Preparation, characterization and biological activity of C8-substituted cytokinins

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F17%3A00476276" target="_blank" >RIV/61389030:_____/17:00476276 - isvavai.cz</a>

Alternative codes found

RIV/61989592:15310/17:73584819

Result on the web

<a href="http://dx.doi.org/10.1016/j.phytochem.2016.12.005" target="_blank" >http://dx.doi.org/10.1016/j.phytochem.2016.12.005</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.phytochem.2016.12.005" target="_blank" >10.1016/j.phytochem.2016.12.005</a>

Result language

angličtina

Original language name

Preparation, characterization and biological activity of C8-substituted cytokinins

Original language description

Naturally occurring cytokinins are adenine-based plant hormones. Although, the effect of various substituents at positions N1, C2, N3, N-6, N7, or N9 on the biological activity of cytokinins has been studied, the C8-substituted compounds have received little attention. Here, we report the synthesis and in vitro biological testing of thirty-one cytokinin derivatives substituted at the C8 position of the adenine skeleton and twenty-seven compounds which served as their N9-tetrahydropyranyl protected precursors. The cytokinin activity of all the compounds was determined in classical cytokinin biotests (wheat leaf senescence, Amaranthus and tobacco callus assays). With some exceptions, the compounds with a N9-tetrahydropyranyl group were generally less active than their de-protected analogs. The latter were further tested for their ability to activate the Arabidopsis cytokinin receptors AHK3 and CRE1/AHK4 in bacterial receptor activation assays. Using this approach, we identified derivatives bearing short aliphatic chains and retaining high cytokinin activity. Such compounds are suitable candidates for fluorescence labeling or as protein-affinity ligands. We further found that some C8-substituted cytokinins exhibited no or lower cytotoxicity toward tobacco cells when compared to their parent compound. Therefore, we also present and discuss the cytotoxicity of all the compounds against three normal human cell lines.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

<a href="/en/project/LO1204" target="_blank" >LO1204: Sustainable development of research in the Centre of the Region Haná</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2017

Confidentiality

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

Name of the periodical

Phytochemistry

ISSN

0031-9422

e-ISSN

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Volume of the periodical

135

Issue of the periodical within the volume

MAR

Country of publishing house

GB - UNITED KINGDOM

Number of pages

13

Pages from-to

115-127

UT code for WoS article

000394197400011

EID of the result in the Scopus database

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