title: Design, synthesis and biological activities of new brassinosteroid analogues with a phenyl group in the side chain.
abstract: 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.
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic. kvasnica@ueb.cas.cz.
authors.forename: M
authors.initials: M
authors.lastname: Kvasnica
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic. kvasnica@ueb.cas.cz.
authors.forename: J
authors.initials: J
authors.lastname: Oklestkova
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic. kvasnica@ueb.cas.cz and Department of Physical Chemistry, Faculty of Science, Palacký University, tř. 17. Listopadu 12, 77146 Olomouc, Czech Republic.
authors.forename: V
authors.initials: V
authors.lastname: Bazgier
authors.affiliation: Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic.
authors.forename: L
authors.initials: L
authors.lastname: Rárová
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic. kvasnica@ueb.cas.cz.
authors.forename: P
authors.initials: P
authors.lastname: Korinkova
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic. kvasnica@ueb.cas.cz.
authors.forename: J
authors.initials: J
authors.lastname: Mikulík
authors.affiliation: Institute of Organic Chemistry and Biochemistry, ASCR, Flemingovo n. 2, 16610 Prague 6, Czech Republic.
authors.forename: M
authors.initials: M
authors.lastname: Budesinsky
authors.affiliation: Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic.
authors.forename: T
authors.initials: T
authors.lastname: Béres
authors.affiliation: Department of Physical Chemistry, Faculty of Science, Palacký University, tř. 17. Listopadu 12, 77146 Olomouc, Czech Republic and Regional Centre of Advanced Technologies and Materials, Department of Physical Chemistry Palacky University in Olomouc, 17. listopadu 1131, Olomouc CZ779 00, Czech Republic.
authors.forename: K
authors.initials: K
authors.lastname: Berka
authors.affiliation: Department of Plant Systems Biology, VIB, 9052 Ghent, Belgium and Department of Plant Biotechnology and Bioinformatics, Ghent University, 9052 Ghent, Belgium.
authors.forename: Q
authors.initials: Q
authors.lastname: Lu
authors.affiliation: Department of Plant Systems Biology, VIB, 9052 Ghent, Belgium and Department of Plant Biotechnology and Bioinformatics, Ghent University, 9052 Ghent, Belgium.
authors.forename: E
authors.initials: E
authors.lastname: Russinova
authors.affiliation: Laboratory of Growth Regulators, Centre of the Region Haná for Biotechnological and Agricultural Research, Institute of Experimental Botany ASCR & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic. kvasnica@ueb.cas.cz.
authors.forename: M
authors.initials: M
authors.lastname: Strnad
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D017360:Arabidopsis / Q000378:metabolism; D029681:Arabidopsis Proteins / Q000378:metabolism; D060406:Brassinosteroids / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D062105:Molecular Docking Simulation; D009369:Neoplasms / Q000188:drug therapy; D010937:Plant Growth Regulators / Q000378:metabolism; D011494:Protein Kinases / Q000378:metabolism
chemical_list: D000970:Antineoplastic Agents; D029681:Arabidopsis Proteins; D060406:Brassinosteroids; D010937:Plant Growth Regulators; D011494:Protein Kinases; C108270:BRI1 protein, Arabidopsis