Artemisinin enhances heme-catalysed oxidation of lipid membranes

Free Radical Biology and Medicine

Volumn 22, Issue 7, 1997, Pages 1283-1288

  Berman, Peter A ^a   Adams, Paul A ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

Artemisinin; Free radicals; Heme; Malaria; Malondialdehyde; Oxygen radicals; Plasmodium falciparum; Qinghaosu; Vitamin E

Indexed keywords

ALPHA TOCOPHEROL; ARTEMISIN; ARTEMISININ; ARTESUNATE; FREE RADICAL; HEME; OXYGEN RADICAL; PEROXIDASE;

ARTICLE; CELL VACUOLE; CHINESE HERB; CONTROLLED STUDY; DRUG MECHANISM; FEVER; HUMAN; HUMAN CELL; LIPID MEMBRANE; MALARIA; OXIDATION REDUCTION REACTION; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL;

ANTIMALARIALS; ARTEMISININS; BENZOTHIAZOLES; ERYTHROCYTE MEMBRANE; FREE RADICAL SCAVENGERS; HEME; HUMANS; HYDROGEN PEROXIDE; LIPID PEROXIDATION; MALONDIALDEHYDE; MEMBRANE LIPIDS; OXIDATION-REDUCTION; PEROXIDASES; SESQUITERPENES; SPECTROPHOTOMETRY; SULFONIC ACIDS; THIOBARBITURATES; VITAMIN E;

ARTESUNATE; PLASMODIUM FALCIPARUM; TRIXIS;

EID: 0030893778     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(96)00508-4     Document Type: Article

References (25)

1. Wyler D. J. Malaria - resurgence, resistance and research. N. Engl. J. Med. 308:1983;875-878.
2. Klayman D. L. Qinghaosu (artemisinin): An antimalarial drug from China. Science. 228:1985;1049-1055.
3. Hien T. T., White N. J. Qinghaosu. Lancet. 341:1993;603-608.
4. Hassan Alin M., Bjorkman A., Landberg-Lindgren A., Ashton M. The effect of artemisinin, its derivatives and mefloquine against chloroquine resistant strains of Plasmodium falciparum in vitro. Trans. R. Soc. Trop. Med. Hyg. 86:1992;365-367.
5. van Thiel P. P. A. M., van Gool T., Hopperus Buma A. P. C. C., Tendeloo C. H., Leentvaar-Kuijpers A., Kager P. A. Artemisinin compounds in treatment of malaria. Lancet. 341:1993;1034-1035.
6. Meshnick S. R., Thomas A., Ranz A., Xu C.-M., Pan H.-Z. Artemisinin (qinghaosu): The role of intracellular hemin in its mechanism of antimalarial action. Mol. Biochem. Parasitol. 49:1991;181-190.
7. Meshnick S. R., Yang Y.-Z., Lima V., Kuypers F., Kamchon-wongpaisan S., Yuthavong Y. Iron-dependant free radical generation from the antimalarial agent artemisinin (qinghaosu). Antimicrobiol. Agents Chemother. 37:1993;1108-1114.
8. Zhang F., Gosser D. K., Meshnick S. R. Hemin-catalysed decomposition of artemisinin. Biochem. Pharmacol. 43:1992;1805-1809.
9. Hong Y.-L., Yang Y.-Z., Meshnick S. R. The interaction of artemisinin with malarial hemozoin. Mol. Biochem. Parasitol. 63:1994;121-128.
10. Yang Y. Z., Asawamahasakda W., Meshnick S. R. Alkylation of human albumin by the antimalarial artemisinin. Biochem. Pharmacol. 46:1993;336-339.
11. Krungkrai S. R., Yuthavong Y. The antimalarial action on Plasmodium falciparum of qinghaosu and artesunate in combination with agents which modulate oxidant stress. Trans. R. Soc. Trop. Med. Hyg. 81:1987;710-714.
12. Levander O. A., Ager A. L., Morris V. C., May R. G. Qinghaosu, dietary vitamin E, selenium, and cod-liver oil: Effect on the susceptibility of mice to the malarial parasite Plasmodium yoelii. Am. J. Clin. Nutr. 50:1989;346-352.
13. Goldberg D. E., Slater A. F. G., Cerami A., Henderson G. B. Hemoglobin degradation in the malaria parasite Plasmodium falciparum: An ordered process in a unique organelle. Proc. Natl. Acad. Sci. USA. 87:1990;2931-2935.
14. Tappel A. L. The mechanism of the oxidation of unsaturated fatty acids catalyzed by hematin compounds. Arch. Biochem. Biophys. 44:1953;378-395.
15. Slater A. F. G., Swiggard W. J., Orton B. R., Flitter W. D., Goldberg D. E., Cerami A., Henderson G. B. An iron-carboxylate bond links the heme units of malaria pigment. Proc. Natl. Acad. Sci. USA. 88:1991;325-329.
16. Slater A., Cerami A. Inhibition by chloroquine of a novel haem polymerase enzyme activity in malaria trophozoites. Nature. 355:1992;167-169.
17. Egan T. J., Ross D. C., Adams P. A. Quinoline antimalarial drugs inhibit spontaneous formation of B-haematin. FEBS Lett. 352:1994;54-57.
18. Yayon A., Cabantchik Z. I., Ginsburg H. Susceptibility of human malaria parasites to chloroquine is pH dependant. Proc. Natl. Acad. Sci. USA. 82:1985;2784-2788.
19. Chou A. C., Chevli R., Fitch C. D. Ferriproto-porphyrin IX fulfills the criteria for identification as the chloroquine receptor of malaria parasites. Biochemistry. 19:1980;1543-1549.
20. Adams P. A., Berman P. A. Reaction between ferriprotoporphyrin IX and the antimalarial endoperoxide artesunate gives an intermediate species with enhanced redox catalytic activity. J. Pharm. Pharmacol. 48:1996;179-183.
21. Scott M. D., Meshnick S. R., Williams R. A., Chiu D. T.-Y., Pan H. C., Lubin B. H., Kuypers F. A. Qinghaosu-mediated oxidation in normal and abnormal erythrocytes. J. Lab. Clin. Med. 114:1989;401-406.
22. Lepage G., Munoz G., Champagne J., Roy C. C. Preparative steps necessary for the accurate measurement of malondialdehyde by high-performance liquid chromatography. Anal. Biochem. 197:1991;277-283.
23. Hoving E. B., Laing C., Rutgers H. M., Teggeler M., van Doormaal J. J., Muskiet F. A. J. Optimized determination of malondialdehyde in plasma lipid extracts using 1,3-diethyl-2-thiobarbituric acid: influence of detection method and relations with lipids and fatty acids in plasma from healthy adults. Clin. Chim. Acta. 208:1992;63-76.
24. Muhia D. K., Thomas C. G., Ward S. A., Edwards G., Mberu E. K., Watkins W. M. Ferriprotoporphyrin catalysed decomposition of artemether: Analytical and pharmacological implications. Biochem. Pharmacol. 48:1994;889-895.
25. Bowry V. W., Ingold K. U., Stocker R. Vitamin E in human low-density lipoprotein - When and how this anti-oxidant becomes a pro-oxidant. Biochem. J. 288:1992;341-344.