Methemoglobin incites primaquine toxicity through single-electron oxidation and modification

Journal of Basic and Clinical Physiology and Pharmacology

Volumn 24, Issue 2, 2013, Pages 105-114

  Balaji, S N ^a   Trivedi, Vishal ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Hemolysis; Methemoglobin; Peroxidase; Primaquine; RBC

Indexed keywords

HEME; HYDROXYL RADICAL; METHEMOGLOBIN; PRIMAQUINE; REACTIVE OXYGEN METABOLITE; TRACE METAL;

ARTICLE; BINDING AFFINITY; BLOOD TOXICITY; CELL MEMBRANE; CHEMICAL MODIFICATION; COMPARATIVE STUDY; ELECTRON TRANSPORT; ENZYME INHIBITION; ERYTHROCYTE; FENTON REACTION; HEMOLYSIS; HUMAN; HUMAN CELL; LIPID PEROXIDATION; MASS SPECTROMETRY; MEMBRANE STRUCTURE; METABOLITE; MOLECULAR MODEL; OSMOTIC STRESS; OXIDATION; OXIDATIVE STRESS; PH; SCANNING ELECTRON MICROSCOPY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

ANTIMALARIALS; ANTIOXIDANTS; CATALASE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ERYTHROCYTE MEMBRANE; ERYTHROCYTES; GLUTATHIONE TRANSFERASE; HEMATOCRIT; HEMOLYSIS; HUMANS; METHEMOGLOBIN; MICROSCOPY, ELECTRON, SCANNING; MODELS, MOLECULAR; OSMOTIC PRESSURE; OXIDATION-REDUCTION; OXIDATIVE STRESS; PRIMAQUINE; PROTEIN BINDING; SPECTRUM ANALYSIS; SUPEROXIDE DISMUTASE;

EID: 84887472172     PISSN: 07926855     EISSN: 21910286     Source Type: Journal    
DOI: 10.1515/jbcpp-2012-0058     Document Type: Article

References (43)

