S-Arachidonoyl-2-thioglycerol synthesis and use for fluorimetric and colorimetric assays of monoacylglycerol lipase

Casida, John E.; Gulevich, Alexander G.; Sarpong, Richmond; Bunnelle, Eric M.

doi:10.1016/j.bmc.2010.01.034

Cited by 10 publications

(10 citation statements)

References 38 publications

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“…Chlorpyrifos oxon was markedly more potent in vitro than paraoxon at inhibiting FAAH (≈ 8-fold) and MAGL (≈ 19-fold). Relatively similar in vitro differences in inhibitory potency against FAAH and MAGL in mouse brain homogenates were previously reported between these two OPs (Quistad et al 2001, 2006; Casida et al 2010). Thus chlorpyrifos oxon may elicit more extensive inhibition of these enzymes in vivo compared to paraoxon.…”

Section: Discussionsupporting

confidence: 83%

“…Activities of AChE and MAGL were measured by a modification of the photometric methods of Ellman and colleagues (1961), Casida and coworkers (2010) and Ulloa and Deutsch (2010). Buffer (PBS, no enzyme blanks) or homogenates in PBS (1:60, 25 µl, approximately 20 µg protein) were added to each well of a 96-well plastic plate on ice in quadruplicate.…”

Section: Methodsmentioning

confidence: 99%

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The cannabinoid receptor antagonist AM251 increases paraoxon and chlorpyrifos oxon toxicity in rats

Liu

Pope

2015

NeuroToxicology

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Organophosphorus anticholinesterases (OPs) elicit acute toxicity by inhibiting acetylcholinesterase (AChE), leading to acetylcholine accumulation and overstimulation of cholinergic receptors. Endocannabinoids (eCBs, e.g., arachidonoyl ethanolamide [AEA] and 2-arachidonoyl glycerol [2-AG]) are neuromodulators that regulate neurotransmission by reducing neurotransmitter release. The eCBs are degraded by the enzymes fatty acid amide hydrolase (FAAH, primarily involved in hydrolysis of AEA) and monoacylglycerol lipase (MAGL, primarily responsible for metabolism of 2-AG). We previously reported that the cannabinoid receptor agonist WIN 55,212-2 reduced cholinergic toxicity after paraoxon exposure. This study compared the effects of the cannabinoid receptor antagonist AM251 on acute toxicity following either paraoxon (PO) or chlorpyrifos oxon (CPO). CPO was more potent in vitro than PO at inhibiting AChE (≈ 2 fold), FAAH (≈ 8 fold), and MAGL (≈ 19 fold). Rats were treated with vehicle, PO (0.3 and 0.6 mg/kg, sc.) or CPO (6 and 12 mg/kg, sc.) and subsets treated with AM251 (3 mg/kg, ip; 30 min after OP). Signs of toxicity were recorded for four hours and rats were then sacrificed. OP-treated rats showed dose-related involuntary movements, with AM251 increasing signs of toxicity with the lower dosages. PO and CPO elicited excessive secretions, but AM251 had no apparent effect with either OP. Lethality was increased by AM251 with the higher dosage of PO, but no lethality was noted with either dosage of CPO, with or without AM251. Both OPs caused extensive inhibition of hippocampal AChE and FAAH (>80–90%), but only CPO inhibited MAGL (37–50%). These results provide further evidence that eCB signaling can influence acute OP toxicity. The selective in vivo inhibition of MAGL by CPO may be important in the differential lethality noted between PO and CPO with AM251 co-administration.

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Section: Discussionsupporting

confidence: 83%

Section: Methodsmentioning

confidence: 99%

The cannabinoid receptor antagonist AM251 increases paraoxon and chlorpyrifos oxon toxicity in rats

Liu

Pope

2015

NeuroToxicology

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“…The activity was followed kinetically for 10 min at 30C by following the appearance of the fluorescent product. The 2-AG-activity was measured in rat brain microsomes using a colorimetric assay as previously described [41]. …”

Section: Methodsmentioning

confidence: 99%

Peripheral FAAH and soluble epoxide hydrolase inhibitors are synergistically antinociceptive

