N-Oleoyldopamine Enhances Glucose Homeostasis through the Activation of GPR119

Chu, Zhi-Liang; Carroll, Christopher J.; Chen, Ruoping; Alfonso, Jean; Gutiérrez, Verónica; He, Hongmei; Lucman, Annette; Xing, Charles; Sebring, Kristen; Zhou, Jingcheng; Wagner, Brandee; Unett, David J.; Jones, Robert M.; Behan, Dominic P.; Leonard, Janet L.

doi:10.1210/me.2009-0239

Cited by 114 publications

(88 citation statements)

References 40 publications

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“…Subsequent reports provided evidence that compounds structurally related to OEA might also be important regulators of GPR119 receptor activity (8,18,19), but no one has reported a complete and thorough evaluation of whether other endogenous endocannabinoid-like lipids can serve as GPR119 ligands. We therefore undertook such a study focusing on compound properties critical for endogenous receptor activation: 1) ability of the ligand to activate GPR119 receptor; 2) translation of the receptor activation into GLP-1 secretion in enteroendocrine cells; 3) the presence of the ligand in the intestinal tissue at levels capable of activating the receptor; and 4) changes in the intestinal ligand concentrations in response to changes in the nutrient load.…”

Section: Discussionmentioning

confidence: 99%

“…OEA is synthesized in the proximal small intestine, where its concentration decreases during food deprivation and increases upon refeeding (16,27). Additional endocannabinoid-like compounds, either amides of long-chain fatty acids or oleoyl-containing lipids, such as 2-oleoylglycerol (2-OG), were subsequently reported to increase GPR119 activity and serve as important endogenous or meal-associated agonists (8,18,19). With a large number of compounds that display different levels of GPR119 activation in vitro in the pharmacological assays, it is unclear which of these endogenous lipids actually mediates physiological activation of GPR119 in the intestine.…”

mentioning

confidence: 99%

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Regulation of GPR119 receptor activity with endocannabinoid-like lipids

Syed

Bui

Beavers

et al. 2012

American Journal of Physiology-Endocrinology and Metabolism

100

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The GPR119 receptor plays an important role in the secretion of incretin hormones in response to nutrient consumption. We have studied the ability of an array of naturally occurring endocannabinoid-like lipids to activate GPR119 and have identified several lipid receptor agonists. The most potent receptor agonists identified were three N-acylethanolamines: oleoylethanolamine (OEA), palmitoleoylethanolamine, and linoleylethanolamine (LEA), all of which displayed similar potency in activating GPR119. Another lipid, 2-oleoylglycerol (2-OG), also activated GPR119 receptor but with significantly lower potency. Endogenous levels of endocannabinoid-like lipids were measured in intestine in fasted and refed mice. Of the lipid GPR119 agonists studied, the intestinal levels of only OEA, LEA, and 2-OG increased significantly upon refeeding. Intestinal levels of OEA and LEA in the fasted mice were low. In the fed state, OEA levels only moderately increased, whereas LEA levels rose drastically. 2-OG was the most abundant of the three GPR119 agonists in intestine, and its levels were radically elevated in fed mice. Our data suggest that, in lean mice, 2-OG and LEA may serve as physiologically relevant endogenous GPR119 agonists that mediate receptor activation upon nutrient uptake.GPR119; linoleoylethanolamine; oleoylethanolamine; 2-oleoylglycerol GUT HORMONES, SUCH AS glucose-dependent insulinotropic polypeptide (GIP), glucagon-like peptide-1 (GLP-1), and peptide YY (PYY), are peptides whose secretion from enteroendocrine intestinal cells is stimulated by the intake of nutrients. Released peptides signal to enhance nutrient metabolism and limit further nutrient consumption. These peptides play a crucial role in the regulation of glucose and lipid metabolism by stimulating insulin secretion, inhibiting glucagon secretion, improving insulin sensitivity, slowing gastric emptying, increasing satiety, and reducing food intake (12,31

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

Regulation of GPR119 receptor activity with endocannabinoid-like lipids

Syed

Bui

Beavers

et al. 2012

American Journal of Physiology-Endocrinology and Metabolism

100

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“…N-Oleoyl dopamine, a commercially available compound with biomedical research interest [25][26][27] was synthesized via the amidation of oleoyl chloride.…”

