Involvement of Cytochrome P-450 in n-Butyl Nitrite-Induced Hepatocyte Cytotoxicity n-Butyl nitrite cytotoxicity
Iranian Journal of Pharmaceutical Sciences,
Vol. 1 No. 1 (2005),
15 January 2005
,
Page 11-19
https://doi.org/10.22037/ijps.v1.39437
Abstract
Addition of n-butyl nitrite to isolated rat hepatocytes caused an immediate glutathione depletion followed by an inhibition of mitochondrial respiration, inhibition
of glycolysis and ATP depletion. At cytotoxic butyl nitrite concentrations, lipid peroxidation occurred before the plasma membrane was disrupted.
Cytochrome P-450 inhibitors inhibited peroxynitrite formation and prevented butyl nitrite-induced mitochondrial respiration inhibition, ATP depletion, lipid
peroxidation and plasma membrane disruption. However, glutathione depletion, S-nitroso-glutathione (GSNO) formation, or the inhibition of glycolysis was not
affected by cytochrome P-450 inhibitors. Glutathione-depleted hepatocytes were resistant to butyl nitrite which suggests that cytotoxicity and peroxynitrite formation results from GSNO formation. Peroxynitrite formation was also inhibited by reactive oxygen scavengers. These findings suggest that cytochrome P-450 isoforms (particularly CYP2E1) act as a source of superoxide anion radicals in the formation of cytotoxic peroxynitrite from nitric oxide.
- n-Butyl nitrite
- Cytochrome P-450
- Nitrosoglutathione
- Peroxynitrite
- Cytotoxicity
- ATP depletion
How to Cite
References
[2] Sigell LT, Kapp FT, Fusaro GA, Nelson ED, Falck RS. Popping and snorting volatile nitrites: a current fad for getting high. Am J Psych 1978; 135: 1216-1218.
[3] Gruetter CA, Kadowitz PJ, Ignarro LJ. Methylene blue inhibits coronary arterial relaxation and guanylate cyclase activation by nitroglycerin, sodium nitrite and amyl nitrite. Can J Physiol Pharmacol 1981; 59: 150-156.
[4] Newell GR, Adams SC, Mansell PWA, Hersh EM. Toxicity, immunosuppressive effects and carcinogenic potential of volatile nitrites: possible relationship to Kaposi’s Sarcoma.
Phrmacotherapy 1984; 4: 284-291.
[5] Moss AR, Osmond D, Bacchetti P, Chermann JC, Barre-Sinoussi F, Carlson J. Risk factors for AIDS and HIV seropositivity in homosexual men. Am J Epidemiol 1987; 125: 1035-1047.
[6] Haverkos HW, Pinsky PF, Dortman DP, Bregman, DJ. Disease manifestation among homosexual men with acquired immunodeficiency syndrome: a possible role of nitrites in Kaposi’s sarcoma. Sex Trans Dis 1985; 12: 203-208.
[7] Hersh EM, Reuben JM, Bogerd H, Rosenblum M, Bielski M, Mansell PW, Rios A, Newell GR, Sonnenfeld, G. Effect of the recreational agent isobutyl nitrite on human peripheral blood leukocytes and on in vitro interferon production. Cancer Res 1983; 43: 1365-1371.
[8] Soderberg LSF, Barnett, JB. Exposure to inhaled isobutyl nitrite reduces T cell blastogenesis and antibody responsiveness. Fund Appl Toxicol 1991; 17: 821-824.
[9] Soderberg LSF, Barnett JB, Chang LW. Inhaled isobutyl nitrite impairs T cell reactivity. Adv Exp Med Biol 1991; 288: 265-269.
[10] Gaworski CL, Aranyi C, Hall A, Levine BS, Jackson CD, Abdo KM. Prechronic inhalation toxicity studies of isobutyl nitrite. Fund Appl Toxicol 1992; 19: 169-175.
[11] Meloche BA, O’Brien PJ. S-nitrosyl glutathione mediated hepatocyte cytotoxicity. Xenobiotica 1993; 23: 863-871.
[12] Niknahad H, O’Brien PJ. (1995) Cytotoxicity induced by N-methyl-N’-nitro-N-nitrosoguanidine may involve S-nitrosyl glutathione and
nitric oxide. Xenobiotica 1995; 25: 91-101.
[13] Moldeus P, Holberg J, Orrenius S. Isolation and use of liver cells. Methods in Enzymol 1978; 52: 60-71.
[14] Khan S, O’Brien PJ. 1-Bromoalkanes as new potent nontoxic glutathione depletors in isolated hepatocytes. Biochem Biophys Res Commun 1991; 179: 436-441.
