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SML2234

Sigma-Aldrich

1S,3R-RSL 3

≥98% (HPLC), powder, GPx4 inhibitor

Synonyme(s) :

RAS-selective lethal, RSL3, (1S, 3R)-2-(2-Chloroacetyl)-2,3,4,9-tetrahydro-1-[4-(methoxycarbonyl)phenyl]-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester

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About This Item

Formule empirique (notation de Hill):
C23H21ClN2O5
Numéro CAS:
1219810-16-8
Poids moléculaire :
440.88
Numéro MDL:
MFCD30187526
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Nom du produit

1S,3R-RSL 3, ≥98% (HPLC)

Essai

≥98% (HPLC)

Forme

powder

Activité optique

[α]/D 9.0 to 15.0°, c = 0.5 in methanol

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

ClCC(=O)N1[C@H](Cc2c3c([nH]c2[C@@H]1c4ccc(cc4)C(=O)OC)cccc3)C(=O)OC

Clé InChI

TXJZRSRTYPUYRW-NQIIRXRSSA-N

Description générale

Ras-selective lethal small molecule 3 (RSL3) induces ferroptosis by inhibiting the activity of glutathione peroxidase 4 (GPx4). RSL3 not only activates ferroptosis but also blocks the activation of the mammalian target of rapamycin (mTOR) signaling pathway through interactions with GPX4. In thyroid cancer cell lines, RSL3 decreases cell viability, inhibits spheroid formation, and disrupts cell migration in vitro.

Application

1S,3R-RSL 3 has been used:
  • as a glutathione peroxidase 4 (GPX4) inhibitor to study its effects on cell death in subventricular glioblastoma multiforme (GBM) lines
  • GPX4 inhibitor and ferroptosis inducer to study its effects on cardiomyocyte death and heart failure in mice
  • as a ferroptosis inducer in HT-1080 cellsin cell viability assay

Actions biochimiques/physiologiques

Ferroptosis inducer; inhibits glutathione peroxidase 4 (GPX4)

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000390804
0000383525
0000336732
0000390804
0000383525

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Consulter la Bibliothèque de documents

Wan Seok Yang et al.
Chemistry & biology, 15(3), 234-245 (2008-03-22)
We screened small molecules to identify two compounds, which we named RSL3 and RSL5, that have increased lethality in the presence of oncogenic RAS. Counter screening with biologically active compounds defined aspects of the mechanism of action for RSL3 and
Nery Jara et al.
Journal of cellular physiology, 236(8), 5801-5817 (2021-01-13)
Glioblastoma multiforme (GBM) is the most common and aggressive brain tumor with a median survival of 14.6 months. GBM is highly resistant to radio- and chemotherapy, and remains without a cure; hence, new treatment strategies are constantly sought. Vitamin C
Inactivation of the glutathione peroxidase GPx4 by the ferroptosis-inducing molecule RSL3 requires the adaptor protein 14-3-3?
Vuckovic AM, et al.
Febs Letters (2020)
Ryosuke Shintoku et al.
Cancer science, 108(11), 2187-2194 (2017-08-25)
In cancer cells the small compounds erastin and RSL3 promote a novel type of cell death called ferroptosis, which requires iron-dependent accumulation of lipid reactive oxygen species. Here we assessed the contribution of lipid peroxidation activity of lipoxygenases (LOX) to
Hao Zheng et al.
Redox biology, 48, 102175-102175 (2021-11-05)
Ferroptosis is a form of regulated cell necrosis, as a consequence of Fe(II)-dependent lipid peroxidation. Although ferroptosis has been linked to cancer cell death, neurodegeneration and reperfusion injury, physiological roles of ferroptosis have not been elucidated to date mostly due
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