Novel cytokinin derivatives do not show negative effects on root growth and proliferation in submicromolar range

PLoS ONE

Volumn 7, Issue 6, 2012, Pages

  Podlešáková, Kateřina ^a   Zalabák, David ^a   Čudejková, Mária ^a   Plíhal, Ondřej ^a   Szüčová, Lucie ^a   Doležal, Karel ^a   Spíchal, Lukáš ^a   Strnad, Miroslav ^a   Galuszka, Petr ^a  

^a PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHOXY ( 6 BENZYLAMINO 9 CHLOROBUTYL)PURINE; 3 METHOXY ( 6 BENZYLAMINO 9 GLUCOSYL)PURINE; 3 METHOXY ( 6 BENZYLAMINO 9 TETRAHYDROPYRAN 2 YL)PURINE; 3 METHOXY(6 BENZYLAMINO)PURINE; CYTOKININ; CYTOKININ DEHYDROGENASE 1; CYTOKININ DEHYDROGENASE 10; CYTOKININ DEHYDROGENASE 6; PURINE; UNCLASSIFIED DRUG;

ARABIDOPSIS; ARTICLE; CONTROLLED STUDY; GENE EXPRESSION PROFILING; GENE FUNCTION; HORMONE METABOLISM; LACZ GENE; MAIZE; NONHUMAN; PHENOTYPE; PLANT GENE; ROOT DEVELOPMENT; ROOT GROWTH; RR GENE; SEEDLING; UPREGULATION;

ARABIDOPSIS; BIOMASS; CELL PROLIFERATION; CYTOKININS; ENZYME ACTIVATION; GENE EXPRESSION PROFILING; GENE EXPRESSION REGULATION, PLANT; OXIDOREDUCTASES; PLANT GROWTH REGULATORS; PLANT LEAVES; PLANT ROOTS; SEEDLING; XYLEM; ZEA MAYS;

EID: 84862497086     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0039293     Document Type: Article

References (54)

