Potent and selective activity of a combination of thymidine and 1843U89, a folate-based thymidylate synthase inhibitor, against Plasmodium falciparum

Antimicrobial Agents and Chemotherapy

Volumn 44, Issue 4, 2000, Pages 1047-1050

  Jiang, Lei ^a   Lee, Pei Chieh ^a   White, John ^a   Rathod, Pradipsinh K ^a  

^a CATHOLIC UNIVERSITY OF AMERICA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [5 [[(1,2 DIHYDRO 3 METHYL 1 OXOBENZO[F]QUINAZOLIN 9 YL)METHYL]AMINO] 1 OXO 2 ISOINDOLINYL]GLUTARIC ACID; FOLIC ACID; METHYLENETETRAHYDROFOLIC ACID; POLYGLUTAMIC ACID; PYRIMIDINE; RALTITREXED; THYMIDINE; THYMIDYLATE SYNTHASE INHIBITOR;

ANIMAL CELL; ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG SELECTIVITY; ENZYME BINDING; LEUKEMIA L 1210; MAMMAL CELL; MOUSE; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; PYRIMIDINE SYNTHESIS;

ANIMALS; CELL DIVISION; ENZYME INHIBITORS; ERYTHROCYTES; FOLIC ACID ANTAGONISTS; INDOLES; KINETICS; LEUKEMIA L1210; MICE; PLASMODIUM FALCIPARUM; QUINAZOLINES; THYMIDINE; THYMIDYLATE SYNTHASE;

EID: 0034019568     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.44.4.1047-1050.2000     Document Type: Article

References (41)

