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  • Structural and conformational studies of the heparan sulfate mimetic PI-88

    Author(s)
    Elli, Stefano
    Stancanelli, Eduardo
    Handley, Paul N
    Carroll, Anthony
    Urso, Elena
    Guerrini, Marco
    Ferro, Vito
    Griffith University Author(s)
    Carroll, Anthony R.
    Year published
    2018
    Metadata
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    Abstract
    The heparan sulfate mimetic PI-88 is a complex mixture of sulfated oligosaccharides with anti-metastatic and anti-angiogenic activity due to its potent inhibition of heparanase and heparan sulfate-dependent angiogenic growth factors. It was recently in Phase III clinical trials for postresection hepatocellular carcinoma. The major oligosaccharide constituents of PI-88 were prepared for the first time by sulfonation of individually purified phosphorylated oligosaccharides isolated from the PI-88 precursor. PI-88 and its components were subjected to detailed 1D and 2D NMR spectroscopic analysis. The spectra of the individual ...
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    The heparan sulfate mimetic PI-88 is a complex mixture of sulfated oligosaccharides with anti-metastatic and anti-angiogenic activity due to its potent inhibition of heparanase and heparan sulfate-dependent angiogenic growth factors. It was recently in Phase III clinical trials for postresection hepatocellular carcinoma. The major oligosaccharide constituents of PI-88 were prepared for the first time by sulfonation of individually purified phosphorylated oligosaccharides isolated from the PI-88 precursor. PI-88 and its components were subjected to detailed 1D and 2D NMR spectroscopic analysis. The spectra of the individual components greatly assisted the assignment of minor resonances in the 1H NMR spectrum of PI-88. The data also showed that the majority of the oligosaccharides in PI-88 are fully sulfated and that undersulfated species present are largely due to anomeric desulfation. The solution conformation of the phosphomannopentaose sulfate (major component) of PI-88 was then determined by a combination of molecular dynamics simulations and NOE measurements which may provide insights into its binding interactions with target proteins.
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    Journal Title
    Glycobiology
    Volume
    28
    Issue
    10
    DOI
    https://doi.org/10.1093/glycob/cwy068
    Subject
    Biological Sciences
    Medical and Health Sciences
    Publication URI
    http://hdl.handle.net/10072/383350
    Collection
    • Journal articles

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