Inhibitors of imidazoleglycerolphosphate dehydratase as herbicides

Weed Science

Volumn 45, Issue 5, 1997, Pages 610-620

  Ohta, Daisaku ^a   Mori, Ichiro ^a   Ward, Eric ^b  

^a CIBA GEIGY LTD   (Switzerland)

^b Ciba Geigy Corporation   (United States)

Author keywords

ARBTH; Enzyme inhibitor; Histidine biosynthesis

Indexed keywords

EID: 0030854175     PISSN: 00431745     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Conference Paper

References (69)

1. Alifano, P., R. Fani, P. Lio, A. Lazcano, M. Bazzicalupo, M. S. Carlomagno, C. B. Bruni. 1996. Histidine biosynthetic pathway and genes: structure, regulation and evolution. Microbiol. Rev. 60:44-69.
2. Ames, B. N. 1957. The biosynthesis of histidine: D-erythro-imidazoleglycerol phosphate dehydratase. J. Biol Chem. 228:131-143.
3. Ames, B. N. and H. K. Mitchell. 1955. The biosynthesis of histidine: imidazoleglycerol phosphate, imidazoleacetol phosphate and histidinol phosphate. J. Biol. Chem. 212:687-697.
4. Berlyn, M. B. 1967. Gene-enzyme relationships in histidine biosynthesis in Aspergillus nidulans. Genetics 57:561-570.
5. Bond, T. J. and J. Akers. 1961. Mechanism of growth inhibition of Escherichia coli by 3-amino 1,2,4-triazole. J. Bacteriol. 81:327-328.
6. Brady, D. R. and L. L. Houston. 1973. Some properties of the catalytic sites of imidazoleglycerol phosphate dehydratase-histidinol phosphate phosphatase, a bifunctional enzyme from Salmonella typhimurium. J. Biol. Chem. 248:2588-2592.
7. Burns, E. R., G. A. Buchanan, and M. C. Carter. 1971. Inhibition of carotenoid synthesis as a mechanism of action of amitrole, dichlormate and pyriclor. Plant Physiol. 47:144-148.
8. Carlomagno, M. S., L. Chiariotti, P. Alifano, A. G. Nappo, and C. B. Bruni. 1988. Structure and function of the Salmonella typhimurium and Escherichia coli K-12 histidine operons. J. Mol. Biol. 203:585-606.
9. Carsiotis, M. and R. F. Jones. 1974. Cross pathway regulation: tryptophane-mediated control of histidine and arginine biosynthetic enzymes in Neurospora crassa. J. Bacteriol. 119:889-892.
10. Chiariotti, L., A. G. Nappo, M. S. Carlomagno, and C. B. Bruni. 1986. Gene structure in the histidine operon of Escherichia coli: Identification and nucleotide sequence of the hisB gene. Mol. Gen. Genet. 202:42-47.
11. 50 values and the type of inhibition for enzyme-catalyzed reactions. Biochem. Med. Metab. Biol. 40:204-212.
12. Duke, S. O. 1990. Overview of herbicide mechanisms of action. Environ. Health Perspect. 87:263-271.
13. Ebbole, D. J., J. L. Paluh, M. Plamann, M. S. Sachs, and C. Yanofsky. 1991. cpc-1, the general regulatory gene for genes of amino acid biosynthesis in Neurospora crassa, is differentially expressed during the asexual life cycle. Mol. Cell Biol. 11:928-934.
14. Fink, G. R. 1964. Gene-enzyme relations in histidine biosynthesis in yeast. Science 146:525-527.
15. Flint, D., M. H. Emptage, M. G. Finnegan, W. Fu, and M. K. Johnson. 1993. The role and properties of the iron-sulfur cluster in Escherichia coli dihydroxy-acid dehydratase. J. Biol. Chem. 268:14732-14742.
16. Glaser, R. D. and L. L. Houston. 1974. Subunit structure and photooxidation of yeast imidazoleglycerolphosphate dehydratase. Biochemistry 13:5145-5152.
17. Gottesman, S. 1984. Bacterial regulation: global regulatory networks. Annu. Rev. Genet. 18:415-441.
