Co-oxidation-mediated xenobiotic activation and cytotoxicity by 12-lipoxygenase in intact platelets

Toxicology

Volumn 247, Issue 2-3, 2008, Pages 154-160

  Lim, Kyung Min ^a   Kim, Jung Sun ^a   Bae, Ok Nam ^a   Noh, Ji Yoon ^a   Chung, Seung Min ^a   Chung, Ka Young ^a   Chung, Jin Ho ^a  

^a Seoul National University   (South Korea)

Author keywords

Naphthol; Co oxidation; Cytotoxicity; Lipoxygenase; Peroxidase mediated bioactivation; Platelets; Prostaglandin H synthase; Reactive metabolite

Indexed keywords

1 NAPHTHOL; ARACHIDONATE 12 LIPOXYGENASE; ARACHIDONIC ACID; PROSTAGLANDIN SYNTHASE; THIOL;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CELL MEMBRANE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; COVALENT BOND; CYTOTOXICITY; FEMALE; MITOCHONDRIAL MEMBRANE POTENTIAL; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; RAT; THROMBOCYTE;

ANIMALS; ARACHIDONATE 12-LIPOXYGENASE; ARACHIDONIC ACID; BIOTRANSFORMATION; BLOOD PLATELETS; FEMALE; NAPHTHOLS; OXIDATION-REDUCTION; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; RATS; RATS, SPRAGUE-DAWLEY; XENOBIOTICS;

EID: 42749089530     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2008.02.015     Document Type: Article

References (37)

