Haematin (haem) polymerization and its inhibition by quinoline antimalarials

Annals of Tropical Medicine and Parasitology

Volumn 91, Issue 5, 1997, Pages 559-566

  Ridley, R G ^a   Dorn, A ^a   Vippagunta, S R ^b   Vennerstrom, J L ^b  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMODIAQUINE; ANTIMALARIAL AGENT; CHLOROQUINE; ENZYME INHIBITOR; HEMATIN; HEME; HEMOGLOBIN; MEFLOQUINE; PRIMAQUINE; PROTEINASE; PYRIMETHAMINE; PYRONARIDINE; QUINOLINE DERIVATIVE; QUINOLINE DERIVED ANTIINFECTIVE AGENT;

ANTIMALARIAL ACTIVITY; CELL MEMBRANE; CELL VACUOLE; CONFERENCE PAPER; DRUG MECHANISM; DRUG PROTEIN BINDING; INTRACELLULAR KILLING; LIPID PEROXIDATION; MALARIA; MEMBRANE STRUCTURE; MULTIDRUG RESISTANCE; NONHUMAN; PLASMODIUM FALCIPARUM; PROTEIN DEGRADATION; PROTEIN POLYMERIZATION; PROTEIN SECRETION; PROTEINASE INHIBITION;

PLASMODIUM FALCIPARUM;

EID: 0030879643     PISSN: 00034983     EISSN: None     Source Type: Journal    
DOI: 10.1080/00034983.1997.11813174     Document Type: Conference Paper

References (45)

