Dihydrofolate reductase and antifolate resistance in malaria

Drug Resistance Updates

Volumn 1, Issue 6, 1998, Pages 397-406

  Sirawaraporn, Worachart ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000715174     PISSN: 13687646     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1368-7646(98)80015-0     Document Type: Review

References (77)

1. WHO Technical Report Series 805. Practical chemotherapy of malaria (1990), WHO 7-8
2. Coggeshall L.T. The selective action of sulfanilamide on the parasites of experimental malaria in monkeys in vivo and in vitro. J Exp Med 71 (1940) 13-20
3. Walker H.A., and van Dyke H.B. Control of malaria infection (P. lophurae) in ducks by sulfonamides. Proc Soc Exp Biol Med 48 (1941) 368-372
4. Maier J., and Riley E. Inhibition of antimalarial action of sulfonamides by p-aminobenzoic acid. Proc Soc Exp Biol Med 50 (1942) 152-154
5. McConkey G.A., Ittarat I., Meshnick S.R., and McCutchan T.F. Auxotrophs of Plasmodium falciparum dependent on p-aminobenzoic acid for growth. Proc Natl Acad Sci USA 91 (1994) 4244-4248
6. Roberts F., Roberts C.W., Johnson J.J., et al. Evidence for the shikimate pathway in apicomplexan parasites. Nature 393 (1998) 801-805
7. Ferone R. Folate metabolism in malaria. Bull WHO 55 (1977) 291-298
8. Krungkrai J., Webster H.K., and Yuthavong Y. De novo and salvage biosynthesis of pteroyl polyglutamates in the human malaria parasite, Plasmodium falciparum. Mol Biochem Parasitol 32 (1989) 25-38
9. Asawamahasakda W., and Yuthavong Y. The methionine synthesis cycle and salvage of methyltetrahydrofolate from host red cells in the malaria parasite (Plasmodium falciparum). Parasitology 107 (1993) 1-10
10. Krungkrai J., Webster H.K., and Yuthavong Y. Guanosine triphosphate cyclohydrolase in Plasmodium falciparum and other Plasmodium species. Mol Biochem Parasitol 17 (1985) 265-276
11. Brooks D.R., Wang P., Read M., et al. Sequence variation of the hydroxymethyldihydropterin pyrophosphokinase: dihydropteroate synthase gene in lines of the human malaria parasite, Plasmodium falciparum, with differing resistance to sulfadoxine. Eur J Biochem 224 (1994) 397-405
12. Triglia T., and Cowman A.F. Primary structure and expression of the dihydropteroate synthase gene of the Plasmodium falciparum. Proc Natl Acad Sci USA 91 (1994) 7149-7153
13. Ferone R. The enzymic synthesis of dihydropteroate and dihydrofolate by Plasmodium berghei. J Protozool 20 (1973) 459-463
14. Triglia T., Menting J.G.T., Wilson C., and Cowman A.F. Mutations in dihydropteroate synthase are responsible for sulfone and sulfonamide resistance in Plasmodium falciparum. Proc Natl Acad Sci USA 94 (1997) 13944-13949
15. Ivanetich K.M., and Santi D.V. Bifunctional thymidylate synthasedihydrofolate reductase in protozoa. FASEB J 4 (1990) 1591-1597
16. Garrett C.E., Coderre J.A., Meek T.D., et al. A bifunctional thymidylate synthetase-dihydrofolate reductase in protozoa. Mol Biochem Parasitol 11 (1984) 257-265
17. Grumont R., Washtien W.L., Caput D., and Santi D.V. Bifunctional thymidylate synthase-dihydrofolate reductase from Leishmania tropica: sequence homology with the corresponding monofunctional proteins. Proc Natl Acad Sci USA 83 (1986) 5387-5391
18. Beverley S.M., Ellenberger T.E., and Cordingley J.S. Primary structure of the gene encoding the bifunctional dihydrofolate reductasethymidylate synthase of Leishmania major. Proc Natl Acad Sci USA 83 (1986) 2584-2588
19. Roos D.S. Primary structure of the dihydrofolate reductasethymidylate synthase gene from Toxoplasma gondii. J Biol Chem 268 (1993) 6269-6280