1. Bedard L.L., Smith G.B., Reid K.R., Petsikas D., and Massey T.E. Investigation of the role of lipoxygenase in bioactivation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human lung. Chem. Res. Toxicol. 15 (2002) 1267-1273
2. Bergmeyer H.U., Bernt E., and Hess B. Methods in Enzymatic Analysis (1965), Academic Press, New York
3. Bieniek G. The presence of 1-naphthol in the urine of industrial workers exposed to naphthalene. Occup. Environ. Med. 51 (1994) 357-359
4. Bloom J.C., and Brandt J.T. Toxic Responses of the Blood. In: Klassen C.D. (Ed). Casarett and Doull's Toxicology-Basic Science of Poisons (2001), McGraw Hill 389-418
5. Brash A.R. A review of possible roles of the platelet 12-lipoxygenase. Circulation 72 (1985) 702-707
6. Brash A.R. Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate. J. Biol. Chem. 274 (1999) 23679-23682
7. Brash A.R. Arachidonic acid as a bioactive molecule. J. Clin. Invest. 107 (2001) 1339-1345
8. Chao Y.C., Kupper L.L., Serdar B., Egeghy P.P., Rappaport S.M., and Nylander-French L.A. Dermal exposure to jet fuel JP-8 significantly contributes to the production of urinary naphthols in fuel-cell maintenance workers. Environ. Health Persp. 114 (2006) 182-185
9. Cho H., Ueda M., Tamaoka M., Hamaguchi M., Aisaka K., Kiso Y., Inoue T., Ogino R., Tatsuoka T., Ishihara T., et al. Novel caffeic acid derivatives: extremely potent inhibitors of 12-lipoxygenase. J. Med. Chem. 34 (1991) 1503-1505
10. Chou D.S., Lee J.J., Hsiao G., Hsieh C.Y., Tsai Y.J., Chen T.F., and Sheu J.R. Baicalein induction of hydroxyl radical formation via 12-lipoxygenase in human platelets: an ESR study. J. Agric. Food Chem. 55 (2007) 649-655
11. Dannhardt G., and Lehr M. In-vitro evaluation of 5-lipoxygenase and cyclo-oxygenase inhibitors using bovine neutrophils and platelets and HPLC. J. Pharm. Pharmacol. 44 (1992) 419-424
12. Degen G.H. Prostaglandin-H synthase containing cell lines as tools for studying metabolism and toxicity of xenobiotics. Toxicology 82 (1993) 243-256
13. Deschamps J.D., Kenyon V.A., and Holman T.R. Baicalein is a potent in vitro inhibitor against both reticulocyte 15-human and platelet 12-human lipoxygenases. Bioorg. Med. Chem. 14 (2006) 4295-4301
14. Doherty M.D., and Cohen G.M. Metabolic activation of 1-naphthol by rat liver microsomes to 1,4-naphthoquinone and covalent binding species. Biochem. Pharmacol. 33 (1984) 3201-3208
15. Doherty M.D., Wilson I., Wardman P., Basra J., Patterson L.H., and Cohen G.M. Peroxidase activation of 1-naphthol to naphthoxy or naphthoxy-derived radicals and their reaction with glutathione. Chem. Biol. Interact. 58 (1986) 199-215
16. Eghbal M.A., Tafazoli S., Pennefather P., and O'Brien P.J. Peroxidase catalysed formation of cytotoxic prooxidant phenothiazine free radicals at physiological pH. Chem. Biol. Interact. 151 (2004) 43-51
17. Eling T.E., Thompson D.C., Foureman G.L., Curtis J.F., and Hughes M.F. Prostaglandin H synthase and xenobiotic oxidation. Annu. Rev. Pharmacol. Toxicol. 30 (1990) 1-45
18. Galati G., Sabzevari O., Wilson J.X., and O'Brien P.J. Prooxidant activity and cellular effects of the phenoxyl radicals of dietary flavonoids and other polyphenolics. Toxicology 177 (2002) 91-104
19. Goldman R., Claycamp G.H., Sweetland M.A., Sedlov A.V., Tyurin V.A., Kisin E.R., Tyurina Y.Y., Ritov V.B., Wenger S.L., Grant S.G., and Kagan V.E. Myeloperoxidase-catalyzed redox-cycling of phenol promotes lipid peroxidation and thiol oxidation in HL-60 cells. Free Radic. Biol. Med. 27 (1999) 1050-1063
20. Guengerich F.P. Cytochromes P450, drugs, and diseases. Mol. Interv. 3 (2003) 194-204
21. Johnson E.N., Brass L.F., and Funk C.D. Increased platelet sensitivity to ADP in mice lacking platelet-type 12-lipoxygenase. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 3100-3105
22. Katoh A., Ikeda H., Murohara T., Haramaki N., Ito H., and Imaizumi T. Platelet-derived 12-hydroxyeicosatetraenoic acid plays an important role in mediating canine coronary thrombosis by regulating platelet glycoprotein IIb/IIIa activation. Circulation 98 (1998) 2891-2898
23. Kenyon V., Chorny I., Carvajal W.J., Holman T.R., and Jacobson M.P. Novel human lipoxygenase inhibitors discovered using virtual screening with homology models. J. Med. Chem. 49 (2006) 1356-1363
24. Kulkarni A.P. Lipoxygenase-a versatile biocatalyst for biotransformation of endobiotics and xenobiotics. Cell. Mol. Life Sci. 58 (2001) 1805-1825
25. Lim K.M., Lee J.Y., Kim J.S., and Chung J.H. Prostaglandin H synthase and lipoxygenase mediated activation of xenobiotics in platelets. Adv. Exp. Med. Biol. 469 (1999) 631-637
26. Maskrey B.H., Bermudez-Fajardo A., Morgan A.H., Stewart-Jones E., Dioszeghy V., Taylor G.W., Baker P.R., Coles B., Coffey M.J., Kuhn H., and O'Donnell V.B. Activated platelets and monocytes generate four hydroxyphosphatidylethanolamines via lipoxygenase. J. Biol. Chem. 282 (2007) 20151-20163
27. Nyby M.D., Sasaki M., Ideguchi Y., Wynne H.E., Hori M.T., Berger M.E., Golub M.S., Brickman A.S., and Tuck M.L. Platelet lipoxygenase inhibitors attenuate thrombin- and thromboxane mimetic-induced intracellular calcium mobilization and platelet aggregation. J. Pharmacol. Exp. Ther. 278 (1996) 503-509
28. O'Brien P.J. Peroxidases. Chem. Biol. Interact. 129 (2000) 113-139
29. Parkinson A. Biotransformation of Xenobiotics. In: Klassen C.D. (Ed). Casarett and Doull's Toxicology-Basic Science of Poisons (2001), McGrawHill 133-224
30. Pidgeon G.P., Tang K., Cai Y.L., Piasentin E., and Honn K.V. Overexpression of platelet-type 12-lipoxygenase promotes tumor cell survival by enhancing alpha(v)beta(3) and alpha(v)beta(5) integrin expression. Cancer Res. 63 (2003) 4258-4267
31. Ross D., and Moldeus P. Generation of reactive species and fate of thiols during peroxidase-catalyzed metabolic activation of aromatic amines and phenols. Environ. Health. Perspect. 64 (1985) 253-257
32. Roy P., and Kulkarni A.P. Co-oxidation of acrylonitrile by soybean lipoxygenase and partially purified human lung lipoxygenase. Xenobiotica 29 (1999) 511-531
33. Sautebin L., Caruso D., Galli G., and Paoletti R. Preferential utilization of endogenous arachidonate by cyclooxygenase in incubations of human platelets. FEBS Lett. 157 (1983) 173-178
34. Tafazoli S., and O'Brien P.J. Prooxidant activity and cytotoxic effects of indole-3-acetic acid derivative radicals. Chem. Res. Toxicol. 17 (2004) 1350-1355
35. Tafazoli S., Wright J.S., and O'Brien P.J. Prooxidant and antioxidant activity of vitamin E analogues and troglitazone. Chem. Res. Toxicol. 18 (2005) 1567-1574
36. Tafazoli S., Spehar D.D., and O'Brien P.J. Oxidative stress mediated idiosyncratic drug toxicity. Drug. Metab. Rev. 37 (2005) 311-325
37. Yu W.K., and Wells P.G. Evidence for lipoxygenase-catalyzed bioactivation of phenytoin to a teratogenic reactive intermediate: in vitro studies using linoleic acid-dependent soybean lipoxygenase, and in vivo studies using pregnant CD-1 mice. Toxicol. Appl. Pharmacol. 131 (1995) 1-12