MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 522662 | Name: TUG-891
Featured New

Description:

WARNING: This product is for research use only, not for human or veterinary use.

TUG-891 is a potent and selective agonist of the free fatty acid receptor 4 (FFA4/GPR120), which demonstrates both potential opportunity and possible challenges to therapeutic agonism. Activation of human FFA4 by TUG-891 also resulted in rapid phosphorylation and internalization of the receptor. TUG-891 was also a potent agonist of mouse FFA4, but it showed only limited selectivity over mouse FFA1, complicating its use in vivo in this species.

Chemical Structure

TUG-891
TUG-891
CAS#1374516-07-0

Theoretical Analysis

MedKoo Cat#: 522662

Name: TUG-891

CAS#: 1374516-07-0

Chemical Formula: C23H21FO3

Exact Mass: 364.1475

Molecular Weight: 364.42

Elemental Analysis: C, 75.81; H, 5.81; F, 5.21; O, 13.17

Price and Availability

Size Price Availability Quantity
10mg USD 90.00 Ready to ship
25mg USD 150.00 Ready to ship
50mg USD 250.00 Ready to ship
100mg USD 450.00 Ready to ship
200mg USD 750.00 Ready to ship
500mg USD 1,650.00 Ready to ship
1g USD 2,650.00 Ready to ship
2g USD 4,650.00 2 weeks
Show More
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
TUG-891; TUG 891; TUG891.
IUPAC/Chemical Name
3-(4-((4-fluoro-4'-methyl-[1,1'-biphenyl]-2-yl)methoxy)phenyl)propanoic acid
InChi Key
LPGBXHWIQNZEJB-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
CC1=CC=C(C2=CC=C(F)C=C2COC3=CC=C(CCC(O)=O)C=C3)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
More Info
Biological target:
TUG-891 is a potent and selective agonist for the long chain free fatty acid (LCFA) receptor 4 (FFA4/GPR120).
In vitro activity:
To investigate whether the GPR120 agonist TUG‐891 directly activates brown adipocytes and to study the downstream intracellular signaling pathways involved, differentiated brown adipocytes were stimulated with TUG‐891. Strikingly, TUG‐891 acutely increased the O2 consumption rate (OCR) of brown adipocytes by more than twofold (Fig 7A). Pretreatment with the GPR120 antagonist AH7614 reduced rather than abolished this response (Fig 7A), indicating that TUG‐891 exhibits both GPR120‐dependent and GPR120‐independent activity. It was investigated whether TUG‐891 functions in a manner similar to LCFAs which can directly activate UCP1 by measuring O2 consumption in isolated BAT mitochondria in conditions mimicking a cellular environment with high purine nucleotide (GDP) content and inhibited UCP1 (Matthias et al, 2000). Indeed, TUG‐891 (≥ 10 μM) increased O2 consumption in mitochondria isolated from WT mice (Fig 7B), suggesting that TUG‐891 has the capacity to overcome purine nucleotide inhibition and activate UCP1 in brown adipocytes. As for Gαq targets, TUG‐891 increased the amount of phosphorylated ERK and AKT (Appendix Fig S9E). Additionally, as Ca2+ could affect mitochondrial polarization, effects of TUG‐891 on mitochondrial membrane potential were investigated. Stimulation with TUG‐891 resulted in fading of the MTR signal while the MTG signal remained intense, indicative of mitochondrial depolarization (Fig 7F). In addition, mitochondria were more fragmented following TUG‐891 stimulation (Fig 7G), pointing toward increased mitochondrial fission, which could explain the GPR120‐dependent increase in respiration. Collectively, these data suggest that activation of brown adipocytes with the GPR120 agonist TUG‐891 is a promising strategy to increase lipid combustion and reduce obesity. Reference: EMBO Mol Med. 2018 Mar; 10(3): e8047. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5840546/
In vivo activity:
