Počet záznamů: 1  

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

  1. 1. 0464462 - UEB-Q 2017 RIV GB eng J - Článek v odborném periodiku
    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
    Grant CEP: GA MŠk(CZ) LO1204; GA ČR GJ15-08202Y; GA MŠk(CZ) LM2015047
    Institucionální podpora: RVO:61389030 ; RVO:61388963
    Klíčová slova: ASYMMETRIC DIHYDROXYLATION * IMMUNOMODULATORY ACTIVITY * BRI1
    Kód oboru RIV: EB - Genetika a molekulární biologie
    Impakt faktor: 3.564, rok: 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.
    Trvalý link: http://hdl.handle.net/11104/0263315