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  • Investigation of the electrophilic reactivity of the cytotoxic marine alkaloid discorhabdin B

    Author(s)
    Lam, Cary F. C.
    Grkovic, Tanja
    Norrie Pearce, A.
    Copp, Brent R.
    Griffith University Author(s)
    Grkovic, Tanja
    Year published
    2012
    Metadata
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    Abstract
    The mechanisms of action of the cytotoxic marine pyrroloiminoquinone alkaloids the discorhabdins are unknown. We have determined that discorhabdin B acts as an electrophile towards biomimetic thiol nucleophiles leading to debrominated adducts. In contrast, less potent cytotoxins discorhabdins D and Q failed to react, supporting an SAR model of cytotoxicity requiring an orchestrated combination of an electrophilic ?1 carbon centre and a nucleophilic N-18 amine for potent activity. The stereospecific nature of nucleophile trapping exhibited by both enantiomers of discorhabdin B implies the biogenesis of ovothiol A substituted ...
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    The mechanisms of action of the cytotoxic marine pyrroloiminoquinone alkaloids the discorhabdins are unknown. We have determined that discorhabdin B acts as an electrophile towards biomimetic thiol nucleophiles leading to debrominated adducts. In contrast, less potent cytotoxins discorhabdins D and Q failed to react, supporting an SAR model of cytotoxicity requiring an orchestrated combination of an electrophilic ?1 carbon centre and a nucleophilic N-18 amine for potent activity. The stereospecific nature of nucleophile trapping exhibited by both enantiomers of discorhabdin B implies the biogenesis of ovothiol A substituted discorhabdins H, H2, K and K2 need not be mediated by enzymatic processes.
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    Journal Title
    Organic and Biomolecular Chemistry
    Volume
    10
    Issue
    15
    DOI
    https://doi.org/10.1039/c2ob07090a
    Subject
    Natural Products Chemistry
    Medicinal and Biomolecular Chemistry
    Organic Chemistry
    Publication URI
    http://hdl.handle.net/10072/48700
    Collection
    • Journal articles

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