URB602 - CAS 565460-15-3
Category: Inhibitor
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Molecular Formula:
C19H21NO2
Molecular Weight:
295.38
COA:
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Targets:
MAGL
Description:
URB602, a cell-permeable N-biphenyl carbamate compound, is a selective inhibitor of monoglycerol lipase (MGL). The IC50 = 28 μM and Km = 20 μM. It does not inhibit fatty acid amide hydrolase (FAAH) at concentrations up to 100 µM or other lipid metabolizing enzymes such as diacylglycerol lipase or COX-2.
Appearance:
Solid powder
Synonyms:
cyclohexyl [1,1'-biphenyl]-3-ylcarbamate; URB602; URB-602; URB 602.
Storage:
Store in a cool and dry place (or refer to the Certificate of Analysis).
MSDS:
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Boiling Point:
416.6±24.0 °C at 760 Torr
Density:
1.14±0.1 g/cm3
InChIKey:
HHVUFQYJOSFTEH-UHFFFAOYSA-N
InChI:
1S/C19H21NO2/c21-19(22-18-12-5-2-6-13-18)20-17-11-7-10-16(14-17)15-8-3-1-4-9-15/h1,3-4,7-11,14,18H,2,5-6,12-13H2,(H,20,21)
Canonical SMILES:
O=C(OC1CCCCC1)NC2=CC(C3=CC=CC=C3)=CC=C2
1.Hyperactivity induced by the dopamine D2/D3 receptor agonist quinpirole is attenuated by inhibitors of endocannabinoid degradation in mice.
Luque-Rojas MJ;Galeano P;Suárez J;Araos P;Santín LJ;de Fonseca FR;Calvo EB Int J Neuropsychopharmacol. 2013 Apr;16(3):661-76. doi: 10.1017/S1461145712000569. Epub 2012 May 30.
The present study was designed to investigate the effect of pharmacological inhibition of endocannabinoid degradation on behavioural actions of the dopamine D2/D3 receptor agonist quinpirole in male C57Bl/6J mice. In addition, we studied the effects of endocannabinoid degradation inhibition on both cocaine-induced psychomotor activation and behavioural sensitization. We analysed the effects of inhibition of the two main endocannabinoid degradation enzymes: fatty acid amide hydrolase (FAAH), using inhibitor URB597 (1 mg/kg); monoacylglycerol lipase (MAGL), using inhibitor URB602 (10 mg/kg). Administration of quinpirole (1 mg/kg) caused a temporal biphasic response characterized by a first phase of immobility (0-50 min), followed by enhanced locomotion (next 70 min) that was associated with the introduction of stereotyped behaviours (stereotyped jumping and rearing). Pretreatment with both endocannabinoid degradation inhibitors did not affect the hypoactivity actions of quinpirole. However, this pretreatment resulted in a marked decrease in quinpirole-induced locomotion and stereotyped behaviours. Administration of FAAH or MAGL inhibitors did not attenuate the acute effects of cocaine.
2.Enhancement of the hypotensive effects of intrathecally injected endocannabinoids by the entourage compound palmitoylethanolamide.
García Mdel C;Adler-Graschinsky E;Celuch SM Eur J Pharmacol. 2009 May 21;610(1-3):75-80. doi: 10.1016/j.ejphar.2009.03.021. Epub 2009 Mar 14.
The intrathecal (i.t.) injection of 50 and 100 nmol anandamide to urethane anesthetized rats induced a dose-dependent decrease in the mean blood pressure (-10.6+/-1.6 mmHg and -15.0+/-1.7 mmHg, respectively; n=6) whereas a lower dose of this endocannabinoid (25 nmol) was devoid of effect. Similar responses were obtained both with the non-metabolizable analog methanandamide and with the endocannabinoid N-arachidonoyldopamine. When the sub-effective dose (25 nmol) of each compound was co-injected with palmitoylethanolamide (100 nmol), significant decreases in the blood pressure were observed (-12.3+1.3 mmHg for anandamide; -12.1+/-0.8 mmHg for methanandamide; -12.1+/-0.8 mmHg for N-arachidonoyldopamine; n=4-6). Palmitoylethanolamide also enhanced the hypotensive responses to the 50 nmol-dose of both anandamide and methanandamide. The hypotensive response induced by co-administration of palmitoylethanolamide and 25 nmol anandamide was prevented both by the cannabinoid CB(1) receptor antagonist SR 144716A (20 nmol; i.t.) and by the vanilloid TRPV1 receptor antagonist capsazepine (20 nmol; i.t.) and enhanced by pretreatment with URB602 (3.5 nmol; i.t.), a putative inhibitor of palmitoylethanolamide degradation.
3.Pharmacological inhibition of MAGL attenuates experimental colon carcinogenesis.
Pagano E;Borrelli F;Orlando P;Romano B;Monti M;Morbidelli L;Aviello G;Imperatore R;Capasso R;Piscitelli F;Buono L;Di Marzo V;Izzo AA Pharmacol Res. 2017 May;119:227-236. doi: 10.1016/j.phrs.2017.02.002. Epub 2017 Feb 11.
Colorectal cancer (CRC) is a major health problem in Western countries. The endocannabinoid 2-arachidonoyl-glycerol (2-AG) exerts antiproliferative actions in a number of tumoral cell lines, including CRC cells. Monoacylglycerol lipase (MAGL), a serine hydrolase that inactivates 2-AG, is highly expressed in aggressive human cancer cells. Here, we investigated the role of MAGL in experimental colon carcinogenesis. The role of MAGL was assessed in vivo by using the xenograft and the azoxymethane models of colon carcinogenesis; MAGL expression was evaluated by RT-PCR and immunohistochemistry; 2-AG levels were measured by liquid chromatography mass spectrometry; angiogenesis was evaluated in tumor tissues [by microvessel counting and by investigating the expression of vascular endothelial growth factor (VEGF) and fibroblast growth factor-2 (FGF-2) proteins] as well as in human umbilical vein endothelial cells (HUVEC); cyclin D1 was evaluated by RT-PCR. MAGL and 2-AG were strongly expressed in tumor tissues. The MAGL inhibitor URB602 reduced xenograft tumor volume, this effect being associated to down-regulation of VEGF and FGF-2, reduction in the number of vessels and down-regulation of cyclin D1.
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CAS 565460-15-3 URB602

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