WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 522660
CAS#: 1236109-67-3
Description: TUG-469 is a potent free fatty acid 1 receptor agonist. TUG-469 showed a 1.7- to 3.0-times higher potency in vitro at 1321N1 cells recombinantly expressing FFA1. Both compounds increased insulin secretion from rat insulinoma INS-1 cells. TUG-469 is > 200-fold selective for FFA1 over FFA4. Finally, a single dose of 5 mg/kg TUG-469 significantly improved glucose tolerance in pre-diabetic NZO mice. TUG-469 turned out as a promising candidate for further drug development of FFA1 agonists for treatment of type 2 diabetes mellitus. Activation of the G protein-coupled free fatty acid receptor 1 (FFA1; formerly known as GPR40) leads to an enhancement of glucose-stimulated insulin secretion from pancreatic β-cells.
MedKoo Cat#: 522660
Name: TUG-469
CAS#: 1236109-67-3
Chemical Formula: C23H23NO2
Exact Mass: 345.1729
Molecular Weight: 345.442
Elemental Analysis: C, 79.97; H, 6.71; N, 4.05; O, 9.26
Synonym: TUG469; TUG 469; TUG-469.
IUPAC/Chemical Name: 3-(4-(((2'-methyl-[1,1'-biphenyl]-3-yl)methyl)amino)phenyl)propanoic acid
InChi Key: RUPXKSLKGSSZCP-UHFFFAOYSA-N
InChi Code: InChI=1S/C23H23NO2/c1-17-5-2-3-8-22(17)20-7-4-6-19(15-20)16-24-21-12-9-18(10-13-21)11-14-23(25)26/h2-10,12-13,15,24H,11,14,16H2,1H3,(H,25,26)
SMILES Code: O=C(O)CCC1=CC=C(NCC2=CC(C3=CC=CC=C3C)=CC=C2)C=C1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 345.442 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Panse M, Gerst F, Kaiser G, Teutsch CA, Dölker R, Wagner R, Häring HU, Ullrich
S. Activation of extracellular signal-regulated protein kinases 1 and 2 (ERK1/2)
by free fatty acid receptor 1 (FFAR1/GPR40) protects from palmitate-induced beta
cell death, but plays no role in insulin secretion. Cell Physiol Biochem.
2015;35(4):1537-45. doi: 10.1159/000373969. Epub 2015 Mar 12. PubMed PMID:
25792236.
2: Urban C, Hamacher A, Partke HJ, Roden M, Schinner S, Christiansen E,
Due-Hansen ME, Ulven T, Gohlke H, Kassack MU. In vitro and mouse in vivo
characterization of the potent free fatty acid 1 receptor agonist TUG-469. Naunyn
Schmiedebergs Arch Pharmacol. 2013 Dec;386(12):1021-30. doi:
10.1007/s00210-013-0899-3. Epub 2013 Jul 17. PubMed PMID: 23861168.
3: Wagner R, Kaiser G, Gerst F, Christiansen E, Due-Hansen ME, Grundmann M,
Machicao F, Peter A, Kostenis E, Ulven T, Fritsche A, Häring HU, Ullrich S.
Reevaluation of fatty acid receptor 1 as a drug target for the stimulation of
insulin secretion in humans. Diabetes. 2013 Jun;62(6):2106-11. doi:
10.2337/db12-1249. Epub 2013 Feb 1. PubMed PMID: 23378609; PubMed Central PMCID:
PMC3661642.
4: Christiansen E, Due-Hansen ME, Urban C, Grundmann M, Schröder R, Hudson BD,
Milligan G, Cawthorne MA, Kostenis E, Kassack MU, Ulven T. Free fatty acid
receptor 1 (FFA1/GPR40) agonists: mesylpropoxy appendage lowers lipophilicity and
improves ADME properties. J Med Chem. 2012 Jul 26;55(14):6624-8. doi:
10.1021/jm3002026. Epub 2012 Jul 13. PubMed PMID: 22724451.
5: Christiansen E, Due-Hansen ME, Urban C, Merten N, Pfleiderer M, Karlsen KK,
Rasmussen SS, Steensgaard M, Hamacher A, Schmidt J, Drewke C, Petersen RK,
Kristiansen K, Ullrich S, Kostenis E, Kassack MU, Ulven T. Structure-Activity
Study of Dihydrocinnamic Acids and Discovery of the Potent FFA1 (GPR40) Agonist
TUG-469. ACS Med Chem Lett. 2010 Jul 2;1(7):345-9. doi: 10.1021/ml100106c.
eCollection 2010 Oct 14. PubMed PMID: 24900217; PubMed Central PMCID: PMC4007913.
