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MedKoo Cat#: 407390 | Name: ES936
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Description:

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

ES936 is a potent NAD(P)H:quinone oxidoreductase inhibitor. ES936 stimulates DNA synthesis in HeLa cells independently on NAD(P)H:quinone oxidoreductase 1 inhibition, through a mechanism involving p38 MAPK. The effect ES936 exerts on DNA synthesis may be either positive or negative depending on the cellular context and growth conditions.

Chemical Structure

ES936
ES936
CAS#192820-78-3

Theoretical Analysis

MedKoo Cat#: 407390

Name: ES936

CAS#: 192820-78-3

Chemical Formula: C18H16N2O6

Exact Mass: 356.1008

Molecular Weight: 356.33

Elemental Analysis: C, 60.67; H, 4.53; N, 7.86; O, 26.94

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
ES936; ES-936; ES 936.
IUPAC/Chemical Name
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
InChi Key
IBLWSLZYYZHSRG-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H16N2O6/c1-10-13(9-26-12-6-4-11(5-7-12)20(23)24)16-17(19(10)2)14(21)8-15(25-3)18(16)22/h4-8H,9H2,1-3H3
SMILES Code
O=C(C(OC)=C1)C2=C(N(C)C(C)=C2COC3=CC=C([N+]([O-])=O)C=C3)C1=O
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
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 356.33 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
1: González-Aragón D, Alcaín FJ, Ariza J, Jódar L, Barbarroja N, López-Pedrera C, Villalba JM. ES936 stimulates DNA synthesis in HeLa cells independently on NAD(P)H:quinone oxidoreductase 1 inhibition, through a mechanism involving p38 MAPK. Chem Biol Interact. 2010 Jul 30;186(2):174-83. doi: 10.1016/j.cbi.2010.04.022. PubMed PMID: 20433816. 2: Dehn DL, Siegel D, Swann E, Moody CJ, Ross D. Biochemical, cytotoxic, and genotoxic effects of ES936, a mechanism-based inhibitor of NAD(P)H:quinone oxidoreductase 1, in cellular systems. Mol Pharmacol. 2003 Sep;64(3):714-20. PubMed PMID: 12920209. 3: Dehn DL, Siegel D, Zafar KS, Reigan P, Swann E, Moody CJ, Ross D. 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, a mechanism-based inhibitor of NAD(P)H:quinone oxidoreductase 1, exhibits activity against human pancreatic cancer in vitro and in vivo. Mol Cancer Ther. 2006 Jul;5(7):1702-9. PubMed PMID: 16891456. 4: Winski SL, Faig M, Bianchet MA, Siegel D, Swann E, Fung K, Duncan MW, Moody CJ, Amzel LM, Ross D. Characterization of a mechanism-based inhibitor of NAD(P)H:quinone oxidoreductase 1 by biochemical, X-ray crystallographic, and mass spectrometric approaches. Biochemistry. 2001 Dec 18;40(50):15135-42. PubMed PMID: 11735396. 5: Guo W, Reigan P, Siegel D, Zirrolli J, Gustafson D, Ross D. Formation of 17-allylamino-demethoxygeldanamycin (17-AAG) hydroquinone by NAD(P)H:quinone oxidoreductase 1: role of 17-AAG hydroquinone in heat shock protein 90 inhibition. Cancer Res. 2005 Nov 1;65(21):10006-15. PubMed PMID: 16267026. 6: Li JZ, Ke Y, Misra HP, Trush MA, Li YR, Zhu H, Jia Z. Mechanistic studies of cancer cell mitochondria- and NQO1-mediated redox activation of beta-lapachone, a potentially novel anticancer agent. Toxicol Appl Pharmacol. 2014 Dec 15;281(3):285-93. doi: 10.1016/j.taap.2014.10.012. PubMed PMID: 25448047. 7: Guo W, Reigan P, Siegel D, Zirrolli J, Gustafson D, Ross D. The bioreduction of a series of benzoquinone ansamycins by NAD(P)H:quinone oxidoreductase 1 to more potent heat shock protein 90 inhibitors, the hydroquinone ansamycins. Mol Pharmacol. 2006 Oct;70(4):1194-203. PubMed PMID: 16825487. 