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Issue 73, 2013
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The bulky side chain of antillatoxin is important for potent toxicity: rational design of photoresponsive cytotoxins based on SAR studies

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Abstract

Antillatoxin is a cyclic peptide with potent neurotoxic and neuritogenic activities. We designed and synthesized six analogues that have photocleavable protecting groups at the terminus of the side chain. Among these compounds, the bis-o-nitrobenzyl acetal derivative was found to exhibit high toxicity and was effectively deactivated by photochemical removal, proving that the biological activity of antillatoxin was modulated by altering the size of the terminal group.

Graphical abstract: The bulky side chain of antillatoxin is important for potent toxicity: rational design of photoresponsive cytotoxins based on SAR studies

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Publication details

The article was received on 30 May 2013, accepted on 12 Jul 2013 and first published on 12 Jul 2013


Article type: Communication
DOI: 10.1039/C3CC44066D
Citation: Chem. Commun., 2013,49, 8024-8026
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    The bulky side chain of antillatoxin is important for potent toxicity: rational design of photoresponsive cytotoxins based on SAR studies

    K. Okura, S. Matsuoka and M. Inoue, Chem. Commun., 2013, 49, 8024
    DOI: 10.1039/C3CC44066D

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