Design, synthesis and biological activities of new brassinosteroid analogues with a phenyl group in the side chain

0464462 - ÚEB 2017 RIV GB eng J - Journal Article
Kvasnica, Miroslav - Oklešťková, Jana - Bazgier, Václav - Rárová, L. - Kořínková, Petra - Mikulík, Jaromír - Buděšínský, Miloš - Béreš, T. - Berka, K. - Lu, Q. - Russinova, E. - Strnad, Miroslav
Design, synthesis and biological activities of new brassinosteroid analogues with a phenyl group in the side chain.
Organic & Biomolecular Chemistry. Roč. 14, č. 37 (2016), s. 8691-8701. ISSN 1477-0520. E-ISSN 1477-0539
R&D Projects: GA MŠMT(CZ) LO1204; GA ČR GJ15-08202Y; GA MŠMT(CZ) LM2015047
Institutional support: RVO:61389030 ; RVO:61388963
Keywords : ASYMMETRIC DIHYDROXYLATION * IMMUNOMODULATORY ACTIVITY * BRI1
Subject RIV: EB - Genetics ; Molecular Biology
Impact factor: 3.564, year: 2016

We have prepared and studied a series of new brassinosteroid derivatives with a p-substituted phenyl group in the side chain. To obtain the best comparison between molecular docking and biological activities both types of brassinosteroids were synthesized; 6-ketones, 10 examples, and B-lactones, 8 examples. The phenyl group was introduced into the steroid skeleton by Horner-Wadsworth-Emmons. The docking studies were carried out using AutoDock Vina 1.05. Plant biological activities were established using different brassinosteroid bioassays in comparison with natural brassinosteroids. Differences in the production of the plant hormone ethylene were also observed in etiolated pea seedlings after treatment with new brassinosteroids. The most active compounds were lactone 8f and 6-oxo derivatives 8c and 9c, their biological activities were comparable or even better than naturally occurring brassinolide. Finally the cytotoxicity of the new derivatives was studied using human normal and cancer cell lines.
Permanent Link: http://hdl.handle.net/11104/0263315