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Preparation, characterization and biological activity of C8-substituted cytokinins
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SYSNO ASEP 0476276 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Preparation, characterization and biological activity of C8-substituted cytokinins Author(s) Zahajská, Lenka (UEB-Q) RID, ORCID
Nisler, Jaroslav (UEB-Q) RID, ORCID
Voller, Jiří (UEB-Q) RID, ORCID
Gucký, Tomáš (UEB-Q) ORCID
Pospíšil, Tomáš (UEB-Q) ORCID
Spíchal, Lukáš (UEB-Q) RID, ORCID
Strnad, Miroslav (UEB-Q) RID, ORCIDNumber of authors 7 Source Title Phytochemistry. - : Elsevier - ISSN 0031-9422
Roč. 135, MAR (2017), s. 115-127Number of pages 13 s. Language eng - English Country GB - United Kingdom Keywords potential purine antagonists ; arabidopsis-thaliana ; nucleosides ; derivatives ; thidiazuron ; specificity ; receptors ; kinetin ; Organic synthesis ; Cytokinin bioassay ; AHK3 and CRE1/AHK4 bacterial receptor assay ; C8-substituted cytokinin Subject RIV CE - Biochemistry OECD category Organic chemistry Institutional support UEB-Q - RVO:61389030 UT WOS 000394197400011 DOI 10.1016/j.phytochem.2016.12.005 Annotation Naturally occurring cytokinins are adenine-based plant hormones. Although, the effect of various substituents at positions N1, C2, N3, N-6, N7, or N9 on the biological activity of cytokinins has been studied, the C8-substituted compounds have received little attention. Here, we report the synthesis and in vitro biological testing of thirty-one cytokinin derivatives substituted at the C8 position of the adenine skeleton and twenty-seven compounds which served as their N9-tetrahydropyranyl protected precursors. The cytokinin activity of all the compounds was determined in classical cytokinin biotests (wheat leaf senescence, Amaranthus and tobacco callus assays). With some exceptions, the compounds with a N9-tetrahydropyranyl group were generally less active than their de-protected analogs. The latter were further tested for their ability to activate the Arabidopsis cytokinin receptors AHK3 and CRE1/AHK4 in bacterial receptor activation assays. Using this approach, we identified derivatives bearing short aliphatic chains and retaining high cytokinin activity. Such compounds are suitable candidates for fluorescence labeling or as protein-affinity ligands. We further found that some C8-substituted cytokinins exhibited no or lower cytotoxicity toward tobacco cells when compared to their parent compound. Therefore, we also present and discuss the cytotoxicity of all the compounds against three normal human cell lines. Workplace Institute of Experimental Botany Contact David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Year of Publishing 2018
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