Abstract
In order to explore the structural determinants for the TRPV1 and TRPA1 agonist properties of gingerols, a series of nineteen analogues (1b-5) of racemic [6]-gingerol (1a) was synthesized and tested on TRPV1 and TRPA1 channels. The exploration of the structure-activity relationships, by modulating the three pharmacophoric regions of [6]-gingerol, led to the identification of some selective TRPV1 agonists/desensitizers of TRPV1 channels (3a, 3f, and 4) and of some full TRPA1 antagonists (2c, 2d, 3b, and 3d).
Copyright © 2011 Elsevier Ltd. All rights reserved.
MeSH terms
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Calcium Channels
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Catechols / chemical synthesis*
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Catechols / chemistry
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Catechols / pharmacology
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Fatty Alcohols / chemical synthesis*
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Fatty Alcohols / chemistry
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Fatty Alcohols / pharmacology
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Humans
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Inhibitory Concentration 50
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Molecular Structure
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Nerve Tissue Proteins / agonists*
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Nerve Tissue Proteins / antagonists & inhibitors
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Protein Binding / drug effects
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Stereoisomerism
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Structure-Activity Relationship
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TRPA1 Cation Channel
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TRPV Cation Channels / agonists*
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TRPV Cation Channels / antagonists & inhibitors
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Transient Receptor Potential Channels / agonists*
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Transient Receptor Potential Channels / antagonists & inhibitors
Substances
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Calcium Channels
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Catechols
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Fatty Alcohols
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Nerve Tissue Proteins
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TRPA1 Cation Channel
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TRPA1 protein, human
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TRPV Cation Channels
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TRPV1 protein, human
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Transient Receptor Potential Channels
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gingerol