UC-1728
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MedKoo CAT#: 555121

CAS#: 948304-40-3

Description: UC-1728, also known as t-TUCB, is a soluble epoxide hydrolase inhibitor. t-TUCB alleviates liver fibrosis and portal pressure in carbon tetrachloride-induced cirrhosis in rats. UC-1728 minimizes ischemia-reperfusion-induced cardiac damage in normal, hypertensive, and diabetic rats.


Chemical Structure

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UC-1728
CAS# 948304-40-3

Theoretical Analysis

MedKoo Cat#: 555121
Name: UC-1728
CAS#: 948304-40-3
Chemical Formula: C21H21F3N2O5
Exact Mass: 438.1403
Molecular Weight: 438.4032
Elemental Analysis: C, 57.53; H, 4.83; F, 13.00; N, 6.39; O, 18.25

Price and Availability

Size Price Availability Quantity
10.0mg USD 120.0 Ready to ship
25.0mg USD 250.0 Ready to ship
50.0mg USD 450.0 Ready to ship
100.0mg USD 750.0 Ready to ship
200.0mg USD 1450.0 Ready to ship
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Synonym: UC-1728; UC 1728; UC1728; t-TUCB.

IUPAC/Chemical Name: 4-(((1r,4r)-4-(3-(4-(trifluoromethoxy)phenyl)ureido)cyclohexyl)oxy)benzoic acid

InChi Key: XDVFKCZZXOGEMN-CZIWCDLHSA-N

InChi Code: InChI=1S/C21H21F3N2O5/c22-21(23,24)31-18-11-5-15(6-12-18)26-20(29)25-14-3-9-17(10-4-14)30-16-7-1-13(2-8-16)19(27)28/h1-2,5-8,11-12,14,17H,3-4,9-10H2,(H,27,28)(H2,25,26,29)/t14-,17-

SMILES Code: FC(F)(F)OC(C=C1)=CC=C1NC(N[C@@H](CC2)CC[C@H]2OC3=CC=C(C(O)=O)C=C3)=O

Appearance: Solid powder

Purity: >99% (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

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

Biological target: UC-1728 (t-TUCB) is an epoxide hydrolase (sEH) Inhibitor (IC50 = 0.9 nM).
In vitro activity: Based on the sEH expression results, it was hypothesized that sEH might play a role in brown adipogenesis in vitro, and sEH inhibition may modulate the process. t-TUCB (Figure 3A), a selective inhibitor of sEH, was chosen for the studies. t-TUCB significantly increased oil red O (ORO) stained differentiated brown adipocyte morphology and lipid accumulation, as assessed by the ORO absorbance (Figure 3B). t-TUCB significantly increased mRNA levels of brown marker genes Ucp1, Pgc-1α, and cell death-inducing DFFA like effector A (Cidea) (Figure 3C). Pparγ mRNA level was significantly increased by t-TUCB only at 20 µM (Figure 3C). Protein expression of UCP1 and PGC-1α were also increased by t-TUCB (Figure 3D). Interestingly, t-TUCB also increased Ephx2 mRNA and sEH protein expression in a dose-dependent manner (Supplemental Figure S1), suggesting that there might be a feedback mechanism between t-TUCB and Ephx2 gene expression. Reference: Int J Mol Sci. 2020 Oct; 21(19): 7039. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7582898/
In vivo activity: Treatment with t-TUCB significantly inhibited mucus secretion with levels similar to that noted in control mice (Fig. 4, A and B). Barrier function of the intestinal epithelium, which is tightly regulated by epithelial junction proteins, plays a crucial role in preventing passage of harmful agents, including dietary antigens, from the lumen of the gut into the mucosal tissues and circulatory system. This study examined expression of epithelial occludin, ZO-1 and E-cadherin in a model of SPI-induced GI allergy by immunofluorescence staining of jejunal sections (Fig. 4, C – E). Consistent with the phenotype associated with GI inflammation, SPI challenge resulted in a marked reduction in expression of epithelial occludin, ZO-1 and E-cadherin relative to control mice (Fig. 4, C and D, middle and top panels, respectively, Fig. 4, E, middle and left panels, respectively). In SPI-challenged mice treated with t-TUCB at 3 mg/kg, loss of occludin and E-cadherin expression was substantially prevented (Fig. 4, C, bottom panels, and E, right panels), while recovery of ZO-1 expression was less striking (Fig. 4, D, bottom panels). Overall, these studies suggest that sEH induced by food allergens such as soy proteins promotes GI allergic responses and inflammation and that inhibition of sEH can attenuate SPI-induced allergic responses. Reference: J Leukoc Biol. 2018 Jul; 104(1): 109–122. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6020675/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 43.84 100.0

