Aromatic indolinic aminoxyls as antioxidants in cardiac sarcoplasmic reticulum lipid and protein oxidation

• Autorzy: Kulawiak-Galaska D. , Wozniak M. , Greci L.
• Języki publikacji: EN

Abstrakty

EN

The results presented demonstrate the influence of aromatic indolinic aminoxyls: 1,2-dihydro-2-ethyl-2-phenyl-3.H-indole-3-phenylimino-1-oxyl (IA-C2) and 1,2-dihydro- 2-octadecyl-2-phenyl-3.H-indole-3-phenylimino-1-oxyl (IA-C18) on oxidation of lipids and proteins of cardiac sarcoplasmic reticulum membranes. We have used doxorubicin and t-butyl hydroperoxide as agents inducing oxidative stress in isolated rat cardiac sarcoplasmic reticulum membrane system. Carbonyl groups were measured as the end product of membrane protein oxidation, and thiobarbituric acid reactive substances were assessed as a marker of lipid pero- xidation. Inhibition of peroxidation of certain membrane components depends on the length of acyl chain. Aminoxyl IA-C2 inhibits the lipid peroxidation process while IA-C18 is an efficient protector against protein oxidation.

Słowa kluczowe

EN

cardiac sarcoplasmic reticulum membrane; doxorubicin; indolinic aminoxyl; lipid oxidation; protein oxidation; antioxidant

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2002
• Tom: 49
• Numer: 1
• Opis fizyczny: p.43-49,fig.

Twórcy

autor

Kulawiak-Galaska D.

• Medical University of Gdansk, Debinki 1, 80-210 Gdansk, Poland

autor

Wozniak M.

autor

Greci L.

Bibliografia

• 1.Singal, P.K., Khaper, N., Palace, V. & Kumar, D. (1998) The role of oxidative stress in the genesis of heart disease. Cardiovascular Res. 40, 426-432.
• 2.Doroshow, J.H. (1983) Effect of anthracycline antibiotics on oxygen radical formation in rat heart. Cancer Res. 43, 460-472.
• 3.Iliskovic, N. & Singal, P.K. (1997) Lipid lowering: An important factor in preventing adriamycin-induced heart failure. Am. J. Pathol. 150, 727-734.
• 4.Minotti, G., Mancuso, C., Frustaci, A., Mordente, A., Santini, S.A., Calafiore, A.M., Liberi, G. & Gentiloni, N. (1996) Paradoxical inhibition of cardiac lipid peroxidation in cancer patient treated with doxorubicin. J. Clin. Invest. 98, 650-661.
• 5.Sugioka, K. & Nakano, M. (1982) Mechanism of phospholipid peroxidation induced by ferric ion-ADP-adriamycin-co- ordination complex. Biochim. Biophys. Acta 713, 333-343.
• 6.Kostoryz,E.L. & Yourtee, D.M. (2001) Oxidative mutagenesis of doxorubicin-Fe(III) complex. Mutat. Res. 490, 131-139.
• 7.Futterman,S. & Rollins, H.H. (1973) A simple biuret method for the estimation of protein in samples containing detergents. Anal. Biochem. 51, 443-447.
• 8.Buege,J.A. & Aust, S T. (1978) Microsomal lipid peroxidation. Meth. Enzymol. 52, 302-310.
• 9.Antosiewicz,J., Bertoli, E., Damiani, E., Greci, L., Popinigis, J., Przybylski, S., Tanfani, F. & Wozniak, M. (1993) Indolinic and quinolinic aminoxyls as protectants against oxidative stress. Free Radic Biol. Med. 15, 203-208.
• 10.Levine,R.L., Garland, D., Oliver, C.N., Amici, A., Climent, I., Lenz, A.-G., Ahn, B.W., Shaltiel, S. & Stadtman, E.R. (1990) Determination of carbonyl content in oxidatively modified proteins. Methods Enzymol. 186, 464-478.
• 11.Berti,C., Colonna, M., Greci, L. & Marchetti, L. (1975) Stable nitroxide radicals from phenyl-isatogen and arylimino derivatives with organometallic compound. Tetrahedron, 31, 1745-1753.
• 12.Antosiewicz,J., Damiani, E., Jassem, W., Wozniak, M., Orena, M. & Greci, L. (1997) Influence of structure on the antioxidant activity of indolinic nitroxide radicals. Free Radic Biol. Med. 22, 249-255.
• 13.Bachur,N.R., Gordon, S.L, Gee, M.V. & Kon, H. (1979) NADPH cytochrome P-450 reductase activation of quinone anticancer agents to free radicals. Proc. Natl. Acad. Sci. U.S.A. 76, 954-957.
• 14.Demant, E.J. & Jensen, P.K. (1983) Destruction of phospholipids and respiratory-chain activity in pig-heart submitochondrial particles induced by an adriamycin-iron complex. Eur. J. Biochem. 132, 551-556.
• 15.Alegria, A.E., Rodriguez, M.S. & Hernandez, J. (1990) Semiquinones derived from anthraquinone-containing antitumor drugs can partition into phosphatidylcholine bilayers. Biochim. Biophys. Acta 1035, 51-55.
• 16.Monti,E., Cova, D., Guido, E., Morelli, R. & Oliva, C. (1996) Protective effect of the nitroxide TEMPOL against the cardiotoxicity of adriamycin. Free Radic Biol. Med. 21, 463-470.
• 17.Chateauneuf,J., Lusztyk, J. & Ingold, K.U. (1988) Absolute rate constants for the reactions of some carbon-centered radicals with 2,2,6,6-tetramethylpiperidine-A/-oxyl. J. Org. Chem. 53, 1629-1632.
• 18.Dean,R.T., Fu, S., Stocker, R. & Davies, M.J. (1997) Biochemistry and pathology of radical-mediated protein oxidation. Biochem. J. 324, 1-18.
• 19.Kang,Y.J., Chen, Y. & Epstein, P.N. (1996) Suppression of doxorubicin cardiotoxicity by overexpression of catalase in the heart of transgenic mice. J. Biol. Chem. 271, 12610-12616.
• 20.Burton,G. & Ingold, K.U. (1986) Vitamin E: Application of the principles of physical organic chemistry to the exploration of its structure and function. Acc. Chem. Res. 19, 194-201.
• 21.Chen,Y., Saari, J.T. & Kang, Y.J. (1994) Weak antioxidant defenses make the heart a target for damage in copper- deficient rats. Free Radic Biol. Med. 17, 529-536.
• 22.Neuzil, J., Gebicki, J.M. & Stocker, R. (1993) Radical-induced chain oxidation of proteins and its inhibition by chain- breaking antioxidant. Biochem. J. 293, 601-606.