20. Bzik D.J., Li W.-B., Horii T., and Inselburg J. Molecular cloning and sequence analysis of the Plasmodium falciparum dihydrofolate reductase-thymidylate synthase gene. Proc Natl Acad Sci USA 84 (1987) 8360-8364
21. Peterson D.S., Walliker D., and Wellems T.E. Evidence that a point mutation in dihydrofolate reductase-thymidylate synthase confers resistance to pyrimethamine in falciparum. Proc Natl Acad Sci USA 85 (1988) 9114-9118
22. Snewin V.A., England S.M., Sims P.F.G., and Hyde J.E. Characterization of the dihydrofolate reductase-thymidylate synthase from human malaria parasites highly resistant to pyrimethamine. Gene 76 (1989) 41-52
23. Hyde J.E. The dihydrofolate reductase-thymidylate synthase gene in the drug resistance of malaria parasites. Pharmacol Ther 48 (1990) 45-59
24. Cowman A.F., Morry M.J., Biggs B.A., Cross G., and Foote S.J. Amino acid changes linked to pyrimethamine resistance in the dihydrofolate reductase-thymidylate synthase gene of Plasmodium falciparum. Proc Natl Acad Sci USA 85 (1988) 9109-9113
25. Eldin de Pecoulas P., Basco L.K., Tahar R., Ouatas T., and Mazabraud A. Analysis of the Plasmodium vivax dihydrofolate reductasethymidylate synthase gene sequence. Gene 211 (1998) 177-185
26. Gutteridge W.E., and Trigg P.I. Action of pyrimethamine and related drugs against Plasmodium knowlesi in vitro. Parasitology 62 (1971) 431-444
27. Bruce-Chwatt L.J., Black R., Canfield C.J., et al. Chemotherapy of Malaria (1986), WHO, Geneva
28. Canfield C.J., Milhous W.K., Ager A.L., et al. A potent, orally active antimalarial from a new class of folic acid antagonists. Am J Trop Med Hyg 49 (1993) 121-126
29. Peter W. Chemotherapy and Drug Resistance in Malaria. In: Peter W. (Ed) (1987), Academic, Geneva
30. Wooden J.M., Hartwell L.H., Vasquez B., and Sibley C.H. Analysis in yeast of antimalarial drugs that the dihydrofolate reductase of Plasmodium falciparum. Mol Biochem Parasitol 85 (1997) 25-40
31. Hekmat-Nejad M., and Rathod P.K. Plasmodium falciparum: kinetic interactions of WR99210 with pyrimethamine-sensitive and pyrimethamine-resistant dihydrofolate reductase. Expt Parasitol 87 (1997) 222-228
32. Fidock D.A., and 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 USA 94 (1997) 10931-10936
33. Diggens S.M., Gutteridge W.E., and Trigg P.I. An altered dihydrofolate reductase associated with a pyrimethamine resistant P. berghei produced in a single step. Nature 228 (1970) 579-580
34. Ferone R. Dihydrofolate from pyrimethamine resistant. P. berghei. J Biol Chem 245 (1970) 850-854
35. Kan S.C., and Siddiqui W.A. Comparative studies on dihydrofolate reductases from Plasmodium falciparum and Aotus trivirgatus. J Protozool 26 (1979) 660-664
36. Sirawaraporn W., and Yuthavong Y. Kinetic and molecular properties of dihydrofolate reductase from pyrimethamine-sensitive and pyrimethamine-resistant Plasmodium chabaudi. Mol Biochem Parasitol 10 (1984) 355-367
37. Walter R.D. Altered dihydrofolate reductase in pyrimethamine-resistant Plasmodium falciparum. Mol Biochem Parasitol 19 (1986) 61-66
38. Chen G.X., Mueller C., Wendlinger M., and Zolg J.W. Kinetic and molecular properties of the dihydrofolate reductase from pyrimethamine-sensitive and pyrimethamine-resistant clones of the human malaria parasite Plasmodium falciparum. Mol Pharmacol 31 (1987) 430-437
39. McCutchan T.F., Welsh J.A., Dame J.B., et al. Mechanism of pyrimethamine resistance in recent isolates of Plasmodium falciparum. Antimicrob Agents Chemother 26 (1984) 656-659
40. Dieckmann A., and Jung A. The mechanism of pyrimethamine resistance in Plasmodium falciparum. Parasitology 93 (1986) 275-278
