Suicidal inactivation of methemoglobin by generation of thiyl radical: Insight into NAC mediated protection in RBC

Current Molecular Medicine

Volumn 13, Issue 6, 2013, Pages 1000-1009

  Balaji, S N ^a   Trivedi, V ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Antioxidant; Free radicals; Hemolysis; Malaria; NAC; RBC

Indexed keywords

ACETYLCYSTEINE; GLUTATHIONE; HYDROGEN PEROXIDE; METHEMOGLOBIN; PEROXIDASE;

ARTICLE; CELL PROTECTION; CONTROLLED STUDY; CYTOLYSIS; DRUG BINDING; ELECTRON TRANSPORT; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVITY; ERYTHROCYTE; HEMOLYSIS; HUMAN; HUMAN CELL; OXIDATION; OXIDATIVE STRESS; SPECTRUM; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 84881346738     PISSN: 15665240     EISSN: 18755666     Source Type: Journal    
DOI: 10.2174/15665240113139990054     Document Type: Article

References (45)

1. MacPherson GG, Warrell MJ, White NJ, Looareesuwan S, Warrell DA. Human cerebral malaria. A quantitative ultrastructural analysis of parasitized erythrocyte sequestration. Am J Pathol 1985; 119(3): 385-401.
2. Pasvol G, Wainscoat JS, Weatherall DJ. Erythrocytes deficiency in glycophorin resist invasion by the malarial parasite Plasmodium falciparum. Nature 1982; 297(5861): 64-66.
3. Garcia-Garcia A, Rodriguez-Rocha H, Madayiputhiya N, Pappa A, Panayiotidis MI, Franco R. Biomarkers of protein oxidation in human disease. Curr Mol Med 2012; 12(6): 681-697.
4. Singer ST, Ataga KI. Hypercoagulability in sickle cell disease and beta-thalassemia. Curr Mol Med 2008; 8(7): 639-645.
5. Stocker R, Hunt NH, Buffinton GD, Weidemann MJ, Lewis Hughes PH, Clark IA. Oxidative stress and protective mechanisms in erythrocytes in relation to Plasmodium vinckei load. Proc Natl Acad Sci USA 1985; 82(2): 548-551.
6. Fibach E, Rachmilewitz E. The role of oxidative stress in hemolytic anemia. Curr Mol Med 2008; 8(7): 609-619.
7. Schofield L, Grau GE. Immunological processes in malaria pathogenesis. Nat Rev Immunol 2005; 5(9): 722-735.
8. Dondorp AM, Kager PA, Vreeken J, White NJ. Abnormal blood flow and red blood cell deformability in severe malaria. Parasitol Today 2000; 16(6): 228-232.
9. Pamplona A, Hanscheid T, Epiphanio S, Mota MM, Vigario AM. Cerebral malaria and the hemolysis/methemoglobin/heme hypothesis: shedding new light on an old disease. Int J Biochem Cell Biol 2009; 41(4): 711-716.
10. Fitri LE, Sardjono TW, Simamora D, Sumarno RP, Setyawati SK. High dose of N-acetylcysteine increase HO and MDA levels and decrease GSH level of HUVECs exposed with malaria serum. Trop Biomed 2011; 28(1): 7-15.
11. Kelly GS. Clinical applications of N-acetylcysteine. Altern Med Rev 1998; 3(2): 114-127.
12. Ziment I. Acetylcysteine: a drug that is much more than a mucokinetic. Biomed Pharmacother 1988; 42(8): 513-519.
13. Mazor D, Golan E, Philip V, et al. Red blood cell permeability to thiol compounds following oxidative stress. Eur J Haematol 1996; 57(3): 241-246.
14. Charunwatthana P, Abul Faiz M, Ruangveerayut R, et al. N-acetylcysteine as adjunctive treatment in severe malaria: a randomized, double-blinded placebo-controlled clinical trial. Crit Care Med 2009; 37(2): 516-522.
15. Arreesrisom P, Dondorp AM, Looareesuwan S, Udomsangpetch R. Suppressive effects of the anti-oxidant N-acetylcysteine on the anti-malarial activity of artesunate. Parasitol Int 2007; 56(3): 221-226.
16. Treeprasertsuk S, Krudsood S, Tosukhowong T, et al. N-acetylcysteine in severe falciparum malaria in Thailand. Southeast Asian J Trop Med Public Health 2003; 34(1): 37-42.
17. Watt G, Jongsakul K, Ruangvirayuth R. A pilot study of N-acetylcysteine as adjunctive therapy for severe malaria. QJM 2002; 95(5): 285-290.
18. Nuchsongsin F, Chotivanich K, Charunwatthana P, et al. Effects of malaria heme products on red blood cell deformability. Am J Trop Med Hyg 2007; 77(4): 617-622.
19. Sheffner AL, Medler EM, Bailey KR, Gallo DG, Mueller AJ, Sarett HP. Metabolic studies with acetylcysteine. Biochem Pharmacol 1966; 15(10): 1523-1535.
20. Parcell S. Sulfur in human nutrition and applications in medicine. Altern Med Rev. 2002 Feb;7(1):22-44.
21. Gaunt SD, Baker DC, Green RA. Clinicopathologic evaluation N-acetylcysteine therapy in acetaminophen toxicosis in the cat. Am J Vet Res 1981; 42(11): 1982-1984.
22. Bolli R, Jeroudi MO, Patel BS, et al. Marked reduction of free radical generation and contractile dysfunction by antioxidant therapy begun at the time of reperfusion. Evidence that myocardial stunning is a manifestation of reperfusion injury. Circ Res 1989; 65(3): 607-622.
