GIT 27 - CAS 6501-72-0
Catalog number:
6501-72-0
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C11H11NO3
Molecular Weight:
205.21
COA:
Inquire
Targets:
Toll-like Receptor (TLR) | Others
Description:
Interferes with TLR4, TLR2/6 signaling; Orally active immunomodulatory agent; Inhibits TNF-α secretion via interference of macrophage TLR4 and TLR 2/6 signaling pathway
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Brife Description:
Interferes with TLR4, TLR2/6 signaling; Orally active immunomodulatory agent; Inhibits TNF-α secretion via interference of macrophage TLR4 and TLR 2/6 signaling pathway
Appearance:
White to Off-White Solid
Synonyms:
5-Dihydro-3-phenyl-5-isoxazoleacetic acid; (S,R)-3-Phenyl-4,5-dihydro-5-isoxazole acetic acid; 3-phenyl-4,5-dihydro-5-isoxazole acetic acid; GIT27; VGX-1027
Solubility:
Soluble to 100 mM in DMSO
Storage:
Store at +4°C
MSDS:
Inquire
Quality Standard:
In-house
Quantity:
Grams-Kilos
Boiling Point:
381.44° C at 760 mmHg (Predicted)
Melting Point:
132.14° C (Predicted)
InChIKey:
MUFJHYRCIHHATF-UHFFFAOYSA-N
InChI:
1S/C11H11NO3/c13-11(14)7-9-6-10(12-15-9)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,14)
Canonical SMILES:
C1C(ON=C1C2=CC=CC=C2)CC(=O)O
1.VGX-1027 modulates genes involved in lipopolysaccharide-induced Toll-like receptor 4 activation and in a murine model of systemic lupus erythematosus.
Fagone P1, Muthumani K, Mangano K, Magro G, Meroni PL, Kim JJ, Sardesai NY, Weiner DB, Nicoletti F. Immunology. 2014 Aug;142(4):594-602. doi: 10.1111/imm.12267.
VGX-1027 [(S,R)-3-phenyl-4,5-dihydro-5-isoxasole acetic acid] is a small molecule compound with immunomodulatory properties, which favourably influences the development of immuno-inflammatory and autoimmune diseases in different animal models such as type 1 diabetes mellitus, pleurisy, rheumatoid arthritis and inflammatory bowel disease. However, the precise mechanism of action of VGX-1027 remains to be ascertained. With this aim, we have studied the immunomodulatory effects of VGX-1027 in vitro, using a genome-wide oligonucleotide microarray approach, and in vivo, using the NZB/NZW F1 model of systemic lupus erythematosus. Microarray data revealed that the administration of VGX-1027 profoundly affected the immune response to exogenous antigens, by modulating the expression of genes that are primarily involved in antigen processing and presentation as well as genes that regulate immune activation. When administered in vivo VGX-1027 ameliorated the course of the disease in the NZB/NZW F1 mice, which correlated with higher per cent survival and improved clinical and histopathological signs.
2.Novel nitric oxide-donating compound (S,R)-3-phenyl-4,5-dihydro-5-isoxazole acetic acid-nitric oxide (GIT-27NO) induces p53 mediated apoptosis in human A375 melanoma cells.
Mijatovic S1, Maksimovic-Ivanic D, Mojic M, Malaponte G, Libra M, Cardile V, Miljkovic D, Harhaji L, Dabideen D, Cheng KF, Bevelacqua Y, Donia M, Garotta G, Al-Abed Y, Stosic-Grujicic S, Nicoletti F. Nitric Oxide. 2008 Sep;19(2):177-83. doi: 10.1016/j.niox.2008.04.004. Epub 2008 May 19.
In this study we evaluated the effects of the new NO donating compound (S,R)-3-phenyl-4,5-dihydro-5-isoxazole acetic acid-nitric oxide (GIT-27NO) on the A375 human melanoma cell line. Treatment with the drug led to concentration-dependent reduction of mitochondrial respiration and number of viable cells in cultures. Decreased cell viability correlated with release and internalization of NO and was neutralized by the extracellular scavenger hemoglobin. GIT-27NO neither influenced cell division nor induced accidental or autophagic cell death. Early signs of apoptosis were observed upon coculture with the drug, and resulting in marked accumulation of hypodiploid cells, suggesting that the induction of apoptosis is one primary mode of action of the compound in A375 cells. GIT-27NO significantly inhibited the expression of the transcription repressor and apoptotic resistant factor YY1 and, in parallel, augmented the presence of total p53. The capacity of GIT-27NO to induce p53-mediated apoptosis along with inhibition of YY1 repressor in A375 melanoma cells indicates that GIT-27NO possesses an important anti-cancer pharmacological profile.
3.Effects of the immunomodulator, VGX-1027, in endotoxin-induced uveitis in Lewis rats.
Mangano K1, Sardesai NY, Quattrocchi C, Mazzon E, Cuzzocrea S, Bendtzen K, Meroni PL, Kim JJ, Nicoletti F. Br J Pharmacol. 2008 Nov;155(5):722-30. doi: 10.1038/bjp.2008.315. Epub 2008 Sep 8.
BACKGROUND AND PURPOSE: VGX-1027 is a novel, low molecular weight, immunomodulatory compound that has shown efficacy against a variety of immuno-inflammatory disease models in animals including autoimmune diabetes in NOD mice, collagen-induced arthritis and chemically induced inflammatory colitis. Here, we have studied the effects of VGX-1027 on the development of endotoxin-induced uveitis (EIU) in male Lewis rats, as a model of inflammatory ocular diseases in humans.
4.Safety, bioavailability, and pharmacokinetics of VGX-1027-A novel oral anti-inflammatory drug in healthy human subjects.
Lee JC1, Menacherry S2, Diehl MC1, Giffear MD1, White CJ3, Juba R1, Bagarazzi ML1, Muthumani K4, Boyer J4, Agarwal V5, Nicoletti F6, Bart S7, Kim JJ1, Weiner DB4, Sardesai NY1. Clin Pharmacol Drug Dev. 2016 Mar;5(2):91-101. doi: 10.1002/cpdd.193. Epub 2015 Jun 8.
VGX-1027, a novel oral immune modulator, is under development for the treatment of rheumatoid arthritis. The safety, tolerability, and pharmacokinetics of single (1-800 mg) and multiple (40-400 mg) oral doses were evaluated in 2 clinical studies. The doses were well tolerated up to 800 mg in a single dose and 200 mg twice daily in multiple doses. Adverse events were mild to moderate in severity with no identifiable dose-related pattern. There were no clinically significant physical or laboratory findings. The pharmacokinetic data indicated that increases in Cmax and AUC0-inf were dose-proportional, and AUC0- τ was approximately dose-proportional. For the single-dose study, median Tmax ranged from 0.5 to 2 hours and mean t1/2 ranged from 4.9 to 8.7 hours. For the multiple-dose study, median Tmax ranged from 0.5 to 2.0 hours and mean t1/2 ranged from 7.05 to 10.05 hours. No accumulation of the drug was observed after day 1, indicating that steady-state concentrations were attained with single and multiple dosing for 5 days.
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Chemical Structure

CAS 6501-72-0 GIT 27

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