Design, synthesis and perception of fluorescently labeled isoprenoid cytokinins
Jazyk angličtina Země Velká Británie, Anglie Médium print-electronic
Typ dokumentu časopisecké články
PubMed
29524794
DOI
10.1016/j.phytochem.2018.02.015
PII: S0031-9422(18)30053-0
Knihovny.cz E-zdroje
- Klíčová slova
- 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-chlor-7-nitrobenzofurazan farmakologie MeSH
- adenin analogy a deriváty chemie MeSH
- Arabidopsis metabolismus MeSH
- barvicí látky chemie MeSH
- cytokininy chemie farmakologie MeSH
- fluorescenční barviva chemie MeSH
- isopentenyladenosin chemická syntéza chemie farmakologie MeSH
- karbocyaniny chemie MeSH
- konfokální mikroskopie MeSH
- kukuřice setá metabolismus MeSH
- molekulární struktura MeSH
- proteiny huseníčku metabolismus MeSH
- puriny chemie MeSH
- receptory cytokinové antagonisté a inhibitory chemie MeSH
- regulace genové exprese u rostlin MeSH
- regulátory růstu rostlin metabolismus MeSH
- rhodaminy chemie MeSH
- semenáček metabolismus MeSH
- terpeny metabolismus MeSH
- vývoj rostlin MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- 4-chlor-7-nitrobenzofurazan MeSH
- 6-((3-methylbut-2-en-1-yl)amino)purine MeSH Prohlížeč
- adenin MeSH
- barvicí látky MeSH
- cyanine dye 5 MeSH Prohlížeč
- cytokininy MeSH
- fluorescenční barviva MeSH
- isopentenyladenosin MeSH
- karbocyaniny MeSH
- N(6)-(delta(2)-isopentenyl)adenine MeSH Prohlížeč
- N(6),N(6)-dimethyladenine MeSH Prohlížeč
- proteiny huseníčku MeSH
- purine MeSH Prohlížeč
- puriny MeSH
- receptory cytokinové MeSH
- regulátory růstu rostlin MeSH
- rhodamine B MeSH Prohlížeč
- rhodaminy MeSH
- terpeny 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.
Citace poskytuje Crossref.org
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