1. 3H chloroquine. American Journal of Pathology, 67, 277-284.
2. ASHONG, J. O., BLENCH, I. P. & WARHURST, D. C. (1989). The composition of haemozoin from Plasmodium falciparum. Transactions of the Royal Society of Tropical Medicine and Hygiene, 83, 167-172.
3. BALASUBRAMANIAN, D., MOHAN RAO, C. & PANJIPAN, B. (1984). The malaria parasite monitored by photoacoustic spectroscopy. Science, 223, 828-830.
4. BASCO, L. K., ANDERSEN, S. L., MILHOUS, W. K., LE BRAS, J. & VENNERSTROM, J. (1994). In vitro activity of bisquinoline WR268,668 against African clones and isolates of Plasmodium falciparum. American Journal of Tropical Medicine and Hygiene, 50, 200-205.
5. BEHERE, D. & GOFF, H. (1984). High affinity binding of quinine to iron (III) porphyrins: novel formation of alkoxide complexes from alcohols and amines. Journal of the American Chemical Society, 106, 4945-4950.
6. BENDRAT, K., BERGER, B. J. & CERAMI, A. (1995). Haem polymerization in malaria. Nature, 378, 138-139.
7. BERENBAUM, M. C. (1978). A method for testing for synergy with any number of agents. Journal of Infectious Diseases, 137, 122-130.
8. BROWN, W. (1911). Malarial pigment (so-called melanin): its nature and mode of production. Journal of Experimental Medicine, 13, 290-299.
9. CHOU, A. C., CHERLI, R. & FITCH, C. D. (1980). Ferriprotoporphyrin IX fulfills the criteria for identification as the chloroquine receptor of malaria parasites. Biochemistry, 19, 1543-1549.
10. COHEN, S., PHIFER, K. & YIELDING, K. (1964). Complex formation between chloroquine and ferrihaemic acid in vitro, and its effect on the antimalarial action of chloroquine. Nature, 202, 805-806.
11. CONSTANTINIDIS, I. & SATTERLEE, J. (1988a). UV-visible and carbon NMR studies of chloroquine binding to urohemin I chloride and uroporphyrin I in aqueous solutions. Journal of the American Chemical Society, 110, 4391-4395.
12. CONSTANTINIDIS, I. & SATTERLEE, J. (1988b). UV-visible and carbon NMR studies of quinine binding to urohemin I chloride and uroporphyrin I in aqueous solutions. Journal of the American Chemical Society, 110, 927-932.
13. DORN, A., STOFFEL, R., MATILE, H., BUBENDORF, A. & RIDLEY, R. G. (1995). Malarial haemozoin/β-haematin supports haem polymerization in the absence of protein. Nature, 374, 269-271.
14. EGAN, T. J., ROSS, D. C. & ADAMS, P. A. (1994). Quinoline anti-malarial drugs inhibit spontaneous formation of β-haematin (malaria pigment). FEBS Letters, 352, 54-57.
15. FITCH, C. D. & KANJANANGGULPAN, P. (1987). The state of ferriprotoporphyrin IX in malaria pigment. Journal of Biological Chemistry, 262, 15 552-15 555.
16. FITCH, C. D., CHEVLI, R., BANYAL, H. S., PHILLIPS, G., PFALLER, M. A. & KROGSTAD, D. J. (1982). Lysis of Plasmodium falciparum by ferriprotoporphyrin IX and a chloroquine-ferriprotoporphyrin IX complex. Antimicrobial Agents and Chemotherapy, 21, 819-822.
17. FU, S. & XIAO, S.-H. (1991). Pyronaridine: a new antimalarial drug. Parasitology Today, 7, 310-313.
18. GABAY, T., KRUGLIAK, M., SHALMIEV, G. & GINSBURG, H. (1994). Inhibition by antimalarial drugs of haemoglobin degradation and iron release in acidified red blood cell lysates - a possible mechanism for their antimalarial effect. Parasitology, 108, 371-381.
19. GEARY, T. & JENSEN, J. B. (1983). Lack of cross-resistance to 4-aminoquinolines in chloroquine resistant Plasmodium falciparum. Journal of Parasitology, 69, 978-105.
20. 3H chloroquine by drug-sensitive and -resistant strains of the human malarial parasite Plasmodium falciparum. Biochemical Pharmacology, 35, 3805-3812.
21. GLUZMAN, I. Y., FRANCIS, S. E., OKSMAN, A., SMITH, C. E., DUFFIN, K. L. & GOLDBERG, D. E. (1994). Order and specificity of the Plasmodium falciparum hemoglobin degradation pathway. Journal of Clinical Investigation, 93, 1602-1608.
22. GOLDIE, J. O., ROTH, E. F., OPPENHEIM, J. & VANDERBERG, J. P. (1990). Biochemical characterization of Plasmodium falciparum haemozoin. American Journal of Tropical Medicine and Hygiene, 83, 584-596.
23. GOOD, M. I. & SCHADER, R. I. (1982). Lethality and behavioural side effects of chloroquine. Journal of Clinical Psychopharmacology, 2, 40-47.