18. Guyer, D., D. Patton, and E. Ward. 1995. Evidence for cross-pathway regulation of metabolic gene expression in plants. Proc. Natl. Acad. Sci. USA 92:4997-5000.
19. Hawkes, T. R., J. M. Cox, N. J. Barnes, et al. 1993. Imidazole glycerol phosphate dehydratase: a herbicidal target. In Proceedings of the Brighton Crop Protection Conference - Weeds. Farnham, Great Britain: British Crop Protection Council, pp. 739-744.
20. Haworth, P. and D. L. Siehl. 1990. Design of enzyme-targeted agrochemicals. J. Agric. Food Chem. 38:1271-1273.
21. Heim, D. R. and I. M. Larrinua. 1989. Primary site of action of amitrole in Arabidopsis thaliana involves inhibition of root elongation but not of histidine or pigment biosynthesis. Plant Physiol. 91:1226-1231.
22. Hilton, J. L. 1969. Inhibitions of growth and metabolism by 3-amino-1,2,4-triazole (amitrole). J. Agric. Food. Chem. 17:182-198.
23. Hilton, J. L., P. C. Kearney, and B. N. Ames. 1965. Mode of action of the herbicide, 3-amino-1,2,4-triazole (amitrole): inhibition of an enzyme of histidine biosynthesis. Arch. Biochem. Biophys. 112:544-547.
24. Hinnebusch, A. G. 1992. The molecular and cellular biology of the yeast Saccharomyces. In E. W. Jones, J. R. Pringle, and J. R. Broach, eds. Gene Expression. Volume II. Plainview, NY: Cold Spring Harbor Laboratory Press, pp. 319-411.
25. Johnston, H. M. and J. R. Roth. 1979. Histidine mutants requiring adenine: selection of mutations with reduced hisG expression in Salmonella typhimurium. Genetics. 92:1-15.
26. Kishore, G. M. and D. M. Shah. 1988. Amino acid biosynthesis inhibitors as herbicides. Annu. Rev. Biochem. 57:627-663.
27. Lam, P.Y.S., P. K. Jadhav, C. J. Eyermann, et al. 1994. Rational design of potent, bioavailable, nonpeptide cyclic ureas as HIV protease inhibitors. Science 263:380-384.
28. Lauble, H., M. C. Kennedy, H. Beinert, and C. D. Stout. 1992. Crystal structures of aconitase with isocitrate and nitroisocitrate bound. Biochemistry 31:2735-2748.
29. Legerton, T. L. and C. Yanofsky. 1985. Cloning and characterization of the multifunctional his3 gene of Neurospora crassa. Gene 39:129-140.
30. Loper, J. C. 1961. Enzyme complementation in mixed extracts of mutants from Salmonella histidine B locus. Proc. Natl. Acad. Sci. USA 46: 1440-1450.
31. Mano, J., M. Hatano, S. Koizumi, S. Tada, M. Hashimoto, and A. Scheidegger. 1993. Purification and properties of a monofunctional imidazoleglycerol-phosphate dehydratase from wheat. Plant Physiol. 103: 733-739.
32. Matringe, M., J.-M. Camadro, P. Labbe, and R. Scalla. 1989. Protoporphyrinogen oxidase as molecular site for diphenyl ether herbicides. Biochem. J. 260:232-235.
33. Mauer, W., H. R. Gerber, and J. Rufener. 1987. CGA 136'872: a new post-emergence herbicide for the selective control of Sorghum spp. and Ecymus repens in Maize. In Proceedings of Brighton Crop Protection Conference - Weeds. Volume 1. Farnham, Great Britain: British Crop Protection Council, pp. 41-48.
34. Miflin, B. J. 1980. Histidine biosynthesis. In B. J. Miflin, ed. The Biochemistry of Plants. Volume 5. Amino Acids and Derivatives. New. York: Academic Press, pp. 533-539.
35. Moore, J. F., A. R. Parker, V. J. Davisson, and J. M. Schwab. 1993. Stereochemical course of the Escherichia coli imidazoleglycerol phosphate dehydrogenase reaction. J. Am. Chem. Soc. 115:3338-3339.
