VGX-1027
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 522453

CAS#: 6501-72-0

Description: VGX-1027 is a small potent nitric oxide-donating compound with potent immunomodulatory properties. VGX-1027, in microarray analysis, modulates the expression of genes that involved in immune activation and the antigen processing and presentation in response to lipopolysaccharide (LPS) stimulation. VGX-1027 is a TLR4 inhibitor. VGX-1027 is a TLR4 and TLR2/6 signaling pathway modulator. In CD4+CD25− T cells, VGX-1027 inhibited cell proliferation induced by enterobacterial antigen.


Price and Availability

Size
Price

100mg
USD 850
1g
USD 3450
Size
Price

200mg
USD 1350
2g
USD 4850
Size
Price

500mg
USD 2150
5g
USD 7850

VGX-1027, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 522453
Name: VGX-1027
CAS#: 6501-72-0
Chemical Formula: C11H11NO3
Exact Mass: 205.07389
Molecular Weight: 205.21
Elemental Analysis: C, 64.38; H, 5.40; N, 6.83; O, 23.39


Synonym: VGX-1027; VGX 1027; VGX1027; GIT 27; GIT-27; GIT27

IUPAC/Chemical Name: 2-(3-phenyl-4,5-dihydroisoxazol-5-yl)acetic acid

InChi Key: MUFJHYRCIHHATF-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(O)CC1CC(C2=CC=CC=C2)=NO1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.90.01


References

1: Fagone P, Muthumani K, Mangano K, Magro G, Meroni PL, Kim JJ, Sardesai NY, Weiner DB, Nicoletti F. VGX-1027 modulates genes involved in lipopolysaccharide-induced Toll-like receptor 4 activation and in a murine model of systemic lupus erythematosus. Immunology. 2014 Aug;142(4):594-602. doi: 10.1111/imm.12267. PubMed PMID: 24527796; PubMed Central PMCID: PMC4107669.

2: Laird MD, Shields JS, Sukumari-Ramesh S, Kimbler DE, Fessler RD, Shakir B, Youssef P, Yanasak N, Vender JR, Dhandapani KM. High mobility group box protein-1 promotes cerebral edema after traumatic brain injury via activation of toll-like receptor 4. Glia. 2014 Jan;62(1):26-38. doi: 10.1002/glia.22581. Epub 2013 Oct 28. PubMed PMID: 24166800; PubMed Central PMCID: PMC4503251.

3: Cha JJ, Hyun YY, Lee MH, Kim JE, Nam DH, Song HK, Kang YS, Lee JE, Kim HW, Han JY, Cha DR. Renal protective effects of toll-like receptor 4 signaling blockade in type 2 diabetic mice. Endocrinology. 2013 Jun;154(6):2144-55. doi: 10.1210/en.2012-2080. Epub 2013 Apr 8. PubMed PMID: 23568555.

4: Mojic M, Mijatovic S, Maksimovic-Ivanic D, Miljkovic D, Stosic-Grujicic S, Stankovic M, Mangano K, Travali S, Donia M, Fagone P, Zocca MB, Al-Abed Y, McCubrey JA, Nicoletti F. Therapeutic potential of nitric oxide-modified drugs in colon cancer cells. Mol Pharmacol. 2012 Oct;82(4):700-10. Epub 2012 Jul 13. PubMed PMID: 22798453.

5: Mijatovic S, Maksimovic-Ivanic D, Timotijevic G, Miljkovic D, Donia M, Libra M, Coco M, McCubrey J, Al-Abed Y, Korac A, Stosic-Grujicic S, Nicoletti F. Induction of caspase-independent apoptotic-like cell death of mouse mammary tumor TA3Ha cells in vitro and reduction of their lethality in vivo by the novel chemotherapeutic agent GIT-27NO. Free Radic Biol Med. 2010 Apr 15;48(8):1090-9. doi: 10.1016/j.freeradbiomed.2010.01.026. Epub 2010 Jan 28. PubMed PMID: 20114073.

6: Donia M, Mijatovic S, Maksimovic-Ivanic D, Miljkovic D, Mangano K, Tumino S, Biondi A, Basile F, Al-Abed Y, Stosic-Grujicic S, Nicoletti F. The novel NO-donating compound GIT-27NO inhibits in vivo growth of human prostate cancer cells and prevents murine immunoinflammatory hepatitis. Eur J Pharmacol. 2009 Aug 1;615(1-3):228-33. doi: 10.1016/j.ejphar.2009.04.069. Epub 2009 May 14. PubMed PMID: 19446546.

7: Mangano K, Sardesai NY, Quattrocchi C, Mazzon E, Cuzzocrea S, Bendtzen K, Meroni PL, Kim JJ, Nicoletti F. Effects of the immunomodulator, VGX-1027, in endotoxin-induced uveitis in Lewis rats. Br J Pharmacol. 2008 Nov;155(5):722-30. doi: 10.1038/bjp.2008.315. Epub 2008 Sep 8. PubMed PMID: 18776919; PubMed Central PMCID: PMC2584921.

8: Mijatovic S, 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. 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. Nitric Oxide. 2008 Sep;19(2):177-83. doi: 10.1016/j.niox.2008.04.004. Epub 2008 May 19. PubMed PMID: 18460348.

9: Mangano K, Sardesai N, D'Alcamo M, Libra M, Malaguarnera L, Donia M, Bendtzen K, Meroni P, Nicoletti F. In vitro inhibition of enterobacteria-reactive CD4+CD25- T cells and suppression of immunoinflammatory colitis in mice by the novel immunomodulatory agent VGX-1027. Eur J Pharmacol. 2008 May 31;586(1-3):313-21. doi: 10.1016/j.ejphar.2008.02.017. Epub 2008 Feb 17. PubMed PMID: 18374912.

10: Maksimovic-Ivanic D, Mijatovic S, Harhaji L, Miljkovic D, Dabideen D, Fan Cheng K, Mangano K, Malaponte G, Al-Abed Y, Libra M, Garotta G, Nicoletti F, Stosic-Grujicic S. Anticancer properties of the novel nitric oxide-donating compound (S,R)-3-phenyl-4,5-dihydro-5-isoxazole acetic acid-nitric oxide in vitro and in vivo. Mol Cancer Ther. 2008 Mar;7(3):510-20. doi: 10.1158/1535-7163.MCT-07-2037. PubMed PMID: 18347138.

11: Stojanovic I, Cuzzocrea S, Mangano K, Mazzon E, Miljkovic D, Wang M, Donia M, Al Abed Y, Kim J, Nicoletti F, Stosic-Grujicic S, Claesson M. 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. Clin Immunol. 2007 Jun;123(3):311-23. Epub 2007 Apr 20. PubMed PMID: 17449326.

12: Stosic-Grujicic S, Cvetkovic I, Mangano K, Fresta M, Maksimovic-Ivanic D, Harhaji L, Popadic D, Momcilovic M, Miljkovic D, Kim J, Al-Abed Y, Nicoletti F. 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 Pharmacol Exp Ther. 2007 Mar;320(3):1038-49. Epub 2006 Dec 5. Erratum in: J Pharmacol Exp Ther. 2007 Apr;321(1):420. Abed, Yousef Al [corrected to Al-Abed, Yousef]. PubMed PMID: 17148780.