41. Inselburg J., Bzik D.J., and Horii T. Pyrimethamine resistant Plasmodium falciparum: overproduction of dihydrofolate reductase by a gene duplication. Mol Biochem Parasitol 26 (1987) 121-134
42. Cowman A.F., and Lew A.M. Antifolate drug selection results in duplication and rearrangement of chromosome 7 in Plasmodium chabaudi. Mol Cell Biol 9 (1989) 5182-5188
43. Tanaka M., Gu H.M., Bzik D.J., et al. Mutant dihydrofolate reductasethymidylate synthase genes in pyrimethamine-resistant Plasmodium falciparum with polymorphic chromosome duplications. Mol Biochem Parasitol 42 (1990) 83-91
44. Thaithong S., Chan S.-W., Songsomboon S., et al. Pyrimethamine resistant mutations in Plasmodium falciparum. Mol Biochem Parasitol 52 (1992) 149-158
45. Zolg J.W., Plitt J.R., Chen G.-X., and Palmer S. Point mutations in the dihydrofolate reductase-thymidylate synthase gene as the molecular basis for pyrimethamine resistance in Plasmodium falciparum. Mol Biochem Parasitol 36 (1989) 253-262
46. Hyde J. Point mutations and pyrimethamine resistance in Plasmodium falciparum. Parasitol Today 5 (1989) 252-255
47. Foote S.J., Galatis D., and Cowman A.F. Amino acids in the dihydrofolate reductase-thymidylate synthase gene of Plasmodium falciparum involved in cycloguanil resistance differ from those involved in pyrimethamine resistance. Proc Natl Acad Sci USA 87 (1990) 3014-3017
48. Basco L.K., de Pecoulas P.E., Wilson C.M., et al. Point mutations in the dihydrofolate reductase-thymidylate synthase gene and pyrimethamine and cycloguanil resistance in Plasmodium falciparum. Mol Biochem Parasitol 69 (1995) 135-138
49. Basco L.K., de Pecoulas P.E., Le Bras J., and Wilson C.M. Plasmodium falciparum: Molecular characterization of multidrug-resistant Cambodian isolates. Expt Parasitol 82 (1996) 97-103
50. Peterson D.S., Milhous W.K., and Wellems T.E. Molecular basis of differential resistance to cycloguanil and pyrimethamine in Plasmodium falciparum malaria. Proc Natl Acad Sci USA 87 (1990) 3018-3022
51. Sirawaraporn W., Sathitkul T., Sirawaraporn R., et al. Antifolate-resistant mutants of Plasmodium falciparum dihydrofolate reductase. Proc Natl Acad Sci USA 94 (1997) 1124-1129
52. Reeder J.C., Rieckmann K.H., Genton B., et al. Point mutations in the dihydrofolate reductase and dihydropteroate synthase genes and in vitro susceptibility to pyrimethamine and cycloguanil of Plasmodium falciparum isolates from Papua New Guinea. Am J Trop Med Hyg 55 (1996) 209-213
53. Zindrou S., Phuong Dung N., Duy Sy N., et al. Plasmodium falciparum: mutation pattern in the dihydrofolate reductase-thymidylate synthase genes of Vietnamese isolates, a novel mutation, and coexistence of two clones in a Thai patient. Expt Parasitol 84 (1996) 56-64
54. Plowe C.V., Cortese J.F., Djimde A., et al. Mutations in Plasmodium falciparum dihydrofolate reductase and dihydropteroate synthase and epidemiologic patterns of pyrimethamine-sulfadoxine use and resistance. J Infect Dis 176 (1997) 1590-1596
55. Wang P., Lee C.-S., Bayoumi R., et al. Resistance to antifolates in Plasmodium falciparum monitored by sequence analysis of dihydropteroate synthetase and dihydrofolate reductase alleles in a large number of field samples of diverse origins. Mol Biochem Parasitol 89 (1997) 161-177
56. Van Dijk M.R., Waters A.P., and Janse C.J. Stable transfection of malaria parasite blood stages. Science 268 (1995) 1358-1362
57. Wu Y., Sifri C.D., Lei H.-H., et al. Transformation of Plasmodium falciparum within human red blood cells. Proc Natl Acad Sci USA 92 (1995) 973-977
58. Van Dijk M.R., Janse C.J., and Waters A.P. Expression of a Plasmodium gene introduced into subtelomic regions of Plasmodium berghei chromosomes. Science 271 (1996) 662-665
