The phenylquinazoline compound S-4893 is a non-competitive cytokinin antagonist that targets Arabidopsis cytokinin receptor CRE1 and promotes root growth in Arabidopsis and rice

Plant and Cell Physiology

Volumn 51, Issue 12, 2010, Pages 2047-2059

  Arata, Yuto ^a   Nagasawa Iida, Asako ^a   Uneme, Hideki ^a   Nakajima, Hiroki ^a   Kakimoto, Tatsuo ^b   Sato, Ryo ^a  

^a SUMITOMO CHEMICAL CO LTD   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

Arabidopsis thaliana; Cytokinin; Cytokinin antagonist; Cytokinin receptor; Plant growth regulator; Root growth promoter

Indexed keywords

6 N (3,3 DIMETHYLALLYL)ADENOSINE; ARABIDOPSIS PROTEIN; CELL SURFACE RECEPTOR; CYTOKININ; N(6) (DELTA(2) ISOPENTENYL)ADENINE; N(6)-(DELTA(2)-ISOPENTENYL)ADENINE; PHYTOHORMONE; PROTEIN KINASE; QUINAZOLINE DERIVATIVE; S 4893 COMPOUND; S-4893 COMPOUND; WOL PROTEIN, ARABIDOPSIS;

ARABIDOPSIS; ARTICLE; BIOSYNTHESIS; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; DRUG SCREENING; GENETICS; GROWTH, DEVELOPMENT AND AGING; ISOLATION AND PURIFICATION; METABOLISM; MOLECULAR LIBRARY; PHYSIOLOGY; PLANT ROOT; PROTEIN BINDING; RICE; SEEDLING; SIGNAL TRANSDUCTION; SYNTHESIS; TRANSGENIC PLANT; YEAST;

ARABIDOPSIS; ARABIDOPSIS PROTEINS; CYTOKININS; DRUG EVALUATION, PRECLINICAL; ISOPENTENYLADENOSINE; ORYZA SATIVA; PLANT GROWTH REGULATORS; PLANT ROOTS; PLANTS, GENETICALLY MODIFIED; PROTEIN BINDING; PROTEIN KINASES; QUINAZOLINES; RECEPTORS, CELL SURFACE; SEEDLING; SIGNAL TRANSDUCTION; SMALL MOLECULE LIBRARIES; YEASTS;

ARABIDOPSIS; ARABIDOPSIS THALIANA;

EID: 78651289515     PISSN: 00320781     EISSN: 14719053     Source Type: Journal    
DOI: 10.1093/pcp/pcq163     Document Type: Article

References (51)

