np8b00284_si_001.pdf (2.22 MB)
Antiangiogenic Activity and Chemical Derivatization of the Neurotoxic Acetogenin Annonacin Isolated from Asimina triloba
journal contribution
posted on 2018-07-20, 17:35 authored by Paige
J. Monsen, Frederick A. LuzzioAnnonacin (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.
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compoundAsimina triloba AnnonacinChemicallaboratorypermesylationrat aortic ring bioassayTetraazidoDerivatizationderivativeevaluationAntiangiogenicantiangiogenicNaturalmembrane permeability assayNorth American pawpawtetraazideiodinationIC 50 valuemicrovesselazide displacement3 μ MmesylationNeurotoxic Acetogenin Annonacin
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