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Caged Capsaicins: New Tools for the Examination of TRPV1 Channels in Somatosensory Neurons
Author(s) -
Gilbert Daniel,
Funk Katharina,
Dekowski Brigitte,
Lechler Ralf,
Keller Sandro,
Möhrlen Frank,
Frings Stephan,
Hagen Volker
Publication year - 2007
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200600437
Subject(s) - capsaicin , pungency , trpv1 , chemistry , extracellular , coumarin , biophysics , nociception , stereochemistry , biochemistry , pharmacology , transient receptor potential channel , receptor , organic chemistry , food science , biology , pepper
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.