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SML2682

Sigma-Aldrich

RIPGBM

≥98% (HPLC)

Synonym(s):

N-(3-(Benzylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-(4-fluorobenzyl)acetamide, N-[1,4-Dihydro-1,4-dioxo-3-[(phenylmethyl)amino]-2-naphthalenyl]-N-[(4-fluorophenyl)methyl]acetamide, cRIPGBM precursor

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About This Item

Empirical Formula (Hill Notation):
C26H21FN2O3
CAS Number:
355406-76-7
Molecular Weight:
428.45
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

faint brown to very dark brown-red

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C1C(N(CC2=CC=C(F)C=C2)C(C)=O)=C(NCC3=CC=CC=C3)C(C4=C1C=CC=C4)=O

Biochem/physiol Actions

RIPGBM is a brain-penetrant, orally available, glioblastoma multiforme (GBM) cancer stem cells (CSCs)-selective apoptosis inducer (GBM-1/-5/-39 EC50 = 220/290/890 nM; human neural progenitor cells (NPCs)/astrocytes/lung fibroblasts EC50 = 1.7/2.8/3.5 μM) with in vivo efficacy against intracranial human GBM orthotopic xenograft tumor growth in mice (50 mg/kg bid. po.). RIPGBM undergoes a cell type-selective metabolic redox conversion to preferentially form in GBM CSCs the derivative cRIPGBM that binds receptor-interacting protein kinase 2 (RIPK2, RIP2) and promotes the formation of a proapoptotic RIPK2/caspase-1 complex.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Natasha C Lucki et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(13), 6435-6440 (2019-03-09)
Glioblastoma multiforme (GBM; grade IV astrocytoma) is the most prevalent and aggressive form of primary brain cancer. A subpopulation of multipotent cells termed GBM cancer stem cells (CSCs) play a critical role in tumor initiation, tumor maintenance, metastasis, drug resistance

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