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5.33469

GPR120 Agonist IV, cpdA

Synonym(s):

GPR120 Agonist IV, cpdA, 2-(3-(2-Chloro-5-(trifluoromethoxy)phenyl)-3-azaspiro[5.5]undecan-9-yl)acetic acid

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Size/SKUAvailabilityPrice
10 mg
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$264.00

About This Item

Empirical Formula (Hill Notation):
C19H23ClF3NO3
CAS Number:
1599477-75-4
Molecular Weight:
405.84
MDL number:
MFCD28975351
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥97% (HPLC)
Form:
solid
Storage condition:
OK to freeze, protect from light

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assay

≥97% (HPLC)

Quality Segment

100

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

off-white

solubility

DMSO: 50 mg/mL

storage temp.

2-8°C

SMILES string

FC(F)(F)Oc1cc(c(cc1)Cl)N2CCC3(CC2)CCC(CC3)CC(=O)O

InChI

1S/C19H23ClF3NO3/c20-15-2-1-14(27-19(21,22)23)12-16(15)24-9-7-18(8-10-24)5-3-13(4-6-18)11-17(25)26/h1-2,12-13H,3-11H2,(H,25,26)

InChI key

WUJVPELCYCESAP-UHFFFAOYSA-N

General description

A cell-permeable azaspiroundecanyl acetic acid compound that acts as a selective Gpr120 (FFAR4) agonist toward both human and murine species (EC50 = 60 nM/IP3 production and 350 nM/β-Arrestin-2 recruitment using cells expressing human or murine Gpr120), while being ineffective toward Gpr40 and is about 100-fold more effective than docosahexaenoic acid/DHA in stimulating serum response element/SRE promoter-mediated reporter transcription in mGPR120-expressing HEK 293. Selectively suppresses (10 µM) chemotaxis toward adipocyte-conditioned medium and LPS-induced inflammatory responses in primary macrophages derived from wt, but not Gpr120-knockout, mice in vitro, including IκB degradation as well as phosphorylations of Tak1, Ikk-β, and JNK, and is efficacious in improving glucose tolerance & insulin sensitivity in vivo among wt, but not Gpr120-knockout, mice on high-fat diet (HFD) when supplemented (30 mg/kg) in the diet for the last 5 wks of a 20-wk HFD period without affecting animal body weight, resulting in decreased hyperinsulinemia, hepatic steatosis, adipose tissue macrophage (ATM) infiltration and inflammation. Unlike the Gpr40/Gpr120 dual agonist DHA, this compound does not stimulate Gpr40-mediated insulin secretion from MIN6 β cell line or ehances Glucose-stimulated insulin secretion (GSIS) from β cells in cultured islets from wt or Gpr120-knockout mice.
A cell-permeable, orally active, non-toxic, azaspiroundecanyl acetic acid based compound that acts as a highly potent, selective and reversible activator of GPR120 in murine and human cells (EC50 = 350 nM for β-arrestin 2 recruitment). Induces concentration-dependent increase in inositol-1,4,5-triphosphate (IP3) production in GRP120 expressing cells. Exhibits about 50-fold higher sensitivity for GRP120 than docosahexaenoic acid, however, it displays very poor affinity towards GRP40. Effectively reduces hepatic steatosis and improves glucose tolerance, hyperinsulinemia, and insulin sensitivity in obese mice fed high fat diet. Strongly inhibits LPS-induced phosphorylation of TAK1, IKKβ & JNK and reduces IκB degradation in macrophages.

Please note that the molecular weight for this compound is batch-specific due to variable water content. Please refer to the vial label or the certificate of analysis for the batch-specific molecular weight. The molecular weight provided represents the baseline molecular weight without water.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
GPR120
Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Oh, D.Y., et al. 2014. Nat. Med.8, 942.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

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GPR120 Agonist IV, cpdA

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GPR119 Agonist, AS1269574 The GPR119 Agonist, AS1269574, also referenced under CAS 330981-72-1, controls the biological activity of GPR119. This small molecule/inhibitor is primarily used for Biochemicals applications.

Sigma-Aldrich

371724

GPR119 Agonist, AS1269574

description

-

description

-

description

-

description

The GPR119 Agonist, AS1269574, also referenced under CAS 330981-72-1, controls the biological activity of GPR119. This small molecule/inhibitor is primarily used for Biochemicals applications.

form

solid

form

powder

form

powder

form

solid

assay

≥97% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥99% (HPLC)

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage condition

OK to freeze, protect from light

storage condition

OK to freeze, protect from light

storage condition

OK to freeze, protect from light

storage condition

OK to freeze, protect from light

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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