Homologues and isomers of noladin ether, a putative novel endocannabinoid:: Interaction with rat cannabinoid CB1 receptors

被引:5
作者
Appendino, G
Ligresti, A
Minassi, A
Daddario, N
Bisogno, T
Di Marzo, V
机构
[1] DiSCAFF, I-28100 Novara, Italy
[2] CNR, Ist Chim Biomol, Endocannabinoid Res Grp, I-80078 Pozzuoli, NA, Italy
关键词
D O I
10.1016/S0960-894X(02)00839-9
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Two regioisomers and 13 analogues of the putative endocannabinoid noladin ether (2-arachidonyl glyceryl ether, 2-AGE, 1) were synthesized and tested for their interaction with CB1 receptors in rat brain membranes. The results showed that a C-20 tetra-unsaturated moiety is necessary for high affinity, and that a series of alkyl glyceryl ethers of potential occurrence in brain tissues have less affinity than 2-AGE for CB1 receptors. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:43 / 46
页数:4
相关论文
共 15 条
[1]   Isolation and expression of a mouse CB1 cannabinoid receptor gene - Comparison of binding properties with those of native CB1 receptors in mouse brain and N18TG2 neuroblastoma cells [J].
Abood, ME ;
Ditto, KE ;
Noel, MA ;
Showalter, VM ;
Tao, Q .
BIOCHEMICAL PHARMACOLOGY, 1997, 53 (02) :207-214
[2]   ISOLATION AND STRUCTURE OF A BRAIN CONSTITUENT THAT BINDS TO THE CANNABINOID RECEPTOR [J].
DEVANE, WA ;
HANUS, L ;
BREUER, A ;
PERTWEE, RG ;
STEVENSON, LA ;
GRIFFIN, G ;
GIBSON, D ;
MANDELBAUM, A ;
ETINGER, A ;
MECHOULAM, R .
SCIENCE, 1992, 258 (5090) :1946-1949
[3]  
Di Marzo V, 1999, CURR MED CHEM, V6, P721
[4]  
FELDER CC, 1995, MOL PHARMACOL, V48, P443
[5]   2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor [J].
Hanus, L ;
Abu-Lafi, S ;
Fride, E ;
Breuer, A ;
Vogel, Z ;
Shalev, DE ;
Kustanovich, I ;
Mechoulam, R .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (07) :3662-3665
[6]   IDENTIFICATION OF AN ENDOGENOUS 2-MONOGLYCERIDE, PRESENT IN CANINE GUT, THAT BINDS TO CANNABINOID RECEPTORS [J].
MECHOULAM, R ;
BENSHABAT, S ;
HANUS, L ;
LIGUMSKY, M ;
KAMINSKI, NE ;
SCHATZ, AR ;
GOPHER, A ;
ALMOG, S ;
MARTIN, BR ;
COMPTON, DR ;
PERTWEE, RG ;
GRIFFIN, G ;
BAYEWITCH, M ;
BARG, J ;
VOGEL, Z .
BIOCHEMICAL PHARMACOLOGY, 1995, 50 (01) :83-90
[7]   Unsaturated long-chain N-acyl-vanillyl-amides (N-AVAMs):: Vanilloid receptor ligands that inhibit anandamide-facilitated transport and bind to CB1 cannabinoid receptors [J].
Melck, D ;
Bisogno, T ;
De Petrocellis, L ;
Chuang, HH ;
Julius, D ;
Bifulco, M ;
Di Marzo, V .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1999, 262 (01) :275-284
[8]   Plasmalogens: biosynthesis and functions [J].
Nagan, N ;
Zoeller, RA .
PROGRESS IN LIPID RESEARCH, 2001, 40 (03) :199-229
[9]   Natural and synthetic endocannabinoids and their structure-activity relationships [J].
Palmer, SL ;
Khanolkar, AD ;
Makriyannis, A .
CURRENT PHARMACEUTICAL DESIGN, 2000, 6 (13) :1381-1397
[10]   Pharmacology of cannabinoid CB1 and CB2 receptors [J].
Pertwee, RG .
PHARMACOLOGY & THERAPEUTICS, 1997, 74 (02) :129-180