Synthesis of New trans-Dehydrocrotonin Nitrogenated Derivatives and their Cytotoxic and DNA-Topoisomerase I Inhibitory Activities
| Autor: | Andressa Esteves-Souza, Kenia Pissinate, Aurea Echevarria, Maria Aparecida Medeiros Maciel |
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| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
0301 basic medicine
Ketone DNA-topoisomerase I Stereochemistry 01 natural sciences 03 medical and health sciences chemistry.chemical_compound Cytotoxic T cell Moiety Hydrazine (antidepressant) cytotoxic activity chemistry.chemical_classification Natural product biology 010405 organic chemistry Topoisomerase trans-dehydrocrotonin diterpenes General Chemistry Oxime 0104 chemical sciences 030104 developmental biology chemistry biology.protein Diterpene Croton cajucara |
| Zdroj: | Journal of the Brazilian Chemical Society v.29 n.1 2018 Journal of the Brazilian Chemical Society Sociedade Brasileira de Química (SBQ) instacron:SBQ Journal of the Brazilian Chemical Society, Volume: 29, Issue: 1, Pages: 133-139, Published: JAN 2018 |
| Popis: | A new series of 19-nor-clerodane diterpene derivatives was synthesized from the natural trans-dehydrocrotonin obtained from stem barks of Croton cajucara (Euphorbiaceae), a native medicinal plant of the Brazilian Amazon. The new derivatives were obtained by changes in the ketone moiety of trans-dehydrocrotonin leading to nitrogenated derivatives which are: three substituted hydrazine diterpenes, oxime, and methyloxime. The cytotoxic effect of the diterpene derivatives was evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against Ehrlich carcinoma and K562 human leukemia cells. The cytotoxic activity of the hydrazine and oxime semi-synthetic derivatives was better than the one of the natural product trans-dehydrocrotonin. Moreover, all diterpenes were tested for their DNA topoisomerase I inhibitory activity, and the most effective one, in general, was observed to the phenyl-hydrazone derivative. Results indicated that the topoisomerase I inhibitory effect is correlated with the cytotoxic activity. |
| Databáze: | OpenAIRE |
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