NSC697923 | CAS# 343351-67-7 | Ubiquitin E2 Inhibitor

MedKoo Cat#: 571062 | Name: NSC697923

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Description:

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

NSC697923 is a ubiquitin-conjugating enzyme E2 (UBE2) inhibitor. It impedes the formation of the Ubc13 and ubiquitin thioester conjugate and suppresses constitutive NF-κB activity in ABC-DLBCL cells. Importantly, NSC697923 inhibits the proliferation and survival of Diffuse Large B-cell Lymphoma cells and has the ability to induce apoptosis. It can also induce nuclear accumulation of p53, which led to its increased transcriptional activity and tumor suppressor function.

Chemical Structure

NSC697923

CAS#343351-67-7

Theoretical Analysis

MedKoo Cat#: 571062

Name: NSC697923

CAS#: 343351-67-7

Chemical Formula: C11H9NO5S

Exact Mass: 267.0201

Molecular Weight: 267.26

Elemental Analysis: C, 49.44; H, 3.39; N, 5.24; O, 29.93; S, 12.00

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 200.00
25mg	USD 290.00

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Related CAS #

No Data

Synonym

NSC697923; NSC 697923; NSC-697923

IUPAC/Chemical Name

2-[(4-Methylphenyl)sulfonyl]-5-nitrofuran

InChi Key

GAUHIPWCDXOLCZ-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H9NO5S/c1-8-2-4-9(5-3-8)18(15,16)11-7-6-10(17-11)12(13)14/h2-7H,1H3

SMILES Code

O=[N+](C1=CC=C(S(=O)(C2=CC=C(C)C=C2)=O)O1)[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

2934.99.9001

More Info

Ubiquitination is an enzymatic post-translational modification in which a ubiquitin protein is attached to a substrate protein. In the protein ubiquitination cascade, ubiquitin (Ub) conjugation to a lysine residue on the target protein is catalyzed three enzymes: ubiquitin-activating enzyme (E1), ubiquitin conjugating enzyme (E2), and ubiquitin ligase (E3). In recent years, a variety of small-molecule inhibitors for ubiquitination have been discovered.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

NSC697923 is a potent UBE2N (ubiquitin-conjugating enzyme E2 N, Ubc13) inhibitor.

In vitro activity:

NSC697923 impedes the formation of the Ubc13 and ubiquitin thioester conjugate and suppresses constitutive NF-κB activity in ABC-DLBCL cells. Importantly, NSC697923 inhibits the proliferation and survival of ABC-DLBCL cells and GCB-DLBCL cells, suggesting the Ubc13-Uev1A may be crucial for DLBCL growth. Reference: Blood. 2012 Aug 23;120(8):1668-77. https://pubmed.ncbi.nlm.nih.gov/22791293/

In vivo activity:

Given the potent cytotoxic effect of NSC697923 on NB cells in vitro, this study proceeded to evaluate its efficacy on inhibiting NB tumor growth in an orthotopic NB mouse model. Two cell lines SH-SY5Y and NGP with stable luciferase gene expression were used in this set of in vivo experiments. At the end of NSC697923 treatment, the xenograft tumors from both control and treatment groups were harvested and weighed. As expected, this study observed significant tumor regression in NSC697923 treatment group of both SH-SY5Y and NGP xenografts (Figures 6a and b). The response of NB xenografts to NSC697923 demonstrates its potent antitumor efficacy as a single agent in vivo. Reference: Cell Death Dis. 2014 Feb 20;5(2):e1079. https://pubmed.ncbi.nlm.nih.gov/24556694/

	Solvent	mg/mL	mM
Solubility
	DMSO	93.2	348.89

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 267.26 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.

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

Formulation protocol:

1. Monda JK, Cheeseman IM. Dynamic regulation of dynein localization revealed by small molecule inhibitors of ubiquitination enzymes. Open Biol. 2018 Sep 26;8(9):180095. doi: 10.1098/rsob.180095. PMID: 30257893; PMCID: PMC6170511. 2. Pulvino M, Liang Y, Oleksyn D, DeRan M, Van Pelt E, Shapiro J, Sanz I, Chen L, Zhao J. Inhibition of proliferation and survival of diffuse large B-cell lymphoma cells by a small-molecule inhibitor of the ubiquitin-conjugating enzyme Ubc13-Uev1A. Blood. 2012 Aug 23;120(8):1668-77. doi: 10.1182/blood-2012-02-406074. Epub 2012 Jul 12. PMID: 22791293; PMCID: PMC3429308. 3. Cao DY, Zhang ZH, Li RZ, Shi XK, Xi RY, Zhang GL, Li F, Wang F. A small molecule inhibitor of caspase-1 inhibits NLRP3 inflammasome activation and pyroptosis to alleviate gouty inflammation. Immunol Lett. 2022 Apr;244:28-39. doi: 10.1016/j.imlet.2022.03.003. Epub 2022 Mar 11. PMID: 35288207. 4. Cheng J, Fan YH, Xu X, Zhang H, Dou J, Tang Y, Zhong X, Rojas Y, Yu Y, Zhao Y, Vasudevan SA, Zhang H, Nuchtern JG, Kim ES, Chen X, Lu F, Yang J. A small-molecule inhibitor of UBE2N induces neuroblastoma cell death via activation of p53 and JNK pathways. Cell Death Dis. 2014 Feb 20;5(2):e1079. doi: 10.1038/cddis.2014.54. PMID: 24556694; PMCID: PMC3944268

