Disposition of amodiaquine and related antimalarial agents in human neutrophils: Implications for drug design

Journal of Pharmacology and Experimental Therapeutics

Volumn 280, Issue 2, 1997, Pages 884-893

  Naisbitt, D J ^a   Ruscoe, J E ^a   Williams, D ^a   O'Neill, P M ^a   Pirmohamed, M ^a   Park, B K ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOPHENOL; AMODIAQUINE; ANTIMALARIAL AGENT; CHLOROQUINE; HALOFANTRINE; MEFLOQUINE; PYRONARIDINE;

AGRANULOCYTOSIS; ANTIGEN ANTIBODY COMPLEX; ANTIMALARIAL ACTIVITY; ARTICLE; BRAIN MALARIA; CELL FUNCTION; CELL ISOLATION; CELL VIABILITY; DRUG ACTIVATION; DRUG DESIGN; DRUG DISPOSITION; HUMAN; HUMAN CELL; LIPOPHILICITY; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL;

AMODIAQUINE; ANTIMALARIALS; CELL SURVIVAL; DRUG DESIGN; GLUTATHIONE; HUMANS; LEUKOCYTES, MONONUCLEAR; MOLECULAR STRUCTURE; NEUTROPHILS; STRUCTURE-ACTIVITY RELATIONSHIP; TETRADECANOYLPHORBOL ACETATE; TRITIUM;

EID: 0030894527     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (51)