Sasso

Wagner

Morisseau

et al. 2015

Pharmacological Research

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We need better medicines to control acute and chronic pain. Fatty acid amide hydrolase (FAAH) and soluble epoxide hydrolase (sEH) catalyze the deactivating hydrolysis of two classes of bioactive lipid mediators - fatty acid ethanolamides (FAEs) and epoxidized fatty acids (EpFAs), respectively - which are biogenetically distinct but share the ability to attenuate pain responses and inflammation. In these experiments, we evaluated the antihyperalgesic activity of small-molecule inhibitors of FAAH and sEH, administered alone or in combination, in two pain models: carrageenan-induced hyperalgesia in mice and streptozocin-induced allodynia in rats. When administered separately, the sEH inhibitor 1-trifluoromethoxyphenyl-3-(1-propionylpiperidine-4-yl)urea (TPPU) and the peripherally restricted FAAH inhibitor URB937 were highly active in the two models. The combination TPPU plus URB937 was markedly synergistic, as assessed using isobolographic analyses. The results of these experiments reveal the existence of a possible functional crosstalk between FAEs and EpFAs in regulating pain responses. Additionally, the results suggest that combinations of sEH and FAAH inhibitors might be exploited therapeutically to achieve greater analgesic efficacy.

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“…An aliquot of the upper aqueous phase (200 μl) was removed, added to 4 ml Scintisafe® scintillation fluid, and counted. AChE and MAGL were measured by a modification of the Ellman method (Ellman et al ., 1961), including modifications based on studies by Casida and coworkers (2010) and Ulloa and Deutsch (2010). PBS or striatal homogenates in PBS (AChE, 10 μg protein; MAGL, approximately 30 μg protein) were added to individual wells of a 96-well plastic plate on ice.…”

Section: Methodsmentioning

confidence: 99%

Comparative effects of parathion and chlorpyrifos on endocannabinoid and endocannabinoid-like lipid metabolites in rat striatum

2015

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Parathion and chlorpyrifos are organophosphorus insecticides (OPs) that elicit acute toxicity by inhibiting acetylcholinesterase (AChE). The endocannabinoids (eCBs, N-arachidonoylethanolamine, AEA; 2-arachidonoylglycerol, 2AG) are endogenous neuromodulators that regulate presynaptic neurotransmitter release in neurons throughout the central and peripheral nervous systems. While substantial information is known about the eCBs, less is known about a number of endocannabinoid-like metabolites (eCBLs, e.g., N-palmitoylethanolamine, PEA; N-oleoylethanolamine, OEA). We report the comparative effects of parathion and chlorpyrifos on AChE and enzymes responsible for inactivation of the eCBs, fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL), and changes in the eCBs AEA and 2AG and eCBLs PEA and OEA, in rat striatum. Adult, male rats were treated with vehicle (peanut oil, 2 ml/kg, sc), parathion (27 mg/kg) or chlorpyrifos (280 mg/kg) 6-7 days after surgical implantation of microdialysis cannulae into the right striatum, followed by microdialysis two or four days later. Additional rats were similarly treated and sacrificed for evaluation of tissue levels of eCBs and eCBLs. Dialysates and tissue extracts were analyzed by LC-MS/MS. AChE and FAAH were extensively inhibited at both time-points (85-96%), while MAGL activity was significantly but lesser affected (37-62% inhibition) by parathion and chlorpyrifos. Signs of toxicity were noted only in parathion-treated rats. In general, chlorpyrifos increased eCB levels while parathion had no or lesser effects. Early changes in extracellular AEA, 2AG and PEA levels were significantly different between parathion and chlorpyrifos exposures. Differential changes in extracellular and/or tissue levels of eCBs and eCBLs could potentially influence a number of signaling pathways and contribute to selective neurological changes following acute OP intoxications.

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S-Arachidonoyl-2-thioglycerol synthesis and use for fluorimetric and colorimetric assays of monoacylglycerol lipase

Cited by 10 publications

References 38 publications

The cannabinoid receptor antagonist AM251 increases paraoxon and chlorpyrifos oxon toxicity in rats

The cannabinoid receptor antagonist AM251 increases paraoxon and chlorpyrifos oxon toxicity in rats

Peripheral FAAH and soluble epoxide hydrolase inhibitors are synergistically antinociceptive

Comparative effects of parathion and chlorpyrifos on endocannabinoid and endocannabinoid-like lipid metabolites in rat striatum

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