Cannabidiolic acid
Cannabidiolic acid inhibits migration of the highly invasive MDA-MB-231 human breast cancer cells, apparently through a mechanism involving inhibition of cAMP-dependent protein kinase A, coupled with an activation of the small GTPase, RhoA. Cannabidiolic acid displays significantly greater potency at inhibiting vomiting in shrews and nausea in rats, and at enhancing 5-HT(1A) receptor activation; it also selectively inhibits cyclooxygenase (COX)-2 activity with an IC(50) value around 2 microM, has 9-fold higher selectivity than COX-1 inhibition. Cannabidiolic acid and cannabidiol have inhibitory actions on the intestines of S. murinus that are not neuronallymediated or mediated via CB1 or CB2 receptors.
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J Toxicol Sci. 2014;39(5):711-6.
Down-regulation of cyclooxygenase-2 (COX-2) by cannabidiolic acid in human breast cancer cells.[Pubmed:
25242400]
Metastases are known to be responsible for approximately 90% of breast cancer-related deaths. Cyclooxygenase-2 (COX-2) is involved not only in inflammatory processes, but also in the metastasis of cancer cells; it is expressed in 40% of human invasive breast cancers.
METHODS AND RESULTS:
To comprehensively analyze the effects of Cannabidiolic acid (CBDA), a selective COX-2 inhibitor found in the fiber-type cannabis plant (Takeda et al., 2008), on COX-2 expression and the genes involved in metastasis, we performed a DNA microarray analysis of human breast cancer MDA-MB-231 cells, which are invasive breast cancer cells that express high levels of COX-2, treated with Cannabidiolic acid for 48 hr at 25 µM. The results obtained revealed that COX-2 and Id-1, a positive regulator of breast cancer metastasis, were down-regulated (0.19-fold and 0.52-fold, respectively), while SHARP1 (or BHLHE41), a suppressor of breast cancer metastasis, was up-regulated (1.72-fold) and CHIP (or STUB1) was unaffected (1.03-fold). These changes were confirmed by real-time RT-PCR analyses.
CONCLUSIONS:
Taken together, the results obtained here demonstrated that i) Cannabidiolic acid had dual inhibitory effects on COX-2 through down-regulation and enzyme inhibition, and ii) Cannabidiolic acid may possess the ability to suppress genes that are positively involved in the metastasis of cancer cells in vitro.
Pharmacol Biochem Behav. 2013 Oct;111:84-9.
Suppression of lithium chloride-induced conditioned gaping (a model of nausea-induced behaviour) in rats (using the taste reactivity test) with metoclopramide is enhanced by cannabidiolic acid.[Pubmed:
24012649]
METHODS AND RESULTS:
We aimed to determine the potential of various doses of metoclopramide (MCP, a dopamine antagonist) to reduce lithium chloride (LiCl)-induced conditioned gaping (a nausea-induced behaviour) in rats, using the taste reactivity test.
We then evaluated whether an ineffective low dose of Cannabidiolic acid (CBDA, 0.1 μg/kg, Rock and Parker, 2013), the potent acidic precursor of cannabidiol (CBD, a non-psychoactive component of cannabis) could enhance the anti-nausea effects of an ineffective low dose of MCP. MCP (3.0 mg/kg) reduced conditioned gaping responses. Coadministration of ineffective doses of MCP (0.3 mg/kg) and Cannabidiolic acid (0.1 μg/kg) enhanced the suppression of conditioned gaping, over that of either drug alone, without interfering with conditioned taste avoidance. MCP dose-dependently reduced nausea-induced conditioned gaping in rats. As well, the suppression of conditioned gaping was enhanced when ineffective doses of MCP and Cannabidiolic acid were coadministered.
CONCLUSIONS:
These data suggest that Cannabidiolic acid could be a powerful adjunct treatment to anti-emetic regimens for chemotherapy-induced nausea.
Psychopharmacology (Berl). 2014 Aug;231(16):3207-15.
