JJKK 048 - CAS 1515855-97-6
Catalog number: 1515855-97-6
Category: Inhibitor
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Molecular Formula:
C23H22N4O5
Molecular Weight:
434.44
COA:
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Targets:
MAGL
Description:
JJKK 048, a benzodioxol derivative, has been found to a MAGL inhibitor that could probably be significant in anticancer and anti-inflammatory studies. IC50: 0.4 nM.
Purity:
98%
Appearance:
Powder
Synonyms:
JJKK048; JJKK-048; JJKK 048; MolPort-035-941-193; BDBM50065646; AKOS025142062; ZINC103287208; [4-[bis(1,3-benzodioxol-5-yl)methyl]piperidin-1-yl]-(1,2,4-triazol-1-yl)methanone
Solubility:
DMSO: 100 mM
Storage:
Store in a cool and dry place and at 0 - 4 °C for short term (days to weeks) or -20 °C for long term (months to years).
MSDS:
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Quality Standard:
In-house standard
Quantity:
Milligram-Grams
InChIKey:
CLSNATLUIXZPMV-UHFFFAOYSA-N
InChI:
InChI=1S/C23H22N4O5/c28-23(27-12-24-11-25-27)26-7-5-15(6-8-26)22(16-1-3-18-20(9-16)31-13-29-18)17-2-4-19-21(10-17)32-14-30-19/h1-4,9-12,15,22H,5-8,13-14H2
Canonical SMILES:
C1CN(CCC1C(C2=CC3=C(C=C2)OCO3)C4=CC5=C(C=C4)OCO5)C(=O)N6C=NC=N6
1.In Vivo Characterization of the Ultrapotent Monoacylglycerol Lipase Inhibitor {4-[bis-(benzo[d][1,3]dioxol-5-yl)methyl]-piperidin-1-yl}(1H-1,2,4-triazol-1-yl)methanone (JJKK-048).
Aaltonen N;Kedzierska E;Orzelska-Górka J;Lehtonen M;Navia-Paldanius D;Jakupovic H;Savinainen JR;Nevalainen T;Laitinen JT;Parkkari T;Gynther M J Pharmacol Exp Ther. 2016 Oct;359(1):62-72. doi: 10.1124/jpet.116.233114. Epub 2016 Jul 22.
Monoacylglycerol lipase (MAGL) is a serine hydrolase that acts as a principal degradative enzyme for the endocannabinoid 2-arachidonoylglycerol (2-AG). In addition to terminating the signaling function of 2-AG, MAGL liberates arachidonic acid to be used as a primary source for neuroinflammatory prostaglandin synthesis in the brain. MAGL activity also contributes to cancer pathogenicity by producing precursors for tumor-promoting bioactive lipids. Pharmacological inhibitors of MAGL provide valuable tools for characterization of MAGL and 2-AG signaling pathways. They also hold great therapeutic potential to treat several pathophysiological conditions, such as pain, neurodegenerative disorders, and cancer. We have previously reported piperidine triazole urea, {4-[bis-(benzo[d][1,3]dioxol-5-yl)methyl]-piperidin-1-yl}(1H-1,2,4-triazol-1-yl)methanone (JJKK-048), to be an ultrapotent and highly selective inhibitor of MAGL in vitro. Here, we characterize in vivo effects of JJKK-048. Acute in vivo administration of JJKK-048 induced a massive increase in mouse brain 2-AG levels without affecting brain anandamide levels. JJKK-048 appeared to be extremely potent in vivo. Activity-based protein profiling revealed that JJKK-048 maintains good selectivity toward MAGL over other serine hydrolases.
2.Piperazine and piperidine triazole ureas as ultrapotent and highly selective inhibitors of monoacylglycerol lipase.
Aaltonen N;Savinainen JR;Ribas CR;Rönkkö J;Kuusisto A;Korhonen J;Navia-Paldanius D;Häyrinen J;Takabe P;Käsnänen H;Pantsar T;Laitinen T;Lehtonen M;Pasonen-Seppänen S;Poso A;Nevalainen T;Laitinen JT Chem Biol. 2013 Mar 21;20(3):379-90. doi: 10.1016/j.chembiol.2013.01.012.
Monoacylglycerol lipase (MAGL) terminates the signaling function of the endocannabinoid, 2-arachidonoylglycerol (2-AG). During 2-AG hydrolysis, MAGL liberates arachidonic acid, feeding the principal substrate for the neuroinflammatory prostaglandins. In cancer cells, MAGL redirects lipid stores toward protumorigenic signaling lipids. Thus MAGL inhibitors may have great therapeutic potential. Although potent and increasingly selective MAGL inhibitors have been described, their number is still limited. Here, we have characterized piperazine and piperidine triazole ureas that combine the high potency attributable to the triazole leaving group together with the bulky aromatic benzodioxolyl moiety required for selectivity, culminating in compound JJKK-048 that potently (IC50 < 0.4 nM) inhibited human and rodent MAGL. JJKK-048 displayed low cross-reactivity with other endocannabinoid targets. Activity-based protein profiling of mouse brain and human melanoma cell proteomes suggested high specificity also among the metabolic serine hydrolases.
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CAS 1515855-97-6 JJKK 048

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