[15] Smith MT, Thor H, Hartizell P, Orrenius S. The measurement of lipid peroxidation in isolated hepatocytes. Biochem Pharmacol 1982; 31: 19-26.
[16] Stocchi V, Cucchiarini L, Magnani M, Chiaranitini PP, Crescentini G. Simultaneous extraction and reverse-phase high-performance liquid chromatographic determination of adenine and pyridine nucleotides in human red blood cells. Anal Biochem 1984; 146: 118-124.
[17] Hohorst HJ. l-(+)-Lactate determination with lactic dehydrogenase and DPN. In: Bergmeyer HU, editor; Methods of enzymatic analysis. New York: Academic Press, 1965; 266-270.
[18] Reed DJ, Babson JR, Beatty PW, Brodie AE, Ellis WW, Potter DW. High-performance liquid chromatography analysis of nanomole levels of glutathione, glutathione disulfide, and related thiols and disulfides. Anal Bioshem 1980; 106: 55-62.
[19] Radi R, Cosgrove TP, Beckman JS, Freeman BA. Peroxynitrite-induced luminol chemiluminescence. Biochem J 1993; 290: 51-57.
[20] Yoshida K, Akaike T, Doi T, Sato K, Ijiri S, Suga M, Ando M, Maeda H. Pronounced enhancement of NO-dependent antimicrobial action by an NO-oxidizing agent, imidazolineoxyl Noxide. Infect Immuonol 1993; 61: 3552-3555.
[21] Meyer DJ, Kramer H, Ketterer B. Human glutathione transferase catalysis of the formation of S-nitrosoglutathione from ogranic nitrites plus glutathione. FEBS Lett 1994; 351: 427-428.
[22] Mayer B, Schrammel A, Klatt P, Koesling D, Schmidt K. Peroxynitrite-induced accumulation of cyclic GMP in endothelial cells and stimulation
of purified soluble guanylate cyclase. Dependence on glutathione and possible role of S-nitrosation. J Biol Chem 1995; 270: 17355- 17360.
[23] Kahl R, Wulff U, Netter KJ. Effect of nitrite on microsomal cytochrome P-450. Xenobiotica 1978; 8: 359-364.
[24]O’Keefe DH, Ebel RE, Peterson JA. Studies of the oxygen binding site of cytochrome P450. Nitric oxide as a spin-label probe. J Biol Chem 1978; 253: 3509-3516.
[25] Radi R, Beckman JS, Bush KM, Freeman BA. Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide. Arch Biochem Biophys 1991;288:481-487.
[26] Koppenol WH, Moreno JJ, Pryor WA, Ischiropoulos H, Beckman JS. Peroxynitrite, a cloaked oxidant formed by nitric oxide and superoxide. Chem Res Toxicol 1992; 5: 834-842.
[27] Floris R, Piersma SR, Yang G, Jones P, Wever R. Interaction of myeloperoxidase with peroxynitrite. A comparison with lactoperoxidase, horseradish
peroxidase and catalase. Eur J Biochem 1993; 215: 267-275.
[28] Lancaster JR Jr, Hibbs JB Jr. EPR demonstration of iron-nitrosyl complex formation by cytotoxic activated macrophages. Proc Natl Acad Sci USA 1990; 87: 1223-1227.
[29] Radi R, Rodriguez M, Castro L, Telleri R. Inhibition of mitochondrial electron transport by peroxynitrite. Arch Biochem Biophys 1994; 308: 89-95.
[30] Bolanos JP, Heales SJ, Land JM, Clark JB. Effect of peroxynitrite on the mitochondrial respiratory chain. J Neurochem 1995; 64: 1965-1972.
[31] Hausladen A, Fridovich I. Superoxide and peroxynitrite inactivate aconitase, but nitric oxide does not: differential susceptibility of neurons and astrocytes in primary cultures. J Biol Chem 1994; 269: 29405-29408.
[32] Castro L, Rodriguez M, Radi R. Aconitase is readily inactivated by peroxynitrite, but not by its precursor, nitric oxide. J Biol Chem 1994; 269: 29409-29415.
[33] Brune B, Lapetina EG. Properties of a novel nitric oxide-stimulated ADP-ribosyltransferase. Arch Biochem Biophys 1990; 279: 286-290.
[34] Dimmeler S, Lottspeich F, Brune B. Nitric oxide causes ADP-ribosylation and inhibition of glyceraldehyde-3-phosphate dehydrogenase. J Biol Chem 1992; 267: 16771-16774.
[35] Mohr S, Stamler JS, Brune B. Mechanism of covalent modification of glyceraldehyde-3-phosphate dehydrogenase at its active site thiol by nitric oxide, peroxynitrite and related nitrosating agents. FEBS Lett 1994; 348: 223-227.
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