1. Becker, D., Kemper, E., Schell, J. and Masterson, R. (1992) New plant binary vectors with selectable markers located proximal to the left T-DNA border. Plant Mol. Biol. 20:1195-1197.
2. Benková, E. and Hejátko, J. (2009) Hormone interactions at the root apical meristem. Plant Mol. Biol. 69:383-396.
3. Choi, J. and Hwang, I. (2007) Cytokinin: perception, signal transduction, and role in plant growth and development. J. Plant Biol. 50:98-108.
4. D'Agostino, I. B., Deruère, J. and Kieber, J. J. (2000) Characterization of the response of the Arabidopsis response regulator gene family to cytokinin. Plant Physiol. 124:1706-1717.
5. Dello Ioio, R., Linhares, F. S., Scacchi, E., Casamitjana-Martinez, E., Heidstra, R., Costantino, P., et al. (2007) Cytokinins determine Arabidopsis root-meristem size by controlling cell differentiation. Curr. Biol. 17:678-682.
6. Ding, Y. and Ma, Q.-H. (2006) Biosynthesis, signal transduction and molecular regulation of cytokinins. Curr. Pharm. Anal. 2:169-182.
7. Dixon, M. and Webb, E. C. (1979) Enzymes. Longman, London.
8. Du, L., Jiao, F., Chu, J., Gulei J., Chen, M. and Wu, P. (2007) The twocomponent signal system in rice (Oryza sativa L.): a genome-wide study of cytokinin signal perception and transduction. Genomics 89:697-707.
9. Ferguson, L. and Lessenger J. E. (2006) Plant growth regulators. In Agricultural Medicine. Edited by Lessenger J. E. pp. 156-166. Springer, New York.
10. Ferreira, F. J. and Kieber, J. J. (2005) Cytokinin signaling. Curr. Opin. Plant Biol. 8:518-525.
11. Gunge, N. and Sakaguchi, K. (1981) Intergeneric transfer of deoxyribonucleic acid killer plasmids, pGKl1 and pGKl2, from Kluyveromyces lactis into Saccharomyces cerevisiae by cell fusion. J. Bacteriol. 147:155-160.
12. Hecht, S. M., Bock, R. M., Schmitz, R. Y., Skoog, F. and Leonard, N. J. (1971) Cytokinins: development of a potent antagonist. Proc. Natl Acad. Sci. USA 68:2608-2610.
13. Higuchi, M., Pischke, M. S., Mahoen, A. P., Miyawaki, K., Hashimoto, Y., Seki, M., et al. (2004) In planta functions of the Arabidopsis cytokinin receptor family. Proc. Natl Acad. Sci. USA 101:8821-8826.
14. Hwang, I. and Sakakibara, H. (2006) Cytokinin biosynthesis and perception. Physiol. Plant. 126:528-583.
15. Iida, A., Seki, M., Kamada, M., Yamada, Y. and Morikawa, H. (1990) Gene delivery into cultured plant cells by DNA-coated gold particles accelerated by a pneumatic particle gun. Theor. Appl. Genet. 80:813-816.
16. Inoue, T., Higuchi, M., Hashimoto, Y., Seki, M., Kobayashi, M., Kato, T., et al. (2001) Identification of CRE1 as a cytokinin receptor from Arabidopsis. Nature 409:1060-1063.
17. Iwamura, H. (1994) Cytokinin antagonists: synthesis and biological activity. In Cytokinins: Chemistry, Activity and Function. Edited by Mok, D. W. S. and Mok, M. C. pp. 43-55. CRC Press, Boca Raton, FL.
18. Iwamura, H., Masuda, N., Koshimizu, K. and Matsubara, S. (1983) Quantitative aspects of the receptor binding of cytokinin agonists and antagonists. J. Med. Chem. 26:838-844.
19. Iwamura, H., Murakami, S., Koga, J., Matsubarab, S. and Koshimizu, K. (1979) Quantitative analysis of anticytokinin activity of 4-substituted 2-methylthiopyrido [2, 3-d] pyrimidines. Phytochemistry 18:1265-1268.
20. Iwamura, H., Murakami, S., Koshimizu, K. and Matsubara, S. (1985) Quantitative structure-activity relationships in cytokinin agonistic and antagonistic pyrido [2, 3-d] pyrimidine derivatives: insights into receptor topology. J. Med. Chem. 28:577-583.
21. Jefferson, R. A., Kavanagh, T. A. and Bevan, M. W. (1987) GUS fusions: β-glucuronidase as a sensitive and versatile gene fusion marker in higher plants. EMBO J. 6:3901-3907.
22. Kakimoto, T. (2001) Identification of plant cytokinin biosynthetic enzymes as dimethylallyl diphosphate: ATP/ADP isopentenyltransferases. Plant Cell Physiol. 42:677-685.
23. Kakimoto, T. (2003) Perception and signal transduction of cytokinins. Annu. Rev. Plant Biol. 54:605-627.
24. Kakimoto, T. and Higuchi, M. (2005) Transformed cell co-expressing cytokinin receptor and cytokinin biosynthesis enzyme. European Patent Application EP1522586.
25. Kakimoto, T., Higuchi, M. and Inoue, T. (2002) Analysis of agonistactivity and antagonist-activity to cytokinin receptor. European Patent Application EP1241182.
26. Karanov, E., Alexieva, V., Golovinsky, E. and Haimova, M. (1993) Cytokinin and anticytokinin activity of some 4-substituted 1H-pyrazoles and 8-aza analogues of adenine. Plant Growth Regul. 13:7-11.
27. Kefford, N. P., Zwar, J. A. and Bruce, M. I. (1968) Antagonism of purine and urea cytokinin activities by derivatives of benzylurea. In Biochemistry and Physiology of Plant Growth Substances. Edited by Wightman, F. and Setterfield, G. pp. 61-69. Runge Press Ltd., Ottawa.