Preparing Stock Solutions

The following data is based on the product molecular weight 438.4032 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. Overby H, Yang Y, Xu X, Graham K, Hildreth K, Choi S, Wan D, Morisseau C, Zeldin DC, Hammock BD, Wang S, Bettaieb A, Zhao L. Soluble Epoxide Hydrolase Inhibition by t-TUCB Promotes Brown Adipogenesis and Reduces Serum Triglycerides in Diet-Induced Obesity. Int J Mol Sci. 2020 Sep 24;21(19):7039. doi: 10.3390/ijms21197039. PMID: 32987880; PMCID: PMC7582898. 2. Minaz N, Razdan R, Hammock BD, Mujwar S, Goswami SK. Impact of diabetes on male sexual function in streptozotocin-induced diabetic rats: Protective role of soluble epoxide hydrolase inhibitor. Biomed Pharmacother. 2019 Jul;115:108897. doi: 10.1016/j.biopha.2019.108897. Epub 2019 May 15. PMID: 31102913; PMCID: PMC6893866. 3. Bastan I, Ge XN, Dileepan M, Greenberg YG, Guedes AG, Hwang SH, Hammock BD, Washabau RJ, Rao SP, Sriramarao P. Inhibition of soluble epoxide hydrolase attenuates eosinophil recruitment and food allergen-induced gastrointestinal inflammation. J Leukoc Biol. 2018 Jul;104(1):109-122. doi: 10.1002/JLB.3MA1017-423R. Epub 2018 Jan 17. PMID: 29345370; PMCID: PMC6020675. 4. Kodani SD, Bhakta S, Hwang SH, Pakhomova S, Newcomer ME, Morisseau C, Hammock BD. Identification and optimization of soluble epoxide hydrolase inhibitors with dual potency towards fatty acid amide hydrolase. Bioorg Med Chem Lett. 2018 Feb 15;28(4):762-768. doi: 10.1016/j.bmcl.2018.01.003. Epub 2018 Jan 4. PMID: 29366648; PMCID: PMC5837813.
In vitro protocol: 1. Overby H, Yang Y, Xu X, Graham K, Hildreth K, Choi S, Wan D, Morisseau C, Zeldin DC, Hammock BD, Wang S, Bettaieb A, Zhao L. Soluble Epoxide Hydrolase Inhibition by t-TUCB Promotes Brown Adipogenesis and Reduces Serum Triglycerides in Diet-Induced Obesity. Int J Mol Sci. 2020 Sep 24;21(19):7039. doi: 10.3390/ijms21197039. PMID: 32987880; PMCID: PMC7582898. 2. Kodani SD, Bhakta S, Hwang SH, Pakhomova S, Newcomer ME, Morisseau C, Hammock BD. Identification and optimization of soluble epoxide hydrolase inhibitors with dual potency towards fatty acid amide hydrolase. Bioorg Med Chem Lett. 2018 Feb 15;28(4):762-768. doi: 10.1016/j.bmcl.2018.01.003. Epub 2018 Jan 4. PMID: 29366648; PMCID: PMC5837813.
In vivo protocol: 1. Minaz N, Razdan R, Hammock BD, Mujwar S, Goswami SK. Impact of diabetes on male sexual function in streptozotocin-induced diabetic rats: Protective role of soluble epoxide hydrolase inhibitor. Biomed Pharmacother. 2019 Jul;115:108897. doi: 10.1016/j.biopha.2019.108897. Epub 2019 May 15. PMID: 31102913; PMCID: PMC6893866. 2. Bastan I, Ge XN, Dileepan M, Greenberg YG, Guedes AG, Hwang SH, Hammock BD, Washabau RJ, Rao SP, Sriramarao P. Inhibition of soluble epoxide hydrolase attenuates eosinophil recruitment and food allergen-induced gastrointestinal inflammation. J Leukoc Biol. 2018 Jul;104(1):109-122. doi: 10.1002/JLB.3MA1017-423R. Epub 2018 Jan 17. PMID: 29345370; PMCID: PMC6020675.