Section: Synthesis Of Oleoyldopaminementioning

confidence: 99%

Myoblast Cell Interaction with Polydopamine Coated Liposomes

et al. 2012

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Liposomes are widely used, from biosensing to drug delivery. Their coating with polymers for stability and functionalization purposes further broadens their set of relevant properties. Poly(dopamine) (PDA), a eumelanin-like material deposited via the “self”-oxidative polymerization of dopamine at mildly basic pH, has attracted considerable interest in the past few years due to its simplicity, flexibility yet fascinating properties. Herein, we characterize the coating of different types of liposomes with PDA depending on the presence of oleoyldopamine in the lipid bilayer and the dopamine hydrochloride concentration. Further, the interaction of these coated liposomes in comparison to their uncoated counterparts with myoblast cells is assessed. Their uptake/association efficiency with these cells is determined. Further, their dose-dependent cytotoxicity with and without entrapped hydrophobic cargo (thiocoraline) is characterized. Taken together, the reported results demonstrate the potential of PDA coated liposomes as a tool in biomedical applications. Supplementary Material 13758_2011_8_MOESM1_ESM.doc (83KB)

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“…However, we have not defined which fatty acid amides elevated by FAAH inhibition are responsible for the effects observed, nor which receptor might in turn be stimulated by such increases. Thus, although we demonstrate that URB597 can elevate AEA, OEA, and PEA, given the actions of these molecules, the effects observed here could be caused by interactions with one or more of the cannabinoid type 1 receptors (Di Marzo, 2009), TRPV1 receptors (van der Stelt andDi Marzo, 2004;Morgese et al, 2007), peroxisome proliferator-activated receptor ␣ (Mascia et al, 2010), G protein-coupled receptor 119 (Chu et al, 2010), G protein-coupled receptor 55 (Whyte et al, 2009), or with an as yet uncharacterized FAA receptor.…”

Section: Discussionmentioning

confidence: 61%

Fatty Acid Amide Hydrolase (FAAH) Inhibition Reduces l-3,4-Dihydroxyphenylalanine-Induced Hyperactivity in the 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine-Lesioned Non-Human Primate Model of Parkinson's Disease

Johnston¹,

Huot²,

Fox³

et al. 2010

J Pharmacol Exp Ther

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Dopaminergic therapies remain the most efficacious symptomatic treatments for Parkinson's disease (PD) but are associated with motor complications, including dyskinesia, and nonmotor complications, such as psychosis, impulse control disorders (ICD), and dopamine dysregulation syndrome (DDS). Nondopaminergic neurotransmitter systems, including the endocannabinoid system, are probably critical to the development of these complications. The role of fatty acid amide hydrolase (FAAH) in mediating L-3,4-dihydroxyphenylalanine (L-DOPA)-induced behaviors was explored in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-lesioned marmoset model of PD. Pharmacodynamic and locomotor effects of the selective FAAH inhibitor [3-(3-carbamoylphenyl)phenyl] N-cyclohexylcarbamate (URB597) were assessed via bioanalytical (liquid chromatography-tandem mass spectrometry) and behavioral observation approaches. URB597 (3, 10, 30, or 60 mg/kg p.o.) increased plasma levels of the FAAH substrates N-arachidonoyl ethanolamide (anandamide), N-oleoyl ethanolamide, and N-palmitoyl ethanolamide by 10.3 Ϯ 0.3-, 7.8 Ϯ 0.2-, and 1.8 Ϯ 0.1-fold (mean of URB597 groups Ϯ S.E.M.), respectively, compared with vehicle (all p Ͻ 0.001) 4 h after administration. Treatment with L-DOPA (20 mg/kg s.c.) alleviated parkinsonism but elicited dyskinesia, psychosis-like-behaviors and hyperactivity, a potential correlate of ICD and DDS. During the 2 to 4 h after L-DOPA, corresponding to 4 to 6 h after URB597 administration, URB597 reduced total L-DOPA-induced activity and the magnitude of hyperactivity by 32 and 52%, respectively, to levels equivalent to those seen in normal animals. Treatment with URB597 (10 mg/kg p.o.) did not modify the antiparkinsonian actions of L-DOPA or L-DOPA-induced dyskinesia and psychosis. URB597 did not alter plasma L-DOPA levels and was without behavioral effects when administered alone. Inhibition of FAAH may represent a novel approach to reducing L-DOPA-induced side effects, such as ICD and DDS, while maintaining the antiparkinsonian benefits of L-DOPA treatment.

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N-Oleoyldopamine Enhances Glucose Homeostasis through the Activation of GPR119

Cited by 114 publications

References 40 publications

Regulation of GPR119 receptor activity with endocannabinoid-like lipids

Regulation of GPR119 receptor activity with endocannabinoid-like lipids

Myoblast Cell Interaction with Polydopamine Coated Liposomes

Fatty Acid Amide Hydrolase (FAAH) Inhibition Reduces l-3,4-Dihydroxyphenylalanine-Induced Hyperactivity in the 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine-Lesioned Non-Human Primate Model of Parkinson's Disease

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