Highly Selective CB1 Cannabinoid Receptor Ligands and Novel CB1/VR1 Vanilloid Receptor “Hybrid” Ligands
Anandamide and the metabolically stabler analogs, (R)-1′-methyl-2′-hydroxy-ethyl-arachidonamide (Met-AEA) and N-(3-methoxy-4-hydroxy-benzyl)-arachidonamide (arvanil), are CB1 cannabinoid and VR1 vanilloid receptors agonists. We synthesized 1′,1′-dimethylheptyl-arvanil (O-1839) and six other AEA anal...
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| Published in | Biochemical and biophysical research communications Vol. 281; no. 2; pp. 444 - 451 |
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| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Elsevier Inc
23.02.2001
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| Subjects | |
| Online Access | Get full text |
| ISSN | 0006-291X 1090-2104 |
| DOI | 10.1006/bbrc.2001.4354 |
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| Abstract | Anandamide and the metabolically stabler analogs, (R)-1′-methyl-2′-hydroxy-ethyl-arachidonamide (Met-AEA) and N-(3-methoxy-4-hydroxy-benzyl)-arachidonamide (arvanil), are CB1 cannabinoid and VR1 vanilloid receptors agonists. We synthesized 1′,1′-dimethylheptyl-arvanil (O-1839) and six other AEA analogs obtained by addition of either a hydroxy, cyano, or bromo group on the C-20 atom of 1,1′-dimethylpentyl-Met-AEA (O-1811, O-1812 and O-1860, respectively) or 1,1′-dimethylpentyl-arvanil (O-1856, O-1895 and O-1861, respectively). The compounds were tested for their (i) affinity for CB1 and CB2 receptors, (ii) capability to activate VR1 receptors, (iii) inhibitory effect on the anandamide hydrolysis and on the anandamide membrane transporter, and (iv) cannabimimetic activity in the mouse ‘tetrad’ of in vivo assays. O-1812 is the first ligand ever proven to be highly (500- to 1000-fold) selective for CB1 vs both VR1 and CB2 receptors, while O-1861 is the first true “hybrid” agonist of CB1/VR1 receptors and a compound with potential therapeutic importance. The activities of the seven compounds in vivo did not correlate with their activities at either CB1 or VR1 receptors, thus suggesting the existence of other brain sites of action mediating some of their neurobehavioral actions in mice. |
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| AbstractList | Anandamide and the metabolically stabler analogs, (R)-1′-methyl-2′-hydroxy-ethyl-arachidonamide (Met-AEA) and N-(3-methoxy-4-hydroxy-benzyl)-arachidonamide (arvanil), are CB1 cannabinoid and VR1 vanilloid receptors agonists. We synthesized 1′,1′-dimethylheptyl-arvanil (O-1839) and six other AEA analogs obtained by addition of either a hydroxy, cyano, or bromo group on the C-20 atom of 1,1′-dimethylpentyl-Met-AEA (O-1811, O-1812 and O-1860, respectively) or 1,1′-dimethylpentyl-arvanil (O-1856, O-1895 and O-1861, respectively). The compounds were tested for their (i) affinity for CB1 and CB2 receptors, (ii) capability to activate VR1 receptors, (iii) inhibitory effect on the anandamide hydrolysis and on the anandamide membrane transporter, and (iv) cannabimimetic activity in the mouse ‘tetrad’ of in vivo assays. O-1812 is the first ligand ever proven to be highly (500- to 1000-fold) selective for CB1 vs both VR1 and CB2 receptors, while O-1861 is the first true “hybrid” agonist of CB1/VR1 receptors and a compound with potential therapeutic importance. The activities of the seven compounds in vivo did not correlate with their activities at either CB1 or VR1 receptors, thus suggesting the existence of other brain sites of action mediating some of their neurobehavioral actions in mice. |
| Author | Brandi, I. Jefferson, R.G. Davis, J.B. Dasse, O. Winckler, R.L. Mahadevan, A. Martin, B.R. Di Marzo, V. De Petrocellis, L. Bisogno, T. Razdan, R.K. |
| Author_xml | – sequence: 1 givenname: V. surname: Di Marzo fullname: Di Marzo, V. organization: Endocannabinoid Research Group, Istituto per la Chimica di Molecole di Interesse Biologico, Istituto di Cibernetica, Consiglio Nazionale delle Ricerche, Via Toiano 6, 80072, Arco Felice (NA), Italy – sequence: 2 givenname: T. surname: Bisogno fullname: Bisogno, T. organization: Endocannabinoid Research Group, Istituto per la Chimica di Molecole di Interesse Biologico, Istituto di Cibernetica, Consiglio Nazionale delle Ricerche, Via Toiano 6, 80072, Arco Felice (NA), Italy – sequence: 3 givenname: L. surname: De Petrocellis fullname: De Petrocellis, L. organization: Endocannabinoid Research Group, Istituto per la Chimica di Molecole di Interesse Biologico, Istituto di Cibernetica, Consiglio Nazionale delle Ricerche, Via Toiano 6, 80072, Arco Felice (NA), Italy – sequence: 4 givenname: I. surname: Brandi fullname: Brandi, I. organization: Endocannabinoid Research Group, Istituto per la Chimica di Molecole di Interesse Biologico, Istituto di Cibernetica, Consiglio Nazionale delle Ricerche, Via Toiano 6, 80072, Arco Felice (NA), Italy – sequence: 5 givenname: R.G. surname: Jefferson fullname: Jefferson, R.G. organization: Department of Pharmacology and Toxicology, Medical College of Virginia Campus, Virginia Commonwealth University, P.O. Box 980613, Richmond, Virginia, 23298 – sequence: 6 givenname: R.L. surname: Winckler fullname: Winckler, R.L. organization: Department of Pharmacology and Toxicology, Medical College of Virginia Campus, Virginia Commonwealth University, P.O. Box 980613, Richmond, Virginia, 23298 – sequence: 7 givenname: J.B. surname: Davis fullname: Davis, J.B. organization: Neuroscience Research, SmithKline Beecham Pharmaceuticals, New Frontiers Science Park, Third Avenue, Harlow, Essex, CM19 5AW, United Kingdom – sequence: 8 givenname: O. surname: Dasse fullname: Dasse, O. organization: Organix Inc. Woburn, Massachusetts, 01801 – sequence: 9 givenname: A. surname: Mahadevan fullname: Mahadevan, A. organization: Organix Inc. Woburn, Massachusetts, 01801 – sequence: 10 givenname: R.K. surname: Razdan fullname: Razdan, R.K. organization: Organix Inc. Woburn, Massachusetts, 01801 – sequence: 11 givenname: B.R. surname: Martin fullname: Martin, B.R. organization: Department of Pharmacology and Toxicology, Medical College of Virginia Campus, Virginia Commonwealth University, P.O. Box 980613, Richmond, Virginia, 23298 |
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| Keywords | endocannabinoid receptor arvanil cannabinoid capsaicin analgesia vanilloid anandamide 2-arachidonoylglycerol |
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| Title | Highly Selective CB1 Cannabinoid Receptor Ligands and Novel CB1/VR1 Vanilloid Receptor “Hybrid” Ligands |
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