t-AUCB | CAS# 885012-33-9 | sEHI

MedKoo Cat#: 565007 | Name: t-AUCB

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Description:

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

t-AUCB is a soluble epoxide hydrolase inhibitor (sEHI), suppressing human glioblastoma cell growth by activating NF-κB-p65.

Chemical Structure

t-AUCB

CAS#885012-33-9

Theoretical Analysis

MedKoo Cat#: 565007

Name: t-AUCB

CAS#: 885012-33-9

Chemical Formula: C24H32N2O4

Exact Mass: 412.2362

Molecular Weight: 412.53

Elemental Analysis: C, 69.88; H, 7.82; N, 6.79; O, 15.51

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00
5mg	USD 600.00
10mg	USD 850.00

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Synonym

t-AUCB; tAUCB; t AUCB; transACUB; trans-ACUB; trans ACUB; UC-1471; UC 1471; UC1471

IUPAC/Chemical Name

trans-4-[4-(3-Adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid

InChi Key

KNBWKJBQDAQARU-KSSCSKLYSA-N

InChi Code

InChI=1S/C24H32N2O4/c27-22(28)18-1-5-20(6-2-18)30-21-7-3-19(4-8-21)25-23(29)26-24-12-15-9-16(13-24)11-17(10-15)14-24/h1-2,5-6,15-17,19,21H,3-4,7-14H2,(H,27,28)(H2,25,26,29)/t15?,16?,17?,19-,21-,24?

SMILES Code

O=C(O)C1=CC=C(O[C@H]2CC[C@H](NC(NC34CC5CC(C4)CC(C5)C3)=O)CC2)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

