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422175

L-165,041

A cell-permeable phenoxyacetic acid derivative that acts as a potent and selective peroxisome proliferator activator receptor δ (PPARδ) agonist (Ki = 6 nM for hPPARδ and 730 nM for hPPARγ).

Synonyme(s) :

L-165,041, Compound P, L165041, 4-[3-(2-Propyl-3-hydroxy-4-acetyl)phenoxy]propyloxyphenoxy-acetic acid, PPAR Agonist VIII, PPARα Agonist III, PPARγ Agonist VII

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A propos de cet article

Formule empirique (notation de Hill) :
C22H26O7
Numéro CAS:
79558-09-1
Poids moléculaire :
402.44
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD04974501
Assay:
≥98% (HPLC)
Form:
solid
Storage condition:
OK to freeze, protect from light
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Quality Segment

100

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

white

solubility

1 M NaOH: 40 mg/mL, DMSO: 5 mg/mL

shipped in

ambient

storage temp.

2-8°C

SMILES string

O(CCCOc2ccc(cc2)OCC(=O)O)c1c(c(c(cc1)C(=O)C)O)CCC

InChI

1S/C22H26O7/c1-3-5-19-20(11-10-18(15(2)23)22(19)26)28-13-4-12-27-16-6-8-17(9-7-16)29-14-21(24)25/h6-11,26H,3-5,12-14H2,1-2H3,(H,24,25)

InChI key

HBBVCKCCQCQCTJ-UHFFFAOYSA-N

General description

A cell-permeable phenoxyacetic acid derivative that acts as a potent and selective peroxisome proliferator activator receptor δ (PPARδ) agonist (Ki = 6 nM for hPPAR δ and 730 nM for hPPARγ). Induces adipocyte differentiation in NIH-PPARδ cells at 500 nM. Also reported to raise total cholesterol in insulin-resistant db/db mice without altering glucose or triglyceride levels. Shown to increase uncoupling protein 3 (UCP3) gene expression in L6 myotubes. Also shown to inhibit cytokine-induced expression of vascular cell adhesion molecule-1 (VCAM-1) and the secretion of monocyte chemotactic protein-1 (MCP-1) in Eahy926 cells.

Biochem/physiol Actions

Cell permeable: yes
Product does not compete with ATP.
Primary Target
Peroxisome proliferator activator receptor δ (PPAR@delta;)
Reversible: no
Target Ki: 6 nM for hPPARδ and 730 nM for hPPARγ

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

Rival, Y., et al. 2002. Eur. J. Pharmacol.435, 143.
Castrillo, A., et al. 2001. J. Biol. Chem.276, 34082.
Hansen, J.B., et al. 2001. J. Biol. Chem.276, 3175.
Son, C., et al. 2001. Endocrinology142, 4189.
Wilkie, N., et al. 2001. J. Neurochem.78, 1135.
Leibowitz, M.D., et al. 2000. FEBS Lett.473, 333.
Berger, J., et al. 1999. J. Biol. Chem.274, 6718.
Lim, H., et al. 1999. Genes Dev.13, 1561.

Legal Information

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

Disclaimer

Toxicity: Irritant (B)

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Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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