36. Morgaliash, E., A. Novogrodsky, and A. Schefter. 1960. Irreversible reaction of 3-amino-1,2,4-triazole and related inhibitors with the protein catalase. Biochem. J. 74:339-350.
37. Mori, I., R. Fonné-Pfister, S. Matsunaga, et al. 1995a. A novel class of herbicide: specific inhibitors of imidazoleglycerol phosphate dehydratase. Plant Physiol. 107:719-723.
38. Mori, I., G. Iwasaki, Y. Kimura, et al. 1995b. Synthesis of inhibitors of imidazoleglycerol phosphate dehydratase. J. Am. Chem. Soc. 117: 4411-4412.
39. Nagai, A., K. Suzuki, E. Ward, M. Moyer, M. Hashimoto, J. Mano, D. Ohta, and A. Scheidegger. 1992a. Overexpression of plant histidinol dehydrogenase using a baculovirus vector system. Arch. Biochem. Biophys. 295:235-239.
40. Nagai, A., K. Suzuki, E. Ward, et al. 1992b. Histidinol dehydrogenase in higher plants. Purification, cloning and expression. In Research in Photosynthesis. Volume IV. Dordrecht, The Netherlands: Kluwer Academic Publishers, pp. 95-98.
41. Niederberger, P., G. Miozzari, and R. Huetter. 1981. Biological role of the general control of amino acid biosynthesis in Saccharomyces cerevisiae. Mol. Cell. Biol. 1:584-593.
42. Parker, A. R., T. Moore, J. Edman, J. M. Schwab, and V. J. Davisson. 1994. Cloning, sequence analysis and expression of the gene encoding imidazoleglycerol phosphate dehydratase in Cryptococcus neoformans. Gene 145:135-138.
43. Patil, S. S., P. E. Kolattukudy, and A. E. Dimond. 1970. Inhibition of ornitine carbamyl transferase from bean plants by the toxin of Pseudomonas phaseolicola. Plant Physiol. 46:752-753.
44. Pillmoor, J. B., K. Wright, and S. D. Lindell. 1991. Herbicide discovery through rational design: some experiences. In Proceedings of the Brighton Crop Protection Conference - Weeds. Farnham, Great Britain: British Crop Protection Council, pp. 857-866.
45. Pinto, J.E.B.P., W. E. Dyer, S. C. Weller, and K. M. Herrmann. 1988. Glyphosate induces 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase in potato (Solanum tuberosum L.) cells grown in suspension culture. Plant Physiol. 87:891-893.
46. Rudiger, W. and J. Benz. 1979. Influence of aminotriazole on the biosynthesis of chlorophyll and phytol. Z. Naturforsch. 34C:1055-1057.
47. Saika, H., T. Früh, G. Iwasaki, S. Koizumi, I. Mori, and K. Hayakawa. 1993. Synthesis of (2R, 3R)-, (2S, 3S) (2R, 3S)-, and (2S, 3R)-imidazole glycerol phosphates (IGP): substrates for IGP-dehydratase (IGPD). Bioorg. Med. Chem. Lett. 3:2129-2134.
48. Shaner, D. L. and B. K. Singh. 1992. How does inhibition of amino acid biosynthesis kill plants? In B. K. Singh, H. E. Flores, and J. C. Shannon, eds. Biosynthesis and Molecular Regulation of Amino Acids in Plants. Rockville, MD: American Society of Plant Physiologists, pp. 174-183.
49. Siehl, D. L. 1992. Considerations in selecting a target site for herbicide design. In B. K. Singh, H. E. Flores, and J. C. Shannon, eds. Biosynthesis and Molecular Regulation of Amino Acids in Plants. Rockville, MD: American Society of Plant Physiologists, pp. 146-162.
50. Sinden, S. L. and R. D. Durbon. 1968. Glutamate synthetase inhibition: possible mode of action of wildfire toxin from Pseudomonas tabaci. Nature (London) 219:379-380.
51. Smith, I. K. 1985. Stimulation of glutathione synthesis in photorespirating plants by catalase inhibitors. Plant Physiol. 79:1044-1047.
