Academic Journal
Preparation, characterization and biological activity of C8-substituted cytokinins
| العنوان: | Preparation, characterization and biological activity of C8-substituted cytokinins |
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| المؤلفون: | Zahajská, L. (Lenka), Nisler, J. (Jaroslav), Voller, J. (Jiří), Gucký, T. (Tomáš), Pospíšil, T. (Tomáš), Spíchal, L. (Lukáš), Strnad, M. (Miroslav) |
| سنة النشر: | 2017 |
| المجموعة: | The Czech Academy of Sciences: Publication Activity (ASEP) / Akademie věd ČR - Publikační činnost |
| مصطلحات موضوعية: | 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 |
| الوصف: | 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. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| تدمد: | 0031-9422 1873-3700 |
| Relation: | urn:pissn: 0031-9422; urn:eissn: 1873-3700; http://hdl.handle.net/11104/0272814 |
| DOI: | 10.1016/j.phytochem.2016.12.005 |
| الاتاحة: | https://doi.org/10.1016/j.phytochem.2016.12.005 http://hdl.handle.net/11104/0272814 |
| Rights: | info:eu-repo/semantics/openAccess |
| رقم الانضمام: | edsbas.A06DCF05 |
| قاعدة البيانات: | BASE |
| تدمد: | 00319422 18733700 |
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| DOI: | 10.1016/j.phytochem.2016.12.005 |