Synthesis and biological activity of brassinosteroid analogues with a nitrogen-containing side chain

0543685 - ÚEB 2022 RIV CH eng J - Journal Article
Diachkov, Mikhail V. - Ferrer, Karoll - Oklešťková, Jana - Rárová, Lucie - Bazgier, Václav - Kvasnica, Miroslav
Synthesis and biological activity of brassinosteroid analogues with a nitrogen-containing side chain.
International Journal of Molecular Sciences. Roč. 22, č. 1 (2021), č. článku 155. E-ISSN 1422-0067
R&D Projects: GA ČR(CZ) GA19-01383S; GA MŠMT(CZ) EF16_019/0000827
Institutional support: RVO:61389030
Keywords : Brassinosteroid * Cytotoxicity * Nitrogen-containing steroid * Organic synthesis * Plant bioassay
OECD category: Organic chemistry
Impact factor: 6.208, year: 2021
Method of publishing: Open access
http://doi.org/10.3390/ijms22010155

Brassinosteroids are a class of plant hormones that regulate a broad range of physiological processes such as plant growth, development and immunity, including the suppression of biotic and abiotic stresses. In this paper, we report the synthesis of new brassinosteroid analogues with a nitrogen-containing side chain and their biological activity on Arabidopis thaliana. Based on molecular docking experiments, two groups of brassinosteroid analogues were prepared with short and long side chains in order to study the impact of side chain length on plants. the derivatives with a short side chain were prepared with amide, amine and ammonium functional groups. the derivatives with a long side chain were synthesized using amide and ammonium functional groups. A total of 25 new brassinosteroid analogues were prepared. All 25 compounds were tested in an Arabidopsis root sensitivity bioassay and cytotoxicity screening. the synthesized substances showed no signifi-cant inhibitory activity compared to natural 24-epibrassinolide. In contrast, in low concentration, several compounds (8a, 8b, 8e, 16e, 22a and 22e) showed interesting growth-promoting activity. the cytotoxicity assay showed no toxicity of the prepared compounds on cancer and normal cell lines.
Permanent Link: http://hdl.handle.net/11104/0320865