3-(4-((3-phenoxybenzyl)amino)phenyl)propanoic acid

3-(4-((3-phenoxybenzyl)amino)phenyl)propanoic acid - Names and Identifiers

Name	3-(4-((3-phenoxybenzyl)amino)phenyl)propanoic acid
Synonyms	GW9508 885101-89-3(GW9508) 3-(4-((3-Phenoxybenzyl)aMino)phenyl)propanoic acid 3-(4-((3-phenoxybenzyl)amino)phenyl)propanoic acid 4-[[(3-Phenoxyphenyl)methyl]amino]benzenepropanoicacid Benzenepropanoic acid, 4-[[(3-phenoxyphenyl)methyl]amino]- GW 9508 4-[[(3-Phenoxyphenyl)methyl]amino]benzenepropanoic acid 4-[[(3-Phenoxyphenyl)methyl]amino]benzenepropanoic acid GW9508
CAS	885101-89-3

3-(4-((3-phenoxybenzyl)amino)phenyl)propanoic acid - Physico-chemical Properties

Molecular Formula	C22H21NO3
Molar Mass	347.41
Melting Point	90-92°C
Solubility	DMSO : ≥ 100 mg/mL (287.84 mM) mother liquor preservation: sub-packaging and freezing to avoid repeated freezing and thawing;-20 ℃,1 month;-80 ℃,6 months (after dilution, the solution temperature is low and storage may precipitate, as far as possible to use it now) Cell experiment: dissolve with DMSO first: dilute with culture medium then, and the dilution process is recommended to be carried out in stages to avoid too fast concentration change leading to compound precipitation. If the compound is precipitated during the dilution process, it can be redissolved by ultrasound. During dilution, ensure that the final concentration of DMSO in the working fluid should be below 0.1% as far as possible, and the maximum should not exceed 0.5%, and set up a DMSO control group with corresponding concentration. Animal experiment: Dissolve with DMSO first: dilute with water or normal saline, etc. The dilution process is recommended to be carried out in sections to avoid excessive concentration cha
Appearance	white powder
Color	Off-white
Storage Condition	2-8°C
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
MDL	MFCD09753282
Use	GW9508 is a potent selective G protein-coupled receptor FFA1 (GPR40) and GPR40 agonist with pEC50 values of 7.32 and 5.46, respectively. GW9508 is about 100 times more selective than GPR120 for GPR40 and is inactive for other GPCR, kinases, proteases, integrins and PPAR. GW9508 is a glucose-sensitive insulin secretagogue and ATP-sensitive potassium (KATP) channel opener. GW9508 has anti-inflammatory and anti-atherosclerotic activities.
Target	GPR120;GPR40(FFA1)
In vitro study	GW9508 stimulates intracellular Ca 2+ mobilization in HEK-293 cells expressing GPR40 (pEC 50 of 7.32) or GPR120 (pEC 50 of 5.46), but not in the parent HEK-293 cell line. GW9508 produces a concentration-dependent increase (pEC 50 of 6.14) in glucose-stimulated insulin secretion at high glucose levels (25 mM). This resulted in a 1.52-fold increase in insulin secretion with 20 μM GW9508 in the presence of 25 mM glucose, compared with 25 mM glucose alone. The ability of GW9508 (10 μM) to enhance insulin secretion from MIN6 cells is significantly enhanced as glucose concentrations are increased. GW9508 inhibits CCL17 and CCL5 expression in a pertussis toxin-sensitive manner. The inhibitory effect by GW9508 is abrogated by depletion of GPR40 with RNA interference. 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.
In vivo study	Administration of GW9508 200 (μM) topically to the skin suppresses ear swelling in a repeated hapten application model (BALB/c and C57BL/6 mice) and contact hypersensitivity with downregulation of CCL5 and CXCL10, respectively.

3-(4-((3-phenoxybenzyl)amino)phenyl)propanoic acid - Risk and Safety

Risk Codes	R22 - Harmful if swallowed R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S39 - Wear eye / face protection. S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets.
UN IDs	UN 3077 9 / PGIII
WGK Germany	3

3-(4-((3-phenoxybenzyl)amino)phenyl)propanoic acid - Reference

Reference

1: Philippe C, Wauquier F, LÃ©otoing L, Coxam V, Wittrant Y. GW9508, a free fatty acid receptor agonist, specifically induces cell death in bone resorbing precursor cells through increased oxidative stress from mitochondrial origin. Exp Cell Res. 2013 Nov 15;319(19):3035-41. doi: 10.1016/j.yexcr.2013.08.013. Epub 2013 Aug 22. PubMed PMID: 23973666.
2: Zhao YF, Wang L, Zha D, Qiao L, Lu L, Yu J, Qu P, Sun Q, Qiu J, Chen C. GW9508 inhibits insulin secretion by activating ATP-sensitive potassium channels in rat pancreatic β-cells. J Mol Endocrinol. 2013 Jun 1;51(1):69-77. doi: 10.1530/JME-13-0019. Print 2013. PubMed PMID: 23628491.
3: Fujita T, Matsuoka T, Honda T, Kabashima K, Hirata T, Narumiya S. A GPR40 agonist GW9508 suppresses CCL5, CCL17, and CXCL10 induction in keratinocytes and attenuates cutaneous immune inflammation. J Invest Dermatol. 2011 Aug;131(8):1660-7. doi: 10.1038/jid.2011.123. Epub 2011 May 19. PubMed PMID: 21593768.
4: Lu SY, Jiang YJ, Zou JW, Luo HB, Wu TX. Insight into analysis of interactions of GW9508 to wild-type and H86F and H137F GPR40: a combined QM/MM study and pharmacophore modeling. J Mol Graph Model. 2011 Apr;29(6):818-25. doi: 10.1016/j.jmgm.2011.01.006. Epub 2011 Feb 1. PubMed PMID: 21334233.

3-(4-((3-phenoxybenzyl)amino)phenyl)propanoic acid - Preparation solution concentration reference

	1mg	5mg	10mg
1 mM	2.878 ml	14.392 ml	28.784 ml
5 mM	0.576 ml	2.878 ml	5.757 ml
10 mM	0.288 ml	1.439 ml	2.878 ml
5 mM	0.058 ml	0.288 ml	0.576 ml

Last Update：2024-01-02 23:10:35

3-(4-((3-phenoxybenzyl)amino)phenyl)propanoic acid - Reference Information

biological activity	GW9508 is an effective selective G protein-coupled receptor FFA1 (GPR40) and GPR40 agonist with pEC50 values of 7.32 and 5.46 respectively. GW9508 is about 100 times more selective than GPR120 for GPR40 and is inactive for other GPCR, kinases, proteases, integrins and PPAR. GW9508 is a glucose-sensitive insulin secretagogue and ATP-sensitive potassium (KATP) channel opener. GW9508 has anti-inflammatory and anti-atherosclerotic activities.
target	pEC50: 7.32 (GPR40) and 5.46 (GPR120)
use	GW9508 is a GPR40 full agonist, used to regulate glucose in rats. Can be applied to the treatment of diabetes type 2. GPR120 selective and potent agonist also used in the treatment of diabetes type 2 due to GPR120 holmium ability to mediate GLP-1 secretion, insulin sensitization and anti-obesity effects.

Last Update：2024-04-09 21:04:16