M.C., Cantelli-Forti G. Analysis of metabolism and genotoxicity of 5-nitro-3-thiophenecarboxanilides in bacterial, mammalian and human cells. Mutagenesis. 10:1995;171-177.
48. Afzal V., Brasch R.C., Nitecki D.E., Wolff S. Nitroxyl spin label contrast enhancers for magnetic resonance imaging. Studies of acute toxicity and mutagenesis. Invest. Radiol. 19:1984;549-554.
49. Johnstone P.A., De Graff W.G., Mitchell J.B. Protection from radiation-induced chromosomal aberrations by the nitroxide TEMPOL. Cancer. 75:1995;2323-2327.
50. De Graff W.G., Krishna M.G., Russo A., Mitchell J.B. Antimutagenicity of a low molecular weight superoxide dismutase mimic against oxidative mutagens. Environ. Mol. Mutagen. 19:1992;21-26.
51. Voest E.E., Van R.E., Van A.B., Neijt J.P., Marx J.J. Increased hydrogen peroxide concentration in human tumor cells due to a nitroxide free radical. Biochim. Biophys. Acta. 1136:1992;113-118.
52. Fuchs J., Groth N., Herrling T. Cutaneous tolerance to nitroxide free radicals in human skin. Free Radic. Biol. Med. 24:1998;643-648.