Basic information Safety Supplier Related

2-(P-AMYLCINNAMOYL)AMINO-4-CHLOROBENZOIC ACID

Basic information Safety Supplier Related

2-(P-AMYLCINNAMOYL)AMINO-4-CHLOROBENZOIC ACID Basic information

Product Name:
2-(P-AMYLCINNAMOYL)AMINO-4-CHLOROBENZOIC ACID
Synonyms:
  • 2-(P-AMYLCINNAMOYL)AMINO-4-CHLOROBENZOIC ACID
  • ONO-RS-082
  • 2-(4-amylcinnamoyl)amino-4-chlorobenzoic acid
  • 2-[[(E)-4-Pentylcinnamoyl]amino]-4-chlorobenzoic acid sodium salt
  • 4-Chloro-2-[[1-oxo-3-(4-pentylphenyl)-2-propen-1-yl]amino]-benzoic acid
  • (E)-4-chloro-2-(3-(4-pentylphenyl)acrylamido)benzoic acid
  • (E)-4-chloro-2-(3-(4-pentylphenyl)acrylamido)benzoic acid(WXC06363)
  • 4-chloro-2-[[(E)-3-(4-pentylphenyl)prop-2-enoyl]amino]benzoic acid
CAS:
99754-06-0
MF:
C21H22ClNO3
MW:
371.86
Mol File:
99754-06-0.mol
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2-(P-AMYLCINNAMOYL)AMINO-4-CHLOROBENZOIC ACID Chemical Properties

Melting point:
175-177℃
storage temp. 
room temp
solubility 
DMSO: ≥20mg/mL
form 
powder
color 
white
Sensitive 
Light Sensitive
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
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Safety Information

Hazard Codes 
N
Risk Statements 
50
Safety Statements 
61
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
2
HazardClass 
9
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2-(P-AMYLCINNAMOYL)AMINO-4-CHLOROBENZOIC ACID Usage And Synthesis

Description

ONO-RS-082 (99754-06-0) is a reversible inhibitor of Ca2+-independent phospholipase A2?(PLA2), IC50=7 μM for guinea pig lung PLA2.1?Inhibits epinephrine-induced thromboxane production in platelets.1?Inhibition of PLA2?by ONO-RS-032 disrupts endosome tubule formation and maintenance of the Golgi complex.2-4?Prevents Xenopus oocyte maturation at stage V.5

Uses

ONO-RS-082 is a potent PLA2 and epinephrine inhibitor.ONO-RS-082 is a phospholipase inhibitor.

in vitro

previous study found that human platelets stimulated by epinephrine led to enhanced turnover of phosphatidylinositol 4,5-bisphosphate, accumulated inositol trisphosphate, diacylglycerol, and phosphatidic acid, indicating stimulation of phospholipase c. it was shown that these responses could be completely blocked by inhibitors of alpha 2-adrenergic receptors including ono-rs-082 or removal of fibrinogen. in addition, epinephrine could evoked an increased turnover of ester-linked arachidonic acid in aspirin treated platelets that was inhibited by ono-rs-082 or the absence of fibrinogen. moreover, it was found that ono-rs-082 at 3.5 μm was able to inhibit epinephrine-stimulated thromboxane production in human platelets. ono-rs-082 could also disrupt endosome tubule formation and maintenance of the golgi complex [1].

in vivo

In vivo long-term activation of KCNK3 by ONO-RS-082 (50 mg/kg/day; preventive treatment, day 0 to day 21) reduces the development of PH in the MCT-PH model[4].
In contrast, in vivo short-term KCNK3 activation by ONO-RS-082 (curative treatment) fails to reduce PH symptoms, which is attributed to the complete loss of KCNK3 expression in MCT-PH rats at days 14 to 21[4].

Animal Model:MCT- pulmonary hypertension (PH) rat model[4]
Dosage:50 mg/kg/day
Administration:
Result:Reduced the development of PH in the MCT-PH model for long-term.

References

[1] H S BANGA. Activation of phospholipases A and C in human platelets exposed to epinephrine: role of glycoproteins IIb/IIIa and dual role of epinephrine.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1986, 83 23: 9197-9201. DOI:10.1073/pnas.83.23.9197
[2] P. DE FIGUEIREDO. Inhibition of Transferrin Recycling and Endosome Tubulation by Phospholipase A2 Antagonists*[J]. The Journal of Biological Chemistry, 2001, 27 1: 47361-47370. DOI:10.1074/jbc.m108508200
[3] JOHN A SCHMIDT. A role for phospholipase A2 activity in membrane tubule formation and TGN trafficking.[J]. Traffic, 2010, 11 12: 1530-1536. DOI:10.1111/j.1600-0854.2010.01115.x
[4] MARIE E BECHLER  William J B. Gβ1γ2 activates phospholipase A2-dependent Golgi membrane tubule formation.[J]. Frontiers in Cell and Developmental Biology, 2014, 2 4: 0004. DOI:10.3389/fcell.2014.00004
[5] AZHARUL ISLAM . The distinct stage-specific effects of 2-(p-amylcinnamoyl)amino-4-chlorobenzoic acid on the activation of MAP kinase and Cdc2 kinase in Xenopus oocyte maturation[J]. Cellular signalling, 2005, 17 4: Pages 507-523. DOI:10.1016/j.cellsig.2004.09.011

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