To investigate the effect of GPR120 activation on energy metabolism in vivo, mice were injected with the GPR120 agonist TUG‐891 daily for a period of 2.5 weeks. TUG‐891 reduced total body weight (Fig 1A), which was due to a large reduction in fat mass (−73%; Fig 1B) and a minor reduction in lean mass (−9.9%; Fig 1C) at week 2.5 compared to vehicle. The reduced lean mass could be due to increased muscle turnover, as TUG‐891 non‐significantly increased expression of markers for both muscle atrophy and regeneration (Appendix Fig S1). During the first week of treatment, food intake was similar in the control and treatment groups (Fig 1D), while fat mass was already reduced by 19% in the TUG‐891‐treated group at day 5. Longer treatment reduced food intake, which further contributed to body weight and fat mass loss. TUG‐891 acutely lowered the respiratory exchange ratio (RER) upon injection, which persisted throughout the dark period (Fig 1E). Accordingly, TUG‐891 lowered glucose oxidation (Fig 1F) and largely increased fat oxidation (Fig 1G). This increase in fat oxidation was supported by histological analysis of adipose tissues, revealing that TUG‐891 administration reduced lipid content in BAT (−28%; Fig 2A), and adipocyte size in both sWAT (−47%; Fig 2B) and gWAT (−38%; Fig 2C). In addition, total organ weights of iBAT (−31%), gWAT (−44%), and liver (−14%) were reduced in TUG‐891‐treated mice as compared to controls (Fig 2D). Ucp1 gene expression (Appendix Fig S3H) and protein staining (Appendix Fig S4) were increased in gWAT of TUG‐891‐treated animals, suggesting GPR120‐mediated browning. Reference: EMBO Mol Med. 2018 Mar; 10(3): e8047. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5840546/
Solvent mg/mL mM
Solubility
DMSO 30.0 82.32
DMF 5.0 13.72
Ethanol 1.0 2.74
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 364.42 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Su XL, Liu YG, Shi M, Zhao YY, Liang XY, Zhang LJ, Wei LL, Zhao YF. The GPR120 Agonist TUG-891 Inhibits the Motility and Phagocytosis of Mouse Alveolar Macrophages. Biomed Res Int. 2020 Feb 20;2020:1706168. doi: 10.1155/2020/1706168. PMID: 32149083; PMCID: PMC7056993. 2. Schilperoort M, van Dam AD, Hoeke G, Shabalina IG, Okolo A, Hanyaloglu AC, Dib LH, Mol IM, Caengprasath N, Chan YW, Damak S, Miller AR, Coskun T, Shimpukade B, Ulven T, Kooijman S, Rensen PC, Christian M. The GPR120 agonist TUG-891 promotes metabolic health by stimulating mitochondrial respiration in brown fat. EMBO Mol Med. 2018 Mar;10(3):e8047. doi: 10.15252/emmm.201708047. PMID: 29343498; PMCID: PMC5840546. 3. Wang L, Ren X, Tian XF, Cheng XL, Zhao YY, Li QY, Duan ZY, Tian LF, Chen Z, Lu JM, Liang XY, Zhao YF, Fu RG. Protective effects of GPR120 agonist-programmed macrophages on renal interstitial fibrosis in unilateral ureteral obstruction (UUO) rats. Biomed Pharmacother. 2019 Sep;117:109172. doi: 10.1016/j.biopha.2019.109172. Epub 2019 Jun 28. PMID: 31261028.
In vitro protocol:
1. Su XL, Liu YG, Shi M, Zhao YY, Liang XY, Zhang LJ, Wei LL, Zhao YF. The GPR120 Agonist TUG-891 Inhibits the Motility and Phagocytosis of Mouse Alveolar Macrophages. Biomed Res Int. 2020 Feb 20;2020:1706168. doi: 10.1155/2020/1706168. PMID: 32149083; PMCID: PMC7056993. 2. Schilperoort M, van Dam AD, Hoeke G, Shabalina IG, Okolo A, Hanyaloglu AC, Dib LH, Mol IM, Caengprasath N, Chan YW, Damak S, Miller AR, Coskun T, Shimpukade B, Ulven T, Kooijman S, Rensen PC, Christian M. The GPR120 agonist TUG-891 promotes metabolic health by stimulating mitochondrial respiration in brown fat. EMBO Mol Med. 2018 Mar;10(3):e8047. doi: 10.15252/emmm.201708047. PMID: 29343498; PMCID: PMC5840546.
In vivo protocol:
