---
_id: '407'
abstract:
- lang: eng
text: 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.
acknowledgement: "This work was supported by the Ministry of Education Youth and Sports,
Czech Republic (grant LO1204 from the National Program of Sustainability I and Agricultural
Research ) and by Czech Science Foundation grants 16-04184S , 501/10/1450 and 13-39982S
and by IGA projects IGA_PrF_2018_033 and IGA_PrF_2018_023 . We would like to thank
Jarmila Balonová, Olga Hustáková and Miroslava Šubová for their skillful technical
assistance and Mgr. Tomáš Pospíšil, Ph.D. for his measurement of 1 H NMR and analysis
of some 2D NMR spectral data. \r\n"
article_processing_charge: No
author:
- first_name: Karolina
full_name: Kubiasová, Karolina
last_name: Kubiasová
- first_name: Václav
full_name: Mik, Václav
last_name: Mik
- first_name: Jaroslav
full_name: Nisler, Jaroslav
last_name: Nisler
- first_name: Martin
full_name: Hönig, Martin
last_name: Hönig
- first_name: Alexandra
full_name: Husičková, Alexandra
last_name: Husičková
- first_name: Lukáš
full_name: Spíchal, Lukáš
last_name: Spíchal
- first_name: Zuzana
full_name: Pěkná, Zuzana
last_name: Pěkná
- first_name: Olga
full_name: Šamajová, Olga
last_name: Šamajová
- first_name: Karel
full_name: Doležal, Karel
last_name: Doležal
- first_name: Ondřej
full_name: Plíhal, Ondřej
last_name: Plíhal
- first_name: Eva
full_name: Benková, Eva
id: 38F4F166-F248-11E8-B48F-1D18A9856A87
last_name: Benková
orcid: 0000-0002-8510-9739
- first_name: Miroslav
full_name: Strnad, Miroslav
last_name: Strnad
- first_name: Lucie
full_name: Plíhalová, Lucie
last_name: Plíhalová
citation:
ama: Kubiasová K, Mik V, Nisler J, et al. Design, synthesis and perception of fluorescently
labeled isoprenoid cytokinins. Phytochemistry. 2018;150:1-11. doi:10.1016/j.phytochem.2018.02.015
apa: Kubiasová, K., Mik, V., Nisler, J., Hönig, M., Husičková, A., Spíchal, L.,
… Plíhalová, L. (2018). Design, synthesis and perception of fluorescently labeled
isoprenoid cytokinins. Phytochemistry. Elsevier. https://doi.org/10.1016/j.phytochem.2018.02.015
chicago: Kubiasová, Karolina, Václav Mik, Jaroslav Nisler, Martin Hönig, Alexandra
Husičková, Lukáš Spíchal, Zuzana Pěkná, et al. “Design, Synthesis and Perception
of Fluorescently Labeled Isoprenoid Cytokinins.” Phytochemistry. Elsevier,
2018. https://doi.org/10.1016/j.phytochem.2018.02.015.
ieee: K. Kubiasová et al., “Design, synthesis and perception of fluorescently
labeled isoprenoid cytokinins,” Phytochemistry, vol. 150. Elsevier, pp.
1–11, 2018.
ista: Kubiasová K, Mik V, Nisler J, Hönig M, Husičková A, Spíchal L, Pěkná Z, Šamajová
O, Doležal K, Plíhal O, Benková E, Strnad M, Plíhalová L. 2018. Design, synthesis
and perception of fluorescently labeled isoprenoid cytokinins. Phytochemistry.
150, 1–11.
mla: Kubiasová, Karolina, et al. “Design, Synthesis and Perception of Fluorescently
Labeled Isoprenoid Cytokinins.” Phytochemistry, vol. 150, Elsevier, 2018,
pp. 1–11, doi:10.1016/j.phytochem.2018.02.015.
short: K. Kubiasová, V. Mik, J. Nisler, M. Hönig, A. Husičková, L. Spíchal, Z. Pěkná,
O. Šamajová, K. Doležal, O. Plíhal, E. Benková, M. Strnad, L. Plíhalová, Phytochemistry
150 (2018) 1–11.
date_created: 2018-12-11T11:46:18Z
date_published: 2018-06-01T00:00:00Z
date_updated: 2023-09-11T12:53:11Z
day: '01'
department:
- _id: EvBe
doi: 10.1016/j.phytochem.2018.02.015
external_id:
isi:
- '000435623400001'
intvolume: ' 150'
isi: 1
language:
- iso: eng
month: '06'
oa_version: None
page: 1-11
publication: Phytochemistry
publication_status: published
publisher: Elsevier
publist_id: '7422'
quality_controlled: '1'
scopus_import: '1'
status: public
title: Design, synthesis and perception of fluorescently labeled isoprenoid cytokinins
type: journal_article
user_id: c635000d-4b10-11ee-a964-aac5a93f6ac1
volume: 150
year: '2018'
...