AUDA

Names

[ Name ]:
AUDA

[Synonym ]:
12-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]-dodecanoic acid
HMS2204E15
12-[(Adamantan-1-ylcarbamoyl)amino]dodecanoic acid
12-{[(3s,5s,7s)-Adamantan-1-ylcarbamoyl]amino}dodecanoic acid
Dodecanoic acid, 12-[[(tricyclo[3.3.1.1]dec-1-ylamino)carbonyl]amino]-
12-(3-adamantan-1-ylureido)dodecanoic acid
Urea-based compound,18
12-[(tricyclo[3.3.1.1]dec-1-ylcarbamoyl)amino]dodecanoic acid
AUDA

Biological Activity

[Description]:

AUDA (compound 43) is a potent soluble epoxide hydrolase (sEH) inhibitor with IC50s of 18 and 69 nM for the mouse and human sEH, respectively[1]. AUDA has anti-inflammatory activity[2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[Target]

IC50: 18 nM (mouse sEH) and 69 nM (human sEH)[1]

[In Vitro]

AUDA (0.3-10 μg/mL; 48 hours) dose-dependently suppresses the proliferation of rat VSMCs exposed to PDGF[2]. AUDA (0.3-10 μg/mL; 30 min) dose-dependently upregulats COX-2 expression[2]. AUDA (10, 50 and 100 μM) augments the migratory ability of HCAECs in a dose-dependent manner[3]. AUDA significantly increases the adhesion ability of HCAECs[3]. Cell Proliferation Assay[2] Cell Line: Vascular smooth muscle cell (VSMC) Concentration: 0.3, 1, 3, 10 μg/mL Incubation Time: 48 hours Result: Dose-dependently suppressed the proliferation of rat VSMCs exposed to PDGF. Western Blot Analysis[2] Cell Line: VSMC Concentration: 1, 3, 10, 30 μg/mL Incubation Time: 30 min Result: Dose-dependently upregulated COX-2 expression.

[In Vivo]

AUDA (i.p.; 10 mg/kg; 14 days) reduces TNF-α, MMP-9 and IL-1β expression levels[3]. Animal Model: Male (wild-type) C57BL/6 mice (age, 4-6 weeks; weight, 18-20 g)[3] Dosage: 10 mg/kg Administration: i.p.; 14 days Result: Reduced TNF-α, MMP-9 and IL-1β expression levels.

[References]

[1]. Morisseau C, et al. Structural refinement of inhibitors of urea-based soluble epoxide hydrolases.Biochem Pharmacol. 2002 May 1;63(9):1599-608.

[2]. Kim HS, et al. Differential Effects of sEH Inhibitors on the Proliferation and Migration of Vascular Smooth Muscle Cells.Int J Mol Sci. 2017 Dec 11;18(12).

[3]. Dai N, et al. Vascular repair and anti-inflammatory effects of soluble epoxide hydrolase inhibitor.Exp Ther Med. 2019 May;17(5):3580-3588.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
592.7±19.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₃H₄₀N₂O₃

[ Molecular Weight ]:
392.575

[ Flash Point ]:
312.3±21.5 °C

[ Exact Mass ]:
392.303894

[ PSA ]:
78.43000

[ LogP ]:
5.61

[ Vapour Pressure ]:
0.0±3.6 mmHg at 25°C

[ Index of Refraction ]:
1.534

[ Storage condition ]:
-20℃

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Intimal smooth muscle cells are a source but not a sensor of anti-inflammatory CYP450 derived oxylipins.

Biochem. Biophys. Res. Commun. 463 , 774-80, (2015)

Vascular pathologies are associated with changes in the presence and expression of morphologically distinct vascular smooth muscle cells. In particular, in complex human vascular lesions and models of...

Alkylphloroglucinol derivatives and triterpenoids with soluble epoxide hydrolase inhibitory activity from Callistemon citrinus.

Fitoterapia 109 , 39-44, (2016)

Phytochemical analysis of the leaves and stems of Callistemon citrinus (Curtis) Skeels led to the isolation of two new alkylphloroglucinols, gallomyrtucommulone E and F (1 and 2), along with four othe...

Therapeutic effects of the soluble epoxide hydrolase (sEH) inhibitor AUDA on atherosclerotic diseases.

Pharmazie 70(1) , 24-8, (2015)

In this study, we aimed to detect the effects of the soluble epoxide hydrolase (sEH) inhibitor 12-(3-adamantan-1-yl-ureido)-dodecanoic acid (AUDA) on atherosclerotic diseases and to explore its mechan...