VGX-1027
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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 Shipping out time Quantity
100mg USD 850 2 Weeks
200mg USD 1350 2 Weeks
500mg USD 2150 2 Weeks
1g USD 3450 2 Weeks
2g USD 4850 2 Weeks
5g USD 7850 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-07-07. Prices are subject to change without notice.

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).

HS Tariff Code:
2934.99.9001


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.