23. Macone A, Fontana M, Barba M, et al. Antioxidant properties of aminoethylcysteine ketimine decarboxylated dimer: a review. Int J Mol Sci 2011; 12(5): 3072-3084.
24. Ates B, Abraham L, Ercal N. Antioxidant and free radical scavenging properties of N-acetylcysteine amide (NACA) and comparison with N-acetylcysteine (NAC). Free Radic Res 2008; 42(4): 372-377.
25. Takashima M, Shichiri M, Hagihara Y, Yoshida Y, Niki E. Reactivity toward oxygen radicals and antioxidant action of thiol compounds. Biofactors 2012; 38(3): 240-248.
26. Aruoma OI, Halliwell B, Hoey BM, Butler J. The antioxidant action of N-acetylcysteine: its reaction with hydrogen peroxide, hydroxyl radical, superoxide, and hypochlorous acid. Free Radic Biol Med 1989; 6(6): 593-597.
27. Kwak HS, Yim HS, Chock PB, Yim MB. Endogenous intracellular glutathionyl radicals are generated in neuroblastoma cells under hydrogen peroxide oxidative stress. Proc Natl Acad Sci USA 1995; 92(10): 4582-4586.
28. Harman LS, Carver DK, Schreiber J, Mason RP. One- and two-electron oxidation of reduced glutathione by peroxidases. J Biol Chem 1986; 261(4): 1642-1648.
29. Sagrista ML, Garcia AE, Africa De Madariaga M, Mora M. Antioxidant and pro-oxidant effect of the thiolic compounds N-acetyl-L-cysteine and glutathione against free radical-induced lipid peroxidation. Free Radic Res 2002; 36(3): 329-340.
30. Subramanian R, Tam J, Aidasani D, Reid DL, Skiles GL. Novel cytochrome p450 bioactivation of a terminal phenyl acetylene group: formation of a one-carbon loss benzaldehyde and other oxidative products in the presence of N-acetyl cysteine or glutathione. Chem Res Toxicol 2011; 24(5): 677-686.
31. Beck JS, Saari JT. Permeability coefficients by the hemolytic method: a correction. Biophys J 1977; 17(3): 281-282.
32. 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(2): 178-185.
33. Trivedi V, Srivastava K, Puri SK, Maulik PR, Bandyopadhyay U. Purification and biochemical characterization of a heme containing peroxidase from the human parasite P. falciparum. Protein Expr Purif 2005; 41(1): 154-161.
34. Gutierrez-Correa J, Stoppani AO. Inactivation of myocardial dihydrolipoamide dehydrogenase by myeloperoxidase systems: effect of halides, nitrite and thiol compounds. Free Radic Res 1999; 30(2): 105-117.
35. Reeder BJ, Svistunenko DA, Cooper CE, Wilson MT. The radical and redox chemistry of myoglobin and hemoglobin: from in vitro studies to human pathology. Antioxid Redox Signal 2004; 6(6): 954-966.
36. Sugita Y, Nomura S, Yoneyama Y. Purification of reduced pyridine nucleotide dehydrogenase from human erythrocytes and methemoglobin reduction by the enzyme. J Biol Chem 1971; 246(19): 6072-6078.
37. 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(50): 41129-41136.
38. Hong SY, Yang JO, Lee EY, Lee ZW. Effects of N-acetyl-L-cysteine and glutathione on antioxidant status of human serum and 3T3 fibroblasts. J Korean Med Sci 2003; 18(5): 649-654.
39. Trivedi V, Chand P, Maulik PR, Bandyopadhyay U. Mechanism of horseradish peroxidase-catalyzed heme oxidation and polymerization (beta-hematin formation). Biochim Biophys Acta 2005; 1723(1-3): 221-228.
40. Jiang JJ, Liu KJ, Jordan SJ, Swartz HM, Mason RP. Detection of free radical metabolite formation using in vivo EPR spectroscopy: evidence of rat hemoglobin thiyl radical formation following administration of phenylhydrazine. Arch Biochem Biophys 1996; 330(2): 266-270.
41. Huang L, Wojciechowski G, Ortiz de Montellano PR. Prosthetic heme modification during halide ion oxidation. Demonstration of chloride oxidation by horseradish peroxidase. J Am Chem Soc 2005; 127(15): 5345-5353.
42. Doerge DR. Mechanism-based inhibition of lactoperoxidase by thiocarbamide goitrogens. Biochemistry 1986; 25(16): 4724-4728.
43. Takeoka S, Sakai H, Kose T, et al. Methemoglobin formation in hemoglobin vesicles and reduction by encapsulated thiols. Bioconjug Chem 1997; 8(4): 539-544.
44. Sprong RC, Winkelhuyzen-Janssen AM, Aarsman CJ, van Oirschot JF, van der Bruggen T, van Asbeck BS. Low-dose N-acetylcysteine protects rats against endotoxin-mediated oxidative stress, but high-dose increases mortality. Am J Respir Crit Care Med 1998; 157(4 Pt 1): 1283-1293.
45. Ator MA, David SK, Ortiz de Montellano PR. Structure and catalytic mechanism of horseradish peroxidase. Regiospecific meso alkylation of the prosthetic heme group by alkylhydrazines. J Biol Chem 1987; 262(31): 14954-14960.