Antimalarial chemotherapy: Young guns or back to the future?

Trends in Parasitology

Volumn 19, Issue 11, 2003, Pages 479-487

  Biagini, Giancarlo A ^a   O'Neill, Paul M ^b   Nzila, Alexis ^b,c   Ward, Stephen A ^a   Bray, Patrick G ^a  

^a LIVERPOOL SCHOOL OF TROPICAL MEDICINE   (United Kingdom)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

^c KENYATTA NATIONAL HOSPITAL   (Kenya)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOQUINOLINE DERIVATIVE; AMODIAQUINE; ANTIMALARIAL AGENT; ARTEETHER; ARTEMETHER; ARTEMISININ DERIVATIVE; ARTEMISONE; ARTESUNATE; ATOVAQUONE; CHLOROQUINE; CHLORPROGUANIL; CHLORPROGUANIL PLUS DAPSONE; DAPSONE; DIHYDROARTEMISININ DERIVATIVE; ENDOPEROXIDE; FANSIDAR; FLUOROAMODIAQUINE; FOLIC ACID ANTAGONIST; FOSMIDOMYCIN; ISOQUINE; MEFLOQUINE; N TERT BUTYLAMODIAQUINE; N [3 (2,4,5 TRICHLOROPHENOXY)PROPOXY] N' ISOPROPYLIMIDOCARBONIMIDIC DIAMIDE; PEROXIDE; PIPERAQUINE; PYRIMETHAMINE; PYRONARIDINE; QUININE; QUINOLINE DERIVATIVE; SODIUM ARTELINATE; TDR 40292; TEBUQUINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; WR 268668;

ANTIBIOTIC RESISTANCE; ANTIMALARIAL ACTIVITY; CELL CYCLE; CELL FUNCTION; CHEMOTHERAPY; COST EFFECTIVENESS ANALYSIS; DRUG BIOAVAILABILITY; DRUG EFFECT; DRUG EFFICACY; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SAFETY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG TARGETING; GENOME; HOST CELL; HUMAN; IC 50; LIVER TOXICITY; MALARIA; MITOCHONDRION; NEUROTOXICITY; NONHUMAN; PLASMA HALF LIFE; PLASTID; PROTEIN DEGRADATION; REVIEW; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TREATMENT OUTCOME;

ARTESUNATE; CINCHONA PUBESCENS; PROTOZOA;

EID: 0142196032     PISSN: 14714922     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.pt.2003.09.011     Document Type: Review

References (74)