24. HAWLEY, S. R., BRAY, P. G., O'NEILL, P., PARK, B. K. & WARD, S. A. (1996a). The role of drug accumulation in 4-aminoquinoline antimalarial potency. Biochemical Pharmacology, 52, 723-733.
25. HAWLEY, S. R., BRAY, P. G. & WARD, S. A. (1996b). Amodiaquine accumulation in Plasmodium falciparum as a possible explanation for its superior antimalarial activity over chloroquine. Molecular and Biochemical Parasitology, 80, 15-25.
26. HEBBEL, R. P. & EATON, J. W. (1989). Pathobiology of heme interaction with the erythrocyte membrane. Seminars in Haematology, 26, 136-149.
27. HYDE, J. E. (1989). Point mutations and pyrimethamine resistance in Plasmodium falciparum. Parasitology Today, 5, 252-255.
28. KELLY, J. C., WASSERMAN, G. S., BERNARD, W. D., SCHULZ, C. & KNAPP, J. F. (1990). Chloroquine poisoning in a child. Annals of Emergency Medicine, 19, 47-50.
29. MESHNICK, S. (1996). Is haemozoin a target for antimalarial drugs? Annals of Tropical Medicine and Parasitology, 90, 367-372.
30. MOREAU, S., PERLY, B. & BIGUET, J. (1982). Interactions de la chloroquine avec la ferriprotoporphyrine. IX. Etude par résonance magnétique nucléaire. Biochimie, 64, 1015-1025.
31. MOREAU, S., PERLY, B., CHACHATY, C. & DELEUZE, C. (1985). A nuclear magnetic resonance study of the interactions of antimalarial drugs with porphyrins. Biochimica et Biophysica Acta, 840, 107-116.
32. OLLIARO, P. L. & GOLDBERG, D. E. (1995). The Plasmodium digestive vacuole: metabolic headquarters and choice drug target. Parasitology Today, 11, 294-297.
33. ORJIH, A. U., BANYAL, H. S., CHEVLI, R. & FITCH, C. D. (1981). Hemin lyses malaria parasites. Science, 214, 667-669.
34. PALMER, K. J., HOLLIDAY, S. M. & BROGDEN, R. N. (1993). Mefloquine. A review of its antimalarial activity, pharmacokinetic properties and therapeutic efficacy. Drugs, 45, 430-475.
35. RIDLEY, R. G. (1996). Haemozoin formation in malaria parasites: is there a haem polymerase? Trends in Microbiology, 4, 253-254.
36. RIDLEY, R. G., HOFHEINZ, W., MATILE, H., JAQUET, C., DORN, A., MASCIADRI, R., JOLIDON, S., RICHTER, W. F., GUENZI, A., GIROMETTA, M.-A., URWYLER, H., HUBER, W., THAITHONG, S. & PETERS, W. (1996). 4-Aminoquinoline analogs of chloroquine with shortened side chains retain activity against chloroquine-resistant Plasmodium falciparum. Antimicrobial Agents and Chemotherapy, 40, 1846-1854.
37. SLATER, A. F. G. (1993). Chloroquine: mechanism of drug action and resistance in Plasmodium falciparum. Pharmacology and Therapeutics, 57, 203-235.
38. SLATER, A. F. G. & CERAMI, A. (1992). Inhibition by chloroquine of a novel haem polymerase enzyme activity in malaria trophozoites. Nature, 355, 167-169.
39. SLATER, A. F. G., SWIGGARD, W. J., ORTON, B, R., FLITTER, W. D., GOLDBERG, D. E., CERAMI, A. & Henderson, G. B. (1991). An iron-carboxylate bond links the heme units of malaria pigment. Proceedings of the National Academy of Sciences of the United States of America, 88, 325-329.
40. SUGIOKA, Y. & SUZUKI, M. (1991). The chemical basis for the ferriprotoporphyrin IX-chloroquine complex induced lipid peroxidation. Biochimica et Biophysica Acta, 1074, 19-24.
41. SUGIOKA, Y., SUZUKI, M. & NAKANO, M. (1987). A ferriprotoporphyrin IX-chloroquine complex promotes membrane phospholipid peroxidation. A possible mechanism for antimalarial action. FEBS Letters, 223, 251-254.
42. SULLIVAN, D. J., GLUZMAN, I. Y. & GOLDBERG, D. E. (1996). Plasmodium hemozoin formation mediated by histidine-rich proteins. Science, 271, 219-222.
43. VEIGNIE, E. & MOREAU, S. (1991). The mode of action of chloroquine. Non-weak base properties of 4-aminoquinolines and antimalarial effects on strains of Plasmodium. Annals of Tropical Medicine and Parasitology, 85, 229-237.
44. VENNERSTROM, J. L., ELLIS, W. Y., AGER JR, A. L., ANDERSEN, S. L., GERENA, L. & MILHOUS, W. (1992). Bisquinolines. 1. N,N-Bis(7-chloroquinolin-4-yl)alkanediamines with potential against chloroquine resistant malaria. Journal of Medicinal Chemistry, 35, 2129-2134.
45. WARD, S. A., BRAY, P. G., MUNGTHIN, M. & HAWLEY, S. R. (1995). Current views on the mechanisms of resistance to quinoline-containing drugs in Plasmodium falciparum. Annals of Tropical Medicine and Parasitology, 89, 121-124.