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OBAA

Names

[ CAS No. ]:
221632-26-4

[ Name ]:
OBAA

[Synonym ]:
(2E)-4-(4-Octadecylphenyl)-4-oxo-2-butenoic acid
2-Butenoic acid, 4-(4-octadecylphenyl)-4-oxo-, (2E)-
(2E)-4-(4-Octadecylphenyl)-4-oxobut-2-enoic acid
4-(4-Octadecylphenyl)-4-oxo-2-butenoic acid

Biological Activity

[Description]:

(2E)-OBAA is a potent phospholipase A2 (PLA2) inhibitor, with an IC50 of 70 nM. (2E)-OBAA induces apoptosis of HUVEC cells. (2E)-OBAA blocks Melittin-induced Ca2+ influx in Trypanosoma brucei, with an IC50 of 0.4 μM[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase
Research Areas >> Inflammation/Immunology

[Target]

PLA2:70 nM (IC50)


[In Vitro]

(2E)-OBAA (5.7 μM) induces apoptotic cell death of human umbilical vein endothelial cells (HUVEC). After 16 h of treatment, almost all of the cells has disintegrated into apoptotic bodies[1].

[In Vivo]

(2E)-OBAA (2.5-7 mg/kg, IV) significantly and dose-dependently inhibits the immunologically induced bronchospasm in guinea pigs[3].

[References]

[1]. J Y Miao, et al. Inhibitors of phospholipase promote apoptosis of human endothelial cells. J Biochem. 1997 Mar;121(3):612-8.

[2]. J Eintracht, et al. Calcium entry in Trypanosoma brucei is regulated by phospholipase A2 and arachidonic acid. Biochem J. 1998 Dec 15;336 ( Pt 3)(Pt 3):659-66.

[3]. T Köhler, et al. Phospholipase A2 inhibition by alkylbenzoylacrylic acids. Biochem Pharmacol. 1992 Aug 18;44(4):805-13.

[4]. Kethineedi VR, et al. Quantum dot-NBD-liposome luminescent probes for monitoring phospholipase A2 activity. Anal Bioanal Chem. 2013 Dec;405(30):9729-37.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
558.6±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C28H44O3

[ Molecular Weight ]:
428.647

[ Flash Point ]:
305.7±26.6 °C

[ Exact Mass ]:
428.329041

[ LogP ]:
11.09

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.508

Related Compounds

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