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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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
2007
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| 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 |
MARC
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| 520 | |a 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. | ||
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| 650 | 4 | |a TRPV1 | |
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