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SML1364

Sigma-Aldrich

KT109

≥98% (HPLC)

Synonym(s):

(4-([1,1′-Biphenyl]-4-yl)-1H-1,2,3-triazol-1-yl)(2-benzylpiperidin-1-yl)methanone

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About This Item

Empirical Formula (Hill Notation):
C27H26N4O
CAS Number:
1402612-55-8
Molecular Weight:
422.52
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(N1CCCCC1Cc2ccccc2)n3cc(nn3)-c4ccc(cc4)-c5ccccc5

InChI

1S/C27H26N4O/c32-27(30-18-8-7-13-25(30)19-21-9-3-1-4-10-21)31-20-26(28-29-31)24-16-14-23(15-17-24)22-11-5-2-6-12-22/h1-6,9-12,14-17,20,25H,7-8,13,18-19H2

InChI key

JKJMWHULJIOKPJ-UHFFFAOYSA-N

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Biochem/physiol Actions

KT109 is a potent and selective inhibitor of Diacylglycerol lipase DAGLβ. Diacylglycerol lipases DAGLα and DAGLβ are serine hydrolases that biosynthesize the endocannabinoid 2-arachidonoylglycerol (2-AG). A lack of selective inhibitors has hampered study of these lipases. KT109 is a potent and selective DAGLβ inhibitor with an IC50 of 42 nM, ~60-fold selectivity for DAGLβ over DAGLα, and negligible activity against FAAH, MGLL and ABHD11, other key enzymes involved in endocannabinoid signaling. KT109 shows some inhibitory activity against PLA2G7 (IC50 = 1 μM) but no inhibitory activity against cytosolic phospholipase A2 (cPLA2 or PLA2G4A). The main off target inhibition against ABHD6 (IC50 = 16 nM) can be controlled for by use of the related compound, KT195, a potent (IC50 = 10 nM) and selective ABHD6 inhibitor with negligible activity against DAGLβ. KT109 disrupts the lipid network involved in macrophage inflammatory responses, lowering 2-AG, as well as arachidonic acid and eicosanoids, in mouse peritoneal macrophages.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H413

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000191887
0000191886
075M4603V

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Ku-Lung Hsu et al.
Nature chemical biology, 8(12), 999-1007 (2012-10-30)
The endocannabinoid 2-arachidonoylglycerol (2-AG) is biosynthesized by diacylglycerol lipases DAGLα and DAGLβ. Chemical probes to perturb DAGLs are needed to characterize endocannabinoid function in biological processes. Here we report a series of 1,2,3-triazole urea inhibitors, along with paired negative-control and
Ku-Lung Hsu et al.
Journal of medicinal chemistry, 56(21), 8257-8269 (2013-10-25)
We have previously shown that 1,2,3-triazole ureas (1,2,3-TUs) act as versatile class of irreversible serine hydrolase inhibitors that can be tuned to create selective probes for diverse members of this large enzyme class, including diacylglycerol lipase-β (DAGLβ), a principal biosynthetic
Bogeon Yun et al.
The Journal of biological chemistry, 289(3), 1491-1504 (2013-12-04)
Perturbation of calcium signaling that occurs during cell injury and disease, promotes cell death. In mouse lung fibroblasts A23187 triggered mitochondrial permeability transition pore (MPTP) formation, lactate dehydrogenase (LDH) release, and necrotic cell death that were blocked by cyclosporin A

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