Tobacco budworm dihydrofolate reductase is a promising target for insecticide discovery

European Journal of Biochemistry

Volumn 267, Issue 2, 2000, Pages 394-403

  Walker, Virginia K ^a   Tyshenko, Michael G ^a   Kuiper, Michael J ^a   Dargar, Ratna V ^b   Yuhas, Debra A ^b   Cruickshank, Philip A ^b   Chaguturu, Rathnam ^b  

^a QUEEN S UNIVERSITY   (Canada)

^b FMC CORPORATION   (United States)

Author keywords

Dihydrofolate reductase; Insecticide; Methotrexate; Molecular modeling

Indexed keywords

DIHYDROFOLATE REDUCTASE; INSECTICIDE;

ARTICLE; ENZYME ANALYSIS; ENZYME BINDING; ENZYME MECHANISM; ENZYME SPECIFICITY; ENZYME STRUCTURE; GENE SEQUENCE; MOLECULAR MODEL; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; SEQUENCE HOMOLOGY;

HELIOTHIS VIRESCENS; HEXAPODA; INSECTA; METAZOA; NICOTIANA TABACUM; VERTEBRATA;

EID: 0033960267     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1327.2000.01009.x     Document Type: Article

References (46)

1. 1. Rancourt, S.L. & Walker, V.K. (1990a) The purification of dihydrofolate reductase from Drosophila melanogaster. Biochim. Biophys. Acta 1039, 261-268.
2. 2. Rancourt, S.L. & Walker, V.K. (1990b) Kinetic characterization of dihydrofolate reductase from Drosophila melanogaster. Biochem. Cell Biol. 68, 1075-1082.
3. 3. Oefner, C., D'Arcy, A. & Winkler, F.K. (1988) Crystal structures of recombinant human dihydrofolate reductase complexed with folate. Eur. J. Biochem. 174, 377-385.
4. 4. Davies, J.F., Delcamp, T.J., Prendergast, N.J., Ashford, V.A., Fresheim, J.H. & Kraut, J. (1990) Crystal structures of recombinant human dihydrofolate reductase complexed with folate and 5-deazafolate. Biochemistry 29, 9467-9479.
5. 5. Cody, V., Galitsky, N., Luft, J.R., Pangborn, W., Rosowsky, A. & Blakley, R.L. (1997) Comparison of two independent crystal structures of human dihydrofolate reductase ternary complexes reduced with nicotinamide adenine dinucleotide phosphate and the very tight-binding inhibitor PT523. Biochemistry 36, 13897-13903.
6. 6. Williams, M.R. (1997) Cotton insect losses, 1979-96. In Proceedings of the Beltwide Cotton Conferences. National Cotton Council, Memphis, TN.
7. 7. Aebersold, R.H., Leavitt, J., Saavedra, R.A., Hood, L.E. & Kent, S.B.H. (1987) Internal amino acid sequence analysis of proteins separated by one-or two-dimensional gel electrophoresis after in situ protease digestion on nitrocellulose. Proc Natl Acad. Sci. USA 84, 6970-6974.
8. 8. Harlow, E. & Lane, D. (1988) Antibodies: a Laboratory Manual, pp. 497-505. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York.
9. 9. Hao, H., Tyshenko, M.G. & Walker, V.K. (1994) Dihydrofolate reductase of Drosophila: cloning and expression of a gene with a rare transcript. J. Biol. Chem. 269, 15179-15185.
10. 10. Chia, W., Karp, R., McGill, S. & Ashburner, M. (1985) Molecular analysis of the Adh region of the genome of Drosophila melanogaster. J. Mol. Biol. 186, 689-706.
11. 11. Saiki, R.K., Gelfand, D.H., Stoffel, S., Scharf, S.J., Higuchi, R., Horn, G.T., Mullis, K.B. & Erlich, H.A. (1988) Primer-directed enzymatic amplification of DNA with a thermostable DNA polymerase. Science 239, 487-491.
12. 12. Innis, M.A. & Gelfand, D.H. (1990) Optimization of PCRs. In PCR Protocols, a Guide to Methods and Applications (Innis, M.A., Gelfand, D.H., Sninsky, J.J. & White, T.J., eds), pp. 3-12. Academic Press Inc, San Diego.
