Chemoenzymatic synthesis and cannabinoid activity of a new diazabicyclic amide of phenylacetylricinoleic acid

Antiallodynic effect of PhAR‐DBH‐Me involves cannabinoid and TRPV1 receptors

“…Our results matched with previously reported data 14 , relating the activation of CB1 receptor on PhAR‐DBH‐Me‐induced anti‐hyperalgesia in mice evaluated by the hot plate test 14 . Furthermore, our results extend the existing data, including the participation of CB2 and TRPV1 receptors as a part of the mechanism of action activated by PhAR‐DBH‐Me.…”

“…PhAR‐DBH‐Me was synthetized at Facultad de Estudios Superiores de Zaragoza ‐ UNAM, as was described by 14 . Capsazepine was acquired from Tocris Bioscience (Ellisville, MO, USA), whereas AM‐251 and AM‐630 were acquired from Sigma Aldrich (San Luis, MO, USA).…”

“…In a previous study, we developed the new synthetic compound ( R,Z )‐18‐((1 S ,4 S )‐5‐methyl‐2,5‐diazabicyclo[2.2.1]heptan‐2‐yl)‐18‐oxooctadec‐9‐en‐7‐ylphenylacetate (PhAR‐DBH‐Me), which is a diazabicyclic amide synthesized from phenylacetylricinoleic acid and (1 S ,4 S )‐2,5‐diazabicyclo[2.2.1]heptane. On the first assays, PhAR‐DBH‐Me produced an antinociceptive effect by activation of the CB1 receptor, suggesting a cannabinergic nature for the compound, similar to anandamide 14 . However, further studies on the nature of this compound such as its antiallodynic effect or its participation on CB2 and TRPV1 receptors have not been performed yet.…”

Characterization of hypotensive and vasorelaxant effects of PHAR-DBH-Me a new cannabinoid receptor agonist

“…PHAR-DBH-Me was synthesized at Facultad de Estudios Superiores de Zaragoza-UNAM, as described by López-Ortiz and co-workers [ 11 ]. All other drugs were purchased from Sigma-Aldrich.…”

“…Those compounds include newly synthesized (R,Z)-18-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-18-oxooctadec-9-en-7-yl phenylacetate (PHAR-DBH-Me) that binds and activates the CB receptor. In a previous paper, it has been reported that amide (PHAR-DBH-Me), an agonist of the CB 1, CB 2 , and TRPV1 receptors, is synthesized from phenylacetylricinoleic acid and (1 S ,4 S )-2,5-diazabicyclo[2.2.1]heptane [ 11 ]. The present study aimed to analyze the effects of the compound PHAR-DBH-Me with different experimental approaches on the cardiovascular system.…”