NOV-002
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MedKoo CAT#: 202030

CAS#: 27025-41-8

Description: NOV-002, also known as 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.


Chemical Structure

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NOV-002
CAS# 27025-41-8

Theoretical Analysis

MedKoo Cat#: 202030
Name: 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

Price and Availability

Size Price Availability Quantity
50.0mg USD 150.0 Same Day
100.0mg USD 250.0 Same Day
1.0g USD 550.0 Same Day
5.0g USD 950.0 Same Day
10.0g USD 1450.0 2 Weeks
50.0g USD 1950.0 2 Weeks
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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

Appearance: white 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 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).

HS Tariff Code: 2934.99.9001

Certificate of Analysis:

Safety Data Sheet (SDS):

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
H2O 10.0 16.3

Preparing Stock Solutions

The following data is based on the product molecular weight 612.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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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.

NOV-002

50.0mg / USD 150.0


Additional Information

 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.