1. AYMARD, J. P., WIOLAND, C., FERRY, R., NETTER, P. AND STREIFF, F.: The in vitro effect of amodiaquine on bone marrow granulocyte-macrophage progenitor cells from normal subjects. Fundam. Clin. Pharmacol. 6: 1-4, 1992.
2. 4-substituted 2,7- (and 2,8-) bis-(trifluoromethyl)-quinolm-4-amines. Aust. J. Chem. 38: 1827-1835, 1985.
3. BASCO, L. K. AND LE BRAS, J.: In vitro activity of pyronaridine against African strains of Plasmodium falciparum. Ann. Trop. Med. Parasitol. 86: 447-454, 1992.
4. BERGQVIST, Y. AND DOMEIJ-NYBERG, B.I Distribution of chloroquine and its metabolite desethyl-chloroquine in human blood cells, and its implications for the quantitative determination of these compounds in serum and plasma. J. Chromatogr. 272: 137-148, 1983.
5. BURCKHALTER, J. H., TENDWICK, J. H., JONES, F. H., JONES, P. A., HOLCOME, W. F. AND RAWLINS, A. L.: Aminoalkylphenols as antimalarials II (heterocyclic-amino)-α-amino-o-cresols: The synthesis of camoquine. J. Am. Chem. Sue. 70: 1363-1373, 1948.
6. CHRISTIE, G., BRECKENRIDGE, A. M. AND PARK, B. K.: Drug protein conjugates. XVIII. Detection of antibodies towards the antimalarial amodiaquine and its quinoneimine metabolite in man and the rat. Biochem. Pharmacol. 38: 1451-1458, 1989.
7. CLARKE, J. B., MAGGS, J. L., KITTERINGHAM, N. R. AND PARK, B. K.: Immunogenicity of amodiaquine in the rat. Int. Arch. Allergy Appl. Immunol. 91: 335-342, 1990.
8. CLARKE, J. B., NEFTEL, K., KITTERINGHAM, N. R. AND PARK, B. K.: Detection of antidrug IgG antibodies in patients with adverse drug reactions to amodiaquine. Int. Arch. Allergy Appl. Immunol. 95: 369-375, 1991.
9. COTGREAVE, I. A. AND MOLDEUS, P.: Methodologies for the application of monobromobimane to the simultaneous analysis of soluble and protein thiol components in biological systems. J. Biochem. Biophys. Methods 13: 231-249, 1986.
10. DOUER, D., SCHWARTZ, E., SHARED, N. AND RAMOT, B.: Amodiaquine induced agranulocytosis: Drug inhibition of myeloid colonies in the presence of patients serum. Isr. J. Med. Sci. 21: 331-334, 1985.
11. ELLIS, M. E., STEED, A. J. AND ADDISON, G. M.: Neutropenia associated with dual antimalarial chemoprophylaxis: Use of bone marrow culture as an aid in further drug management. J. Infect. 15: 147-152, 1987.
12. HARRISON, A. C., KITTERINGHAM, N. R., CLARKE, J. B. AND PARK, B. K.: The mechanism of bioactivation and antigen formation of amodiaquine in the rat. Biochem. Pharmacol. 43: 1421-1430, 1992.
13. HATTON, C. S. R., PETO, T. E. A., BUNCH, C. AND PASVOL, G.: Frequency of severe neutropenia associated with amodiaquine prophylaxis against malaria. Lancet 1: 411-413, 1986.
14. HAWLEY, S. R., BRAY, P. G., O'NEILL, P. M., NAISBITT, D. J., PARK, B. K. AND WARD, S. A.: Manipulation of the N-alkyl substituent in amodiaquine to overcome the verapamil-sensitive chloroquine resistance component. Antimicrob. Agents Chemother. 40: 2345-2349, 1996a.
15. HAWLEY, S. R., BRAY, P. G., O'NEILL, P. M., PARK, B. K. AND WARD, S. A.: The role of drug accumulation in 4-aminoquinoline antimalarial potency, Biochem. Pharmacol. 55: 723-722, 1996b.
16. HOFSTRA, A. H. AND UETRECHT, J. P.: Myeloperoxidase-mediated activation of xenobiotics by human leucocytes. Toxicology 82: 221-242, 1993.
17. HOUGH, S., KITTERINGHAM, N. R. AND PARK, B. K.: The role of bioactivation in amodiaquine immunogenicity (Abstract). Hum. Exp. Toxicol. 15: 650, 1996.
18. JEWELL, H., MAGGS, J. L., HARRISON, A. C., O'NEILL, P. M., RUSCOE, J. E. AND PARK, B. K.: The role of hepatic metabolism in the bioactivation and detoxification of amodiaquine. Xenobiotica 25: 199-217, 1995.
19. KLEBANOFF, S. J. AND CLARK, R. A.: Nitroblue tetrazolium reduction. In The Neutrophil: Function and Clinical Disorders, pp. 308-314, North Holland Publishing Co., Amsterdam, 1978.
20. KLEMPNER, M. S. AND STYRT, B.: Alkalinizing the intralysosomal pH inhibits degranulation of human neutrophils. J. Clin. Invest. 72: 1793-1800, 1983.
21. LABRO, M. T. AND BABIN-CHEVAYE, C.: Effects of amodiaquine, chloroquine and mefloquine on human polymorphonuclear neutrophil function in vitro. Antimicrob. Agents Chemother. 32: 1124-1130, 1988.
22. LARREY, D., CASTOT, A., PESSAYRE, D., MERIGOT, P., MACHAYEKHY, J. P., FELDAMN, G., LENOIR, A., RUELT, B. AND BENHAMOV, J. P.: Amodiaquine-induced hepatitis. Ann. Intern. Med. 104: 801-803, 1986.
23. LAURENT, F., SAIVAN, S., CHRETIEN, P., MAGNAVEL, J. F., PEYRON, F., SQALLI, A., TUFENKJI, A. E., CULAIS, Y., BABA, H., CAMPISTRON, G., REGIS, H., AMBROISETHOMAS, P., BRYSKIER, A. AND HOUIN, G.: Pharmacokinetic and pharmacodynamic study of amodiaquine and its two metabolites after single oral dose in human volunteers. Arzneim.-Forsch./Drug Res. 43: 612-616, 1993.
24. LULLMANN, H., LULLMANN-RAUCH, R. AND WASSERMANN, O.: Drug induced phos- pholipidosis. Crit. Rev. Toxicol. 4: 185-218, 1975.
25. MAGGS, J. L., TINGLE, M. D., KITTERINGHAM, N. R. AND PARK, B. K.: Drug-protein conjugates. XIV. Mechanisms of formation of protein-arylating intermediates from amodiaquine, a myelotoxin and hepatotoxin in man. Biochem. Pharmacol. 37: 303-311, 1988.