28. Koren, B., Stanovnik, B. and Tisler, M. (1987) Transformations of 1, 2, 4-thiadiazolo [2, 3-x] azines. Heterocycles 26:689-697.
29. Koshioka, M., Takeuchi, Y., Saka, H. and Kamuro, Y. (2005) Mutual and close relationship between basic studies and practical application on plant growth substances. Regul. Plant Growth Dev. 40:111-123.
30. Kuroha, T., Ueguchi, C., Sakakibara, H. and Satoh, S. (2006) Cytokinin receptors are required for normal development of auxin-transporting vascular tissues in the hypocotyl but not in adventitious roots. Plant Cell Physiol. 47:234-243.
31. Kwon, S., Ikeda, F. and Isagawa, K. (1973) Cyclization of quinazoline derivatives. Nippon Kagaku Kaishi 10:1944-1948.
32. Kyozuka, J. (2007) Control of shoot and root meristem function by cytokinin. Curr. Opin. Plant Biol. 10:442-446.
33. Li, X., Mo, X., Shou, H. and Wu, P. (2006) Cytokinin-mediated cell cycling arrest of pericycle founder cells in lateral root initiation of Arabidopsis. Plant Cell Physiol. 47:1112-1123.
34. Lineweaver, H. and Burk, D. (1934) The determination of enzyme dissociation constants. J. Amer. Chem. Soc. 56:658-666.
35. Maeda, T., Wurgler-Murphy, S. M. and Saito, H. (1994) A twocomponent system that regulates an osmosensing MAP kinase cascade in yeast. Nature 369:187-188.
36. Mähönen, A. P., Higuchi, M., Törmäkangas, K., Miyawaki, K., Pischke, M. S., Sussman, M. R., et al. (2006) Cytokinins regulate a bidirectional phosphorelay network in Arabidopsis. Curr. Biol. 11:1116-1122.
37. Miyawaki, K., Tarkowski, P., Matsumoto-Kitano, M., Kato, T., Sato, S., Tarkowska, D., et al. (2006) Roles of Arabidopsis ATP/ADP isopentenyltransferases and tRNA isopentenyltransferases in cytokinin biosynthesis. Proc. Natl Acad. Sci. USA 103:16598-16603.
38. Mumberg, D., Müller, R. and Funk, M. (1995) Yeast vectors for the controlled expression of heterologous proteins in different genetic backgrounds. Gene 156:119-122.
39. Nishimura, C., Ohashi, Y., Sato, S., Kato, T., Tabata, S. and Ueguchi, C. (2004) Histidine kinase homologs that act as cytokinin receptors possess overlapping functions in the regulation of shoot and root growth in Arabidopsis. Plant Cell 16:1365-1377.
40. Nisler, J., Zatloukal, M., Popa, I., Doležal, K., Strnad, M. and Spíchal, L. (2010) Cytokinin receptor antagonists derived from 6-benzylaminopurine. Phytochemistry 71:823-830.
41. Riefler, M., Novak, O., Strnad, M. and Schmülling, T. (2006) Arabidopsis cytokinin receptor mutants reveal functions in shoot growth, leaf senescence, seed size, germination, root development, and cytokinin metabolism. Plant Cell 18:40-54.
42. Romanov, G. A., Lomin, S. N. and Schmülling, T. (2006) Biochemical characteristics and ligand-binding properties of Arabidopsis cytokinin receptor AHK3 compared to CRE1/AHK4 as revealed by a direct binding assay. J. Exp. Bot. 57:4051-4040.
43. Romanov, G. A., Spíchal, L., Lomin, S. N., Strnad, M. and Schmülling, T. (2005) A live cell hormone-binding assay on transgenic bacteria expressing a eukaryotic receptor protein. Anal. Biochem. 347:129-134.
44. Spíchal, L., Krystof, V., Paprskárová, M., Lenobel, R., Stýskala, J., Binarová, P., et al. (2007) Classical anticytokinins do not interact with cytokinin receptors but inhibit cyclin-dependent kinases. J. Biol. Chem. 282:14356-14363.
45. Spíchal, L., Werner, T., Popa, I., Riefler, M., Schmülling, T. and Strnad, M. (2009) The purine derivative PI-55 blocks cytokinin action via receptor inhibition. FEBS J. 276:244-253.
46. Stanovnik, B. and Tisler, M. (1972) A new synthesis of pyrido [1, 2-a]-1, 3, 5-triazines. Synthesis 6:308-309.
47. Takei, K., Sakakibara, H. and Sugiyama, T. (2001) Identification of genes encoding adenylate isopentenyltransferase, a cytokinin biosynthesis enzyme, in Arabidopsis thaliana. J. Biol. Chem. 276:26405-26410.
48. Werner, T., Motyka, V., Laucou, V., Smets, R., Van Onckelen H. and Schmülling, T. (2003) Cytokinin-deficient transgenic Arabidopsis plants show multiple developmental alterations indicating opposite functions of cytokinins in the regulation of shoot and root meristem activity. Plant Cell 15:2532-2550.
49. Werner, T., Motyka, V., Strnad, M. and Schmülling, T. (2001) Regulation of plant growth by cytokinin. Proc. Natl Acad. Sci. USA 98:10487-10492.
50. Yamada, H., Suzuki, T., Terada, K., Takei, K., Ishikawa, K., Miwa, K., et al. (2001) The Arabidopsis AHK4 histidine kinase is a cytokinin-binding receptor that transduces cytokinin signals across the membrane. Plant Cell Physiol. 42:1017-1023.
51. Yoshida, S., Forno, D. A., Cock, J. H. and Gomez, K. A. (1972) Laboratory Manual for Physiological Studies of Rice, 2nd edn. pp. 53-57. The International Rice Research Institute, Philippines.