| Identification | Back Directory | [Name]
trans-ACUB | [CAS]
885012-33-9 | [Synonyms]
t-AUCB
trans-ACUB
trans-AUCB
trans-4-(4-[3-Adamantan-1-yl-ureido]-cyclohexyloxy)-benzoic acid
4-(((trans-4-(3-(Adamantan-1-yl)ureido)cyclohexyl)oxy)benzoic acid
4-(((1R,4r)-4-(3-((3S,5S,7S)-adamantan-1-yl)ureido)cyclohexyl)oxy)benzoic acid
Benzoic acid, 4-[[trans-4-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]cyclohexyl]oxy]- | [Molecular Formula]
C24H32N2O4 | [MDL Number]
MFCD18633310 | [MOL File]
885012-33-9.mol | [Molecular Weight]
412.52 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
≤30mg/ml in DMSO;20mg/ml in dimethyl formamide | [form ]
crystalline solid | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
trans-ACUB is a potent inhibitor of soluble epoxide hydrolase (sEH) which is known to convert epoxides to their corresponding diols. Inhibitors of sEH act as anti-inflammatory, anti-hypertensive and cardioprotective agents. | [Biological Activity]
trans-aucb is a potent inhibitor of soluble epoxide hydrolase (seh).soluble epoxide hydrolase (seh) can convert epoxides to their corresponding diols. inhibitors of seh have anti-hypertensive, anti-inflammatory, neuroprotective, and cardioprotective effects. | [in vitro]
a previous study showed that the pretreatment with dapt could substantially potentiate the growth inhibition caused by t-aucb in u251 and u87 cells. moreover, the pretreatment with dapt markedly increased t-aucb-induced apoptosis of u251 and u87 cells. moreover, t-aucb alone did not obviously affect caspase-3 activity in the cells, but t-aucb plus dapt pretreatment caused significant increase of caspase-3 activity. in addition, the pretreatment with dapt was able to completely block t-aucb-induced phosphorylation of p38 mapk, mapkapk2 and hsp27 in the cells [1]. | [in vivo]
a previous animal study was conducted to investigate the effects of acute seh inhibition by t-aucb on infarct volume, functional outcome, and changes in cerebral blood flow (cbf) in a rat model of ischemic stroke. it was found that t-aucb could significantly reduce cortical infarct volume by 35%, elevate cumulative epoxyeicosatrienoic acids-to-dihydroxyeicosatrienoic acids ratio in brain cortex by twofold, and improve functional outcome in arm-flexion test when compared with that of the vehicle-treated group [2]. | [IC 50]
0.5 nm | [References]
[1] li jy, li rj, wang hd. γ-secretase inhibitor dapt sensitizes t-aucb-induced apoptosis of human glioblastoma cells in vitro via blocking the p38 mapk/mapkapk2/hsp27 pathway. acta pharmacol sin. 2014 jun;35(6):825-31.
[2] shaik js, ahmad m, li w, rose me, foley lm, hitchens tk, graham sh, hwang sh, hammock bd, poloyac sm. soluble epoxide hydrolase inhibitor trans-4-[4-(3-adamantan-1-yl-ureido)-cyclohexyloxy]-benzoic acid is neuroprotective in rat model of ischemic stroke. am j physiol heart circ physiol. 2013 dec 1;305(11):h1605-13. |
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