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Merck
CN

SML2681

cRIPGBM

≥98% (HPLC)

Synonym(s):

1-Benzyl-3-(4-fluorobenzyl)-2-methyl-4,9-dioxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-ium chloride, RIPGBM proapoptic metabolite

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About This Item

Empirical Formula (Hill Notation):
C26H20ClFN2O2
CAS Number:
2361988-77-2
Molecular Weight:
446.90
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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InChI

1S/C26H20FN2O2.ClH/c1-17-28(15-18-7-3-2-4-8-18)23-24(29(17)16-19-11-13-20(27)14-12-19)26(31)22-10-6-5-9-21(22)25(23)30;/h2-14H,15-16H2,1H3;1H/q+1;/p-1

InChI key

IHNGETPFBJHWFE-UHFFFAOYSA-M

SMILES string

O=C1C2=C([N+](CC3=CC=C(F)C=C3)=C(C)N2CC4=CC=CC=C4)C(C5=C1C=CC=C5)=O.[Cl-]

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Biochem/physiol Actions

Apoptosis inducer that binds receptor-interacting protein kinase 2 (RIPK2, RIP2) and promotes the proapoptotic RIPK2/caspase-1 complex formation.
cRIPGBM is an apoptosis inducer (GBM-1/-5/-39 EC50 = 63/95/290 nM; human neural progenitor cells (NPCs)/astrocytes/lung fibroblasts EC50 = 190/710/960 nM) that binds receptor-interacting protein kinase 2 (RIPK2, RIP2) and promotes the formation of a proapoptotic RIPK2/caspase-1 complex. Cell type-selective metabolic redox conversion of RIPGBM to cRIPGBM in glioblastoma multiforme (GBM) cancer stem cells (CSCs) form the basis of selective GBM CSCs apoptosis induction by RIPGBM over non-GBM cultures.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000093064
0000093065
0000080971

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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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