Abstract
The first biologically relevant clickable probe related to the antitumor marine lipid jaspine B is reported. The concise synthetic route to both enantiomers relied on the supercritical fluid chromatography (SFC) enantiomeric resolution of racemic materials. The eutomeric dextrogyre derivative represents the first jaspine B analogue with enhanced cytotoxicity with IC50 down to 30 nm. These enantiomeric probes revealed a chiralitydependent cytoplasmic imaging of U2OS cancer cells by in situ click labeling.
Keywords:
Jaspine B; bioorthogonality; click chemistry; fluorescent probes; pachastrissamine.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkynes / chemical synthesis
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Alkynes / chemistry*
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Alkynes / toxicity
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry*
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Antineoplastic Agents / toxicity
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Cell Line, Tumor
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Click Chemistry
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Fluorescent Dyes / chemical synthesis
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Fluorescent Dyes / chemistry*
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Fluorescent Dyes / toxicity
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Humans
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Molecular Probes / chemical synthesis
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Molecular Probes / chemistry*
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Molecular Probes / toxicity
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Sphingosine / analogs & derivatives*
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Sphingosine / chemical synthesis
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Sphingosine / toxicity
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Stereoisomerism
Substances
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Alkynes
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Antineoplastic Agents
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Fluorescent Dyes
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Molecular Probes
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pachastrissamine
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Sphingosine