A comparison of cannabidiolic acid with other treatments for anticipatory nausea using a rat model of contextually elicited conditioned gaping.[Pubmed:
24595502]
The effectiveness of Cannabidiolic acid (CBDA) was compared with other potential treatments for anticipatory nausea (AN), using a rat model of contextually elicited conditioned gaping reactions. The potential of ondansetron (OND), Δ(9)-tetrahydrocannabinol (THC), chlordiazepoxide (CDP), Cannabidiolic acid, and co-administration of Cannabidiolic acid and tetrahydrocannabinolic acid (THCA) to reduce AN and modify locomotor activity was evaluated.
METHODS AND RESULTS:
Following four pairings of a novel context with lithium chloride (LiCl), the rats were given a test for AN. On the test trial, they received pretreatment injections of the following: vehicle, OND (0.1 or 1.0 mg/kg), THC (0.5 mg/kg), Cannabidiolic acid (0.0001, 0.001, 0.01, 0.1 mg/kg or 1.0 mg/kg), CDP (1, 5, or 10 mg/kg) or co-administration of subthreshold doses of Cannabidiolic acid (0.1 μg/kg), and THCA (5 μg/kg). Immediately following the AN test trial in all experiments, rats were given a 15 min locomotor activity test. Finally, the potential of Cannabidiolic acid (0.001, 0.01, 0.1, and 1 mg/kg) to attenuate conditioned freezing to a shock-paired tone was assessed. THC, Cannabidiolic acid, and CDP, but not OND, reduced contextually elicited gaping reactions. Co-administration of subthreshold doses of Cannabidiolic acid and THCA also suppressed AN, and this effect was blocked by pretreatment with either a cannabinoid receptor 1 (CB1) receptor antagonist or a 5-hydroxytryptamine 1A (5-HT1A) receptor antagonist. CDP (but not Cannabidiolic acid, THC or Cannabidiolic acid and THCA) also suppressed locomotor activity at effective doses. Cannabidiolic acid did not modify the expression of conditioned fear.
CONCLUSIONS:
Cannabidiolic acid has therapeutic potential as a highly potent and selective treatment for AN without psychoactive or locomotor effects.
Br J Pharmacol. 2013 Jun;169(3):685-92.
Effect of low doses of cannabidiolic acid and ondansetron on LiCl-induced conditioned gaping (a model of nausea-induced behaviour) in rats.[Pubmed:
23488964]
To determine the minimally effective dose of Cannabidiolic acid (CBDA) that effectively reduces lithium chloride (LiCl)-induced conditioned gaping reactions (nausea-induced behaviour) in rats and to determine if these low systemic doses of Cannabidiolic acid (5-0.1 μg·kg⁻¹) relative to those of CBD could potentiate the anti-nausea effects of the classic 5-hydroxytryptamine 3 (5-HT₃) receptor antagonist, ondansetron (OND).
METHODS AND RESULTS:
We investigated the efficacy of low doses of Cannabidiolic acid to suppress acute nausea, assessed by the establishment of conditioned gaping to a LiCl-paired flavour in rats. The potential of threshold and subthreshold doses of Cannabidiolic acid to enhance the reduction of nausea-induced conditioned gaping by OND were then determined. Cannabidiolic acid (at doses as low as 0.5 μg·kg⁻¹) suppressed nausea-induced conditioned gaping to a flavour. A low dose of OND (1.0 μg·kg⁻¹) alone reduced nausea-induced conditioned gaping, but when it was combined with a subthreshold dose of Cannabidiolic acid (0.1 μg·kg⁻¹) there was an enhancement in the suppression of LiCl-induced conditioned gaping.
CONCLUSIONS:
Cannabidiolic acid potently reduced conditioned gaping in rats, even at low doses and enhanced the anti-nausea effect of a low dose of OND. These findings suggest that combining low doses of Cannabidiolic acid and OND will more effectively treat acute nausea in chemotherapy patients.
