Caged capsaicins:: New tools for the examination of TRPV1 channels in somatosensory neurons
Caged capsaicins:: New tools for the examination of TRPV1 channels in somatosensory neurons
复制标题
DOI：
10.1002/cbic.200600437
复制
发表时间：
2007-01-02
期刊：
影响因子：
3.2
通讯作者：
Hagen, Volker
中科院分区：
文献类型：
--
作者：
Gilbert, Daniel;Funk, Katharina;Hagen, Volker
香兰素辣椒素，N-（4-羟基-3-甲氧基苄基）-8-甲基非-6-氨基酰胺，是辣椒的刺激性成分，作为痛觉神经元热敏转导通道的激活配体用于疼痛研究。本文介绍了两种以香兰基基基羟基为修饰基的辣椒素衍生物的合成和应用。α -羟基-4,5-二甲氧基-2-硝基苯笼（cdmnb笼）辣椒素和{7-[双（羧甲基）氨基]香豆素-4-基}甲氧羰基笼（bcmacmoc笼）辣椒素。这些化合物的辣度显著降低，但在紫外线照射下释放出活性辣椒素。cdmnb笼型辣椒素可用于进行浓度跳跃实验，而bcmacmoc笼型辣椒素是膜不相关的，可以选择性地应用于质膜的细胞内或细胞外。这两种化合物都可以作为疼痛生理学的有价值的研究工具。
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. alpha-corboxy-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.