Design, synthesis and perception of fluorescently labeled isoprenoid cytokinins
Language English Country Great Britain, England Media print-electronic
Document type Journal Article
PubMed
29524794
DOI
10.1016/j.phytochem.2018.02.015
PII: S0031-9422(18)30053-0
Knihovny.cz E-resources
- Keywords
- 6-[(3-methylbut-2-en-1-yl)amino]purine, ARR5:GUS, Competitive receptor bioassay, Cytokinin, Fluorescent label, Fluorescent probe, Isoprenoid, Linker, Live cell confocal microscopy, N(6)-isopentenyladenine,
- MeSH
- 4-Chloro-7-nitrobenzofurazan pharmacology MeSH
- Adenine analogs & derivatives chemistry MeSH
- Arabidopsis metabolism MeSH
- Coloring Agents chemistry MeSH
- Cytokinins chemistry pharmacology MeSH
- Fluorescent Dyes chemistry MeSH
- Isopentenyladenosine chemical synthesis chemistry pharmacology MeSH
- Carbocyanines chemistry MeSH
- Microscopy, Confocal MeSH
- Zea mays metabolism MeSH
- Molecular Structure MeSH
- Arabidopsis Proteins metabolism MeSH
- Purines chemistry MeSH
- Receptors, Cytokine antagonists & inhibitors chemistry MeSH
- Gene Expression Regulation, Plant MeSH
- Plant Growth Regulators metabolism MeSH
- Rhodamines chemistry MeSH
- Seedlings metabolism MeSH
- Terpenes metabolism MeSH
- Plant Development MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- 4-Chloro-7-nitrobenzofurazan MeSH
- 6-((3-methylbut-2-en-1-yl)amino)purine MeSH Browser
- Adenine MeSH
- Coloring Agents MeSH
- cyanine dye 5 MeSH Browser
- Cytokinins MeSH
- Fluorescent Dyes MeSH
- Isopentenyladenosine MeSH
- Carbocyanines MeSH
- N(6)-(delta(2)-isopentenyl)adenine MeSH Browser
- N(6),N(6)-dimethyladenine MeSH Browser
- Arabidopsis Proteins MeSH
- purine MeSH Browser
- Purines MeSH
- Receptors, Cytokine MeSH
- Plant Growth Regulators MeSH
- rhodamine B MeSH Browser
- Rhodamines MeSH
- Terpenes MeSH
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.
References provided by Crossref.org
Auxins and Cytokinins-The Role of Subcellular Organization on Homeostasis
