Design, synthesis and perception of fluorescently labeled isoprenoid cytokinins
| Autor: | Martin Hönig, Miroslav Strnad, Václav Mik, Jaroslav Nisler, Lukáš Spíchal, Zuzana Pěkná, Olga Šamajová, Karolina Kubiasová, Alexandra Husičková, Karel Doležal, Eva Benková, Ondřej Plíhal, Lucie Plíhalová |
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| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Cytokinins Arabidopsis Plant Development Plant Science Horticulture Biochemistry Zea mays 03 medical and health sciences chemistry.chemical_compound Isopentenyladenosine Plant Growth Regulators Gene Expression Regulation Plant Rhodamine B heterocyclic compounds Fluorescein Receptors Cytokine Receptor Coloring Agents Molecular Biology Fluorescent Dyes Microscopy Confocal biology Molecular Structure Chemistry Arabidopsis Proteins Rhodamines Terpenes Adenine fungi food and beverages General Medicine Carbocyanines biology.organism_classification Coumarin Fluorescence 030104 developmental biology 4-Chloro-7-nitrobenzofurazan Purines Seedlings Cytokinin Linker |
| Zdroj: | Phytochemistry. 150 |
| ISSN: | 1873-3700 |
| Popis: | Isoprenoid cytokinins play a number of crucial roles in the regulation of plant growth and development. To study cytokinin receptor properties in plants, we designed and prepared fluorescent derivatives of 6-[(3-methylbut-2-en-1-yl)amino]purine (N6-isopentenyladenine, iP) with several fluorescent labels attached to the C2 or N9 atom of the purine moiety via a 2- or 6-carbon linker. The fluorescent labels included dansyl (DS), fluorescein (FC), 7-nitrobenzofurazan (NBD), rhodamine B (RhoB), coumarin (Cou), 7-(diethylamino)coumarin (DEAC) and cyanine 5 dye (Cy5). All prepared compounds were screened for affinity for the Arabidopsis thaliana cytokinin receptor (CRE1/AHK4). Although the attachment of the fluorescent labels to iP via the linkers mostly disrupted binding to the receptor, several fluorescent derivatives interacted well. For this reason, three derivatives, two rhodamine B and one 4-chloro-7-nitrobenzofurazan labeled iP were tested for their interaction with CRE1/AHK4 and Zea mays cytokinin receptors in detail. We further showed that the three derivatives were able to activate transcription of cytokinin response regulator ARR5 in Arabidopsis seedlings. The activity of fluorescently labeled cytokinins was compared with corresponding 6-dimethylaminopurine fluorescently labeled negative controls. Selected rhodamine B C2-labeled compounds 17, 18 and 4-chloro-7-nitrobenzofurazan N9-labeled compound 28 and their respective negative controls (19, 20 and 29, respectively) were used for in planta staining experiments in Arabidopsis thaliana cell suspension culture using live cell confocal microscopy. |
| Databáze: | OpenAIRE |
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