SML2682
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:
Molecular Weight:
428.45
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
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
InChI
1S/C26H21FN2O3/c1-17(30)29(16-19-11-13-20(27)14-12-19)24-23(28-15-18-7-3-2-4-8-18)25(31)21-9-5-6-10-22(21)26(24)32/h2-14,28H,15-16H2,1H3
InChI key
COATXBHZYVUJQP-UHFFFAOYSA-N
Biochem/physiol Actions
Orally active, brain-penetrant, GBM CSCs-selective apoptosis inducer with efficacy in a murine orthotopic xenograft model of glioblastoma multiforme in vivo.
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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SML2682-25MG | 04061841217367 |
| SML2682-5MG | 04061841217374 |