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Description: Necroptosis inhibitor; also inhibits pyroptosis
Chemical Name: (2E)-N-[4-[[(3-Methoxy-2-pyrazinyl)amino]sulfonyl]phenyl]-3-(5-nitro-2-thienyl)-2-propenamide
Purity: ≥98% (HPLC)
Citations (19)
Reviews (1)
Literature (1)
Pathways (1)

Biological Activity for Necrosulfonamide

Necrosulfonamide is a necroptosis inhibitor. Blocks mixed lineage kinase domain-like protein (MLKL), a critical substrate of receptor-interacting serine-threonine kinase 3 (RIP3) during necrosis. Prevents MLKL-RIP1-RIP3 necrosome complex from interacting with downstream necrosis effectors. Binds and inhibits gasdermin D. Inhibits pyroptosis.

Technical Data for Necrosulfonamide

M. Wt 461.47
Formula C18H15N5O6S2
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 1360614-48-7
PubChem ID 1566236
Smiles O=C(NC2=CC=C(S(NC3=C(OC)N=CC=N3)(=O)=O)C=C2)/C=C/C1=CC=C([N+]([O-])=O)S1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for Necrosulfonamide

Solvent Max Conc. mg/mL Max Conc. mM
DMSO 9.23 20

Preparing Stock Solutions for Necrosulfonamide

The following data is based on the product molecular weight 461.47. 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.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.2 mM 10.83 mL 54.17 mL 108.35 mL
1 mM 2.17 mL 10.83 mL 21.67 mL
2 mM 1.08 mL 5.42 mL 10.83 mL
10 mM 0.22 mL 1.08 mL 2.17 mL

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Product Datasheets for Necrosulfonamide

Certificate of Analysis / Product Datasheet
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References for Necrosulfonamide

References are publications that support the biological activity of the product.

Zhou et al (2012) New components of the necroptotic pathway. Protein Cell 3 811 PMID: 23073834

Sun et al (2012) Mixed lineage kinase domain-like protein mediates necrosis signaling downstream of RIP3 kinase. Cell 148 213 PMID: 22265413

Kreuzaler et al (2012) Killing a cancer: what are the alternatives? Nat.Rev.Cancer. 12 411 PMID: 22576162

Pandeya et al (2019) Gasdermin D (GSDMD) as a new target for the treatment of infection. Medchemcomm 10 660 PMID: 31191857

If you know of a relevant reference for Necrosulfonamide, please let us know.

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Keywords: Necrosulfonamide, Necrosulfonamide supplier, non-apoptotic, cell, death, necroptosis, necrosis, necrosome, mixed, lineage, kinase, domain-like, protein, MLKL, receptor, interacting, serine, threonine, kinases, 3, RIP3, Gasdermin, D, GSDMD, pyroptosis, inhibitors, inhibits, Necroptosis, Inflammasomes, 5025, Tocris Bioscience

19 Citations for Necrosulfonamide

Citations are publications that use Tocris products. Selected citations for Necrosulfonamide include:

Kevin S et al (2020) Influenza-Induced Oxidative Stress Sensitizes Lung Cells to Bacterial-Toxin-Mediated Necroptosis. Cell Rep 32 108062 PMID: 32846120

Tanya A et al (2020) Lytic Cell Death Mechanisms in Human Respiratory Syncytial Virus-Infected Macrophages: Roles of Pyroptosis and Necroptosis. Viruses 12 PMID: 32854254

Kyung-Min et al (2020) Combined the SMAC mimetic and BCL2 inhibitor sensitizes neoadjuvant chemotherapy by targeting necrosome complexes in tyrosine aminoacyl-tRNA synthase-positive breast cancer. Breast Cancer Res 22 130 PMID: 33239070

James et al (2020) Locking mixed-lineage kinase domain-like protein in its auto-inhibited state prevents necroptosis. Proc Natl Acad Sci U S A 117 33272-33281 PMID: 33318170

