From synthesis to the biological effect of isoprenoid 2′-deoxyriboside and 2′,3′-dideoxyriboside cytokinin analogues

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F23%3A00569181" target="_blank" >RIV/61389030:_____/23:00569181 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61989592:15310/23:73616759

Výsledek na webu

<a href="https://doi.org/10.1016/j.phytochem.2022.113481" target="_blank" >https://doi.org/10.1016/j.phytochem.2022.113481</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.phytochem.2022.113481" target="_blank" >10.1016/j.phytochem.2022.113481</a>

Jazyk výsledku

angličtina

Název v původním jazyce

From synthesis to the biological effect of isoprenoid 2′-deoxyriboside and 2′,3′-dideoxyriboside cytokinin analogues

Popis výsledku v původním jazyce

Isoprenoid cytokinins are a class of naturally occurring plant signaling molecules. A series of prepared compounds derived from isoprenoid cytokinins (isopentenyladenine, trans-zeatin and cis-zeatin) with attached 2′-deoxy-D-ribose or 2′,3′-dideoxy-D-ribose at the N9 position of the purine were prepared and their biological activities were examined. Different synthetic approaches were employed. The final compounds were characterized with variety of physicochemical methods (TLC, HPLC-MS, and NMR) and their cytokinin activity was determined in classical bioassays such as Amaranthus, tobacco callus, detached wheat leaf senescence and Arabidopsis thaliana root elongation inhibition assay. In addition, compounds were screened for activation of the cytokinin signaling pathway (bacterial receptor, competitive ligand binding and ARR5::GUS assay) to provide a detailed assessment of CK structure-activity relationship. The prepared compounds were found to be non-toxic to human cells and the majority of assays exhibited the highest activity of free bases while 2′,3′-dideoxyribosides had very weak or no activity. In contrast to the free bases, all 2′-deoxyriboside derivatives were not toxic to tobacco callus even at the highest tested concentration (10−4 moL/l) and compound 1 (iPdR) induced betacyanin synthesis at higher concentration even stronger than iP free base in the Amaranthus bioassay. The general cytokinin activity pattern base > riboside >2′-deoxyriboside > 2′,3′-dideoxyriboside was distinguished.

Název v anglickém jazyce

From synthesis to the biological effect of isoprenoid 2′-deoxyriboside and 2′,3′-dideoxyriboside cytokinin analogues

Popis výsledku anglicky

Isoprenoid cytokinins are a class of naturally occurring plant signaling molecules. A series of prepared compounds derived from isoprenoid cytokinins (isopentenyladenine, trans-zeatin and cis-zeatin) with attached 2′-deoxy-D-ribose or 2′,3′-dideoxy-D-ribose at the N9 position of the purine were prepared and their biological activities were examined. Different synthetic approaches were employed. The final compounds were characterized with variety of physicochemical methods (TLC, HPLC-MS, and NMR) and their cytokinin activity was determined in classical bioassays such as Amaranthus, tobacco callus, detached wheat leaf senescence and Arabidopsis thaliana root elongation inhibition assay. In addition, compounds were screened for activation of the cytokinin signaling pathway (bacterial receptor, competitive ligand binding and ARR5::GUS assay) to provide a detailed assessment of CK structure-activity relationship. The prepared compounds were found to be non-toxic to human cells and the majority of assays exhibited the highest activity of free bases while 2′,3′-dideoxyribosides had very weak or no activity. In contrast to the free bases, all 2′-deoxyriboside derivatives were not toxic to tobacco callus even at the highest tested concentration (10−4 moL/l) and compound 1 (iPdR) induced betacyanin synthesis at higher concentration even stronger than iP free base in the Amaranthus bioassay. The general cytokinin activity pattern base > riboside >2′-deoxyriboside > 2′,3′-dideoxyriboside was distinguished.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10608 - Biochemistry and molecular biology

Projekt

<a href="/cs/project/EF16_019%2F0000827" target="_blank" >EF16_019/0000827: Rostliny jako prostředek udržitelného globálního rozvoje</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

Phytochemistry

ISSN

0031-9422

e-ISSN

1873-3700

Svazek periodika

205

Číslo periodika v rámci svazku

JAN

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

12

Strana od-do

113481

Kód UT WoS článku

000883907500002

EID výsledku v databázi Scopus

2-s2.0-85141317708