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SML2732

Sigma-Aldrich

DO34

≥98% (HPLC)

Sinónimos:

(2-Benzyl-4-{[(2-methyl-2-propanyl)oxy]carbonyl}piperazinyl){4-[(4-trifluoromethoxy)phenyl]-1H-1,2,3-triazol-1-yl}methanone, 3-(Phenylmethyl)-4-[[4-[4-(trifluoromethoxy)phenyl]-1H-1,2,3-triazol-1-yl]carbonyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester

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About This Item

Fórmula empírica (notación de Hill):
C26H28F3N5O4
Número de CAS:
1848233-58-8
Peso molecular:
531.53
Número MDL:
MFCD31807614
Código UNSPSC:
12352200
NACRES:
NA.77

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

color

white to beige

solubilidad

DMSO: 2 mg/mL, clear

temp. de almacenamiento

−20°C

cadena SMILES

O=C(N1CCN(CC1CC2=CC=CC=C2)C(OC(C)(C)C)=O)N3N=NC(C4=CC=C(C=C4)OC(F)(F)F)=C3

InChI

1S/C26H28F3N5O4/c1-25(2,3)38-24(36)32-13-14-33(20(16-32)15-18-7-5-4-6-8-18)23(35)34-17-22(30-31-34)19-9-11-21(12-10-19)37-26(27,28)29/h4-12,17,20H,13-16H2,1-3H3

Clave InChI

CQGMWUWJVBKTRM-UHFFFAOYSA-N

Acciones bioquímicas o fisiológicas

Brain-penetrant, selective and highly potent diacylglycerol lipase (DAGLα/β, DAGLalpha & DAGLbeta) inhibitor in vitro and in vivo.
DO34 is a brain-penetrant, selective and highly potent diacylglycerol lipase inhibitor (recom human DAGLα/β pIC50 = 8.2/8.1 by SAG hydrolysis; mouse brain DAGLα/β pIC50 = 9.1-9.3/8.6 by ABPP ReDiMe) with detectable off-target activity toward only ABHD6 & PLA2G7 among all mouse brain serine hydrolases and little affinity toward cannabinoid receptors CB1/2. DO34 blocks depolarization-induced suppression of excitation (DSE IC50 = 0.18 μM) and inhibition (100% DSI blockage at 1 μM) in mouse cerebellar and hippocampal slices ex vivo, and attenuate LPS-induced neuroinflammatory responses by lowering brain 2-AG & PGE2 level in mice in vivo (50 mg/kg, i.p).

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000181991
0000152076
0000152076
0000181991
0000133902

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Carol A Gianessi et al.
Addiction biology, 25(3), e12768-e12768 (2019-05-06)
Individuals with alcohol use disorder exhibit compulsive habitual behaviors that are thought to be, in part, a consequence of chronic and persistent use of alcohol. The endocannabinoid system plays a critical role in habit learning and in ethanol self-administration, but
Jayme R McReynolds et al.
Biological psychiatry, 84(2), 85-94 (2017-11-05)
Clinical reports suggest that rather than directly driving cocaine use, stress may create a biological context within which other triggers for drug use become more potent. We hypothesize that stress-induced increases in corticosterone "set the stage" for relapse by promoting
Jenny L Wilkerson et al.
The Journal of pharmacology and experimental therapeutics, 363(3), 394-401 (2017-10-04)
Diacylglycerol lipase (DAGL) α and β, the major biosynthetic enzymes of the endogenous cannabinoid (endocannabinoid) 2-arachidonylglycerol (2-AG), are highly expressed in the nervous system and immune system, respectively. Genetic deletion or pharmacological inhibition of DAGL-β protects against lipopolysaccharide (LPS)-induced inflammatory
Daisuke Ogasawara et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(1), 26-33 (2015-12-17)
Diacylglycerol lipases (DAGLα and DAGLβ) convert diacylglycerol to the endocannabinoid 2-arachidonoylglycerol. Our understanding of DAGL function has been hindered by a lack of chemical probes that can perturb these enzymes in vivo. Here, we report a set of centrally active
Victoria S Cavener et al.
Frontiers in neuroscience, 12, 479-479 (2018-08-16)
Elucidating the underlying molecular mechanisms regulating fear and extinction learning may offer insights that can lead to novel treatments for debilitating anxiety and trauma-related disorders including posttraumatic stress disorder. The endocannabinoid (eCB) system is a retrograde inhibitory signaling pathway involved
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