Antiangiogenic Activity and Chemical Derivatization
of the Neurotoxic Acetogenin Annonacin Isolated from Asimina
triloba
Posted on 2018-07-20 - 17:35
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.
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Monsen, Paige
J.; Luzzio, Frederick A. (2018). Antiangiogenic Activity and Chemical Derivatization
of the Neurotoxic Acetogenin Annonacin Isolated from Asimina
triloba. ACS Publications. Collection. https://doi.org/10.1021/acs.jnatprod.8b00284
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AUTHORS (2)
PM
Paige
J. Monsen
FL
Frederick A. Luzzio
KEYWORDS
compoundAsimina triloba AnnonacinChemicallaboratorypermesylationrat aortic ring bioassayTetraazidoDerivatizationderivativeevaluationAntiangiogenicantiangiogenicNaturalmembrane permeability assayNorth American pawpawtetraazideiodinationIC 50 valuemicrovesselazide displacement3 μ MmesylationNeurotoxic Acetogenin Annonacin