Heme binding contributes to antimalarial activity of bis-quaternary ammoniums

Antimicrobial Agents and Chemotherapy

Volumn 47, Issue 8, 2003, Pages 2584-2589

  Biagini, Giancarlo A ^a   Richier, Eric ^b   Bray, Patrick G ^a   Calas, Michèle ^b   Vial, Henri ^b   Ward, Stephen A ^a  

^a LIVERPOOL SCHOOL OF TROPICAL MEDICINE   (United Kingdom)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,12 DODECANEMETHYLENE BIS(4 METHYL 5 ETHYLTHIAZOLIUM)DIIODIDE; ANTIMALARIAL AGENT; BISQUARTERNARY AMMONIUM; FUROSEMIDE; HEMATIN; HEME; HEMOZOIN; PHOSPHATIDYLCHOLINE; QUATERNARY AMMONIUM DERIVATIVE; T16; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; BINDING AFFINITY; BINDING SITE; CELL VACUOLE; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG DISTRIBUTION; DRUG MECHANISM; ERYTHROCYTE; ERYTHROCYTE MEMBRANE; HUMAN; HUMAN CELL; MEMBRANE PERMEABILITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; SCATCHARD PLOT;

ANIMALS; ANTIMALARIALS; ERYTHROCYTE MEMBRANE; ERYTHROCYTES; HEME; HEMEPROTEINS; HEMIN; HUMANS; PLASMODIUM FALCIPARUM; PROTEIN BINDING; QUATERNARY AMMONIUM COMPOUNDS; REGRESSION ANALYSIS; SPECTROPHOTOMETRY, ULTRAVIOLET; THIAZOLES; VACUOLES;

EID: 0041767496     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.47.8.2584-2589.2003     Document Type: Article

References (27)

