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Design, synthesis and perception of fluorescently labeled isoprenoid cytokinins

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F18%3A73591288" target="_blank" >RIV/61989592:15310/18:73591288 - isvavai.cz</a>

  • Alternative codes found

    RIV/61389030:_____/18:00492202

  • Result on the web

    <a href="https://www.sciencedirect.com/science/article/abs/pii/S0031942218300530" target="_blank" >https://www.sciencedirect.com/science/article/abs/pii/S0031942218300530</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1016/j.phytochem.2018.02.015" target="_blank" >10.1016/j.phytochem.2018.02.015</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Design, synthesis and perception of fluorescently labeled isoprenoid cytokinins

  • Original language description

    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 (N-6-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.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    20401 - Chemical engineering (plants, products)

Result continuities

  • Project

    Result was created during the realization of more than one project. More information in the Projects tab.

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2018

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    PHYTOCHEMISTRY

  • ISSN

    0031-9422

  • e-ISSN

  • Volume of the periodical

    150

  • Issue of the periodical within the volume

    JUN

  • Country of publishing house

    GB - UNITED KINGDOM

  • Number of pages

    11

  • Pages from-to

    1-11

  • UT code for WoS article

    000435623400001

  • EID of the result in the Scopus database

    2-s2.0-85042918796