Locostatin

Names

[ Name ]:
Locostatin

[Synonym ]:
(4S)-N-Crotonyl-4-benzyl-2-oxazolidinone
(R)-4-BENZYL-3-CROTONYL-2-OXAZOLIDINONE
(S,E)-3-(but-2'-enoyl)-4-benzyloxazolidin-2-one
(S)-3-((E)-but-2-enoyl)-4-benzyloxazolidin-2-one
4-(S)-benzyl-((E)-2'-butenoyl)-1,3-oxazolidin-2-one
(4S)-3-((E)-2-butenoyl)-4-(phenylmethyl)-2-oxazolidinone
(4S)-3-[(E)-BUT-2-ENOYL]-4-BENZYL-2-OXAZOLIDINONE
(4S)-N-[(2E)-but-2-enoyl]-4-phenylmethyl-1,3-oxazolidin-2-one
(N-CROTONYL)-(4S)-BENZYL-2-OXAZOLIDINONE
UIC-1005
(S,E)-4-benzyl-3-(but-2-enoyl)oxazolidin-2-one
MFCD00278769
(S)-3-((E)-but-2-enoyl)-4-benzyloxazolidinone
(N-Crotonyl)-(R)-4-benzyl-2-oxazolidinone
(S)-(+)-4-BENZYL-3-CROTONYL-2-OXAZOLIDINONE

Biological Activity

[Description]:

Locostatin (UIC-1005) is a potent RKIP inhibitor. Locostatin binds Raf kinase inhibitor RKIP protein and disrupts the interaction of RKIP with Raf-1 kinase and G protein-coupled receptor kinase 2. Locostatin inhibits cell proliferation and migration. Locostatin can be used to synthesize chemical probes toward PEBP-proteins. Locostatin aggravates thioacetamide (HY-Y0698)-induced acute liver failure in mice [1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[Target]

RKIP[3]

[In Vitro]

Locostatin (200 µM；37 °C；6 小时) 破坏 RKIP 与 Raf-1 和 GRK2 的相互作用[1]。 Locostatin (50 µM；0-48 小时) 抑制 MDCK 细胞的增殖和迁移[2]。 Cell Proliferation Assay[2] Cell Line: MDCK cells Concentration: 50 µM Incubation Time: 0-48 h Result: Inhibited cell proliferation and sheet migration.

[In Vivo]

Locostatin (0.5 mg/kg；腹腔注射；每天一次，连续 7 天) 加重硫代乙酰胺 (HY-Y0698) 诱导的小鼠急性肝衰竭[3]。 Animal Model: 6 weeks, 18-22 g, male ICR mice (TAA model; injected intraperitoneally with 300 mg/kg TAA once a day for 2 days)[3] Dosage: 0.5 mg/kg Administration: I.p.; once a day for 7 days Result: Decreased the expression of RKIP, led to more severe damage, such as steatosis and hepatic lesions, increased the production of ROS in the liver and TNF-α, IL-6 and IL-1β in the sera of mice with acute liver injury, inhibitd Nrf2 and HO-1 expression in the livers of mice, induced NF-κB activation in the livers of mice,increased the phosphorylation of JNK, p38 and ERK in liver tissues.

[References]

[1]. Beshir AB, et al. Locostatin Disrupts Association of Raf Kinase Inhibitor Protein With Binding Proteins by Modifying a Conserved Histidine Residue in the Ligand-Binding Pocket. For Immunopathol Dis Therap. 2011;2(1):47-58.

[2]. Mc Henry KT, et al. A non-antibacterial oxazolidinone derivative that inhibits epithelial cell sheet migration. Chembiochem. 2002 Nov 4;3(11):1105-11.

[3]. Lin X, et al. Inhibition of RKIP aggravates thioacetamide-induced acute liver failure in mice. Exp Ther Med. 2018 Oct;16(4):2992-2998.

Chemical & Physical Properties

[ Density]:
1.205 g/cm3

[ Boiling Point ]:
351ºC at 760 mmHg

[ Melting Point ]:
84-88ºC(lit.)

[ Molecular Formula ]:
C₁₀H₁₅NO₃

[ Molecular Weight ]:
197.23100

[ Flash Point ]:
166.1ºC

[ Exact Mass ]:
197.10500

[ PSA ]:
46.61000

[ LogP ]:
1.29870

[ Appearance of Characters ]:
white to off-white

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: ≥30mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Risk Phrases ]:
24/25

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
29349990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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