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大麻素酸、类似物及内源性对应物。

The cannabinoid acids, analogs and endogenous counterparts.

作者信息

Burstein Sumner H

机构信息

Department of Biochemistry and Molecular Pharmacology, The University of Massachusetts Medical School, Worcester, MA 01605, USA.

出版信息

Bioorg Med Chem. 2014 May 15;22(10):2830-43. doi: 10.1016/j.bmc.2014.03.038. Epub 2014 Apr 1.

DOI:10.1016/j.bmc.2014.03.038
PMID:24731541
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4351512/
Abstract

The cannabinoid acids are a structurally heterogeneous group of compounds some of which are endogenous molecules and others that are metabolites of phytocannabinoids. The prototypic endogenous substance is N-arachidonoyl glycine (NAgly) that is closely related in structure to the cannabinoid agonist anandamide. The most studied phytocannabinoid is Δ(9)-THC-11-oic acid, the principal metabolite of Δ(9)-THC. Both types of acids have in common several biological actions such as low affinity for CB1 anti-inflammatory activity and analgesic properties. This suggests that there may be similarities in their mechanism of action, a point that is discussed in this review. Also presented are reports on analogs of the acids that provide opportunities for the development of novel therapeutic agents, such as ajulemic acid.

摘要

大麻素酸是一类结构异质的化合物，其中一些是内源性分子，另一些是植物大麻素的代谢产物。典型的内源性物质是N-花生四烯酰甘氨酸（NAgly），其结构与大麻素激动剂花生四烯乙醇胺密切相关。研究最多的植物大麻素是Δ(9)-四氢大麻酚-11-酸，它是Δ(9)-四氢大麻酚的主要代谢产物。这两类酸都具有多种生物学作用，如对CB1亲和力低、抗炎活性和镇痛特性。这表明它们的作用机制可能存在相似性，本综述将讨论这一点。还介绍了关于这些酸的类似物的报告，这些类似物为开发新型治疗药物提供了机会，如阿珠莫酸。

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本文引用的文献

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Front Pharmacol. 2014 Jan 2;4:162. doi: 10.3389/fphar.2013.00162. eCollection 2014.
2
Urinary cannabinoid disposition in occasional and frequent smokers: is THC-glucuronide in sequential urine samples a marker of recent use in frequent smokers?偶尔吸烟者和频繁吸烟者尿液中大麻素的分布：频繁吸烟者尿样中 THC-葡糖苷酸是否是近期使用的标志物？
Clin Chem. 2014 Feb;60(2):361-72. doi: 10.1373/clinchem.2013.214106. Epub 2013 Nov 1.
3
Bioorg Med Chem. 2015 Jan 1;23(1):241-63. doi: 10.1016/j.bmc.2014.11.002. Epub 2014 Nov 8.
Control of spasticity in a multiple sclerosis model using central nervous system-excluded CB1 cannabinoid receptor agonists.
使用中枢神经系统排除型 CB1 cannabinoid 受体激动剂控制多发性硬化模型中的痉挛。
FASEB J. 2014 Jan;28(1):117-30. doi: 10.1096/fj.13-239442. Epub 2013 Oct 11.
4
Investigation of the transformation of 11-nor-9-carboxy-Δ(9)-tetrahydrocannabinol during water chlorination by liquid chromatography-quadrupole-time-of-flight-mass spectrometry.采用液相色谱-四极杆飞行时间质谱法研究 11-去甲-9-羧基-Δ(9)-四氢大麻酚在水氯化过程中的转化。
J Hazard Mater. 2013 Oct 15;261:628-36. doi: 10.1016/j.jhazmat.2013.08.006. Epub 2013 Aug 12.
5
Quinolones and non-steroidal anti-inflammatory drugs interacting with copper(II), nickel(II), cobalt(II) and zinc(II): structural features, biological evaluation and perspectives.喹诺酮类和非甾体抗炎药与铜（II）、镍（II）、钴（II）和锌（II）的相互作用：结构特征、生物评价及前景展望。
Dalton Trans. 2013 May 14;42(18):6252-76. doi: 10.1039/c3dt50268f.
6
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Br J Pharmacol. 2013 Jun;169(4):933-48. doi: 10.1111/bph.12180.
7
A GPR18-based signalling system regulates IOP in murine eye.基于 GPR18 的信号系统调节小鼠眼内压。
Br J Pharmacol. 2013 Jun;169(4):834-43. doi: 10.1111/bph.12136.
8
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J Cell Sci. 2013 Feb 15;126(Pt 4):879-88. doi: 10.1242/jcs.118075. Epub 2012 Dec 13.
9
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Mol Pharmacol. 2013 Jan;83(1):267-82. doi: 10.1124/mol.112.081182. Epub 2012 Oct 25.
10
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J Mol Signal. 2012 Jul 26;7(1):10. doi: 10.1186/1750-2187-7-10.