52. Staples, M. A. and L. L. Houston. 1979. Proteolytic degradation of imidazoleglycerol phosphate dehydratase-histidinol phosphatase from Salmonella typhymurium and the isolation of a resistant bifunctional core enzyme. J. Biol. Chem. 254:1395-1401.
53. Steinruecken, H. and N. Amrhein. 1980. The herbicide glyphosate is a potent inhibitor of 5-enolpyruvyl-shikimic acid 3-phosphate synthase. Biochem. Biophys. Res. Commun. 94:1207-1212.
54. Struhl, K. 1985. Nucleotide sequence and transcriptional mapping of the yeast pet56-his3-ded1 gene region. Nucleic Acids Res. 13:8587-8601.
55. Struhl, K., J. R. Cameron, and R. W. Davis. 1976. Functional genetic expression of eukaryotic DNA in Escherichia coli. Proc. Natl. Acad. Sci. USA 73:1471-1475.
56. Struhl, K. and R. W. Davis. 1977. Production of a functional eukaryotic enzyme in Escherichia coli: cloning and expression of the yeast structural gene for imidazoleglycerol phosphate dehydratase (his3). Proc. Natl. Acad. Sci. USA 74:5255-5259.
57. Struhl, K. and R. W. Davis. 1981. Transcription of the his3 gene region in Saccharomyces cerevisiae. J. Mol. Biol. 152:535-552.
58. Tada, S., M. Hatano, Y. Nakayama, S. Volrath, D. Guyer, E. Ward, and D. Ohta. 1995. Insect cell expression of recombinant imidazoleglycerol phosphate dehydratase of Arabidopsis and wheat and inhibition by triazole herbicides. Plant Physiol. 109:153-159.
59. Tada, S., S. Volrath, D. Guyer, A. Scheidegger, J. Ryals, D. Ohta, and E. Ward. 1994. Isolation and characterization of cDNAs encoding imidazoleglycerolphosphate dehydratase from Arabidopsis thaliana. Plant Physiol. 105:579-583.
60. von Heijne, G. and K. Nishikawa. 1991. Chloroplast transit peptides: the perfect random coil? FEBS Lett. 278:1-3.
61. von Itzstein, M., W. Y. Wu, G. B. Kok, et al. 1993. Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature (London) 363:418-423.
62. Walsh, C. 1979. Enzymatic reaction mechanisms. New York: W. H. Freeman, p. 542.
63. Ward, E., S. Volrath, S. Koizumi, S. Tada, I. Mori, and G. Iwasaki, inventors; Ciba-Geigy Corp., assignee. 1994 Apr 29. Herbicide resistant transgenic plants and their preparation. WO 9426909.
64. Wei, T. F., T. S. Ramasubramanian, F. Pu, and J. W. Golden. 1993. Anabaena sp. strain PCC 7120 bifA gene encoding a sequence specific DNA binding protein cloned by in vivo transcriptional interference selection. J. Bacteriol. 175:4025-4035.
65. Wiater, A., D. Hulanicka, and T. Klopotowski. 1971a. Structural requirements for inhibition of yeast imidazoleglycerol phosphate dehydratase by triazole and anion inhibitors. Acta. Biochim. Pol. 18:289-297.
66. Wiater, A., T. Klopotowski, and G. Bagdasarian. 1971b. Synergistic inhibition of plant imidazoleglycerol phosphate dehydratase by aminotriazole and phosphate. Acta. Biochim. Pol. 18:309-314.
67. Wiater, A., K. Krajewska-Grynkiewicz, and T. Klopotowski. 1971c. Histidine biosynthesis and its regulation in plants. Acta. Biochim. Pol. 18: 299-307.
68. Winkler, M. E. 1987. Biosynthesis of histidine. In Escherichia coli and Salmonella typhimurium. In F. C. Neidhardt, J. L. Ingraham, K. B. Low, B. Magasanik, M. Schaechter, and H. E. Umbarger, eds. Cellular and Molecular Biology. Volume I. Washington, DC: American Society of Microbiology, pp. 395-411.
69. Wolfner, M., D. Yep, F. Messenguy, and G. R. Fink. 1975. Integration of amino acid biosynthesis into the cell cycle of Saccharomyces cerevisiae. J. Mol. Biol. 96:273-290.