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1: Guedes AGP, Aristizabal F, Sole A, Adedeji A, Brosnan R, Knych H, Yang J, Hwang SH, Morisseau C, Hammock BD. Pharmacokinetics and antinociceptive effects of the soluble epoxide hydrolase inhibitor t-TUCB in horses with experimentally induced radiocarpal synovitis. J Vet Pharmacol Ther. 2017 Oct 25. doi: 10.1111/jvp.12463. [Epub ahead of print] PubMed PMID: 29067696.

2: Zhang CH, Zheng L, Gui L, Lin JY, Zhu YM, Deng WS, Luo M. Soluble epoxide hydrolase inhibition with t-TUCB alleviates liver fibrosis and portal pressure in carbon tetrachloride-induced cirrhosis in rats. Clin Res Hepatol Gastroenterol. 2017 Oct 11. pii: S2210-7401(17)30187-0. doi: 10.1016/j.clinre.2017.09.001. [Epub ahead of print] PubMed PMID: 29031875.

3: Deng W, Zhu Y, Lin J, Zheng L, Zhang C, Luo M. Inhibition of soluble epoxide hydrolase lowers portal hypertension in cirrhotic rats by ameliorating endothelial dysfunction and liver fibrosis. Prostaglandins Other Lipid Mediat. 2017 Jul;131:67-74. doi: 10.1016/j.prostaglandins.2017.08.004. Epub 2017 Aug 16. PubMed PMID: 28822809.

4: Huang Y, Qin J, Sun D, Jiang H, Zheng L, He Y, Gui L, Qian B, Zhang C, Luo M. Inhibition of soluble epoxide hydrolase reduces portal pressure by protecting mesenteric artery myogenic responses in cirrhotic rats. Prostaglandins Other Lipid Mediat. 2017 Jul;131:17-24. doi: 10.1016/j.prostaglandins.2017.03.007. Epub 2017 May 1. PubMed PMID: 28473204.

5: Kandhi S, Zhang B, Froogh G, Qin J, Alruwaili N, Le Y, Yang YM, Hwang SH, Hammock BD, Wolin MS, Huang A, Sun D. EETs promote hypoxic pulmonary vasoconstriction via constrictor prostanoids. Am J Physiol Lung Cell Mol Physiol. 2017 Aug 1;313(2):L350-L359. doi: 10.1152/ajplung.00038.2017. Epub 2017 Apr 27. PubMed PMID: 28450284; PubMed Central PMCID: PMC5582931.

6: Islam O, Patil P, Goswami SK, Razdan R, Inamdar MN, Rizwan M, Mathew J, Inceoglu B, Stephen Lee KS, Hwang SH, Hammock BD. Inhibitors of soluble epoxide hydrolase minimize ischemia-reperfusion-induced cardiac damage in normal, hypertensive, and diabetic rats. Cardiovasc Ther. 2017 Jun;35(3). doi: 10.1111/1755-5922.12259. PubMed PMID: 28296232; PubMed Central PMCID: PMC5597338.

7: Guedes A, Galuppo L, Hood D, Hwang SH, Morisseau C, Hammock BD. Soluble epoxide hydrolase activity and pharmacologic inhibition in horses with chronic severe laminitis. Equine Vet J. 2017 May;49(3):345-351. doi: 10.1111/evj.12603. Epub 2016 Aug 16. PubMed PMID: 27338788; PubMed Central PMCID: PMC5580818.

8: Qin J, Sun D, Jiang H, Kandhi S, Froogh G, Hwang SH, Hammock BD, Wolin MS, Thompson CI, Hintze TH, Huang A. Inhibition of soluble epoxide hydrolase increases coronary perfusion in mice. Physiol Rep. 2015 Jun;3(6). pii: e12427. doi: 10.14814/phy2.12427. PubMed PMID: 26071213; PubMed Central PMCID: PMC4510629.