1. Sachs J, Malaney P. The economic and social burden of malaria. Nature 2002;415: 680-5. (Pubitemid 34136401)
2. White NJ. Determinants of relapse periodicity in Plasmodium vivax malaria. Malar J 2011;10:297.
3. Baird JK, Hoffman SL. Primaquine therapy for malaria. Clin Infect Dis 2004;39: 1336-45. (Pubitemid 39458520)
4. Sinclair D, Donegan S, Isba R, Lalloo DG. Artesunate versus quinine for treating severe malaria. Cochrane Database Syst Rev 2012;6:CD005967.
5. Anthony MP, Burrows JN, Duparc S, Moehrle J, Wells TN. The global pipeline of new medicines for the control and elimination of malaria. Malar J 2012;11:316.
6. Baird JK. Primaquine toxicity forestalls effective therapeutic management of the endemic malarias. Int J Parasitol 2012;42: 1049-54.
7. Taylor WR, White NJ. Antimalarial drug toxicity: a review. Drug Saf 2004;27: 25-61. (Pubitemid 38186936)
8. Stanton RC. Glucose-6-phosphate dehydrogenase, NADPH, and cell survival. IUBMB Life 2012;64: 362-9.
9. Beutler E, Duparc S. Glucose-6-phosphate dehydrogenase deficiency and antimalarial drug development. Am J Trop Med Hyg 2007;77: 779-89. (Pubitemid 351844308)
10. Mihaly GW, Ward SA, Edwards G, Orme ML, Breckenridge AM. Pharmacokinetics of primaquine in man: identification of the carboxylic acid derivative as a major plasma metabolite. Br J Clin Pharmacol 1984;17: 441-6. (Pubitemid 14055274)
11. Frischer H, Mellovitz RL, Ahmad T, Nora MV. The conversion of primaquine into primaquine-aldehyde, primaquine-alcohol, and carboxyprimaquine, a major plasma metabolite. J Lab Clin Med 1991;117: 468-76.
12. Fletcher KA, Barton PF, Kelly JA. Studies on the mechanisms of oxidation in the erythrocyte by metabolites of primaquine. Biochem Pharmacol 1988;37: 2683-90.
13. Bowman ZS, Jollow DJ, McMillan DC. Primaquine-induced hemolytic anemia: role of splenic macrophages in the fate of 5-hydroxyprimaquine-treated rat erythrocytes. J Pharmacol Exp Ther 2005;315: 980-6. (Pubitemid 41635383)
14. Bowman ZS, Morrow JD, Jollow DJ, McMillan DC. Primaquineinduced hemolytic anemia: role of membrane lipid peroxidation and cytoskeletal protein alterations in the hemotoxicity of 5-hydroxyprimaquine. J Pharmacol Exp Ther 2005;314: 838-45. (Pubitemid 41043869)
15. Bowman ZS, Oatis JE Jr., Whelan JL, Jollow DJ, McMillan DC. Primaquine-induced hemolytic anemia: susceptibility of normal versus glutathione-depleted rat erythrocytes to 5-hydroxyprimaquine. J Pharmacol Exp Ther 2004;309: 79-85. (Pubitemid 38393117)
16. Croft S. Antimalarial chemotherapy: mechanisms of action, resistance and new directions in drug discovery. Drug Discov Today 2001;6:1151.
17. Ganesan S, Tekwani BL, Sahu R, Tripathi LM, Walker LA. Cytochrome P(450)-dependent toxic effects of primaquine on human erythrocytes. Toxicol Appl Pharmacol 2009;241: 14-22.
18. Ganesan S, Chaurasiya ND, Sahu R, Walker LA, Tekwani BL. Understanding the mechanisms for metabolism-linked hemolytic toxicity of primaquine against glucose 6-phosphate dehydrogenase deficient human erythrocytes: evaluation of eryptotic pathway. Toxicology 2012;294: 54-60.
19. Anstey NM, Hassanali MY, Mlalasi J, Manyenga D, Mwaikambo ED. Elevated levels of methaemoglobin in Tanzanian children with severe and uncomplicated malaria. Trans R Soc Trop Med Hyg 1996;90: 147-51. (Pubitemid 26141084)
20. Reeder BJ. The redox activity of hemoglobins: from physiologic functions to pathologic mechanisms. Antioxid Redox Signal 2010 1;13: 1087-123.
21. Carmona-Fonseca J, Alvarez G, Maestre A. Methemoglobinemia and adverse events in Plasmodium vivax malaria patients associated with high doses of primaquine treatment. Am J Trop Med Hyg 2009;80: 188-93.
22. Balaji SN, Trivedi V. Extracellular methemoglobin mediated ROS spike extracellular methemoglobin mediated early ROS spike triggers osmotic fragility and RBC destruction: an insight into the enhanced hemolysis during malaria. Indian J Clin Biochem 2012;27: 178-85.
23. Laurie AT, Jackson RM. Q-SiteFinder: an energy-based method for the prediction of protein-ligand binding sites. Bioinformatics 2005;21: 1908-16. (Pubitemid 40668026)
24. Schneidman-Duhovny D, Inbar Y, Nussinov R, Wolfson HJ. PatchDock and SymmDock: servers for rigid and symmetric docking. Nucleic Acids Res 2005;33:W363-7. (Pubitemid 44529944)
25. Andrusier N, Nussinov R, Wolfson HJ. FireDock: fast interaction refinement in molecular docking. Proteins 2007;69: 139-59. (Pubitemid 47339146)
26. Dongre VG, Karmuse PP, Rao PP, Kumar A. Development and validation of UPLC method for determination of primaquine phosphate and its impurities. J Pharm Biomed Anal 2008;46: 236-42.
27. Trivedi V, Chand P, Srivastava K, Puri SK, Maulik PR, Bandyopadhyay U. Clotrimazole inhibits hemoperoxidase of Plasmodium falciparum and induces oxidative stress. Proposed antimalarial mechanism of clotrimazole. J Biol Chem 2005;280: 41129-36. (Pubitemid 41832165)
28. Monk LS, Fagerstedt KV, Crawford RM. Superoxide dismutase as an anaerobic polypeptide: a key factor in recovery from oxygen deprivation in Iris pseudacorus? Plant Physiol 1987; 85: 1016-20.
29. Habig WH, Pabst MJ, Jakoby WB. Glutathione S-transferases. The first enzymatic step in mercapturic acid formation. J Biol Chem 1974;249: 7130-9.
30. Beers RF Jr., Sizer IW. A spectrophotometric method for measuring the breakdown of hydrogen peroxide by catalase. J Biol Chem 1952;195: 133-40.
31. Hortola P. SEM analysis of red blood cells in aged human bloodstains. Forensic Sci Int 1992;55: 139-59.
32. Rodkey FL, Hill TA, Pitts LL, Robertson RF. Spectrophotometric measurement of carboxyhemoglobin and methemoglobin in blood. Clin Chem 1979;25: 1388-93. (Pubitemid 9247020)
33. Parcell S. Sulfur in human nutrition and applications in medicine. Altern Med Rev 2002;7: 22-44. (Pubitemid 34203978)
34. Kiefer CR, Snyder LM. Oxidation and erythrocyte senescence. Curr Opin Hematol 2000;7: 113-6. (Pubitemid 30106543)
35. Strother A, Fraser IM, Allahyari R, Tilton BE. Metabolism of 8-aminoquinoline antimalarial agents. Bull World Health Organ 1981;59: 413-25. (Pubitemid 11024765)
36. Carson PE, Hohl R, Nora MV, Parkhurst GW, Ahmad T, Scanlan S, et al. Toxicology of the 8-aminoquinolines and genetic factors associated with their toxicity in man. Bull World Health Organ 1981;59: 427-37. (Pubitemid 11024766)
37. Lee CC, Kinter LD, Heiffer MH. Subacute toxicity of primaquine in dogs, monkeys, and rats. Bull World Health Organ 1981; 59: 439-48. (Pubitemid 11024767)
38. Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM. Identification of human cytochrome P(450) s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol 2003;59: 429-42. (Pubitemid 37214951)
39. Beaudoin RL, Aikawa M. Primaquine-induced changes in morphology of exoerythrocytic stages of malaria. Science 1968;160: 1233-4.
40. Kamchonwongpaisan S, Samoff E, Meshnick SR. Identification of hemoglobin degradation products in Plasmodium falciparum. Mol Biochem Parasitol 1997;86: 179-86. (Pubitemid 27245179)
41. Hall AH, Kulig KW, Rumack BH. Drug- and chemical-induced methaemoglobinaemia. Clinical features and management. Med Toxicol 1986;1: 253-60. (Pubitemid 16005258)
42. Wagner MA, Andemariam B, Desai SA. A two-compartment model of osmotic lysis in Plasmodium falciparum-infected erythrocytes. Biophys J 2003;84: 116-23. (Pubitemid 36026384)
43. Brumen M, Heinrich R. A metabolic osmotic model of human erythrocytes. Biosystems 1984;17: 155-69. (Pubitemid 15222415)