In vitro protocol:

In vivo protocol:

1. Cao DY, Zhang ZH, Li RZ, Shi XK, Xi RY, Zhang GL, Li F, Wang F. A small molecule inhibitor of caspase-1 inhibits NLRP3 inflammasome activation and pyroptosis to alleviate gouty inflammation. Immunol Lett. 2022 Apr;244:28-39. doi: 10.1016/j.imlet.2022.03.003. Epub 2022 Mar 11. PMID: 35288207. 2. Cheng J, Fan YH, Xu X, Zhang H, Dou J, Tang Y, Zhong X, Rojas Y, Yu Y, Zhao Y, Vasudevan SA, Zhang H, Nuchtern JG, Kim ES, Chen X, Lu F, Yang J. A small-molecule inhibitor of UBE2N induces neuroblastoma cell death via activation of p53 and JNK pathways. Cell Death Dis. 2014 Feb 20;5(2):e1079. doi: 10.1038/cddis.2014.54. PMID: 24556694; PMCID: PMC3944268

1: Hodge CD, Edwards RA, Markin CJ, McDonald D, Pulvino M, Huen MS, Zhao J, Spyracopoulos L, Hendzel MJ, Glover JN. Covalent Inhibition of Ubc13 Affects Ubiquitin Signaling and Reveals Active Site Elements Important for Targeting. ACS Chem Biol. 2015 Jul 17;10(7):1718-28. doi: 10.1021/acschembio.5b00222. Epub 2015 May 1. PubMed PMID: 25909880; PubMed Central PMCID: PMC4506735. 2: Pulvino M, Liang Y, Oleksyn D, DeRan M, Van Pelt E, Shapiro J, Sanz I, Chen L, Zhao J. Inhibition of proliferation and survival of diffuse large B-cell lymphoma cells by a small-molecule inhibitor of the ubiquitin-conjugating enzyme Ubc13-Uev1A. Blood. 2012 Aug 23;120(8):1668-77. doi: 10.1182/blood-2012-02-406074. Epub 2012 Jul 12. PubMed PMID: 22791293; PubMed Central PMCID: PMC3429308. 3: Gombodorj N, Yokobori T, Yoshiyama S, Kawabata-Iwakawa R, Rokudai S, Horikoshi I, Nishiyama M, Nakano T. Inhibition of Ubiquitin-conjugating Enzyme E2 May Activate the Degradation of Hypoxia-inducible Factors and, thus, Overcome Cellular Resistance to Radiation in Colorectal Cancer. Anticancer Res. 2017 May;37(5):2425-2436. PubMed PMID: 28476810. 4: Cheng J, Fan YH, Xu X, Zhang H, Dou J, Tang Y, Zhong X, Rojas Y, Yu Y, Zhao Y, Vasudevan SA, Zhang H, Nuchtern JG, Kim ES, Chen X, Lu F, Yang J. A small-molecule inhibitor of UBE2N induces neuroblastoma cell death via activation of p53 and JNK pathways. Cell Death Dis. 2014 Feb 20;5:e1079. doi: 10.1038/cddis.2014.54. PubMed PMID: 24556694; PubMed Central PMCID: PMC3944268. 5: Maculins T, Carter N, Dorval T, Hudson K, Nissink JW, Hay RT, Alwan H. A Generic Platform for Cellular Screening Against Ubiquitin Ligases. Sci Rep. 2016 Jan 8;6:18940. doi: 10.1038/srep18940. PubMed PMID: 26743172; PubMed Central PMCID: PMC4705515. 6: Ritorto MS, Ewan R, Perez-Oliva AB, Knebel A, Buhrlage SJ, Wightman M, Kelly SM, Wood NT, Virdee S, Gray NS, Morrice NA, Alessi DR, Trost M. Screening of DUB activity and specificity by MALDI-TOF mass spectrometry. Nat Commun. 2014 Aug 27;5:4763. doi: 10.1038/ncomms5763. PubMed PMID: 25159004; PubMed Central PMCID: PMC4147353. 7: Pontrelli P, Conserva F, Papale M, Oranger A, Barozzino M, Vocino G, Rocchetti MT, Gigante M, Castellano G, Rossini M, Simone S, Laviola L, Giorgino F, Grandaliano G, Di Paolo S, Gesualdo L. Lysine 63 ubiquitination is involved in the progression of tubular damage in diabetic nephropathy. FASEB J. 2017 Jan;31(1):308-319. doi: 10.1096/fj.201600382RR. Epub 2016 Oct 24. PubMed PMID: 27881486. 8: Chen H, Wu G, Gao S, Guo R, Zhao Z, Yuan H, Liu S, Wu J, Lu X, Yuan X, Yu Z, Zu X, Xie N, Yang N, Hu Z, Sun Q, Zhang W. Discovery of Potent Small-Molecule Inhibitors of Ubiquitin-Conjugating Enzyme UbcH5c from α-Santonin Derivatives. J Med Chem. 2017 Aug 2. doi: 10.1021/acs.jmedchem.6b01829. [Epub ahead of print] PubMed PMID: 28696694.