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Caged capsaicins: new tools for the examination of TRPV1 channels in somatosensory neurons

The vanilloid capsaicin, N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide, is the pungent ingredient of chili peppers and is used in pain research as an activating ligand of heat-sensitive transduction channels in nociceptive neurons. Here we describe the synthesis and application of two capsaici...

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Bibliographic Details
Main Authors: Gilbert, Daniel (Author) , Lehmeyer-Funk, Katharina (Author) , Möhrlen, Frank (Author) , Frings, Stephan (Author)
Format: Article (Journal)
Language:English
Published: 2007
In: ChemBioChem
Year: 2007, Volume: 8, Issue: 1, Pages: 89-97
ISSN:1439-7633
DOI:10.1002/cbic.200600437
Online Access:Verlag, Volltext: http://dx.doi.org/10.1002/cbic.200600437
Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/cbic.200600437/abstract
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Author Notes:Daniel Gilbert, Katharina Funk, Brigitte Dekowski, Ralf Lechler, Sandro Keller, Frank Möhrlen, Stephan Frings, and Volker Hagen
Description
Summary:The vanilloid capsaicin, N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide, is the pungent ingredient of chili peppers and is used in pain research as an activating ligand of heat-sensitive transduction channels in nociceptive neurons. Here we describe the synthesis and application of two capsaicin derivatives modified at the hydroxy function of the vanillyl motif: α-carboxy-4,5-dimethoxy-2-nitrobenzyl-caged (CDMNB-caged) capsaicin and {7-[bis(carboxymethyl)amino]coumarin-4-yl}methoxycarbonyl-caged (BCMACMOC-caged) capsaicin. These compounds show dramatically reduced pungency, but release active capsaicin upon irradiation with UV light. CDMNB-caged capsaicin can be used to perform concentration-jump experiments, while BCMACMOC-caged capsaicin is membrane-impermeant and can be applied selectively to the intracellular or extracellular sides of a plasma membrane. Both compounds can serve as valuable research tools in pain physiology.
Item Description:Gesehen am 16.05.2017
Physical Description:Online Resource
ISSN:1439-7633
DOI:10.1002/cbic.200600437

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