9: Harris TR, Bettaieb A, Kodani S, Dong H, Myers R, Chiamvimonvat N, Haj FG, Hammock BD. Inhibition of soluble epoxide hydrolase attenuates hepatic fibrosis and endoplasmic reticulum stress induced by carbon tetrachloride in mice. Toxicol Appl Pharmacol. 2015 Jul 15;286(2):102-11. doi: 10.1016/j.taap.2015.03.022. Epub 2015 Mar 28. PubMed PMID: 25827057; PubMed Central PMCID: PMC4458210.

10: López-Vicario C, Alcaraz-Quiles J, García-Alonso V, Rius B, Hwang SH, Titos E, Lopategi A, Hammock BD, Arroyo V, Clària J. Inhibition of soluble epoxide hydrolase modulates inflammation and autophagy in obese adipose tissue and liver: role for omega-3 epoxides. Proc Natl Acad Sci U S A. 2015 Jan 13;112(2):536-41. doi: 10.1073/pnas.1422590112. Epub 2014 Dec 30. PubMed PMID: 25550510; PubMed Central PMCID: PMC4299190.

11: Kim J, Yoon SP, Toews ML, Imig JD, Hwang SH, Hammock BD, Padanilam BJ. Pharmacological inhibition of soluble epoxide hydrolase prevents renal interstitial fibrogenesis in obstructive nephropathy. Am J Physiol Renal Physiol. 2015 Jan 15;308(2):F131-9. doi: 10.1152/ajprenal.00531.2014. Epub 2014 Nov 5. PubMed PMID: 25377915; PubMed Central PMCID: PMC4338924.

12: Wagner K, Yang J, Inceoglu B, Hammock BD. Soluble epoxide hydrolase inhibition is antinociceptive in a mouse model of diabetic neuropathy. J Pain. 2014 Sep;15(9):907-14. doi: 10.1016/j.jpain.2014.05.008. Epub 2014 Jun 9. PubMed PMID: 24924124; PubMed Central PMCID: PMC4150748.

13: Shrestha A, Krishnamurthy PT, Thomas P, Hammock BD, Hwang SH. Soluble epoxide hydrolase inhibitor, t-TUCB, protects against myocardial ischaemic injury in rats. J Pharm Pharmacol. 2014 Sep;66(9):1251-8. doi: 10.1111/jphp.12251. Epub 2014 Apr 2. PubMed PMID: 24697323; PubMed Central PMCID: PMC4134728.

14: Sun D, Cuevas AJ, Gotlinger K, Hwang SH, Hammock BD, Schwartzman ML, Huang A. Soluble epoxide hydrolase-dependent regulation of myogenic response and blood pressure. Am J Physiol Heart Circ Physiol. 2014 Apr 15;306(8):H1146-53. doi: 10.1152/ajpheart.00920.2013. Epub 2014 Feb 21. PubMed PMID: 24561863; PubMed Central PMCID: PMC3989753.

15: Guedes AG, Morisseau C, Sole A, Soares JH, Ulu A, Dong H, Hammock BD. Use of a soluble epoxide hydrolase inhibitor as an adjunctive analgesic in a horse with laminitis. Vet Anaesth Analg. 2013 Jul;40(4):440-8. doi: 10.1111/vaa.12030. Epub 2013 Mar 7. PubMed PMID: 23463912; PubMed Central PMCID: PMC3956586.

16: Sanders WG, Morisseau C, Hammock BD, Cheung AK, Terry CM. Soluble epoxide hydrolase expression in a porcine model of arteriovenous graft stenosis and anti-inflammatory effects of a soluble epoxide hydrolase inhibitor. Am J Physiol Cell Physiol. 2012 Aug 1;303(3):C278-90. doi: 10.1152/ajpcell.00386.2011. Epub 2012 May 23. PubMed PMID: 22621785; PubMed Central PMCID: PMC3423029.

17: Wang L, Yang J, Guo L, Uyeminami D, Dong H, Hammock BD, Pinkerton KE. Use of a soluble epoxide hydrolase inhibitor in smoke-induced chronic obstructive pulmonary disease. Am J Respir Cell Mol Biol. 2012 May;46(5):614-22. doi: 10.1165/rcmb.2011-0359OC. Epub 2011 Dec 28. PubMed PMID: 22180869; PubMed Central PMCID: PMC3359909.

UC-1728

10.0mg / USD 120.0