Design and synthesis of the CB1 selective cannabinoid antagonist AM281: A potential human SPECT ligand

Ruoxi Lan1, Qian Lü1, Pusheng Fan1, John Gatley2, Nora D. Volkow2, Susanthi R. Fernando3, Roger G. Pertwee3, Alexandros Makriyannis4
1Department of Pharmaceutical Sciences and Molecular and Cell Biology, U-92, University of Connecticut, 06269, Storrs, CT
2Medical Department, Brookhaven National Laboratory, 11973, Upton, NY
3Department of Biomedical Sciences, University of Aberdeen, AB9 1AS, Aberdeen, Scotland
4Institute of Material Sciences, University of Connecticut, 06269, Storrs, CT

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Martin BR. Cellular effects of cannabinoids. Pharmacol Rev. 1986;38:45–74.

Devane WA, Dysarz FA, 3d., Johnson MR, Melvin LS, Howlett AC. Determination and characterization of a cannabinoid receptor in rat brain. Mol Pharmacol. 1988;34:605–613.

Munro S, Thomas KL, Abu-Shaar M. Molecular characterization of a peripheral receptor for cannabinoids. Nature (London) 1993;365:61–65.

Barth F, Casellas P, Congy C, Martinez S, Rinaldi M, Anne-Archard G. Pyrazole derivatives, method of preparing them and pharmaceutical compositions in which they are present. US Patent 5,624,941 Apr. 29, 1997.

Rinaldi-Carmona M, Barth F, Héaulme M, Shire D, Calandra B, Congy C, Martinez S, Maruani J, Néliat G, Caput D, Ferrara P, Soubrié P, Breliere JC, Le Fur G. SR141716A. A potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett 1994;350:240–244.

Rinaldi-Carmona M, Barth F, Heaulme M, Alonso R, Shire D, Congy C, Soubrié P, Breliere JC, Le Fur G. Biochemical and pharmacological characterization of SR141716A, the first potent and selective brain cannabinoid receptor antagonist. Life Sci. 1995;56:1941–1947.

Shire D, Calandra B, Delpech M, Dumont X, Kaghad M, Le Fur G, Caput D, Ferrara P. Structural features of the central cannabinoid CB1 receptor involved in the binding of the specific CB1 antagonist SR 141716A. J Biol Chem. 1996;271:6941–6946.

Rinaldi-Carmona M, Pialot F, Congy C, Redon E, Barth F, Bachy A, Breliere JC, Soubrié P, Le Fur G. Characterization and distribution of binding sites for [3H]-SR 141716A, a selective brain (CB1) cannabinoid receptor antagonist, in rodent brain. Life Sci. 1996;58:1239–1247.

Gatley SJ, Gifford AN, Volkow ND, Lan R, Makriyannis A. 123I-Labeled AM251. a radioiodinated ligand which binds in vivo to mouse brain cannabinoid CB1 receptors. Eur J Pharmacol. 1996;307:331–338.

Lan R, Gatley SJ, Makriyannis A. Preparation of iodine-123 labeled AM251: a potential SPECT radioligand for the brain cannabinoid CB1 receptor. J Label Compds Radiopharma 1996;38:875–881.

Gatley SJ, Lan R, Pyatt B, Gifford AN, Volkow ND, Makriyannis A. Binding of the non-classical cannabinoid CP 55,940, and the diarylpyrazole AM251 to rodent brain cannabinoid receptors. Life Sci. 1997;61:PL191–197.

Herkenham M, Lynn AB, Little MD, Johnson MR, Melvin LS, DeCosta BR, Rice KC. Cannabinoid receptor localization in brain. Proc Natl Acad Sci. 1990;87:1932–1936.

Herkenham M, Lynn AB, Johnson MR, Melvin LS, DeCosta BR, Rice KC. Characterization and localization of cannabinoid receptors in rat brain: a quantitative in vitro autoradiographic study: J Neurosci. 1991;11:563–583.

Gatley SJ, Lan R, Volkow ND, Pappas N, King P, Wong CT, Gifford AN, Pyatt B, Dewey SL, Makriyannis A. Imaging the brain marijuana receptor: Development of a radioligand that binds to cannabinoid CB1 receptors in vivo. J Neurochem. 1998;70:417–23.

Hanson RN, El-Wakil H. Electrophilic destannylation: stereospecific introduction of electrophiles at the 21 position of (17α)-19-Norpregna-1,3,5(10),20-tetraene-3-17β-diols. J Org Chem. 1987;52:3687–3688.

Pertwee, RG, Fernando, SR, Nash, JE, Coutts, AA. Further evidence for the presence of cannabinoid CB1 receptors in guinea-pig small intestine. Br J Pharmacol. 1996;118:2199–2205.

Gifford AN, Tang Y, Gatley SJ, Volkow ND, Lan R. Makriyannis A. Effect of the cannabinoid receptor SPECT agent, AM 281, on hippocampal acetylcholine release from rat brain slices Neurosci Lett. 1997;238:84–86.

Drake DJ, Jensen RS, Busch-Peterson J, Kawakami JK, Fernandez-Garcia MC, Fan P, Makriyannis A, Tius MA Classical nonclassical hydrid cannabinoids: southern aliphatic chamfunctionalized C-6β methyl, ethyl, and propyl analogues. J Med Chem 1998;41:3596–3608.

Abadji V, Lin S, Taha G, Griffin G, Stevenson LA, Pertwee RG, Makriyannis A. (R)-methanandamide a chiral novel anandamide possessing higher potency and metabolic stability. J Med Chem 1994;37:1889–1893.

Dodd PR, Hardy JA, Oakley AE, Edwardson JA, Perry EK, Delaunoy JP. A rapid method for preparing synaptosomes: comparison, with alternative procedures. Brain Res. 1981;226:107–118.

Charalambous A, Guo Y, Houston DB, Howlett AC, Compton DR, Martin BR, Makriyannis A. 5-Azido-Δ8-THC: a novel photoaffinity label for the cannabinoid receptor. J Med Chem 1992;35:3076–3079.

Cheng Y, Prusoff WH, Relationship between the inhibition constant (K i) and the concentration of inhibitor which causes 50 per cent (IC50) of an enzymatic reaction. Biochem Pharmacol 1973;22:3099–3108.

Coutts AA, Pertwee RG. Inhibition by cannabinoid receptor agonists of acetylcholine release from the guinea-pig Myenteric plexus. Br J Pharmacol. 1997;21:1557–1566.

Tallarida RJ, Cowan A, Adler MW. pA2 and receptor differentiation: a statistical analysis of competitive antagonism. Life Sci. 1979;25:637–654.

Colquhoun D. Lectures on Biostatistics. Oxford: Oxford University Press; 1971.