Synthesis and cytotoxicity screening of substituted isobenzofuranones designed from anacardic acids
| Autor: | Bruno C. Cavalcanti, Maria Lucilia dos Santos, Letícia V. Costa-Lotufo, Luiz Antonio Soares Romeiro, Camila O. Santos, Cláudia Pessoa, O. Manoel de Moraes, Lucio Paulo Lima Logrado, José Roberto de Oliveira Ferreira, Arinice M. Costa |
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| Rok vydání: | 2010 |
| Předmět: |
DNA damage
Cell Survival Drug Evaluation Preclinical Antineoplastic Agents Apoptosis Chemical synthesis chemistry.chemical_compound Inhibitory Concentration 50 Cell Line Tumor Drug Discovery Animals Humans MTT assay Cytotoxicity Benzofurans Cell Proliferation Pharmacology chemistry.chemical_classification Cell growth Organic Chemistry General Medicine Anacardic acids Anacardic Acids Oxygen chemistry Biochemistry Cell culture Drug Design Hydrophobic and Hydrophilic Interactions Lactone |
| Zdroj: | European journal of medicinal chemistry. 45(8) |
| ISSN: | 1768-3254 |
| Popis: | This work is part of a large program, which seeks to discover new antitumor isobenfuranones designed from anacardic acids. The synthetic strategy for the construction of the title compounds takes into consideration the use of inexpensive anacardic acids (2), the major natural cashew (Anacardium occidentale) nut-shell phenolic lipid, and features one-pot construction of fused-ring aromatic gamma-lactones, phthalides. The cytotoxicity screening in different human cancer cell lines (HL-60 leukemia, SF295 glioblastoma and MDA-MB435 melanoma) by the MTT assay showed that acyclic precursor (6), and isobenfuranones (1a and 1b) are active compounds. Interestingly, 1a exhibits significant antiproliferative effect against HL-60 cells and moderate activity against SF295 and MDA-MB435 cell lines. Analysis of mechanisms involved in the cytotoxic activity showed that active compounds were leading to DNA damage, triggering apoptosis or necrosis induction. |
| Databáze: | OpenAIRE |
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