CAS 885101-89-3|GW9508

Introduction：Basic information about CAS 885101-89-3|GW9508, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. GW9508 BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Articles11
6. Synonyms

Common Name	GW9508
CAS Number	885101-89-3	Molecular Weight	347.407
Density	1.2±0.1 g/cm3	Boiling Point	538.4±45.0 °C at 760 mmHg
Molecular Formula	C₂₂H₂₁NO₃	Melting Point	/
MSDS	ChineseUSA	Flash Point	279.4±28.7 °C
Symbol	GHS05, GHS07, GHS09	Signal Word	Danger

Names

Name	3-[4-[(3-phenoxyphenyl)methylamino]phenyl]propanoic acid
Synonym	More Synonyms

GW9508 BiologicalActivity

Description	GW9508 is a potent and selective agonist for FFA1 (GPR40) with pEC50 of 7.32, 100-fold selective against GPR120, stimulates insulin secretion in a glucose-sensitive manner.IC50 value: 7.32 (pEC50) [1]Target: GPR40GW9508 is shown to be at least 100-fold selective against 220 other GPCRs, 60 kinases, 63 proteases, seven integrins and 20 nuclear receptors including PPARα, δ and γ (pEC50 4.0, 4 and 4.9, respectively). GW9508 produces a concentration-dependent increase in intracellular Ca2+ concentrations via GPR40 receptor activation and the GPR120 receptor. GW9508 is active as an agonist at both GPR40 and GPR120, it is approximately 100-fold selective for GPR40 with respect to GPR120. GW9508 produces a concentration-dependent increase (pEC50=6.14) in glucose-stimulated insulin secretion at high glucose levels (25 mM). GW9508 dose dependently stimulated insulin secretion in a glucose-sensitive manner in MIN6 cells. Furthermore, GW9508 is able to potentiate the KCl-mediated increase in insulin secretion in MIN6 cells. [1] GW9508 induced hyperpolarization and opening of KATP channels in rat β-cells. [2] GW9508 inhibits CCL17 and CCL5 expression in a pertussis toxin-sensitive manner. GW9508 further suppresses expression of IL-11, IL-24, and IL-33 induced in HaCaT cells by TNF-α and IFN-γ. GW9508 also inhibits CCL5 and CXCL10 production by normal human epidermal keratinocytes. [3]
Related Catalog	Signaling Pathways >>GPCR/G Protein >>GPR40Research Areas >>Metabolic Disease
References	[1]. Briscoe CP, et al. Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules. Br J Pharmacol. 2006 Jul;148(5):619-28. [2]. Zhao YF, et al. Activation of ATP-sensitive potassium channels in rat pancreatic beta-cells by linoleic acid through both intracellular metabolites and membrane receptor signalling pathway. J Endocrinol, 2008, 198(3), 533-540. [3]. Fujita T, et al. A GPR40 agonist GW9508 suppresses CCL5, CCL17, and CXCL10 induction in keratinocytes and attenuates cutaneous immune inflammation. J Invest Dermatol, 2011, 131(8), 1660-1667.

Description

GW9508 is a potent and selective agonist for FFA1 (GPR40) with pEC50 of 7.32, 100-fold selective against GPR120, stimulates insulin secretion in a glucose-sensitive manner.IC50 value: 7.32 (pEC50) [1]Target: GPR40GW9508 is shown to be at least 100-fold selective against 220 other GPCRs, 60 kinases, 63 proteases, seven integrins and 20 nuclear receptors including PPARα, δ and γ (pEC50 4.0, 4 and 4.9, respectively). GW9508 produces a concentration-dependent increase in intracellular Ca2+ concentrations via GPR40 receptor activation and the GPR120 receptor. GW9508 is active as an agonist at both GPR40 and GPR120, it is approximately 100-fold selective for GPR40 with respect to GPR120. GW9508 produces a concentration-dependent increase (pEC50=6.14) in glucose-stimulated insulin secretion at high glucose levels (25 mM). GW9508 dose dependently stimulated insulin secretion in a glucose-sensitive manner in MIN6 cells. Furthermore, GW9508 is able to potentiate the KCl-mediated increase in insulin secretion in MIN6 cells. [1] GW9508 induced hyperpolarization and opening of KATP channels in rat β-cells. [2] GW9508 inhibits CCL17 and CCL5 expression in a pertussis toxin-sensitive manner. GW9508 further suppresses expression of IL-11, IL-24, and IL-33 induced in HaCaT cells by TNF-α and IFN-γ. GW9508 also inhibits CCL5 and CXCL10 production by normal human epidermal keratinocytes. [3]

Related Catalog

Signaling Pathways >>GPCR/G Protein >>GPR40Research Areas >>Metabolic Disease

References

[1]. Briscoe CP, et al. Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules. Br J Pharmacol. 2006 Jul;148(5):619-28.

[2]. Zhao YF, et al. Activation of ATP-sensitive potassium channels in rat pancreatic beta-cells by linoleic acid through both intracellular metabolites and membrane receptor signalling pathway. J Endocrinol, 2008, 198(3), 533-540.

[3]. Fujita T, et al. A GPR40 agonist GW9508 suppresses CCL5, CCL17, and CXCL10 induction in keratinocytes and attenuates cutaneous immune inflammation. J Invest Dermatol, 2011, 131(8), 1660-1667.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	538.4±45.0 °C at 760 mmHg
Molecular Formula	C₂₂H₂₁NO₃
Molecular Weight	347.407
Flash Point	279.4±28.7 °C
Exact Mass	347.152130
PSA	58.56000
LogP	4.74
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.641
InChIKey	DGENZVKCTGIDRZ-UHFFFAOYSA-N
SMILES	O=C(O)CCc1ccc(NCc2cccc(Oc3ccccc3)c2)cc1
Storage condition	Store at RT
Water Solubility	DMSO: >20mg/mL

Safety Information

Symbol	GHS05, GHS07, GHS09
Signal Word	Danger
Hazard Statements	H302-H315-H318-H335-H410
Precautionary Statements	P261-P273-P280-P305 + P351 + P338-P501
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes	Xn,N
Risk Phrases	22-37/38-41-50/53
Safety Phrases	26-39-60-61
RIDADR	UN 3077 9 / PGIII

Articles11

Omega-3 fatty acids and other FFA4 agonists inhibit growth factor signaling in human prostate cancer cells.

J. Pharmacol. Exp. Ther. 352(2) , 380-94, (2015)

Omega-3 fatty acids (n-3 FAs) are proposed to have many beneficial effects on human health. However, the mechanisms underlying their potential cancer preventative effects are unclear. G protein-couple...

Short-chain fatty acid sensing in rat duodenum.

J. Physiol. 593(3) , 585-99, (2015)

Luminal lipid in the duodenum modulates gastroduodenal functions via the release of gut hormones and mediators such as cholecystokinin and 5-HT. The effects of luminal short-chain fatty acids (SCFAs) ...

Novel identification of the free fatty acid receptor FFAR1 that promotes contraction in airway smooth muscle.

Am. J. Physiol. Lung Cell. Mol. Physiol. 309 , L970-82, (2015)

Obesity is one of the major risk factors for asthma. Previous studies have demonstrated that free fatty acid levels are elevated in the plasma of obese individuals. Medium- and long-chain free fatty a...

Synonyms

Benzenepropanoic acid, 4-[[(3-phenoxyphenyl)methyl]amino]-

3-{4-[(3-Phenoxybenzyl)amino]phenyl}propanoic acid

gw9508

GW-9508

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