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Hlavní dokumenty

SML1914

Sigma-Aldrich

TUG-891

≥98% (HPLC)

Synonyma:

3-(4-((4-Fluoro-4-methyl-[1,1-biphenyl]-2-yl)methoxy)phenyl)-propanoic acid, 4-[(4-Fluoro-4′-methyl[1,1′-biphenyl]-2-yl)methoxy]-benzenepropanoic acid, TUG 891, TUG891

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About This Item

Empirický vzorec (Hillův zápis):
C23H21FO3
Číslo CAS:
1374516-07-0
Molekulová hmotnost:
364.41
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

room temp

SMILES string

Fc1cc(c(cc1)c3ccc(cc3)C)COc2ccc(cc2)CCC(=O)O

InChI

1S/C23H21FO3/c1-16-2-7-18(8-3-16)22-12-9-20(24)14-19(22)15-27-21-10-4-17(5-11-21)6-13-23(25)26/h2-5,7-12,14H,6,13,15H2,1H3,(H,25,26)

InChI key

LPGBXHWIQNZEJB-UHFFFAOYSA-N

Biochem/physiol Actions

Orally active, potent and selective agonist for long chain free fatty acid (FFA) receptor FFA4 (GPR120).
TUG-891 is an orally active, potent and selective agonist for human long chain free fatty acid (FFA) receptor FFA4/GPR120 (pEC50 of receptor β-arrestin-2 recruitment = 7.36/FFA4 vs. 4.19/FFA1 HEK transfectants; pEC50 of calcium mobilization = 7.02/FFA4 vs. 5.30/FFA1 transfectants), while exhibiting no activity toward human short-chain FFA receptors FFA2/GPR43 and FFA3/GPR41. TUG-891 also exhibits potent partial agonist activity toward murine FFA4 (pEC50 = 7.77, 75% efficacy by β-arrestin-2 recruitment assay; pEC50 = 6.89 by calcium mobilization), albeit with a reduced selectivity over mFFA1 (pEC50 = 5.92 by β-arrestin-2 recruitment and 6.41 by by calcium mobilization). When administered via water intake (~20 mg/kg/day), TUG-891 is reported to reverse food intake increases and body weight gains among mice subjected to sleep fragmentation, and significantly attenuate visceral white adipose tissue inflammation as well as insulin resistance.
TUG-891, a GPR120 agonist helps to stimulate metabolic health by inducing mitochondrial respiration in brown fat. It is capable of enhancing lipid oxidation and decreasing fat mass in mice.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Osvědčení o analýze (COA)

Lot/Batch Number
0000182920
0000193071

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Navštívit knihovnu dokumentů

D Gozal et al.
International journal of obesity (2005), 40(7), 1143-1149 (2016-03-17)
Sleep fragmentation (SF), a frequent occurrence in multiple sleep and other diseases leads to increased food intake and insulin resistance via increased macrophage activation and inflammation in visceral white adipose tissue (VWAT). Free fatty acid receptor 4 (FFA4) is reduced
Bharat Shimpukade et al.
Journal of medicinal chemistry, 55(9), 4511-4515 (2012-04-24)
GPR120 is a receptor of unsaturated long-chain fatty acids reported to mediate GLP-1 secretion, insulin sensitization, anti-inflammatory, and anti-obesity effects and is therefore emerging as a new potential target for treatment of type 2 diabetes and metabolic diseases. Further investigation
The GPR120 agonist TUG-891 promotes metabolic health by stimulating mitochondrial respiration in brown fat
Schilperoort M, et al.
EMBO Molecular Medicine, 10(3) (2018)
Brian D Hudson et al.
Molecular pharmacology, 84(5), 710-725 (2013-08-28)
TUG-891 [3-(4-((4-fluoro-4'-methyl-[1,1'-biphenyl]-2-yl)methoxy)phenyl)propanoic acid] was recently described as a potent and selective agonist for the long chain free fatty acid (LCFA) receptor 4 (FFA4; previously G protein-coupled receptor 120, or GPR120). Herein, we have used TUG-891 to further define the function

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