1. Szüčová L, Spíchal L, Doležal K, Zatloukal M, Greplová J, et al. (2009) Synthesis, characterization and biological activity of ring-substituted 6-benzylamino-9-tetrahydropyran-2-yl and 9-tetrahydrofuran-2-ylpurine derivatives. Bioorgan Med Chem 17: 1938-1947.
2. West T, Preece JE, (2004) Effects of thidiazuron and nutrient salt formulations on micropropagation of hardy hibiscus (Hibiscus moscheutos L.). Acta Hortic 630: 293-297.
3. Debnath SC, (2008) Zeatin-induced one-step in vitro cloning affects the vegetative growth of cranberry (Vaccinium macrocarpon Ait.) micropropagules over stem cuttings. Plant Cell Tiss Org 93: 231-240.
4. Robert-Seilaniantz A, Navarro L, Bari R, Jones JD, (2007) Pathological hormone imbalances. Curr Opin Plant Biol 10: 372-379.
5. Bairu MW, Fennell CW, van Staden J, (2006) The effect of plant growth regulators on somaclonal variation in Cavendish banana (Musa AAA cv. 'Zelig'). Sci Hortic-Amterdam 108: 347-351.
6. Galuszka P, Popelková H, Werner T, Frébortová J, Pospíšilová H, et al. (2007) Biochemical characterization and histochemical localization of cytokinin oxidases/dehydrogenases from Arabidopsis thaliana expressed in Nicotiana tabaccum L. J Plant Growth Regul 26: 255-267.
7. Werbrouck SPO, Strnad M, van Onckelen HA, Debergh PC, (1996) Meta-topolin, an alternative to benzyladenine in tissue culture? Physiol Plantarum 98: 291-297.
8. Bairu MW, Stirk WA, Doležal K, van Staden J, (2008) The role of topolins in micropropagation and somaclonal variation of banana cultivars 'Williams' and 'Grand Naine' (Musa spp. AAA). Plant Cell Tiss Org 95: 373-379.
9. Valero-Aracama C, Kane ME, Wilson SB, Philman NL, (2010) Substitution of benzyladenine with meta-topolin during shoot multiplication increases acclimatization of difficult- and easy-to-acclimatize sea oats (Uniola paniculata L.) genotypes. Plant Growth Regul 60: 43-49.
10. Holub J, Hanuš J, Hanke DE, Strnad M, (1998) Biological activity of cytokinins derived from ortho- and meta-hydroxybenzyladenine. Plant Growth Regul 26: 109-115.
11. Mok MC, Martin RC, Dobrev PI, Vaňková R, Ho PS, et al. (2005) Topolins and hydroxylated thidiazuron derivatives are substrates of cytokinin O-glucosyltransferase with position specificity related to receptor recognition. Plant Physiol 137: 1057-1066.
12. Spíchal L, Rakova NY, Riefler M, Mizuno T, Romanov GA, et al. (2004) Two cytokinin receptors of Arabidopsis thaliana, CRE1/AHK4 and AHK3, differ in their ligand specificity in a bacterial assay. Plant Cell Physiol 45: 1299-1305.
13. Werbrouck SPO, van der Jeugt B, Dewitte W, Prinsen E, van Onckelen HA, (1995) The metabolism of benzyladenine in Spathiphyllum floribundum 'Schott Petite' in relation to acclimatisation problems. Plant Cell Rep 14: 662-665.
14. Auer CA, (1996) Cytokinin inhibition of Arabidopsis root growth: An examination of genotype, cytokinin activity, and N-6-benzyladenine metabolism. J Plant Growth Regul 15: 201-206.
15. Cary AJ, Liu WN, Howell SH, (1995) Cytokinin action is coupled to ethylene in its effects on the inhibition of root and hypocotyl elongation in Arabidopsis thaliana seedlings. Plant Physiol 107: 1075-1082.
16. Bertell G, Eliasson L, (1992) Cytokinin effects on root growth and possible interactions with ethylene and indole-3-acetic acid. Physiol Plantarum 84: 255-261.
17. Růžička K, Ljung K, Vanneste S, Podhorská R, Beeckman T, et al. (2007) Ethylene regulates root growth through effects on auxin biosynthesis and transport-dependent auxin distribution. Plant Cell 7: 2197-2212.
18. Růžička K, Šimašková M, Duclercq J, Petrášek J, Zažímalová E, et al. (2009) Cytokinin regulates root meristem activity via modulation of the polar auxin transport. P Natl Acad Sci USA 106: 4284-4289.
19. Zhang R, Letham DS, (1989) Cytokinin biochemistry in relation to leaf senescence. III. The senescence-retarding activity and metabolism of 9-substituted 6-benzylaminopurines in soybean leaves. J Plant Growth Regul 8: 181-197.
20. Corse J, Pacovsky RS, Lyman ML, Brandon DL, (1989) Biological activity of several 9-nonglycosidic-substituted natural cytokinins. J Plant Growth Regul 8: 211-223.
21. Fox JE, Sood CK, Buckwalter B, McChesney JD, (1971) The metabolism and biological activity of a 9-substituted cytokinin. Plant Physiol 47: 275-281.
22. Pietraface WJ, Blaydes DF, (1981) Activity and metabolism of 9-substituted cytokinins during lettuce seed germination. Physiol Plantarum 53: 249-254.
23. Sul IW, Korban SS, (1994) Effect of different cytokinins on axillary shoot proliferation and elongation of several genotypes of Sequoia sempervirens. In Vitro Cell Dev-Pl 30: 131-135.
24. Weaver RJ, Overbeek RM, Pool RM, (1965) Induction of fruit set in Vitis vinifera L. by a kinin. Nature 206: 952-953.
25. Letham DS, Summons RE, Entsch B, Gollnow BI, Parker CW, et al. (1978) Glycosylation of cytokinin analogues. Phytochemistry 17: 2053-2057.
