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Merck
CN

SML4250

t-TUCB

≥97% (HPLC), powder, hydrolase (sEH) inhibitor

Synonym(s):

4-[[trans-4-[[[[4-(Trifluoromethoxy)phenyl]amino]carbonyl]amino]cyclohexyl]oxy]benzoic acid, trans-4-[4-[3-(4-Trifluoromethoxyphenyl)ureido]cyclohexyloxy]benzoic acid, EC 1728, EC-1728, EC1728, UC 1728, UC-1728, UC1728

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About This Item

Empirical Formula (Hill Notation):
C21H21F3N2O5
CAS Number:
Molecular Weight:
438.40
MDL number:
NACRES:
NA.21
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Product Name

t-TUCB, ≥97% (HPLC), powder, hydrolase (sEH) inhibitor

Quality Level

assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Application

t-TUCB may be used in in vitro studies to examine lipid accumulation and its interaction with omega-3 epoxides in regulating autophagy and endoplasmic reticulum (ER) stress markers.

Biochem/physiol Actions

t-TUCB is an orally active and potent soluble epoxide hydrolase (sEH) inhibitor (h/m/r IC50 = 0.9/1.3/16 nM). t-TUCB modulates inflammation and autophagy in adipose tissue and liver in obese fat-1 mice (10 μg/mL in drinking water, ∼1.67 mg/kg/d). When administered at 10 mg/kg via s.c. t-TUCB is substantially more effective than t-AUCB and APAU in a diabetic neuropathy model in rats.

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Cristina López-Vicario et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(2), 536-541 (2015-01-01)
Soluble epoxide hydrolase (sEH) is an emerging therapeutic target in a number of diseases that have inflammation as a common underlying cause. sEH limits tissue levels of cytochrome P450 (CYP) epoxides derived from omega-6 and omega-3 polyunsaturated fatty acids (PUFA)
Karen Wagner et al.
European journal of pharmacology, 700(1-3), 93-101 (2013-01-02)
Epoxy-fatty acids have been recognized as important cell signaling molecules with multiple biological effects including anti-nociception. The main degradation pathway of these signaling molecules is via the soluble epoxide hydrolase (sEH) enzyme. Inhibitors of sEH extend the anti-nociceptive effects of
Sung Hee Hwang et al.
Journal of medicinal chemistry, 50(16), 3825-3840 (2007-07-10)
A series of N,N'-disubstituted ureas having a conformationally restricted cis- or trans-1,4-cyclohexane alpha to the urea were prepared and tested as soluble epoxide hydrolase (sEH) inhibitors. This series of compounds showed low nanomolar to picomolar activities against recombinant human sEH.

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