26. MAGGS, J. L., WILLIAMS, D., PIRMOHAMED, M. AND PARK, B. K.: The metabolic formation of reactive intermediates from clozapine, a drug associated with agranulocytosis in man. J. Pharmacol. Exp. Ther. 270: 1463-1475, 1995.
27. MEERHOF, L. J. AND ROOS, D.: Heterogenicity in chronic granulomatous disease detected with an improved nitroblue tetrazolium slide test. J. Leukocyte Biol. 39: 699-711, 1986.
28. NEFTEL, K. A., WOODTLY, W., SCHMID, M., FRICK, P. G. AND FEHR, J.: Amodiaquine induced agranulocytosis and liver damage. Br. Med. J. 292: 721-723, 1986.
29. O'DoNNELL, C. A., FOSTER, A. L. AND COLEMAN, J. W.: Penicillamine and penicillin can generate antigenic determinants on rat peritoneal cells in vitro. Immunology 72: 571-576, 1991.
30. O'NEILL, P. M.: The effect of chemical substitution on the metabolism and antimalarial activity of amodiaquine and primaquine. Ph.D. thesis, The University of Liverpool, Liverpool, UK, 1995.
31. O'NEILL, P. M., HARRISON, A. C., STORR, R. C., HAWLEY, S. R., WARD, S. A. AND PARK, B. K.: The effect of fluorine substitution on the metabolism and antimalarial activity of amodiaquine. J. Med. Chem. 37: 1363-1370, 1994.
32. O'NEILL, P. M., HAWLEY, S. R., STORR, R. C., WARD, S. A. AND PARK, B. K.: The effect of fluorine substitution on the antimalarial activity of tebuquine. Bioorg. Med. Chem. Lett. 6: 391-392, 1996.
33. O'NEILL, P. M., WILLOCK, D. J., HAWLEY, S. R., BRAY, P. G., STORR, R. C., WARD, S. A. AND PARK, B. K.: Synthesis, antimalarial activity and molecular modelling of tebuquine analogues. J. Med. Chem., in press, 1996.
34. PETERS, W.: Chemotherapy and Drug Resistance in Malaria. Academic Press, London, 1970.
35. PIRMOHAMED, M., GRAHAM, A., ROBERTS, P., SMITH, D., CHADWICK, D., BRECKENRIDGE, A. M. AND PARK, B. K.: Carbamazepine hypersensitivity assessment of clinical and in vitro chemical cross-reactivity with phenytoin and oxcarbazepine. Br. J. Clin. Pharmacol. 32: 741-749, 1991.
36. PIRMOHAMED, M., KITTERINGHAM, N. R. AND PARK, B. K.: The role of active metabolites in drug toxicity. Drug Safety 11: 114-144, 1994.
37. RHODES, E. G. H., BALL, J. AND FRANKLIN, I. M.: Amodiaquine induced agranulocytosis: Inhibition of colony growth in bone marrow by antimalarial agents. Br. Med. J. 292: 717-718, 1986.
38. RILEY, R. J., LAMBERT, C., MAGGS, J. L., KITTERINGHAM, N. R. AND PARK, B. K.: An in vitro study of the microsomal metabolism and cellular toxicity of phenytoin, sorbinil, and mianserin. Br. J. Clin. Pharmacol. 28: 577-588, 1988.
39. +-ATPases: An improved fluorescence assay. Biochem. Biophys. Acta 1183: 161-170, 1993.
40. ROUVEIX, B., COULOMBEL, L., AVMARD, J. P., CHAU, F. AND ABEL, L.: Amodiaquine-induced immune agranulocytosis. Br. J. Haematol. 71: 7-11, 1989.
41. RUSCOE, J. E., JEWELL, H., MAGGS, J. L., O'NEILL, P. M., STORR, C. R., WARD, S. A. AND PARK, B. K.: The effect of chemical substitution on the metabolic activation, metabolic detoxification, and pharmacological activity of amodiaquine in the mouse. J. Pharmacol. Exp. Ther. 273: 393-404, 1995.
42. SHAO, B. R.: A review of the antimalarial drug pyronaridine. Chin. Med. J. 103: 428-434, 1990.
43. SLATER, A. F. G.: Chloroquine: Mechanism of drug action and resistance in Plasmodium falciparum. Pharmacol. Ther. 57: 203-236, 1993.
44. SUREDA, A., HERNANDEZ-MADRID, A., PÉREZ VAQUERO, M. A., PEREZ DE OTEYZA, J., ESCRIBANO, L. AND ODRIOZOLA, J.: Quinidine-induced agranulocytosis of abrupt onset. Acta Haematol. 84: 43-44, 1990.
45. THOMPSON, D., CONSTANTIN-TEODOSIU, D., NORBECK, K., SVENSSON, B. AND MOLDEUS, P.: Metabolic activation of eugenol by myeloperoxidase and polymorphonuclear leukocytes, Chem. Res. Toxicol. 2: 186-192, 1989.
46. TINGLE, M. D., JEWELL, H., MAGGS, J. L., O'NEILL, P. M. AND PARK, B. K.: The bioactivation of amodiaquine by human polymorphonuclear leucocytes in vitro: Chemical mechanisms and the effects of fluorine substitution. Biochem. Pharmacol. 50: 1113-1119, 1995.
47. UETRECHT, J. P., ZAHID, N. AND RUBIN, R.: Metabolism of procainamide to a hydroxylamine by human neutrophils and mononuclear leukocytes. Chem. Res. Toxicol. 1: 74-78, 1988.
48. WATKINS, W. M., SIXSMITH, D. G., SPENCER, H. C., BORIGA, D. A., KARIUKI, D. M., KIPINGOR, T. AND KOECH, D. K.: Effectiveness of amodiaquine as treatment for chloroquine-resistant Plasmodium falciparum infections in Kenya. Lancet 1: 357-359, 1984.
49. WERBEL, L. M., COOK, P. D., ELSLAGER, E. F., HUNG, J. H., JOHNSON, J. L., KESTON, S. J., MCNAMARA, D. J., ORTWINE, D. F. AND WORTH, D. F.: Synthesis, antimalarial activity and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3[(alkylamino)methyl][1,1′-biphenyl]-2- ols and N-oxides. J. Med. Chem. 29: 924-939, 1986.
50. WINSTANLEY, P. A., EDWARDS, I. G., ORME, M. L. AND BRECKENRIDGE, A. M.: The disposition of amodiaquine in man after oral administration. Br. J. Pharm. Pharmacol. 23: 1-7, 1987.
51. YAMAMOTO, A., ADACHI, S., MATSUZAWA, Y., KITANI, T., HIRAOKA, A. AND SEKI, K.: Studies on drug induced lipidosis. VII. Effects of bis-β-diethyl-aminoethyl-ether of hexestrol, chloroquine, homochlorocyclizine, prenylamine and diazacholestrol on the lipid composition of rat liver and kidney. Lipids 11: 616-622, 1976.