1. Wellems T., Plowe C.V. Chloroquine-resistant malaria. J. Infect. Dis. 184:2001;770-776.
2. O'Neill P.M., et al. The 4-aminoquinolines-past, present and future: a chemical perspective. Pharmacol. Ther. 77:1998;29-58.
3. O'Neill P.M., et al. The effect of fluorine substitution on the metabolism and antimalarial activity of amodiaquine. J. Med. Chem. 37:1994;1362-1370.
4. Ruscoe J.E., et al. Effect of disposition of mannich antimalarial agents on their pharmacology and toxicology. Antimicrob. Agents Chemother. 42:1998;2410-2416.
5. Raynes K.J., et al. New 4-aminoquinoline mannich base antimalarials 1. effect of an alkyl substituent in the 5′-position of the 4(-hydroxylanilino side chain. J. Med. Chem. 42:1999;2747-2751.
6. De D., et al. Aminoquinolines that circumvent resistance in Plasmodium falciparum in vitro. Am. J. Trop. Med. Hyg. 55:1996;579-583.
7. Ridley R.G., et al. 4-aminoquinoline analogues of chloroquine with shortened side chains retain activity against chloroquine resistant plasmodium falciparum. Antimicrob. Agents Chemother. 40:1996;1846-1854.
8. Stocks P.A., et al. Novel short chain chloroquine analogues retain activity against chloroquine resistant K1 Plasmodium falciparum. J. Med. Chem. 45:2002;4975-4983.
9. Foley M., Tilley L. Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents. Pharmacol. Ther. 79:1998;55-87.
10. Bornstik K., et al. Antimalarial chemotherapeutic peroxides: artemisinin, yingzhaosu A and related compounds. Int. J. Parasitol. 32:2002;1661-1667.
11. Posner G.H., et al. Evidence for Fe(IV)=O in the molecular mechanism of action of the trioxane antimalarial artemisinin. J. Am. Chem. Soc. 117:1995;5885-5886.
12. Haynes R.K., et al. Ring opening of artemisinin (qinghaosu) and dihydroartemisinin and interception of the open hydroperoxides with formation of N-oxides - a chemical model for antimalarial mode of action. Tetrahedron Lett. 40:1999;4715-4718.
13. Hindley S., et al. mechanism-based design of parasite targeted artemisinin derivatives: synthesis and antimalarial activity of new diamine containing analogues. J. Med. Chem. 45:2002;1052-1063.
14. Haynes R.K. Artemisinin and derivatives: the future for malaria treatment? Curr. Opin. Infect. Dis. 14:2001;719-726.
15. Posner G.H., et al. Orally active, water-soluble antimalarial 3-aryltrioxanes: short synthesis and preclinical efficacy testing in rodents. J. Med. Chem. 45:2002;3824-3828.
16. Bachi M.D., et al. A short synthesis and biological evaluation of potent and nontoxic antimalarial bridged bicyclic -sulfonyl-endoperoxides. J. Med. Chem. 46:2003;2516-2533.
17. Robert A., et al. From mechanistic studies on artemisinin derivatives to new modular antimalarial drugs. Acc. Chem. Res. 35:2002;167-174.
18. Bzik D.J., et al. Molecular cloning and sequence analysis of the Plasmodium falciparum dihydrofolate reductase-thymidylate synthase gene. Proc. Natl. Acad. Sci. U. S. A. 84:1987;8360-8364.
19. Triglia T., Cowman A.F. Primary structure and expression of the dihydropteroate synthetase gene of Plasmodium falciparum. Proc. Natl. Acad. Sci. U. S. A. 91:1994;7149-7153.
20. Sibley C.H., et al. Pyrimethamine-sulfadoxine resistance in Plasmodium falciparum: what next? Trends Parasitol. 17:2001;582-588.
21. Mutabingwa T., et al. Chlorproguanil-dapsone for treatment of drug-resistant falciparum malaria in Tanzania. Lancet. 358:2001;1218-1223.
22. Watkins A., et al. The efficacy of antifolate antimalarial combinations in Africa: a predictive model based on pharmacodynamic and pharmacokinetic analyses. Parasitol. Today. 13:1997;459-464.
23. Knight D.J., Williamson P. The antimalarial activity of N-benzyl-oxydihydrotriazines. IV. The development of resistance to BRL 6231 (4,6-diamino-1,2-dihyydro-2-,2-dimethyl-1-(2,4,5-trichloropropyloxy)-1,3,5 triazine hydrochloride) by Plasmodium berghei. Ann. Trop. Med. Parasitol. 76:1982;9-14.
24. Winstanley P.A., et al. In vitro activities of novel antifolate drug combinations against Plasmodium falciparum and human granulocyte CFUs. Antimicrob. Agents Chemother. 39:1995;948-952.
