Metabolites of acetaminophen trigger Ca2+ release from liver microsomes

Toxicology Letters

Volumn 106, Issue 1, 1999, Pages 23-29

  Stoyanovsky, Detcho A ^a   Cederbaum, Arthur I ^a  

^a MOUNT SINAI SCHOOL OF MEDICINE   (United States)

Author keywords

Acetaminophen; Ca2+ release; Liver microsomes; Metabolites

Indexed keywords

1,4 BENZOQUINONE; ADENOSINE TRIPHOSPHATASE (CALCIUM MAGNESIUM); DRUG METABOLITE; PARACETAMOL; RYANODINE; RYANODINE RECEPTOR;

ANIMAL TISSUE; ARTICLE; CALCIUM TRANSPORT; CONTROLLED STUDY; IN VITRO STUDY; LIVER MICROSOME; LIVER TOXICITY; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

ACETAMINOPHEN; ANALGESICS, NON-NARCOTIC; ANIMALS; BENZOQUINONES; CA(2+) MG(2+)-ATPASE; CALCIUM; IMINES; MALE; MICROSOMES, LIVER; RATS; RATS, SPRAGUE-DAWLEY; RYANODINE;

EID: 0032942437     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-4274(99)00009-0     Document Type: Article

References (24)

1. Abramson J.J., Buck E., Salama G., Casida J.E., Pessah I.N. Mechanism of anthraquinone-induced calcium release from skeletal muscle sarcoplasmic reticulum. J. Biol. Chem. 263:1988;18750-18758.
2. Burcham P.C., Harman A.W. Effect of acetaminophen hepatotoxicity on hepatic mitochondrial and microsomal calcium contents in mice. Toxicol. Lett. 44:1988;91-99.
3. Burcham P.C., Harman A.W. Mitochondrial dysfunction in paracetamol hepatotoxicity: in vitro studies in isolated mouse hepatocytes. Toxicol. Lett. 50(15):1990;37-48.
4. Dahlin D.C., Nelson S.D. Synthesis, decomposition kinetics, and preliminary toxicological studies of pure N-acetyl-p-benzoquinone imine, a proposed toxic metabolite of acetaminophen. J. Med. Chem. 25(1):1982;85-87.
5. Dai Y., Cederbaum A.I. Cytotoxicity of acetaminophen in human cytochrome P4502E1-transfected HepG2 cells. J. Pharmacol. Exp. Ther. 273:1995;1497-1505.
6. Grewal K.K., Racz W.J. Intracellular calcium disruption as a second event in acetaminophen-induced hepatotoxicity. Can. J. Physiol. Pharmacol. 71:1993;26-33.
7. Henry T.R., Wallace K. Differential mechanisms of induction of the mitochondrial permeability transition by quinones of varying chemical reactivities. Toxicol. Appl. Pharmacol. 134:1995;195-203.
8. Kaplin A.I., Ferris C.D., Voglmaier S.M., Snyder S.H. Purified reconstituted inositol 1,4,5-trisphosphate receptors. Thiol reagents act directly on receptor protein. J. Biol. Chem. 269:1994;28972-28978.
9. Lilly L.B., Gollan J.L. Ryanodine-induced calcium release from hepatic microsomes and permeabilized hepatocytes. Am. J. Physiol. 268:1995;1017-1024.
10. 2+ release induced by benzoquinone derivatives. Arch. Biochem. Biophys. 259:1987;283-295.
11. 2+ release by rat liver mitochondria. Arch. Biochem. Biophys. 267:1988;539-550.
12. Parmar D.V., Ahmed G., Khandkar M.A., Katyare S.S. Mitochondrial ATPase: a target for paracetamol-induced hepatotoxicity. Eur. J. Pharmacol. 293(19):1995;225-229.
13. Pumford N.R., Roberts D.W., Benson R.W., Hinson J.A. Immunochemical quantitation of 3-(cystein-S-yl)acetaminophen protein adducts in subcellular liver fractions following a hepatotoxic dose of acetaminophen. Biochem. Pharmacol. 40:1990;573-579.
14. Shoshan-Barmatz V. High affinity ryanodine binding sites in rat liver endoplasmic reticulum. FEBS Lett. 263:1990;317-320.
15. Shoshan-Barmatz V., Pressley T.A., Higham S., Kraus-Friedmann N. Distinct ryanodine- and inositol 1,4,5-trisphosphate-binding sites in hepatic microsomes. Biochem. J. 276:1991;41-46.
16. 3.radical. J. Biol. Chem. 265:1990;8392-8399.
17. 2+ release from liver microsomes. Biochemistry. 35:1996;15839-15845.
18. Stoyanovsky D.A., Cederbaum A.I. Redox-cycling of iron ions triggers calcium release from liver microsomes. Free Radic. Biol. Med. 24:1998;745-753.
19. 2+ sequestration by toxic agents. Biochem. Pharmacol. 34:1985;3717-3723.
20. Tirmenstein M.A., Nelson S.D. Subcellular binding and effects on calcium homeostasis produced by acetaminophen and a nonhepatotoxic regioisomer, 3′-hydroxyacetanilide, in mouse liver. J. Biol. Chem. 264:1989;9814-9819.
21. Tsokos-Kuhn J.O., Todd E.L., McMillin-Wood J.B., Mitchell J.R. ATP-dependent calcium uptake by rat liver plasma membrane vesicles. Effect of alkylating hepatotoxins in vivo. Mol. Pharmacol. 28:1985;56-61.
22. Wallace K.B., Eells J.T., Madeira V.M., Cortopassi G., Jones D.P. Mitochondria-mediated cell injury. Symposium overview. Fundam. Appl. Toxicol. 38:1997;23-37.
23. 2+ release from sarcoplasmic reticulum via an oxidation reaction. J. Biol. Chem. 264:1989;21725-21736.
24. 2+ sequestering. Relation to SH groups. J. Biol. Chem. 265:1990;2184-2189.