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N9037

Sigma-Aldrich

Necrostatin-1

≥98% (HPLC)

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Synonym(s):
5-(1H-Indol-3-ylmethyl)-3-methyl-2-thioxo-4-Imidazolidinone, 5-(Indol-3-ylmethyl)-3-methyl-2-thio-Hydantoin, MTH-DL-Tryptophan
Empirical Formula (Hill Notation):
C13H13N3OS
CAS Number:
Molecular Weight:
259.33
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

solubility

DMSO: >10 mg/mL

storage temp.

−20°C

SMILES string

CN1C(=S)NC(Cc2c[nH]c3ccccc23)C1=O

InChI

1S/C13H13N3OS/c1-16-12(17)11(15-13(16)18)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,14H,6H2,1H3,(H,15,18)

InChI key

TXUWMXQFNYDOEZ-UHFFFAOYSA-N

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Necrostatin-1 ≥98% (HPLC)

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Necrostatin-1 Necrostatin-1, CAS 4311-88-0, is a cell-permeable, potent, and selective blocker of necroptosis (EC₅₀ = 494 nM in FADD-deficient Jurkat cells treated with TNF-α).

480065

Necrostatin-1

form

powder

form

powder

form

powder

form

crystalline solid

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: >10 mg/mL

solubility

DMSO: ≥5 mg/mL

solubility

DMSO: >5 mg/mL

solubility

DMSO: 10 mg/mL, methanol: 5 mg/mL

Application

Necrostatin-1has been used to investigate its effect on the regulation of interleukin (IL)-33 expression during liver injury in mice in vivo and in hepatic stellate cells in vitro. It has also been used as an inhibitor of receptor-interacting protein kinase 1 (RIPK1) in experimental studies.

Biochem/physiol Actions

Necrostatin-1(Nec-1) might exhibit therapeutic benefit against patients with traumatic brain injury (TBI). In addition, it might also be used to treat other acute central nervous system (CNS) disorders that feature necroptosis as a mode of cell death. It is extensively used to study the effect of receptor-interacting protein kinase 1 (RIPK1) on cell death and inflammation in experimental disease models. Nec‐1 protects hippocampal (HT‐22) cells from glutamate‐induced oxytosis via increasing cellular glutathione (GSH) levels, decreasing reactive oxygen species production, inhibiting the nuclear translocation of apoptosis‐inducing factor and B-cell lymphoma 2 (Bcl‐2) /adenovirus E1B 19kDa‐interacting protein 3‐related pathways.
Necrostatin-1 is an inhibitor of necroptosis (non-apoptotic cell death pathway).

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Necrostatin-1

Sorafenib-induced defective autophagy promotes cell death by necroptosis
Kharaziha P, et al.
Testing, 6(35), 37066-37066 (2015)
The chemical inhibitors of cellular death, PJ34 and Necrostatin-1, down-regulate IL-33 expression in liver
Arshad MI, et al.
Journal of Molecular Medicine, 93(8), 867-878 (2015)
T Suzuki et al.
Canadian journal of biochemistry, 55(5), 521-527 (1977-05-01)
Proton magnetic resonance spectra of methylthiohydantoin (3-methyl-2-thiohydantoin), thiohydantoin (2-thiohydantoin), and hydantoin derivatives of amino acids were studied in dimethyl sulfoxide-d6. Their parent amino acids could be identified by the spectra. An application to the N- and C-terminal amino acid analysis
Anahita Kyani et al.
ChemMedChem, 13(2), 164-177 (2017-12-14)
Protein disulfide isomerase (PDI) is overexpressed in glioblastoma, the most aggressive form of brain cancer, and folds nascent proteins responsible for the progression and spread of the disease. Herein we describe a novel nanomolar PDI inhibitor, pyrimidotriazinedione 35G8, that is
Necrostatin-1 analogues: critical issues on the specificity, activity and in vivo use in experimental disease models
Takahashi N, et al.
Cell Death & Disease, 3(11), e437-e437 (2012)

Articles

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

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