Skip to Content
Merck

SML2234

1S,3R-RSL 3

≥98% (HPLC), powder, GPx4 inhibitor

Synonym(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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C23H21ClN2O5
CAS Number:
1219810-16-8
Molecular Weight:
440.88
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD30187526
Assay:
≥98% (HPLC)
Form:
powder

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

1S,3R-RSL 3, ≥98% (HPLC)

SMILES string

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

InChI key

TXJZRSRTYPUYRW-NQIIRXRSSA-N

assay

≥98% (HPLC)

form

powder

optical activity

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

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

Related Categories

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

Biochem/physiol Actions

Ferroptosis inducer; inhibits glutathione peroxidase 4 (GPX4)

General description

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

SML2234-BULK: + SML2234-25MG: + SML2234-VAR: + SML2234-5MG:

jan

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000481959
0000481959
0000476723
0000476722
0000476722

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
Enyong Dai et al.
Biochemical and biophysical research communications, 522(2), 415-421 (2019-11-26)
Ferroptosis is a form of regulated cell death that is triggered by iron accumulation and lipid peroxidation. Although plasma membrane injuries represent an important event in cell death, the impact of membrane repair mechanisms on ferroptosis remains unidentified. Here, we
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service