8: Siegel D, Shieh B, Yan C, Kepa JK, Ross D. Role for NAD(P)H:quinone oxidoreductase 1 and manganese-dependent superoxide dismutase in 17-(allylamino)-17-demethoxygeldanamycin-induced heat shock protein 90 inhibition in pancreatic cancer cells. J Pharmacol Exp Ther. 2011 Mar;336(3):874-80. doi: 10.1124/jpet.110.176438. PubMed PMID: 21156818; PubMed Central PMCID: PMC3061536. 9: Zhou H, Dehn D, Kepa JK, Siegel D, Scott DE, Tan W, Ross D. NAD(P)H:quinone oxidoreductase 1-compromised human bone marrow endothelial cells exhibit decreased adhesion molecule expression and CD34+ hematopoietic cell adhesion. J Pharmacol Exp Ther. 2010 Jul;334(1):260-8. doi: 10.1124/jpet.110.167841. PubMed PMID: 20378716; PubMed Central PMCID: PMC2912043. 10: Kolossov VL, Ponnuraj N, Beaudoin JN, Leslie MT, Kenis PJ, Gaskins HR. Distinct responses of compartmentalized glutathione redox potentials to pharmacologic quinones targeting NQO1. Biochem Biophys Res Commun. 2017 Jan 29;483(1):680-686. doi: 10.1016/j.bbrc.2016.12.082. PubMed PMID: 27986568; PubMed Central PMCID: PMC5253246. 11: Okubo A, Yasuhira S, Shibazaki M, Takahashi K, Akasaka T, Masuda T, Maesawa C. NAD(P)H dehydrogenase, quinone 1 (NQO1), protects melanin-producing cells from cytotoxicity of rhododendrol. Pigment Cell Melanoma Res. 2016 May;29(3):309-16. doi: 10.1111/pcmr.12461. PubMed PMID: 26847926. 12: Gustafson DL, Siegel D, Rastatter JC, Merz AL, Parpal JC, Kepa JK, Ross D, Long ME. Kinetics of NAD(P)H:quinone oxidoreductase I (NQO1) inhibition by mitomycin C in vitro and in vivo. J Pharmacol Exp Ther. 2003 Jun;305(3):1079-86. PubMed PMID: 12649308. 13: Park EJ, Min KJ, Choi KS, Kwon TK. Dicoumarol sensitizes renal cell carcinoma Caki cells to TRAIL-induced apoptosis through down-regulation of Bcl-2, Mcl-1 and c-FLIP in a NQO1-independent manner. Exp Cell Res. 2014 Apr 15;323(1):144-54. doi: 10.1016/j.yexcr.2014.01.009. PubMed PMID: 24462458. 14: Anwar A, Dehn D, Siegel D, Kepa JK, Tang LJ, Pietenpol JA, Ross D. Interaction of human NAD(P)H:quinone oxidoreductase 1 (NQO1) with the tumor suppressor protein p53 in cells and cell-free systems. J Biol Chem. 2003 Mar 21;278(12):10368-73. PubMed PMID: 12529318. 15: Reigan P, Colucci MA, Siegel D, Chilloux A, Moody CJ, Ross D. Development of indolequinone mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1): NQO1 inhibition and growth inhibitory activity in human pancreatic MIA PaCa-2 cancer cells. Biochemistry. 2007 May 22;46(20):5941-50. PubMed PMID: 17455910. 16: Moffit JS, Aleksunes LM, Kardas MJ, Slitt AL, Klaassen CD, Manautou JE. Role of NAD(P)H:quinone oxidoreductase 1 in clofibrate-mediated hepatoprotection from acetaminophen. Toxicology. 2007 Feb 12;230(2-3):197-206. PubMed PMID: 17188792; PubMed Central PMCID: PMC1885461. 17: Zhu H, Jia Z, Mahaney JE, Ross D, Misra HP, Trush MA, Li Y. The highly expressed and inducible endogenous NAD(P)H:quinone oxidoreductase 1 in cardiovascular cells acts as a potential superoxide scavenger. Cardiovasc Toxicol. 2007;7(3):202-11. PubMed PMID: 17901563. 18: Siegel D, Kepa JK, Ross D. NAD(P)H:quinone oxidoreductase 1 (NQO1) localizes to the mitotic spindle in human cells. PLoS One. 2012;7(9):e44861. doi: 10.1371/journal.pone.0044861. PubMed PMID: 22984577; PubMed Central PMCID: PMC3439439. 19: Bello RI, Gómez-Díaz C, López-Lluch G, Forthoffer N, Córdoba-Pedregosa MC, Navas P, Villalba JM. Dicoumarol relieves serum withdrawal-induced G0/1 blockade in HL-60 cells through a superoxide-dependent mechanism. Biochem Pharmacol. 2005 Jun 1;69(11):1613-25. PubMed PMID: 15896341. 20: Choi TY, Sohn KC, Kim JH, Kim SM, Kim CH, Hwang JS, Lee JH, Kim CD, Yoon TJ. Impact of NAD(P)H:quinone oxidoreductase-1 on pigmentation. J Invest Dermatol. 2010 Mar;130(3):784-92. doi: 10.1038/jid.2009.280. PubMed PMID: 19759547.