ChemicalBook Product Catalog Biochemical Engineering Biochemical Reagents Agonist Inhibitors 4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid

4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid

Product Name4,5-Dihydro-3-phenyl-5-isoxazoleaceticacid
CAS6501-72-0
MFC11H11NO3
MW205.21
EINECS
MOL File6501-72-0.mol

Chemical Properties

Melting point	157-158℃
Boiling point	381.438±34.00 °C(Press: 760.00 Torr)(predicted)
Density	1.295±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
storage temp.	Sealed in dry,2-8°C
solubility	Soluble in DMSO (up to 30 mg/ml).
form	solid
pka	4.380±0.10(predicted)
color	White
Stability	Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

Safety Information

Hazard Codes	Xn
Risk Statements	22-43
Safety Statements	36/37
HS Code	2934.99.4400

Usage And Synthesis

Description

VGX-1027 (6501-72-0) is an immunomodulator that inhibits secretion of IL-1β, TNF-α, and IL-10 from murine macrophages stimulated with LPS and spares T cell function.1Ameliorates the course of acute and chronic immunoinflammatory conditions such as carrageenan-induced pleurisy, LPS-induced lethality, and type II collagen-induced arthritis in mouse models.1Prevents spontaneous and accelerated forms of autoimmune diabetes in a NOD mouse model.2Modulates genes involved in LPS-induced Toll-like receptor 4 activation in a mouse Lupus model.3Displays protective effects in particulate matter-induced acute lung injury by blocking TLR4 signaling.4

Uses

2-(3-Phenyl-4,5-dihydroisoxazol-5-yl)acetic Acid reduces the secretion of IL-1β, TNF-α and IL-10 from purified murine macrophages but not of T cells; and reduces the activation of NF-κB and p38 MAP kinase pathways along with up-regulation of ERK pathways. 2-(3-Phenyl-4,5-dihydroisoxazol-5-yl)acetic Acid inhibits proliferation of enterobacterial antigen-reactive CD4+CD25- T cells in vitro .

in vivo

VGX-1027 (10, 20 mg/kg of i.p. for 12 day or 100 mg/kg of p.o. for 11 day) successfully counteractes the development of destructive insulitis and hyperglycemia^[1].
VGX-1027 (25mg/kg; ip; single dose) counteracts the uveitis-inducing effect of LPS in eight-week-old male Lewis rats (180-220g)^[3].

Animal Model:	Adult male mice, at 6 to 8 weeks of age with 25 to 30 g^[1]
Dosage:	10, 20 mg/kg for i.p. or 100 mg/kg for p.o.
Administration:	IP daily for 12 consecutive day or PO daily for 11 consecutive day
Result:	Successfully counteracted the development of destructive insulitis and hyperglycemia to the mice made diabetic with multiple low doses of Streptozotocin.

IC 50

IL-1β; IL-10

storage

Store at +4°C

References

[1] IVANA STOJANOVIC . In vitro, ex vivo and in vivo immunopharmacological activities of the isoxazoline compound VGX-1027: Modulation of cytokine synthesis and prevention of both organ-specific and systemic autoimmune diseases in murine models[J]. Clinical immunology, 2007, 123 3: Pages 311-323. DOI:10.1016/j.clim.2007.03.004
[2] STANISLAVA STOSIC-GRUJICIC. A potent immunomodulatory compound, (S,R)-3-Phenyl-4,5-dihydro-5-isoxazole acetic acid, prevents spontaneous and accelerated forms of autoimmune diabetes in NOD mice and inhibits the immunoinflammatory diabetes induced by multiple low doses of streptozotocin in CBA/H mice.[J]. Journal of Pharmacology and Experimental Therapeutics, 2007, 320 3: 1038-1049. DOI:10.1124/jpet.106.109272
[3] PAOLO FAGONE. VGX-1027 modulates genes involved in lipopolysaccharide-induced Toll-like receptor 4 activation and in a murine model of systemic lupus erythematosus[J]. Immunology, 2014, 142 4: 594-602. DOI:10.1111/imm.12267
[4] MENGMENG XU . Protective effects of VGX-1027 in PM2.5-induced airway inflammation and bronchial hyperresponsiveness[J]. European journal of pharmacology, 2019, 842: Pages 373-383. DOI:10.1016/j.ejphar.2018.11.010

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