The cannabinoid acids, analogs and endogenous counterparts

被引：15
作者：
Burstein, Sumner H. [1 ]
机构：
[1] Univ Massachusetts, Sch Med, Dept Biochem & Mol Pharmacol, Worcester, MA 01605 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2014年 / 22卷 / 10期
基金：
美国国家卫生研究院;
关键词：
Cannabinoid; Delta(9)-THC-11-oic acid; Ajulemic acid; NAgly; Lipoamino acid; Prostaglandin; Lipoxin; N-ARACHIDONOYL GLYCINE; ACTIVATED RECEPTOR-GAMMA; HUMAN-LUNG FIBROBLASTS; AJULEMIC ACID; PPAR-GAMMA; TETRAHYDROCANNABINOLIC ACID; PROSTAGLANDIN SYNTHESIS; OXIDATIVE-METABOLISM; INVIVO METABOLITES; NITRIC-OXIDE;
D O I：
10.1016/j.bmc.2014.03.038
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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 Delta(9)-THC-11-oic acid, the principal metabolite of Delta(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. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2830 / 2843
页数：14
相关论文
共 114 条
[91]   Pain measurements and side effect profile of the novel cannabinoid ajulemic acid [J].
Salim, K ;
Schneider, U ;
Burstein, S ;
Hoy, L ;
Karst, M .
NEUROPHARMACOLOGY, 2005, 48 (08) :1164-1171
[92]   Simultaneous quantification of free and glucuronidated cannabinoids in human urine by liquid chromatography tandem mass spectrometry [J].
Scheidweiler, Karl B. ;
Desrosiers, Nathalie A. ;
Huestis, Marilyn A. .
CLINICA CHIMICA ACTA, 2012, 413 (23-24) :1839-1847
[93]   Resolution phase of inflammation: Novel endogenous anti-inflammatory and proresolving lipid mediators and pathways [J].
Serhan, Charles N. .
ANNUAL REVIEW OF IMMUNOLOGY, 2007, 25 :101-137
[94]   Resolvins and Protectins in Inflammation Resolution [J].
Serhan, Charles N. ;
Petasis, Nicos A. .
CHEMICAL REVIEWS, 2011, 111 (10) :5922-5943
[95]   Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor [J].
Sheskin, T ;
Hanus, L ;
Slager, J ;
Vogel, Z ;
Mechoulam, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (05) :659-667
[96]   Oleoyl serine, an endogenous N-acyl amide, modulates bone remodeling and mass [J].
Smoum, Reem ;
Bar, Arik ;
Tan, Bo ;
Milman, Garry ;
Attar-Namdar, Malka ;
Ofek, Orr ;
Stuart, Jordyn M. ;
Bajayo, Alon ;
Tam, Joseph ;
Kram, Vardit ;
O'Dell, David ;
Walker, Michael J. ;
Bradshaw, Heather B. ;
Bab, Itai ;
Mechoulam, Raphael .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (41) :17710-17715
[97]   Ajulemic acid, a synthetic cannabinoid acid, induces an antiinflammatory profile of eicosanoids in human synovial cells [J].
Stebulis, Judith A. ;
Johnson, David R. ;
Rossetti, Ronald G. ;
Burstein, Sumner H. ;
Zurier, Robert B. .
LIFE SCIENCES, 2008, 83 (19-20) :666-670
[98]   A novel synthetic, noripsychoactive cannabinoid acid (HU-320) with antiinflammatory properties in murine collagen-induced arthritis [J].
Sumariwalla, PF ;
Gallily, R ;
Tchilibon, S ;
Fride, E ;
Mechoulam, R ;
Feldmann, M .
ARTHRITIS AND RHEUMATISM, 2004, 50 (03) :985-998
[99]   N-arachidonoyl glycine induces macrophage apoptosis via GPR18 [J].
Takenouchi, Rina ;
Inoue, Kazuhiko ;
Kambe, Yuki ;
Miyata, Atsuro .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2012, 418 (02) :366-371
[100]   Identification of endogenous acyl amino acids based on a targeted lipidomics approach [J].
Tan, Bo ;
O'Dell, David K. ;
Yu, Y. William ;
Monn, M. Francesca ;
Hughes, H. Velocity ;
Burstein, Sumner ;
Walker, J. Michael .
JOURNAL OF LIPID RESEARCH, 2010, 51 (01) :112-119
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