Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain
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-cont...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-12-01
|
| Series: | International Journal of Molecular Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-0067/22/1/155 |
| _version_ | 1797543525814894592 |
|---|---|
| author | Mikhail V. Diachkov Karoll Ferrer Jana Oklestkova Lucie Rarova Vaclav Bazgier Miroslav Kvasnica |
| author_facet | Mikhail V. Diachkov Karoll Ferrer Jana Oklestkova Lucie Rarova Vaclav Bazgier Miroslav Kvasnica |
| author_sort | Mikhail V. Diachkov |
| collection | DOAJ |
| description | 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 <i>Arabidopis thaliana</i>. 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 significant 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. |
| first_indexed | 2024-03-10T13:45:53Z |
| format | Article |
| id | doaj.art-cf71572ab6f54d12a987397b9f2d27bb |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T13:45:53Z |
| publishDate | 2020-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-cf71572ab6f54d12a987397b9f2d27bb2023-11-21T02:36:32ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672020-12-0122115510.3390/ijms22010155Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side ChainMikhail V. Diachkov0Karoll Ferrer1Jana Oklestkova2Lucie Rarova3Vaclav Bazgier4Miroslav Kvasnica5Laboratory of Growth Regulators, The Czech Academy of Sciences, Institute of Experimental Botany & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech RepublicLaboratory of Growth Regulators, The Czech Academy of Sciences, Institute of Experimental Botany & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech RepublicLaboratory of Growth Regulators, The Czech Academy of Sciences, Institute of Experimental Botany & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech RepublicLaboratory of Growth Regulators, The Czech Academy of Sciences, Institute of Experimental Botany & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech RepublicLaboratory of Growth Regulators, The Czech Academy of Sciences, Institute of Experimental Botany & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech RepublicLaboratory of Growth Regulators, The Czech Academy of Sciences, Institute of Experimental Botany & Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech RepublicBrassinosteroids 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 <i>Arabidopis thaliana</i>. 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 significant 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.https://www.mdpi.com/1422-0067/22/1/155brassinosteroidorganic synthesisnitrogen-containing steroidplant bioassaycytotoxicity |
| spellingShingle | Mikhail V. Diachkov Karoll Ferrer Jana Oklestkova Lucie Rarova Vaclav Bazgier Miroslav Kvasnica Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain International Journal of Molecular Sciences brassinosteroid organic synthesis nitrogen-containing steroid plant bioassay cytotoxicity |
| title | Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain |
| title_full | Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain |
| title_fullStr | Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain |
| title_full_unstemmed | Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain |
| title_short | Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain |
| title_sort | synthesis and biological activity of brassinosteroid analogues with a nitrogen containing side chain |
| topic | brassinosteroid organic synthesis nitrogen-containing steroid plant bioassay cytotoxicity |
| url | https://www.mdpi.com/1422-0067/22/1/155 |
| work_keys_str_mv | AT mikhailvdiachkov synthesisandbiologicalactivityofbrassinosteroidanalogueswithanitrogencontainingsidechain AT karollferrer synthesisandbiologicalactivityofbrassinosteroidanalogueswithanitrogencontainingsidechain AT janaoklestkova synthesisandbiologicalactivityofbrassinosteroidanalogueswithanitrogencontainingsidechain AT lucierarova synthesisandbiologicalactivityofbrassinosteroidanalogueswithanitrogencontainingsidechain AT vaclavbazgier synthesisandbiologicalactivityofbrassinosteroidanalogueswithanitrogencontainingsidechain AT miroslavkvasnica synthesisandbiologicalactivityofbrassinosteroidanalogueswithanitrogencontainingsidechain |