13. 13. Frohman, M. (1990) Amplification of flanking sequences by inverse PCR. In PCR Protocols, a Guide to Methods and Applications (Innis, M.A., Gelfand, D.H., Sninsky, J.J. & White, T.J., eds), pp. 219-227. Academic Press Inc, San Diego.
14. 14. Sambrook, J., Fritsch, E.F. & Maniatis, T. (1989) Molecular Cloning: a Laboratory Manual, 2nd edn. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York.
15. 15. Bjourson, A.J. & Cooper, J.E. (1992) Band-stab PCR: a simple technique for purification of individual PCR products. Nucleic Acids Res. 20, 4675.
16. 16. Hao, H., Tyshenko, M.G. & Walker, V.K. (1996) Isolation and characterization of a dihydrofolate reductase gene mutation in methotrexate-resistant Drosophila cells. Gene Expression 6, 231-239.
17. 17. Kaufman, B.T. & Gardiner, R.C. (1966) Studies on dihydrofolate reductase I purification and properties of dihydrofolate reductase from chicken liver. J. Biol. Chem. 241, 1319-1328.
18. 18. Shotoski, FA. & Fallon, A.M. (1991) An amplified insect dihydrofolate reductase gene contains a single intron. Eur. J. Biochem. 201, 151-160.
19. 19. Martinez, P., Martin, W. & Cerff, R. (1989) Structure, evolution and anaerobic regulation of a nuclear gene encoding cytosolic glyceraldehyde-3-phosphate. J. Mol. Biol. 208, 551-565.
20. 20. Logsdon, J.M., Tyshenko, M.G., Dixon, C., D.-Jafari, J., Walker, V.K. & Palmer, J.D. (1995) Seven newly discovered intron positions in the triose-phosphate isomerase gene; evidence for the introns-late theory. Proc. Natl Acad. Sci. USA 92, 8507-8511.
21. 21. Breathnach, R., Benoist, C., O'Hare, K., Gannon, F. & Chambon, P. (1978) Ovalbumin gene: evidence for a leader sequence in mRNA and DNA sequences at the exon-intron boundaries. Proc. Natl Acad. Sci. USA 75, 4853-4857.
22. 22. Tyshenko, M.G. & Walker, V.K. (1997) Towards a reconciliation of the introns early or late views: triosephosphate isomerase genes from insects. Biochim. Biophys. Acta 1353, 131-136.
23. 23. Matthews, D.A., Bolin, J.T., Burridge, J.M., Filman, D.J., Volz, K.W. & Kraut, J. (1985) Refined crystal structures of Escherichia coli and chicken liver dihydrofolate reductase containing bound trimethoprim. J. Biol. Chem. 260, 392-399.
24. 24. Barclay, B.J., Huang, T., Nagel, M.G., Misener, V.L., Game, J.C. & Wahl. G.M. (1988) Mapping and sequencing of the dihydrofolate reductase gene (DFR1) of Saccharomyces cerevisiae. Gene 63, 175-185.
25. 25. Duffy, T.H., Beckman, S.B., Peterson, S.M., Vitols, K.S. & Huennekens, F.M. (1987) L1210 dihydrofolate reductase: kinetics and mechanism of activation by various agents. J. Biol. Chem. 262, 7028-7033.
26. 26. Wu, J.W. & Wang. Z.X. (1998) Activation mechanism and modification kinetics of Chinese hamster dihydrofolate reductase by p-chloromercuribenzoate. Biochem. J. 335, 81-189.
27. 27. Bednar, R.A., Fried, W.B., Lock, Y.W. & Pramanik, B. (1989) Chemical modification of chalcone isomerase by mercurials and tetrathionate: evidence for a single cysteine residue in the active site. J. Biol. Chem. 264, 14272-14276.
28. 28. Chen, M.J., Shimada, T., Moulton, A.D., Cline, A., Humphries, R.K., Maizel, J. & Nienhuis, A.W. (1984) The functional human dihydrofolate reductase gene. J. Biol. Chem. 259, 3933-3943.
