Antiangiogenic Activity and Chemical Derivatization of the Neurotoxic Acetogenin Annonacin Isolated from Asimina triloba
| Autor: | Paige J. Monsen, Frederick A. Luzzio |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
0301 basic medicine
Asimina Membrane permeability Annonacin Pharmaceutical Science Angiogenesis Inhibitors Aorta Thoracic In Vitro Techniques Analytical Chemistry Lactones Structure-Activity Relationship 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Drug Discovery Animals Structure–activity relationship Bioassay Furans Derivatization Pharmacology Chromatography Molecular Structure biology Plant Extracts Organic Chemistry biology.organism_classification Capillaries Rats 030104 developmental biology Complementary and alternative medicine chemistry Fruit Seeds Acetogenin Molecular Medicine Azide 030217 neurology & neurosurgery |
| Zdroj: | Journal of Natural Products. 81:1905-1909 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.8b00284 |
| Popis: | Annonacin (1) was isolated from the North American pawpaw (Asimina triloba), as reported earlier from these laboratories. Natural 1 was submitted to the rat aortic ring bioassay for evaluation of antiangiogenic activity and was found to inhibit microvessel growth (IC50 value of 3 μM). 4,10,15,20-Tetraazido derivatives of 1 were prepared by permesylation followed by azide displacement or by iodination followed by azide displacement. The tetraazide derived from mesylation/azidation was antiangiogenic, while that derived from iodination/azidation exhibited no appreciable activity. The membrane permeability of natural 1 was evaluated using the parallel artificial membrane permeability assay and was found to be marginally permeable as compared to several clinically relevant compounds. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|