26. Suzuki T, Miwa K, Ishikawa K, Yamada H, Aiba H, et al. (2001) The Arabidopsis sensor His-kinase, AHK4, can respond to cytokinins. Plant Cell Physiol 42: 107-113.
27. Yonekura-Sakakibara K, Kojima M, Yamaya T, Sakakibara H, (2004) Molecular characterization of cytokinin-responsive histidine kinases in maize. Differential ligand preferences and response to cis-zeatin. Plant Physiol 134: 1654-1661.
28. Gallie DR, Young TE, (2004) The ethylene biosynthetic and perception machinery is differentially expressed during endosperm and embryo development in maize. Mol Genet Genomics 271: 267-281.
29. Suttle JC, Mornet R, (2005) Mechanism-based irreversible inhibitors of cytokinin dehydrogenase. J Plant Physiol 162: 1189-1196.
30. Kopečný D, Briozzo P, Popelková H, Šebela M, Končitíková R, et al. (2010) Phenyl- and benzylurea cytokinins as competitive inhibitors of cytokinin oxidase/dehydrogenase: a structural study. Biochimie 92: 1052-1062.
31. Romanov GA, Lomin SN, 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: 4051-4058.
32. Tarkowská D, Doležal K, Tarkowski P, Åstot C, Holub J, et al. (2003) Identification of new aromatic cytokinins in Arabidopsis thaliana and Populus x canadensis leaves by LC-(+)ESI-MS and capillary liquid chromatography/frit-fast atom bombardment mass spectrometry. Physiol Plantarum 117: 579-590.
33. Higuchi M, Pischke MS, Mähonen AP, Miyawaki K, Hashimoto Y, et al. (2004) In planta functions of the Arabidopsis cytokinin receptor family. P Natl Acad Sci USA 101: 8821-8826.
34. Hothorn M, Dabi T, Chory J, (2011) Structural basis for cytokinin recognition by Arabidopsis thaliana histidine kinase 4. Nat Chem Biol 7: 766-768.
35. Kudo T, Kiba T, Sakakibara H, (2010) Metabolism and long-distance translocation of cytokinins. J Integr Plant Biol 52: 53-60.
36. Saleem M, Lamkemeyer T, Schützenmeister A, Madlung J, Sakai H, et al. (2010) Specification of cortical parenchyma and stele of maize (Zea mays L.) primary roots by asymmetric levels of auxin, cytokinin and cytokinin-regulated proteins. Plant Physiol 152: 4-18.
37. Laplaze L, Benková E, Casimiro I, Maes L, Vanneste S, et al. (2007) Cytokinins act directly on lateral root founder cells to inhibit root initiation. Plant Cell 19: 3889-3900.
38. Mik V, Szüčová L, Šmehilová M, Zatloukal M, Doležal K, et al. (2011) N9-substituted derivatives of kinetin: Effective anti-senescence agents. Phytochemistry 72: 821-831.
39. Vyroubalová Š, Václavíková K, Turečková V, Novák O, Šmehilová M, et al. (2009) Characterization of new maize genes putatively involved in cytokinin metabolism and their expression during osmotic stress in relation to cytokinin levels. Plant Physiol 51: 433-447.
40. Spíchal L, Werner T, Popa I, Riefler M, Schmülling T, et al. (2009) The purine derivative PI-55 blocks cytokinin action via receptor inhibition. FEBS J 276: 244-253.
41. Nisler J, Zatloukal M, Popa I, Doležal K, Strnad M, et al. (2010) Cytokinin receptor antagonists derived from 6-benzylaminopurine. Phytochemistry 71: 823-830.
42. Riefler M, Novák O, Strnad M, 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.
43. Werner T, Motyka V, Laucou V, Smets R, Van Onckelen H, et al. (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.
44. McGaw BA, Heald JK, Horgan R, (1984) Dihydrozeatin metabolism in radish seedlings. Phytochemistry 23: 1373-1377.
45. McGaw BA, Horgan R, Heald JK, (1985) Cytokinin metabolism and the modulation of cytokinin activity in radish. Phytochemistry 24: 9-13.
46. Winkler R, Sandermann H, (1992) N-Glucosyl conjugates of chlorinated anilines: spontaneous formation and cleavage. J Agr Food Chem 40: 2008-2012.
47. Brzobohatý B, Moore I, Kristoffersen P, Bako L, Campos N, et al. (1993) Release of active cytokinin by a beta-glucosidase localized to the maize root meristem. Science 12: 1051-1054.
48. Cairns JRK, Esen A, (2010) β-Glucosidases. Cell Mol Life Sci 67: 3389-3405.
49. Filipi T, Mazura P, Janda L, Kiran NS, Brzobohatý B, (2012) Engineering the cytokinin-glucoside specificity of the maize β-D-glucosidase Zm-p60.1 using site-directed random mutagenesis. Phytochemistry 74: 40-48.
50. Faiss M, Zalubilová J, Strnad M, Schmülling T, (1997) Conditional transgenic expression of the ipt gene indicates a function of cytokinins in paracrine signaling in whole tobacco plants. Plant J 12: 401-415.
51. Novák O, Hauserová E, Amakorová P, Doležal K, Strnad M, (2008) Cytokinin profiling in plant tissues using ultra-performance liquid chromatography-electrospray tandem mass spectrometry. Phytochemistry 69: 2214-2224.
52. Yamada H, Suzuki T, Terada K, Takei K, Ishikawa 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.
53. Benjamini Y, Hochberg Y, (1995) Controlling the false discovery rate: a practical and powerful approach to multiple testing. J Roy Stat Soc B Met 57: 289-300.
54. Kurakawa T, Ueda N, Maekawa M, Kobayashi K, Kojima M, et al. (2007) Direct control of shoot meristem activity by a cytokinin-activating enzyme. Nature 445: 652-655.