1. Ancelin, M. L., M. Parant, M. J. Thuet, J. R. Philippot, and H. J. Vial. 1991. Increased permeability to choline in simian erythrocytes after Plasmodium knowlesi infection. Biochem. J. 273:701-709.
2. Ancelin, M. L., M. Calas, J. Bompart, G. Cordina, D. Martin, M. Ben Bari, T. Jei, P. Druilhe, and H. Vial. 1998. Antimalarial activity of 77 phospholipid polar head analogues: close correlation between inhibition of phospholipid metabolism and in vitro Plasmodium falciparum growth. Blood 91:1426-1437.
3. Berenbaum, M. C. 1978. A method for testing for synergy with any number of agents. J. Infect. Dis. 137:122-130.
4. Bray, P. G., O. Janneh, K. J. Raynes, M. Mungthin, H. Ginsburg, and S. A. Ward. 1999. Cellular uptake of chloroquine is dependent on binding to ferriprotoporphyrin IX and is independent of NHE activity in Plasmodium falciparum. J. Cell Biol. 145:363-376.
5. Calas, M., G. Cordina, J. Bompart, M. Ben Bari, T. Jei, M. L. Ancelin, and H. Vial. 1997. Antimalarial activity of molecules interfering with Plasmodium falciparum phospholipid metabolism-structure-activity relationship analysis. J. Med. Chem. 40:3557-3566.
6. Calas, M., M. L. Ancelin, G. Cordina, P. Portefaix, G. Piquet, V. Vidal-Sailhan, and H. Vial. 2000. Antimalarial activity of compounds interfering with Plasmodium falciparum phospholipid metabolism: comparison between mono- and bisquaternary ammonium salts. J. Med. Chem. 43:505-516.
7. Desai, S. A., S. M. Bezrukov, and J. Zimmerberg. 2000. A voltage-dependent channel involved in nutrient uptake by red blood cells infected with the malaria parasite. Nature 406:1001-1005.
8. Desjardins, R. E., C. J. Canfield, J. D. Haynes, and J. D. Chulay. 1979. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob. Agents Chemother. 16:710-718.
9. Foley, M., and L. Tilley. 1998. Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents. Pharmacol. Ther. 79:55-87.
10. Francis, S. E., D. J. Sullivan, Jr., and D. E. Goldberg. 1997. Hemoglobin metabolism in the malaria parasite Plasmodium falciparum. Annu. Rev. Microbiol. 51:97-123.
11. Ginsburg, H., M. Krugliak, O. Eidelman, and Z. I. Cabantchik. 1983. New permeability pathways induced in membranes of Plasmodium falciparum-infected erythrocytes. Mol. Biochem. Parasitol. 8:177-190.
12. Ginsburg, H., O. Famin, J. Zhang, and M. Krugliak. 1998. Inhibition of glutathione-dependent degradation of heme by chloroquine and amodiaquine as a possible basis for their antimalarial mode of action. Biochem. Pharmacol. 56:1305-1313.
13. Kirk, K. 2001. Membrane transport in the malaria-infected erythrocyte. Physiol. Rev. 81:495-537.
14. Kirk, K., and H. A. Horner. 1995. Novel anion dependence of induced cation transport in malaria-infected erythrocytes. J. Biol. Chem. 270:24270-24275.
15. Lambros, C., and J. P. Vanderberg. 1979. Synchronisation of Plasmodium falciparum erythrocyte stages in culture. J. Parasitol. 65:418-420.
16. Moon, R. P., L. Tyas, U. Certa, K. Rupp, D. Bur, C. Jacquet, H. Matile, H. Loetscher, F. Grueninger-Leitch, J. Kay, B. M. Dunn, C. Berry, and R. G. Ridley. 1997. Expression and characterisation of plasmepsin I from Plasmodium falciparum. Eur. J. Biochem. 244:552-560.
17. O'Neill, P. M., D. J. Willock, S. R. Hawley, P. G. Bray, R. C. Storr, S. A. Ward, and B. K. Park. 1997. Synthesis, antimalarial activity, and molecular modeling of tebuquine analogues. J. Med. Chem. 40:437-448.
18. Ridley, R. G. 2002. Medical need, scientific opportunity and the drive for antimalarial drugs. Nature 415:686-693.
19. Saliba, K. J., P. I. Folb, and P. J. Smith. 1998. Role for the Plasmodium falciparum digestive vacuole in chloroquine resistance. Biochem. Pharmacol. 56:313-320.
20. Saliba, K. J., H. A. Horner, and K. Kirk. 1998. Transport and metabolism of the essential vitamin pantothenic acid in human erythrocytes infected with the malaria parasite Plasmodium falciparum. J. Biol. Chem. 273:10190-10195.
21. Slater, A. F. 1993. Chloroquine: mechanism of drug action and resistance in Plasmodium falciparum. Pharmacol. Ther. 57:203-235.
22. Staines, H. M., C. Rae, and K. Kirk. 2000. Increased permeability of the malaria-infected erythrocyte to organic cations. Biochim. Biophys. Acta 1463:88-98.
23. Stead, A. M., P. G. Bray, I. G. Edwards, H. P. DeKoning, B. C. Elford, P. A. Stocks, and S. A. Ward. 2001. Diamidine compounds: selective uptake and targeting in Plasmodium falciparum. Mol. Pharmacol. 59:1298-1306.
24. Sullivan, D. J., Jr., I. L. Gluzman, D. G. Russell, and D. E. Goldberg. 1996. On the molecular mechanisms of chloroquine's antimalarial action. Proc. Natl. Acad. Sci. USA 93:11865-11870.
25. Trager, W., and J. B. Jenson. 1976. Human malaria parasites in continuous culture. Science 193:673-675.
26. Wengelnik, K., V. Vidal, M. L. Ancelin, A. M. Cathiard, J. L. Morgat, C. H. Kocken, M. Calas, S. Herrera, A. W. Thomas, and H. J. Vial. 2002. A class of potent antimalarials and their specific accumulation in infected erythrocytes. Science 295:1311-1314.
27. Yayon, A., R. Timberg, S. Friedman, and H. Ginsburg. 1984. Effects of chloroquine on the feeding mechanism of the intraerythrocytic human malarial parasite Plasmodium falciparum. J. Protozool. 31:367-372.