Shelf Life

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 412.53 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: Bah TM, Davis CM, Allen EM, Borkar RN, Perez R, Grafe MR, Raber J, Pike MM, Alkayed NJ. Soluble epoxide hydrolase inhibition reverses cognitive dysfunction in a mouse model of metabolic syndrome by modulating inflammation. Prostaglandins Other Lipid Mediat. 2024 Aug;173:106850. doi: 10.1016/j.prostaglandins.2024.106850. Epub 2024 May 10. PMID: 38735559; PMCID: PMC11218661. 2: Norman JE, Nuthikattu S, Milenkovic D, Rutledge JC, Villablanca AC. Sex- Specific Response of the Brain Free Oxylipin Profile to Soluble Epoxide Hydrolase Inhibition. Nutrients. 2023 Feb 28;15(5):1214. doi: 10.3390/nu15051214. PMID: 36904213; PMCID: PMC10005333. 3: Nuthikattu S, Milenkovic D, Norman JE, Rutledge J, Villablanca A. High Glycemia and Soluble Epoxide Hydrolase in Females: Differential Multiomics in Murine Brain Microvasculature. Int J Mol Sci. 2022 Oct 27;23(21):13044. doi: 10.3390/ijms232113044. PMID: 36361847; PMCID: PMC9655872. 4: Han WW, Wang XR, He YF, Zhang HS, Cong X, Xiang RL, Wu LL, Yu GY, Liu LM, Zhang Y. Soluble epoxide hydrolase inhibitor, t-AUCB, improves salivary gland function by ameliorating endothelial injury. Life Sci. 2022 Nov 1;308:120942. doi: 10.1016/j.lfs.2022.120942. Epub 2022 Sep 9. PMID: 36096247. 5: Nuthikattu S, Milenkovic D, Norman JE, Rutledge J, Villablanca A. The Brain's Microvascular Response to High Glycemia and to the Inhibition of Soluble Epoxide Hydrolase Is Sexually Dimorphic. Nutrients. 2022 Aug 23;14(17):3451. doi: 10.3390/nu14173451. PMID: 36079709; PMCID: PMC9460226. 6: Wang X, Han W, Zhang Y, Zong Y, Tan N, Zhang Y, Li L, Liu C, Liu L. Soluble Epoxide Hydrolase Inhibitor t-AUCB Ameliorates Vascular Endothelial Dysfunction by Influencing the NF-κB/miR-155-5p/eNOS/NO/IκB Cycle in Hypertensive Rats. Antioxidants (Basel). 2022 Jul 15;11(7):1372. doi: 10.3390/antiox11071372. PMID: 35883863; PMCID: PMC9311992. 7: Tian Y, Li S, Dong K, Su X, Fu S, Lv X, Duan M, Yang T, Han Y, Hu G, Liu J, Sun Y, Yue H, Sun Y, Zhang H, Du Z, Miao Z, Tong M, Liu Y, Qin M, Gong P, Hou Y, Gao Z, Zhao Y. Discovery of benzamide derivatives containing urea moiety as soluble epoxide hydrolase inhibitors. Bioorg Chem. 2022 Oct;127:105898. doi: 10.1016/j.bioorg.2022.105898. Epub 2022 May 24. PMID: 35792317. 8: Tian Y, Li S, Yang P, Su X, Liu J, Lv X, Dong K, Yang T, Duan M, Hu G, Yue H, Sun Y, Sun Y, Zhang H, Du Z, Miao Z, Tong M, Hou Y, Gao Z, Zhao Y. Synthesis and biological evaluation of new series of benzamide derivatives containing urea moiety as sEH inhibitors. Bioorg Med Chem Lett. 2022 Aug 15;70:128805. doi: 10.1016/j.bmcl.2022.128805. Epub 2022 May 19. PMID: 35598794. 9: Nuthikattu S, Milenkovic D, Norman JE, Rutledge J, Villablanca A. Inhibition of Soluble Epoxide Hydrolase Is Protective against the Multiomic Effects of a High Glycemic Diet on Brain Microvascular Inflammation and Cognitive Dysfunction. Nutrients. 2021 Nov 1;13(11):3913. doi: 10.3390/nu13113913. PMID: 34836168; PMCID: PMC8622784. 10: Chen Y, Liu Q, Yang T, Shen L, Xu D. Soluble Epoxide Hydrolase Inhibitors Regulate Ischemic Arrhythmia by Targeting MicroRNA-1. Front Physiol. 2021 Sep 27;12:717119. doi: 10.3389/fphys.2021.717119. PMID: 34646152; PMCID: PMC8502875. 11: Davis CM, Zhang WH, Allen EM, Bah TM, Shangraw RE, Alkayed NJ. Soluble Epoxide Hydrolase Blockade after Stroke Onset Protects Normal but Not Diabetic Mice. Int J Mol Sci. 2021 May 21;22(11):5419. doi: 10.3390/ijms22115419. PMID: 34063817; PMCID: PMC8196561. 12: Hamzaoui M, Roche C, Coquerel D, Duflot T, Brunel V, Mulder P, Richard V, Bellien J, Guerrot D. Soluble Epoxide Hydrolase Inhibition Prevents Experimental Type 4 Cardiorenal Syndrome. Front Mol Biosci. 2021 Mar 11;7:604042. doi: 10.3389/fmolb.2020.604042. PMID: 33777999; PMCID: PMC7991096. 13: Wu J, Fan Z, Zhao Y, Chen Q, Xiao Q. Inhibition of soluble epoxide hydrolase (sEH) protects hippocampal neurons and reduces cognitive decline in type 2 diabetic mice. Eur J Neurosci. 2021 Apr;53(8):2532-2540. doi: 10.1111/ejn.15150. Epub 2021 Mar 22. PMID: 33595911. 14: Duflot T, Laurent C, Soudey A, Fonrose X, Hamzaoui M, Iacob M, Bertrand D, Favre J, Etienne I, Roche C, Coquerel D, Le Besnerais M, Louhichi S, Tarlet T, Li D, Brunel V, Morisseau C, Richard V, Joannidès R, Stanke-Labesque F, Lamoureux F, Guerrot D, Bellien J. Preservation of epoxyeicosatrienoic acid bioavailability prevents renal allograft dysfunction and cardiovascular alterations in kidney transplant recipients. Sci Rep. 2021 Feb 12;11(1):3739. doi: 10.1038/s41598-021-83274-1. PMID: 33580125; PMCID: PMC7881112. 15: Hanif A, Agba SO, Ledent C, Tilley SL, Morisseau C, Nayeem MA. Adenosine A2A receptor and vascular response: role of soluble epoxide hydrolase, adenosine A1 receptor and angiotensin-II. Mol Cell Biochem. 2021 May;476(5):1965-1978. doi: 10.1007/s11010-021-04049-w. Epub 2021 Jan 28. PMID: 33511551. 16: Han Y, Huang D, Xu S, Li L, Tian Y, Li S, Chen C, Li Y, Sun Y, Hou Y, Sun Y, Qin M, Gong P, Gao Z, Zhao Y. Ligand-based optimization to identify novel 2-aminobenzo[d]thiazole derivatives as potent sEH inhibitors with anti- inflammatory effects. Eur J Med Chem. 2021 Feb 15;212:113028. doi: 10.1016/j.ejmech.2020.113028. Epub 2020 Nov 17. PMID: 33248848. 17: Zhang X, Liao C, Sun K, Liu L, Xu D. A Soluble Epoxide Hydrolase Inhibitor Upregulated KCNJ12 and KCNIP2 by Downregulating MicroRNA-29 in a Mouse Model of Myocardial Infarction. Heart Surg Forum. 2020 Aug 12;23(5):E579-E585. doi: 10.1532/hsf.2999. PMID: 32990585. 18: Varennes O, Mentaverri R, Duflot T, Kauffenstein G, Objois T, Lenglet G, Avondo C, Morisseau C, Brazier M, Kamel S, Six I, Bellien J. The Metabolism of Epoxyeicosatrienoic Acids by Soluble Epoxide Hydrolase Is Protective against the Development of Vascular Calcification. Int J Mol Sci. 2020 Jun 17;21(12):4313. doi: 10.3390/ijms21124313. PMID: 32560362; PMCID: PMC7352784. 19: Jiang XS, Xiang XY, Chen XM, He JL, Liu T, Gan H, Du XG. Inhibition of soluble epoxide hydrolase attenuates renal tubular mitochondrial dysfunction and ER stress by restoring autophagic flux in diabetic nephropathy. Cell Death Dis. 2020 May 21;11(5):385. doi: 10.1038/s41419-020-2594-x. PMID: 32439839; PMCID: PMC7242354. 20: Wu J, Zhao Y, Fan Z, Chen Q, Chen J, Sun Y, Jiang X, Xiao Q. Soluble epoxide hydrolase inhibitor protects against blood-brain barrier dysfunction in a mouse model of type 2 diabetes via the AMPK/HO-1 pathway. Biochem Biophys Res Commun. 2020 Apr 2;524(2):354-359. doi: 10.1016/j.bbrc.2020.01.085. Epub 2020 Jan 28. PMID: 32001002.