25. Canfield C.J., et al. PS-15: a potent, orally active antimalarial from a new class of folic acid antagonists. Am. J. Trop. Med. Hyg. 49:1993;121-126.
26. Banerjee D., et al. Novel aspects of resistance to drugs targeted to dihydrofolate reductase and thymidylate synthase. Biochim. Biophys. Acta. 1587:2002;164-173.
27. Kinyanjui S.M., et al. The antimalarial triazine WR99210 and the prodrug PS-15: folate reversal of in vitro activity against Plasmodium falciparum and a non-antifolate mode of action of the prodrug. Am. J. Trop. Med. Hyg. 60:1999;943-947.
28. van Hensbroek M.B., et al. Iron, but not folic acid, combined with effective antimalarial therapy promotes haematological recovery in African children after acute falciparum malaria. Trans. R. Soc. Trop. Med. Hyg. 89:1995;672-676.
29. Wang P., et al. A modified in vitro sulfadoxine susceptibility assay for Plasmodium falciparum suitable for investigating Fansidar resistance. Parasitology. 115:1997;223-230.
30. Nzila A., et al. Chemosensitization of Plasmodium falciparum by Probenecid in vitro. Antimicrob. Agents Chemother. 47:2003;2108-2112.
31. Golenser J., et al. Plasmodium falciparum: in vitro induction of resistance to aminopterin. Exp. Parasitol. 52:1981;371-377.
32. Fidock D.A., Wellems T.E. Transformation with human dihydrofolate reductase renders malaria parasites insensitive to WR99210 but does not affect the intrinsic activity of proguanil. Proc. Natl. Acad. Sci. U. S. A. 94:1997;10931-10936.
33. Patel, O. et al. Sulfa drugs strike more than once. Trends Parasitol. (in press).
34. Roland S., et al. The characteristics and significance of sulfonamides as substrates for Escherichia coli dihydropteroate synthase. J. Biol. Chem. 254:1979;10337-10345.
35. Barnes M.J., et al. Impact of polyglutamation on sensitivity to raltitrexed and methotrexate in relation to drug-induced inhibition of de novo thymidylate and purine biosynthesis in CCRF-CEM cell lines. Clin. Cancer Res. 5:1999;2548-2558.
36. Vial H.J., et al. Transport of phospholipid synthesis precursors and lipid trafficking into malaria-infected erythrocytes. Novartis Found. Symp. 226:1999;74-83.
37. Ancelin M.L., et al. Antimalarial activity of 77 phospholipid polar head analogs: close correlation between inhibition of phospholipid metabolism and in vitro Plasmodium falciparum growth. Blood. 91:1998;1426-1437.
38. Wengelnik K., et al. A class of potent antimalarials and their specific accumulation in infected erythrocytes. Science. 295:2002;1311-1314.
39. Stead A.M., et al. Diamidine compounds: selective uptake and targeting in Plasmodium falciparum. Mol. Pharmacol. 59:2001;1298-1306.
40. Biagini G.A., et al. Haem binding contributes to the antimalarial activity of bis-quaternary ammoniums. Antimicrob. Agents Chemother. 47:2003;2584-2589.
41. Fichera M.E., Roos D.S. A plastid organelle as a drug target in apicomplexan parasites. Nature. 390:1997;407-409.
42. Delwiche C.F., Palmer J.D. The origin of plastids and their spread via secondary endosymbiosis. Plant Syst. Evol. 11:1997;51-86.
43. Waller R.F., et al. Nuclear-encoded proteins target to the plastid in Toxoplasma gondii and Plasmodium falciparum. Proc. Natl. Acad. Sci. U. S. A. 95:1998;12352-12357.
44. McLeod R., et al. Triclosan inhibits the growth of Plasmodium falciparum and Toxoplasma gondii by inhibition of apicomplexan Fab I. Int. J. Parasitol. 31:2001;109-113.
45. Surolia N., Surolia A. Triclosan offers protection against blood stages of malaria by inhibiting enoyl-ACP reductase of Plasmodium falciparum. Nat. Med. 7:2001;167-173.
46. Waller R.F., et al. A type II pathway for fatty acid biosynthesis presents drug targets in Plasmodium falciparum. Antimicrob. Agents Chemother. 47:2003;297-301.
47. Krugliak M., et al. Intraerythrocytic Plasmodium falciparum utilizes only a fraction of the amino acids derived from the digestion of host cell cytosol for the biosynthesis of its proteins. Mol. Biochem. Parasitol. 119:2002;249-256.
48. Greenbaum D.C., et al. A role for the protease falcipain 1 in host cell invasion by the human malaria parasite. Science. 298:2002;2002-2006.
49. Klemba M., Goldberg D.E. Biological roles of proteases in parasitic protozoa. Annu. Rev. Biochem. 71:2002;275-305.
