Involvement of myeloperoxidase and NADPH oxidase in the covalent binding of amodiaquine and clozapine to neutrophils: Implications for drug-induced agranulocytosis

Chemical Research in Toxicology

Volumn 27, Issue 4, 2014, Pages 699-709

  Lobach, Alexandra R ^a   Uetrecht, Jack ^a,b  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMODIAQUINE; CLOZAPINE; MYELOPEROXIDASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE; PEROXIDASE; PROTEIN BINDING;

AGRANULOCYTOSIS; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BONE MARROW CELL; CONTROLLED STUDY; COVALENT BOND; DRUG BINDING; EX VIVO STUDY; FEMALE; HUMAN; HUMAN CELL; KNOCKOUT MOUSE; LEUKOCYTE ACTIVATION; MALE; NEUTROPHIL; NONHUMAN; PERIPHERAL LYMPHOCYTE; RAT; RESPIRATORY BURST; ANIMAL; CHEMICALLY INDUCED; ENZYME LINKED IMMUNOSORBENT ASSAY; METABOLISM; MOUSE; POLYACRYLAMIDE GEL ELECTROPHORESIS; SPRAGUE DAWLEY RAT;

AGRANULOCYTOSIS; AMODIAQUINE; ANIMALS; CLOZAPINE; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ENZYME-LINKED IMMUNOSORBENT ASSAY; FEMALE; MICE; MICE, KNOCKOUT; NADPH OXIDASE; NEUTROPHILS; PEROXIDASE; PROTEIN BINDING; RATS; RATS, SPRAGUE-DAWLEY;

EID: 84899416857     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx500019u     Document Type: Article

References (21)

1. Tesfa, D., Keisu, M., and Palmblad, J. (2009) Idiosyncratic drug-induced agranulocytosis: Possible mechanisms and management Am. J. Hematol. 84, 428-434
2. Uetrecht, J. and Naisbitt, D. J. (2013) Idiosyncratic adverse drug reactions: Current concepts Pharmacol. Rev. 65, 779-808
3. Ng, W., Lobach, A. R., Zhu, X., Chen, X., Liu, F., Metushi, I. G., Sharma, A., Li, J., Cai, P., Ip, J., Novalen, M., Popovic, M., Zhang, X., Tanino, T., Nakagawa, T., Li, Y., and Uetrecht, J. (2012) Animal models of idiosyncratic drug reactions Adv. Pharmacol. 63, 81-135
4. Liu, Z. C. and Uetrecht, J. P. (1995) Clozapine is oxidized by activated human neutrophils to a reactive nitrinium ion that irreversibly binds to the cells J. Pharmacol. Exp. Ther. 275, 1476-1483
5. Lai, W. G., Zahid, N., and Uetrecht, J. P. (1999) Metabolism of trimethoprim to a reactive iminoquinone methide by activated human neutrophils and hepatic microsomes J. Pharmacol. Exp. Ther. 291, 292-299
6. Ju, C. and Uetrecht, J. (1998) Oxidation of a metabolite of indomethacin (desmethyldeschlorobenzoylindomethacin) to reactive intermediates by activated neutrophils, hypochlorus acid and the myeloperoxidase system Drug Metab. Dispos. 27, 676-680
7. Hampton, M. B., Kettle, A. J., and Winterbourn, C. C. (1998) Inside the neutrophil phagosome: Oxidants, myeloperoxidase, and bacterial killing Blood 92, 3007-3017
8. Gardner, I., Leeder, J. S., Chin, T., Zahid, N., and Uetrecht, J. P. (1998) A comparison of the covalent binding of clozapine and olanzapine to human neutrophils in vitro and in vivo Mol. Pharmacol. 53, 999-1008
9. Tingle, M. D., Jewell, H., Maggs, J. L., O'Neill, P. M., and Park, B. K. (1995) The bioactivation of amodiaquine by human polymorphonuclear leucocytes in vitro: chemical mechanisms and the effects of fluorine substitution Biochem. Pharmacol. 50, 1113-1119
10. Naisbitt, D. J., Ruscoe, J. E., Williams, D., O'Neill, P. M., Pirmohamed, M., and Park, B. K. (1997) Disposition of amodiaquine and related antimalarial agents in human neutrophils: Implications for drug design J. Pharmacol. Exp. Ther. 280, 884-893
11. Dettling, M., Sachse, C., Muller-Oerlinghausen, B., Roots, I., Brockmoller, J., Rolfs, A., and Cascorbi, I. (2000) Clozapine-induced agranulocytosis and hereditary polymorphisms of clozapine metabolizing enzymes: No association with myeloperoxidase and cytochrome P4502D6 Pharmacopsychiatry 33, 218-220
12. Mosyagin, I., Dettling, M., Roots, I., Mueller-Oerlinghausen, B., and Cascorbi, I. (2004) Impact of myeloperoxidase and NADPH-oxidase polymorphisms in drug-induced agranulocytosis J. Clin. Psychopharmacol. 24, 613-617
13. Glogauer, M., Marchal, C. C., Zhu, F., Worku, A., Clausen, B. E., Foerster, I., Marks, P., Downey, G. P., Dinauer, M., and Kwiatkowski, D. J. (2003) Rac1 deletion in mouse neutrophils has selective effects on neutrophils functions J. Immunol. 170, 5652-5657
14. Harrison, A. C., Kitteringham, N. R., Clarke, J. B., and Park, B. K. (1992) The mechansim of bioactivation and antigen formation of amodiaquine in the rat Biochem. Pharmacol. 43, 1421-1430
15. Gray, L., van den Buuse, M., Scarr, E., Dean, B., and Hannan, A. J. (2009) Clozapine reverses schizophrenia-related behaviours in the metabotropic glutamate receptor 5 knockout mouse: Association with N-methyl- d -aspartic acid receptor up-regulation Int. J. Neuropsychopharmacol. 12, 45-60
16. Bedard, K. and Krause, K.-H. (2007) The NOX family of ROS-generating NADPH oxidases: Physiology and pathophysiology Physiol. Rev. 87, 245-313
17. Uetrecht, J. P. and Trager, W. (2007) Drug Metabolism: Chemical and Enzymatic Aspects, Informa Healthcare, New York.
18. Hofstra, A. H. and Uetrecht, J. P. (1993) Myeloperoxidase-mediated activation of xenobiotics by human leukocytes Toxicology 82, 221-242
19. Christie, G., Breckenridge, A. M., and Park, B. K. (1989) Drug-protein conjugates-XVIII. Detection of antibodies towards the antimalarial amodiaquine and its quinone imine metabolite in man and the rat Biochem. Pharmacol. 38, 1451-1458
20. Clarke, J. B., Maggs, J. L., Kitteringham, N. R., and Park, B. K. (1990) Immunogenicity of amodiaquine in the rat Int. Arch. Allergy Appl. Immunol. 91, 335-342
21. Maggs, J. L., Tingle, M. D., Kitteringham, N. R., and Park, B. K. (1988) Drug-protein conjugates-XIV. Mechanisms of formation of protein-arylating intermediates from amodiaquine, a myelotoxin and hepatotoxin in man Biochem. Pharmacol. 37, 303-311