59. Wu Y., Kirkman L.A., and Wellems T.E. Transformation of Plasmodium falciparum malaria parasites by homologous integration of plasmids that confer resistance to pyrimethamine. Proc Natl Acad Sci USA 93 (1996) 1130-1134
60. Raynolds M.G., and Roos D.S. A biochemical and genetic model for parasite resistance to antifolates. Toxoplasma dondii provides insights into pyrimethamine and cycloguanil resistance in Plasmodium falciparum. J Biol Chem 273 (1998) 3461-3469
61. Sirawaraporn W., Prapunwattana P., Sirawaraporn R., et al. The dihydrofolate reductase domain of Plasmodium falciparum thymidylate synthase-dihydrofolate reductase: gene synthesis, expression, and anti-folate resistant mutants. J Biol Chem 268 (1993) 21637-21644
62. Hall S.J., Sim P.F.G., and Hyde J.E. Functional expression of the dihydrofolate reductase and thymidylate synthetase of the human malaria parasite Plasmodium falciparum in Escherichia coli. Mol Biochem Parasitol 45 (1991) 317-330
63. Sano G.I., Morimatsu K., and Horii T. Purification and characterization of dihydrofolate reductase of Plasmodium falciparum expressed by a synthetic gene in Escherichia coli. Mol Biochem Parasitol 63 (1994) 265-273
64. Hekmat-Nejad M., Lee P.-C., and Rathod P.K. Plasmodium falciparum: direct cloning and expression of pyrimethamine-sensitive and pyrimethamine-resistant dihydrofolate reductase domains. Expt Parasitol 85 (1997) 303-305
65. Knighton D.R., Kan C.-C., Howland E., et al. Structure of and kinetic channelling in bifunctional dihydrofolate reductase-thymidylate synthase. Nature Struct Biol 1 (1994) 186-194
66. Smith D.R., and Calvo J.M. Nucleotide sequence of the E. coli gene coding for dihydrofolate reductase. Nucleic Acids Res 8 (1980) 2255-2274
67. Kumar A.A., Blankenship D.T., Kaufman B.T., and Freisheim J.H. Primary structure of chicken liver dihydrofolate reductase. Biochemistry 19 (1980) 667-678
68. Masters J.N., and Attardi G. The nucleotide sequence of cDNA coding for the human dihydrofolic acid reductase. Gene 21 (1983) 59-63
69. Chen M.-J., Shimada T., Moulton A.D., et al. The functional human dihydrofolate reductase gene. J Biol. Chem. 259 (1984) 3933-3943
70. Edman J.C., Edman U., Cao M., et al. Isolation and expression of the Pneumocystis carinii dihydrofolate reductase gene. Proc Natl Acad Sci USA 86 (1989) 8625-8629
71. Freisheim J.H., Bitar K.G., Reddy A.V., and Blankenship D.T. Dihydrofolate reductase from amethopterin-resistant Lactobacillus casei. sequences of the cyanogen bromide peptides and complete sequences of the enzyme. J Biol Chem 253 (1978) 6437-6444
72. Kuntz I.D., Blaney J.M., Oatley S.J., et al. A geometric approach to macromolecule-ligand interactions. J Mol Biol 161 (1982) 269-288
73. Meng E.C., Shoichet B.K., and Kuntz I.D. Automated docking with gridbased energy evaluation. J Comp Chem 13 (1992) 505-524
74. Shoichet B.K., Bodian D.L., and Kuntz I.D. Molecular docking using shape description. J Comp Chem 13 (1992) 380-397
75. Leach A.R. The use of molecular modelling to discover and design new molecules. In: Leach A.R. (Ed). Molecular Modellings: Principles and Applications (1996), Addison Wesley Longman Limited, Edinburgh 543-583
76. Toyoda T., Brobey R.K.B., Sano G.-I., and Horii T. Lead discovery of inhibitors of the dihydrofolate reductase domain of Plasmodium falciparum dihydrofolate reductase-thymidylate synthase. Biochem Biophys Res Comm 235 (1997) 515-519
77. McKie J.H., Douglas K.T., Chan C., et al. Rational drug design approach for overcoming drug resistance: application to pyrimethamine resistance in malaria. J Med Chem 41 (1998) 1367-1370