50. Le Bonniec S., et al. Plasmepsin II, an acidic hemoglobinase from the Plasmodium falciparum food vacuole, is active at neutral pH on the host erythrocyte membrane skeleton. J. Biol. Chem. 274:1999;14218-14223.
51. Rosenthal P.J., et al. Cysteine proteases of malaria parasites: targets for chemotherapy. Curr. Pharm. Des. 8:2002;1659-1672.
52. Li R., et al. Structure-based design of parasitic protease inhibitors. Bioorg. Med. Chem. 4:1996;1421-1427.
53. Carroll C.D., et al. Identification of potent inhibitors of Plasmodium falciparum plasmepsin II from an encoded statine combinatorial library. Bioorg. Med. Chem. Lett. 8:1998;2315-2320.
54. Nezami A., et al. Identification and characterization of allophenylnorstatine-based inhibitors of plasmepsin II, an antimalarial target. Biochemistry. 41:2002;2273-2280.
55. Jiang S., et al. New class of small nonpeptidyl compounds blocks Plasmodium falciparum development in vitro by inhibiting plasmepsins. Antimicrob. Agents Chemother. 45:2001;2577-2584.
56. Wu Y., et al. Data-mining approaches reveal hidden families of proteases in the genome of malaria parasite. Genome Res. 13:2003;601-616.
57. Le Roch K., et al. Activation of a Plasmodium falciparum cdc2-related kinase by heterologous p25 and cyclin H. Functional characterization of a P. falciparum cyclin homologue. J. Biol. Chem. 275:2000;8952-8958.
58. Waters N.C., Geyer J.A. Cyclin-dependent protein kinases as therapeutic drug targets for antimalarial drug development. Expert Opin. Ther. Targets. 7:2003;7-17.
59. Harmse L., et al. Structure-activity relationships and inhibitory effects of various purine derivatives on the in vitro growth of Plasmodium falciparum. Biochem. Pharmacol. 62:2001;341-348.
60. Kirk K. Membrane transport in the malaria-infected erythrocyte. Physiol. Rev. 81:2001;495-537.
61. Efron L., et al. Direct interaction of dermaseptin S4 aminoheptanoyl derivative with intraerythrocytic malaria parasite leading to increased specific antiparasitic activity in culture. J. Biol. Chem. 277:2002;24067-24072.
62. Saliba K.J., Kirk K. Uptake of an antiplasmodial protease inhibitor into Plasmodium falciparum-infected human erythrocytes via a parasite-induced pathway. Mol. Biochem. Parasitol. 94:1998;297-301.
63. Gero A.M., et al. New malaria chemotherapy developed by utilization of a unique parasite transport system. Curr. Pharm. Des. 9:2003;867-877.
64. Gelb M.H., et al. Protein farnesyl and N-myristoyl transferases: piggy-back medicinal chemistry targets for the development of antitrypanosomatid and antimalarial therapeutics. Mol. Biochem. Parasitol. 126:2003;155-163.
65. Jomaa H., et al. Inhibitors of the nonmevalonate pathway of isoprenoid biosynthesis as antimalarial drugs. Science. 285:1999;1573-1576.
66. Lell B., et al. Fosmidomycin, a novel chemotherapeutic agent for malaria. Antimicrob. Agents Chemother. 47:2003;735-738.
67. Fry M., et al. Effect of mitochondrial inhibitors on adenosinetriphosphate levels in Plasmodium falciparum. Comp. Biochem. Physiol. B. 96:1990;775-782.
68. 2+ transport, and fatty acid-induced uncoupling in malaria parasites mitochondria. J. Biol. Chem. 275:2000;9709-9715.
69. Ellis J.E. Coenzyme Q homologs in parasitic protozoa as targets for chemotherapeutic attack. Parasitol. Today. 10:1994;296-301.
70. Syafruddin D., et al. Mutations in the Cytochrome b gene of Plasmodium berghei conferring resistance to atovaquone. Mol. Biochem. Parasitol. 104:1999;185-194.
71. Looareesuwan S., et al. Malarone (atovaquone and proguanil hydrochloride): a review of its clinical development for treatment of malaria. Am. J. Trop. Med. Hyg. 60:1999;533-541.
72. Krungkrai J., et al. Antimalarial activity of orotate analogs that inhibit dihydroorotase and dihydroorotate dehydrogenase. Biochem. Pharmacol. 43:1992;1295-1301.
73. Murphy A.D., et al. Plasmodium falciparum: cyanide-resistant oxygen consumption. Exp. Parasitol. 87:1997;112-120.
74. Kita K., et al. Role of complex II in anaerobic respiration of the parasite mitochondria from Ascaris suum and Plasmodium falciparum. Biochim. Biophys. Acta. 1553:2002;123-139.