Gonzalez-Juarbe et al (2015) Pore-Forming Toxins Induce Macrophage Necroptosis during Acute Bacterial Pneumonia. Channels (Austin) 11 e1005337 PMID: 26659062

Simon et al (2023) PRMT5-mediated regulatory arginine methylation of RIPK3. Cell Death Discov 9 14 PMID: 36658119

Yuan et al (2023) Necroptotic kinases are involved in the reduction of depression-induced astrocytes and fluoxetine's inhibitory effects on necroptotic kinases. Front Pharmacol 13 1060954 PMID: 36686688

Bittner et al (2016) Death receptor 3 mediates necroptotic cell death. Cellular and Molecular Life Sciences PMID: 27592300

Bagnjuk et al (2019) Necroptosis in primate luteolysis: a role for ceramide. Cell Death Discov 5 67 PMID: 30774995

Greer et al (2018) ONC201 kills breast cancer cells in vitro by targeting mitochondria. Oncotarget 9 18454 PMID: 29719618

Heulot et al (2016) The TAT-RasGAP317-326 anti-cancer peptide can kill in a caspase-, apoptosis-, and necroptosis-independent manner. Oncotarget 7 64342 PMID: 27602963

Junying et al (2021) RIPK1 Promotes Energy Sensing by the mTORC1 Pathway. Mol Cell 81 370-385.e7 PMID: 33271062

Ferenc et al (2021) Caspase-9 acts as a regulator of necroptotic cell death. FEBS J 288 6476-6491 PMID: 33899329

Michael E et al (2021) Overexpression screen of interferon-stimulated genes identifies RARRES3 as a restrictor of Toxoplasma gondii infection. Elife 10 PMID: 34871166

Chefetz et al (2019) A Pan-ALDH1A Inhibitor Induces Necroptosis in Ovarian Cancer Stem-like Cells. Cell Rep 26 3061 PMID: 30865894

Gonzalez-Juarbe et al (2017) Pore-forming toxin-mediated ion dysregulation leads to death receptor-independent necroptosis of lung epithelial cells during bacterial pneumonia. Cell Death Differ 24 917 PMID: 28387756

Xie et al (2017) The Tumor Suppressor p53 Limits Ferroptosis by Blocking DPP4 Activity. Cell Rep 20 1692 PMID: 28813679

Svetlana et al (2022) A family of conserved bacterial virulence factors dampens interferon responses by blocking calcium signaling. Cell 185 2354-2369.e17 PMID: 35568036

Charles E et al (2019) Upregulation of human glycolipid transfer protein (GLTP) induces necroptosis in colon carcinoma cells. Biochim Biophys Acta Mol Cell Biol Lipids 1864 158-167 PMID: 30472325

Do you know of a great paper that uses Necrosulfonamide from Tocris? Please let us know.

Reviews for Necrosulfonamide

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Necrosulfonamide work well to block pyroptosis.
By Xiaogang Wang on 06/12/2020
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: THP-1 cell line

We used Necrosulfonamide as a positive control to inhibit the induction of pyroptosis by staphylococcal cytolysin. Differentiated THP-1 cells were pretreated with 25uM Necrosulfonamide (NSA) for 1 h before treating with or without 1 ug/ml Staphylococcal pore-forming toxin for 4 h. The LDH release in culture supernatants of treated cells was measured. Our data indicated that Necrosulfonamide treatment can significantly inhibit staphylococcal cytolysin induced pyroptosis.

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Literature in this Area

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Programmed Cell Death Poster

Programmed Cell Death Poster

There are two currently recognized forms of programmed cell death: apoptosis and necroptosis. This poster summarizes the signaling pathways involved in apoptosis, necroptosis and cell survival following death receptor activation, and highlights the influence of the molecular switch, cFLIP, on cell fate.

Pathways for Necrosulfonamide

Toll-like Receptor Signaling Pathway

Toll-like Receptor Signaling Pathway

TLR signaling is involved in the cellular response to threatening molecules such as bacteria and viruses. It results in an inflammatory and immmunological response.