1999
DOI: 10.1038/sj.bjp.0702836
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Structural determinants of the partial agonist‐inverse agonist properties of 6′‐azidohex‐2′‐yne‐Δ8‐tetrahydrocannabinol at cannabinoid receptors

Abstract: We have extended previous investigations of four analogues of Δ8‐tetrahydrocannabinol (Δ8‐THC): 6′‐azidohex‐2′‐yne‐Δ8‐THC (O‐1184), 6′‐azidohex‐cis‐2′‐ene‐Δ8‐THC (O‐1238) and octyl‐2′‐yne‐Δ8‐THC (O‐584) and its 1‐deoxy‐analogue (O‐1315). O‐1184, O‐1238 and O‐584 displaced [3H]‐CP55940 from specific binding sites on Chinese hamster ovary (CHO) cell membranes expressing CB1 or CB2 cannabinoid receptors, with pKi values of 8.28 to 8.45 (CB1) and 8.03 to 8.13 (CB2). The pKi values of O‐1315 were significantly less… Show more

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Cited by 57 publications
(63 citation statements)
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“…At concentrations up to 10 M, HU-308 had no effect on forskolin-stimulated cyclic AMP production in cells that had not been transfected with cannabinoid receptors (n ϭ 3). These data provide strong evidence that HU-308 shares the ability of established cannabinoid receptor agonists to inhibit cyclic AMP production (19), and they confirm that it interacts significantly more readily with CB 2 than with CB 1 receptors.…”
Section: Resultssupporting
confidence: 66%
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“…At concentrations up to 10 M, HU-308 had no effect on forskolin-stimulated cyclic AMP production in cells that had not been transfected with cannabinoid receptors (n ϭ 3). These data provide strong evidence that HU-308 shares the ability of established cannabinoid receptor agonists to inhibit cyclic AMP production (19), and they confirm that it interacts significantly more readily with CB 2 than with CB 1 receptors.…”
Section: Resultssupporting
confidence: 66%
“…The ability of HU-308 to inhibit forskolinstimulated cyclic AMP production in Chinese hamster ovary (CHO) cells, stably transfected with human CB 1 or CB 2 receptors, was measured by a method we have used previously for the bioassay of other cannabinoids (19). The effect of HU-308 on cyclic AMP production has been expressed in percentage terms and mean values for EC 50 ; maximal effects (E max ) and the SEM or 95% confidence limits of these values have been calculated by nonlinear regression analysis with the equation for a sigmoid concentration-response curve (PRISM software from GraphPad, San Diego) (19).…”
Section: Methodsmentioning
confidence: 99%
“…Thus, unlike SR141716A (Pertwee et al 1996b), O-2654 does not increase the amplitude of electrically evoked contractions of this preparation. Nor does it share the ability of the CB 1 partial agonist, O-1184, to inhibit these contractions (Ross et al 1999b). O-2050, a sulphonamide analogue of ∆ 8 -THC with an acetylenic side chain also behaves as a neutral CB 1 receptor antagonist in the mouse vas deferens .…”
Section: Neutral Antagonism At Cannabinoid Receptorsmentioning
confidence: 98%
“…3.2: AM251 (Vásquez et al 2003), AM281 (Cosenza et al 2000;Gifford et al 1997;Izzo et al 2000;Vásquez et al 2003), LY320135 (Felder et al 1998) and AM630 (Sect. 3.2.2) at CB 1 receptors and SR144528 Rinaldi-Carmona et al 1998;Ross et al 1999b), AM630 (New and Wong 2003;Ross et al 1999a) and AM251 (New and Wong 2003) at CB 2 receptors. These effects include SR141716A-and AM281-induced hyperkinesia in rats and/or mice Cosenza et al 2000;Costa and Colleoni 1999) and the attenuation in vitro of CB 1 or CB 2 receptor signalling.…”
Section: Inverse Agonism At Cannabinoid Receptorsmentioning
confidence: 98%
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