Glutathione disulfide (NOV-002)
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MedKoo CAT#: 202030

CAS#: 27025-41-8

Description: Glutathione disulfide, also known as NOV-002, glutathione disulfide, GSSG; oxidized glutathione, is a dimer of glutathione with potential chemoprotective and immunomodulating activities. Mimicking endogenous GSSG, glutathione disulfide acts as a competitive substrate for gamma-glutamyl-transpeptidase (GGT), which may result in the S-glutathionylation of proteins, predominantly actin, a redox stress on endoplasmic reticulum (ER), and ER stress-induced apoptosis; S-glutathionylation may be stimulated by reactive oxygen species (ROS) liberated by a glutathione disulfide NOV-002-induced increase in GGT activity. Glutathione disulfide NOV-002 may also induce phosphorylation of proteins such as ERK and p38, two kinases that play critical regulatory roles in cell proliferation and apoptosis.


Price and Availability

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Price

10mg
USD 150
100mg
USD 550
1g
USD 950
Size
Price

25mg
USD 250
200mg
USD 650
2g
USD 1450
Size
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50mg
USD 450
500mg
USD 750
5g
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Glutathione disulfide (NOV-002), purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 200mg may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 202030
Name: Glutathione disulfide (NOV-002)
CAS#: 27025-41-8
Chemical Formula: C20H32N6O12S2
Exact Mass: 612.15196
Molecular Weight: 612.63
Elemental Analysis: C, 39.21; H, 5.26; N, 13.72; O, 31.34; S, 10.47


Synonym: NOV002; NOV-002; NOV 002; glutathione disulfide; GSSG; oxidized glutathione; glutathione dimer; Gluthoxim; Glutoxim.

IUPAC/Chemical Name: (2S,2'S)-5,5'-(((2R,2'R)-disulfanediylbis(1-((carboxymethyl)amino)-1-oxopropane-3,2-diyl))bis(azanediyl))bis(2-amino-5-oxopentanoic acid)

InChi Key: YPZRWBKMTBYPTK-XOGOEWOHSA-N

InChi Code: InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12?/m0/s1

SMILES Code: O=C(NCC(O)=O)[C@@H](NC(CC[C@H](N)C(O)=O)=O)CSSC[C@H](NC(CC[C@H](N)C(O)=O)=O)C(NCC(O)=O)=O


Technical Data

Appearance:
white solid powder

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

Certificate of Analysis:

Safety Data Sheet (MSDS):

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 water.

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in water

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

Harmonized System Code:
293490


Additional Information

 
 


References

1: Gumireddy K, Li A, Cao L, Yan J, Liu L, Xu X, Pazoles C, Huang Q. NOV-002, A Glutathione Disulfide Mimetic, Suppresses Tumor Cell Invasion and Metastasis. J Carcinog Mutagen. 2013 Apr 30;2013. pii: S7-002. PubMed PMID: 24377058; PubMed Central PMCID: PMC3872994.  

2: Grek CL, Townsend DM, Uys JD, Manevich Y, Coker WJ 3rd, Pazoles CJ, Tew KD. S-glutathionylated serine proteinase inhibitors as plasma biomarkers in assessing response to redox-modulating drugs. Cancer Res. 2012 May 1;72(9):2383-93. doi: 10.1158/0008-5472.CAN-11-4088. Epub 2012 Mar 8. PubMed PMID: 22406622.

3: Diaz-Montero CM, Wang Y, Shao L, Feng W, Zidan AA, Pazoles CJ, Montero AJ, Zhou D. The glutathione disulfide mimetic NOV-002 inhibits cyclophosphamide-induced hematopoietic and immune suppression by reducing oxidative stress. Free Radic Biol Med. 2012 May 1;52(9):1560-8. doi: 10.1016/j.freeradbiomed.2012.02.007. Epub 2012 Feb 15. PubMed PMID: 22343421; PubMed Central PMCID: PMC3341494.

4: Montero AJ, Diaz-Montero CM, Deutsch YE, Hurley J, Koniaris LG, Rumboldt T, Yasir S, Jorda M, Garret-Mayer E, Avisar E, Slingerland J, Silva O, Welsh C, Schuhwerk K, Seo P, Pegram MD, Glück S. Phase 2 study of neoadjuvant treatment with NOV-002 in combination with doxorubicin and cyclophosphamide followed by docetaxel in patients with HER-2 negative clinical stage II-IIIc breast cancer. Breast Cancer Res Treat. 2012 Feb;132(1):215-23. doi: 10.1007/s10549-011-1889-0. Epub 2011 Dec 3. PubMed PMID: 22138748; PubMed Central PMCID: PMC3697917.

5: Montero AJ, Jassem J. Cellular redox pathways as a therapeutic target in the treatment of cancer. Drugs. 2011 Jul 30;71(11):1385-96. doi: 10.2165/11592590-000000000-00000. Review. PubMed PMID: 21812504.

6: Sönmez MF, Savranlar Y. Letter to the editor regarding the article by Jenderny et al. Biomed Pharmacother. 2011 Aug;65(5):385. doi: 10.1016/j.biopha.2011.04.002. Epub 2011 Jun 28. PubMed PMID: 21782378.

7: Uys JD, Manevich Y, Devane LC, He L, Garret TE, Pazoles CJ, Tew KD, Townsend DM. Preclinical pharmacokinetic analysis of NOV-002, a glutathione disulfide mimetic. Biomed Pharmacother. 2010 Sep;64(7):493-8. doi: 10.1016/j.biopha.2010.01.003. Epub 2010 Feb 24. PubMed PMID: 20359856; PubMed Central PMCID: PMC2921589.

8: Jenderny S, Lin H, Garrett T, Tew KD, Townsend DM. Protective effects of a glutathione disulfide mimetic (NOV-002) against cisplatin induced kidney toxicity. Biomed Pharmacother. 2010 Jan;64(1):73-6. doi: 10.1016/j.biopha.2009.09.009. Epub 2009 Oct 17. PubMed PMID: 19896793; PubMed Central PMCID: PMC3388846.

9: Townsend DM, Tew KD. Pharmacology of a mimetic of glutathione disulfide, NOV-002. Biomed Pharmacother. 2009 Feb;63(2):75-8. doi: 10.1016/j.biopha.2008.08.019. Epub 2008 Sep 17. PubMed PMID: 18851905; PubMed Central PMCID: PMC2657662.

10: Townsend DM, Pazoles CJ, Tew KD. NOV-002, a mimetic of glutathione disulfide. Expert Opin Investig Drugs. 2008 Jul;17(7):1075-83. doi: 10.1517/13543784.17.7.1075 . PubMed PMID: 18549343.

11: Townsend DM, He L, Hutchens S, Garrett TE, Pazoles CJ, Tew KD. NOV-002, a glutathione disulfide mimetic, as a modulator of cellular redox balance. Cancer Res. 2008 Apr 15;68(8):2870-7. doi: 10.1158/0008-5472.CAN-07-5957. PubMed PMID: 18413755; PubMed Central PMCID: PMC3397193.

12: Townsend DM, Findlay VL, Tew KD. Glutathione S-transferases as regulators of kinase pathways and anticancer drug targets. Methods Enzymol. 2005;401:287-307. Review. PubMed PMID: 16399394.