Design, synthesis and perception of fluorescently labeled isoprenoid cytokinins

Kubiasová, K.; Mik, V.; Nisler, Jaroslav; Hönig, Martin; Husičková, A.; Spíchal, L.; Pěkná, Z.; Šamajová, O.; Doležal, Karel; Plíhal, O.; Benková, E.; Strnad, Miroslav; Plíhalová, Lucie

doi:https://dx.doi.org/10.1016/j.phytochem.2018.02.015

Number of the records: 1

Design, synthesis and perception of fluorescently labeled isoprenoid cytokinins

1.

SYSNO ASEP	0492202
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Design, synthesis and perception of fluorescently labeled isoprenoid cytokinins
Author(s)	Kubiasová, K. (CZ) Mik, V. (CZ) Nisler, Jaroslav (UEB-Q)_{RID, ORCID} Hönig, Martin (UEB-Q)_{RID, ORCID} Husičková, A. (CZ) Spíchal, L. (CZ) Pěkná, Z. (CZ) Šamajová, O. (CZ) Doležal, Karel (UEB-Q)_{RID, ORCID} Plíhal, O. (CZ) Benková, E. (AT) Strnad, Miroslav (UEB-Q)_{RID, ORCID} Plíhalová, Lucie (UEB-Q)_{ORCID, RID}
Number of authors	13
Source Title	Phytochemistry. - : Elsevier - ISSN 0031-9422 Roč. 150, JUN (2018), s. 1-11
Number of pages	11 s.
Language	eng - English
Country	GB - United Kingdom
Keywords	barley aleurone protoplasts ; endoplasmic-reticulum ; nodule organogenesis ; histidine kinase ; arabidopsis ; receptor ; binding ; probe ; ahk4 ; identification ; 6-[(3-methylbut-2-en-1-yl)amino]purine ; N-6-isopentenyladenine ; Isoprenoid ; Cytokinin ; Fluorescent label ; Fluorescent probe ; Linker ; Competitive receptor bioassay ; arr5:gus ; Live cell confocal microscopy
Subject RIV	EB - Genetics ; Molecular Biology
OECD category	Plant sciences, botany
R&D Projects	LO1204 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
	GA16-04184S GA ČR - Czech Science Foundation (CSF)
	GAP501/10/1450 GA ČR - Czech Science Foundation (CSF)
Institutional support	UEB-Q - RVO:61389030
UT WOS	000435623400001
EID SCOPUS	85042918796
DOI	10.1016/j.phytochem.2018.02.015
Annotation	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.
Workplace	Institute of Experimental Botany
Contact	David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469
Year of Publishing	2019

Number of the records: 1