1. Wang L, Ren X, Tian XF, Cheng XL, Zhao YY, Li QY, Duan ZY, Tian LF, Chen Z, Lu JM, Liang XY, Zhao YF, Fu RG. Protective effects of GPR120 agonist-programmed macrophages on renal interstitial fibrosis in unilateral ureteral obstruction (UUO) rats. Biomed Pharmacother. 2019 Sep;117:109172. doi: 10.1016/j.biopha.2019.109172. Epub 2019 Jun 28. PMID: 31261028. 2. Schilperoort M, van Dam AD, Hoeke G, Shabalina IG, Okolo A, Hanyaloglu AC, Dib LH, Mol IM, Caengprasath N, Chan YW, Damak S, Miller AR, Coskun T, Shimpukade B, Ulven T, Kooijman S, Rensen PC, Christian M. The GPR120 agonist TUG-891 promotes metabolic health by stimulating mitochondrial respiration in brown fat. EMBO Mol Med. 2018 Mar;10(3):e8047. doi: 10.15252/emmm.201708047. PMID: 29343498; PMCID: PMC5840546.
1: Hopkins MM, Zhang Z, Liu Z, Meier KE. Eicosopentaneoic Acid and Other Free Fatty Acid Receptor Agonists Inhibit Lysophosphatidic Acid- and Epidermal Growth Factor-Induced Proliferation of Human Breast Cancer Cells. J Clin Med. 2016 Jan 26;5(2). pii: E16. doi: 10.3390/jcm5020016. PubMed PMID: 26821052; PubMed Central PMCID: PMC4773772. 2: Anbazhagan AN, Priyamvada S, Gujral T, Bhattacharyya S, Alrefai WA, Dudeja PK, Borthakur A. A Novel Anti-inflammatory Role of GPR120 in Intestinal Epithelial Cells. Am J Physiol Cell Physiol. 2016 Jan 20:ajpcell.00123.2015. doi: 10.1152/ajpcell.00123.2015. [Epub ahead of print] PubMed PMID: 26791484. 3: Gao B, Huang Q, Jie Q, Lu WG, Wang L, Li XJ, Sun Z, Hu YQ, Chen L, Liu BH, Liu J, Yang L, Luo ZJ. GPR120: A bi-potential mediator to modulate the osteogenic and adipogenic differentiation of BMMSCs. Sci Rep. 2015 Sep 14;5:14080. doi: 10.1038/srep14080. PubMed PMID: 26365922; PubMed Central PMCID: PMC4568495. 4: Mizuta K, Zhang Y, Mizuta F, Hoshijima H, Shiga T, Masaki E, Emala CW Sr. Novel identification of the free fatty acid receptor FFAR1 that promotes contraction in airway smooth muscle. Am J Physiol Lung Cell Mol Physiol. 2015 Nov 1;309(9):L970-82. doi: 10.1152/ajplung.00041.2015. Epub 2015 Sep 4. PubMed PMID: 26342087; PubMed Central PMCID: PMC4628981. 5: Song T, Peng J, Ren J, Wei HK, Peng J. Cloning and characterization of spliced variants of the porcine G protein coupled receptor 120. Biomed Res Int. 2015;2015:813816. doi: 10.1155/2015/813816. Epub 2015 May 17. PubMed PMID: 26075265; PubMed Central PMCID: PMC4449883. 6: Liu Z, Hopkins MM, Zhang Z, Quisenberry CB, Fix LC, Galvan BM, Meier KE. Omega-3 fatty acids and other FFA4 agonists inhibit growth factor signaling in human prostate cancer cells. J Pharmacol Exp Ther. 2015 Feb;352(2):380-94. doi: 10.1124/jpet.114.218974. Epub 2014 Dec 9. PubMed PMID: 25491146; PubMed Central PMCID: PMC4293432. 7: Cornall LM, Mathai ML, Hryciw DH, McAinch AJ. GPR120 agonism as a countermeasure against metabolic diseases. Drug Discov Today. 2014 May;19(5):670-9. doi: 10.1016/j.drudis.2013.11.021. Epub 2013 Dec 4. Review. PubMed PMID: 24315954. 8: Hudson BD, Shimpukade B, Mackenzie AE, Butcher AJ, Pediani JD, Christiansen E, Heathcote H, Tobin AB, Ulven T, Milligan G. The pharmacology of TUG-891, a potent and selective agonist of the free fatty acid receptor 4 (FFA4/GPR120), demonstrates both potential opportunity and possible challenges to therapeutic agonism. Mol Pharmacol. 2013 Nov;84(5):710-25. doi: 10.1124/mol.113.087783. Epub 2013 Aug 26. PubMed PMID: 23979972; PubMed Central PMCID: PMC3807074. 9: Shimpukade B, Hudson BD, Hovgaard CK, Milligan G, Ulven T. Discovery of a potent and selective GPR120 agonist. J Med Chem. 2012 May 10;55(9):4511-5. doi: 10.1021/jm300215x. Epub 2012 May 2. PubMed PMID: 22519963.

View History

Parimifasor

Parimifasor

PU-H54-iso

PU-H54-iso

Formylmethionyl-alanyl-leucine

Formylmethionyl-alanyl-leucine

Tubulysin F

Tubulysin F

Oxidopamine Free Base

Oxidopamine Free Base

Oxypendyl

Oxypendyl