29. 29. Stone, D., Paterson, S.J., Raper, J.H. & Phillips, A.W. (1979) The amino acid sequence of dihydrofolate reductase from the mouse lymphoma L1210. J. Biol. Chem. 254, 480-488.
30. 30. Smith, D.R. & Calvo, J.M. (1980) Nucleotide sequence of the E. coli gene coding for dihydrofolate reductase. Nucleic Acids Res. 8, 2255-2274.
31. 31. Kaufman, B.T. & Kemerer, V.F. (1977) Characterization of chicken liver dihydrofolate reductase after purification by affinity chromatography and isoelectric focusing. Arch. Biochem. Biophys. 179, 420-430.
32. 32. Stone, S.R. & Morrison, J.F. (1986) Mechanism of inhibition of dihydrofolate reductase from bacterial and vertebrate sources by various classes of folate analogues. Biochim. Biophys. Acta 869, 275-285.
33. 2-terminal amino acid sequences. J. Biol. Chem. 255, 6542-6545.
34. 34. Kaufman, B.T. (1963) Activation of dihydrofolate reductase by urea and formamide. Biochem. Biophys. Res. Commun. 10, 449-453.
35. 35. Barbehenn, E.K. & Kaufman, B.T. (1978) Activation of chicken liver dihydrofolate reductase by tetrathionate. Biochem. Biophys. Res. Commun. 85, 402-407.
36. 36. Srimatkandada, S., Medina, W.D., Cashmore, A.R., Whyte, W., Engle, D., Moronson, B.A., Franco, C.T., Dube, S.K. & Bertinio, J.R. (1983) Amplification and organization of dihydrofolate reductase genes in a human leukemic cell line, K-562, resistant to methotrexate. Biochemistry 22, 5774-5781.
37. 37. Prendergast, N.J., Appleman, J.R., Delcamp, T.J., Blakley, R.L. & Freisheim, J.H. (1989) Effects of conversion of phenylalanine-31 to leucine on the function of human dihydrofolate reductase. Biochemistry 28, 4645-4650.
38. 38. Tan, X.H., Huang, S.M., Ratnam, M., Thompson, P.D. & Freisheim, J.H. (1990) The importance of loop region residues 40-60 in human dihydrofolate reductase as revealed by site-directed mutagenesis. J. Biol. Chem. 265, 8027-8032.
39. 39. Delcamp, T.J., Susten, S.S., Blankenship, D.T. & Freisheim, J.H. (1983) Purification and characterization of dihydrofolate reductase from methotrexate-resistant human lymphoblastoid cells. Biochemistry 22, 633-639.
40. 40. Hansch, C. & Klein, T.E. (1991) Quantitative structure-activity relationships and molecular graphics in evaluation of enyme-ligand interactions. Methods Enzymol. 202, 512-543.
41. 41. Baccanari, D., Phillips, A., Smith, S., Sinski, D. & Burchall, J. (1975) Purification and properties of Escherichia coli dihydrofolate reductase. Biochemistry 14, 5267-5273.
42. 42. Baccanari, D.P. & Joyner, S.S. (1981) Dihydrofolate reductase hysteresis and its effect on inhibitor binding analyses. Biochemistry 20, 1710-1716.
43. 43. Poe, M., Greenfield, N.J., Hirschfield, J.M., Williams, M.N. & Hoogsteen, K. (1972) Dihydrofolate reductase: purification and characterization of the enzyme from an amethopterin-resistant mutant of Escherichia coli. Biochemistry 11, 1023-1030.
44. 44. Bowden, K., Hall, A.D., Birdsall, B., Feeney, J. & Roberts, G.C. (1989) Interactions between inhibitors of dihydrofolate reductase. Biochem. J. 258, 35-342.
45. 45. Dwivedi, C.M. & Murti, C.R.K. (1979) Inhibition of E. coli DHFR by some newer pyrimidine analogues. In Chemistry and Biology of Pteridines (Kisluik, R.L. & Brown, G.M., eds), pp. 401-405. Elsevier, New York.
46. 46. Frieden, C. (1990) Refolding of Escherichia coli dihydrofolate reductase: sequential formation of substrate binding sites. Proc. Natl Acad. Sci. USA 87, 4413-4416.