1. Bzik, D. J., W. B. Li, T. Horii, and J. Inselburg. 1987. Molecular cloning and sequence analysis of the Plasmodium falciparum dihydrofolate reductase-thymidylate synthase gene. Proc. Natl. Acad. Sci. USA 84:8360-8364.
2. Carreras, C. W., and D. V. Santi. 1945. The catalytic mechanism and structure of thymidylate synthase. Annu. Rev. Biochem. 64:721-762.
3. Chen, G. X., and J. W. Zolg. 1987. Purification of the bifunctional thymidylate synthase-dihydrofolate reductase complex from the human malaria parasite Plasmodium fakipanim. Mol. Pharmacol. 32:723-730.
4. Coderre, J. A., S. M. Beverley, R. T. Schimke, and D. V. Santi. 1983. Overproduction of a bifunctional thymidylate synthetase-dihydrofolate reductase and DNA amplification in methotrexate-resistant Leishmania tropica. Proc. Natl. Acad. Sci. USA 80:2132-2136.
5. 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.
6. Diggens, S. M., W. E. Gutleridge, and P. I. Trigg. 1970. Altered dihydrofolate reductase associated with a pyrimethamine-resistant Plasmodium berghei berghei produced in a single step. Nature 228:579-580.
7. Duch, D. S., S. Banks, I. K. Dev, S. H. Dickerson, R. Ferone, L. S. Heath, J. Humphreys, V. Knick, W. Pendergast, S. Singer, et al. 1993. Biochemical and cellular pharmacology of 1843U89, a novel benzoquinazoline inhibitor of thymidylate synthase. Cancer Res. 53:810-818.
8. Evans, R. M., J. D. Laskin, and M. T. Hakala. 1980. Assessment of growth-limiting events caused by 5-fluorouracil in mouse cells and in human cells. Cancer Res. 40:4113-4122.
9. Ferone, R. 1970. Dihydrofolate reductase from pyrimethamine-resistant Plasmodium berghei. J. Biol. Chem. 245:850-354.
10. Foote, S. J., D. Galatis, and A. F. Cowman. 1990. 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 87:3014-3017.
11. Gassis, S., and P. K. Rathod. 1996. Frequency of drug resistance in Plasmodium falciparum: a nonsynergistic combination of 5-fluoroorotate and atovaquone suppresses in vitro resistance. Antimicrob. Agents Chemother. 40: 914-919.
12. Gomez, Z. M., and P. K. Rathod. 1990. Antimalarial activity of a combination of 5-fluoroorotate and uridine in mice. Antimicrob. Agents Chemother. 34:1371-1375.
13. Heidelberger, C., P. V. Danenberg, and R. G. Moran. 1983. Fluorinated pyrimidines and their nucleosides. Adv. Enzymol. Relat. Areas Mol. Biol. 54:58-119.
14. Hekmat-Nejad, M., and P. K. Rathod. 1996. Kinetics of Plasmodium falciparum thymidylate synthase: interactions with high-affinity metabolites of 5-fluoroorotate and D1694. Antimicrob. Agents Chemother. 40:1628-1632.
15. Houghton, P. J., G. S. Germain, B. J. Hazelton, J. W. Pennington, and J. A. Houghton. 1989. Mutants of human colon adenocarcinoma, selected for thymidylate synthase deficiency. Proc. Natl. Acad. Sci. USA 86:1377-1381.
16. Ingraham, H. A., L. Dickey, and M. Goulian. 1986. DNA fragmentation and cytotoxicity from increased cellular deoxyuridylate. Biochemistry 25:3225-3230.
17. Jackman, A. L., G. A. Taylor, W. Gibson, R. Kimbell, M. Brown, A. H. Calvert, I. R. Judson, and L. R. Hughes. 1991. ICI D1694, a quinazoline antifolate thymidylate synthase inhibitor that is a potent inhibitor of L1210 tumor cell growth in vitro and in vivo: a new agent for clinical study. Cancer Res. 51:5579-5586.
18. Krungkrai, J., S. R. Krungkrai, and K. Phakanont. 1992. Antimalarial activity of orotate analogs that inhibit dihydroorotase and dihydroorotate dehydrogenase. Biochem. Pharmacol. 43:1295-1301.
19. Kunz, B. A., S. E. Kohalmi, T. A. Kunkel, C. K. Mathews, E. M. McIntosh, and J. A. Reidy. 1994. International Commission for Protection Against Environmental Mutagens and Carcinogens. Deoxyribonucleoside triphosphate levels: a critical factor in the maintenance of genetic stability. Mutat. Res. 318:1-64.
20. Parker, W. B., and Y. C. Cheng. 1990. Metabolism and mechanism of action of 5-fluorouracil. Pharmacol. Ther. 48:381-395.
21. Peterson, D. S., W. K. Milhous, and T. E. Wellems. 1990. Molecular basis of differential resistance to cycloguanil and pyrimethamine in Plasmodium falciparum malaria. Proc. Natl. Acad. Sci. USA 87:3018-3022.
22. Queen, S. A., D. L. VanderJagt, and P. Reyes. 1990. In vitro susceptibilities of Plasmodium falciparum to compounds which inhibit nucleotide metabolism. Antimicrob. Agents Chemother. 34:1393-1398.
23. Rathod, P. K., and Z. M. Gomez. 1991. Plasmodium yoelii: oral delivery of 5-fluoroorotate to treat malaria in mice. Exp. Parasitol. 73:512-514.
24. Rathod, P. K., A. Khatri, T. Hubbert, and W. K. Milhous. 1989. Selective activity of 5-fluoroorotic acid against Plasmodium falciparum in vitro. Antimicrob. Agents Chemother. 33:1090-1094.
25. Rathod, P. K., M. Khosla, S. Gassis, R. D. Young, and C. Lutz. 1994. Selection and characterization of 5-fluoroorotate-resistant Plasmodium falciparum. Antimicrob. Agents Chemother. 38:2871-2876.
26. Rathod, P. K., N. P. Leffers, and R. D. Young. 1992. Molecular targets of 5-fluoroorotate in the human malaria parasite, Plasmodium falciparum. Antimicrob. Agents Chemother. 36:704-711.
27. Rathod, P. K., T. McErlean, and P. C. Lee. 1997. Variations in frequencies of drug resistance in Plasmodium falciparum. Proc. Natl. Acad. Sci. USA 94:9389-9393.
28. Rathod, P. K., and S. Reshmi. 1994. Susceptibility of Plasmodium falciparum to a combination of thymidine and ICI D1694, a quinazoline antifolate directed at thymidylate synthase. Antimicrob. Agents Chemother. 38:476-480.
29. Reyes, P., and C. Heidelberger. 1965. Fluorinated pyrimidines. XXVI. Mammalian thymidylate synthetase: its mechanism of action and inhibition by fluorinated nucleotides. Mol. Pharmacol. 1:14-30.
30. Reyes, P., P. K. Rathod, D. J. Sanchez, J. E. Mrema, K. H. Rieckmann, and H. G. Heidrich. 1982. Enzymes of purine and pyrimidine metabolism from the human malaria parasite, Plasmodium falciparum. Mol. Biochem. Parasitol. 5:275-290.
31. Roberts, D. 1966. An isotopic assay for thymidylate synthetase. Biochemistry 5:3546-3548.
32. Seymour, K. K., S. D. Lyons, L. Phillips, K. H. Rieckmann, and R. I. Christopherson. 1994. Cytotoxic effects of inhibitors of de novo pyrimidine biosynthesis upon Plasmodium falciparum. Biochemistry 33:5268-5274.
33. 32a. Shallom, S. L., K. Zhang, L. Jiang, and P. K. Rathod. 1999. Essential protein-protein interactions between Plasmodium falciparum thymidylate synthase and dihydrofolate reductase domains. J. Biol. Chem. 274:37781-37786.
34. Sherman, I. W. 1998. Purine and pyrimidine metabolism of asexual stages, p. 177-184. In I. W. Sherman (ed.), Malaria: parasite biology, pathogenesis, and protection. ASM Press, Washington, D.C.
35. Srivastava, I. K., and A. B. Vaidya. 1999. A mechanism for the synergistic antimalarial action of atovaquone and proguanil. Antimicrob. Agents Chemother. 43:1334-1339.
36. Trager, W., and J. B. Jensen. 1976. Human malaria parasites in continuous culture. Science 193:673-675.
37. Trigg, P. I., and A. V. Kondrachine. 1998. The current global malaria situation, p. 11-22 In I. W. Sherman (ed.), Malaria: parasite biology, pathogenesis, and protection. ASM Press, Washington, D.C.
38. Ward, W. H., R. Kimbell, and A. L. Jackman. 1992. Kinetic characteristics of ICI D1694: a quinazoline antifolate which inhibits thymidylate synthase. Biochem. Pharmacol. 43:2029-2031.
39. White, N. J. 1992. Antimalarial drug resistance: the pace quickens. J. Antimicrob. Chemother. 30:571-585.
40. Wu, Y., L. A. Kirkman, and T. E. Wellems. 1996. Transformation of Plasmodium falciparum malaria parasites by homologous integration of plasmids that confer resistance to pyrimethamine. Proc. Natl. Acad. Sci. USA 93: 1130-1134.
41. Yoshioka, A., S. Tanaka, O. Hiraoka, Y. Koyama, Y. Hirota, D. Ayusawa, T. Seno, C. Garrett, and Y. Wataya. 1987. Deoxyribonucleoside triphosphate imbalance. 5-Fluorodeoxyuridine-induced DNA double strand breaks in mouse FM3A cells and the mechanism of cell death. J. Biol. Chem. 262: 8235-8241.