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SML1071

Sigma-Aldrich

ML240

≥98% (HPLC)

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Synonym(s):
2-(2-Amino-1H-benzimidazol-1-yl)-8-methoxy-N-(phenylmethyl)-4-quinazolinamine, CID-49830258
Empirical Formula (Hill Notation):
C23H20N6O
CAS Number:
1346527-98-7
Molecular Weight:
396.44
MDL number:
MFCD28137687
UNSPSC Code:
12352200
PubChem Substance ID:
329825650
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

, white to yellow to light brown

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

NC1=NC2=C(C=CC=C2)N1C3=NC4=C(OC)C=CC=C4C(NCC5=CC=CC=C5)=N3

InChI

1S/C23H20N6O/c1-30-19-13-7-10-16-20(19)27-23(28-21(16)25-14-15-8-3-2-4-9-15)29-18-12-6-5-11-17(18)26-22(29)24/h2-13H,14H2,1H3,(H2,24,26)(H,25,27,28)

InChI key

NHAMBLRUUJAFOY-UHFFFAOYSA-N

Application

ML240 has been used as an inhibitor of D2 ATPase activity of valosin-containing protein.

Biochem/physiol Actions

ML240 is a selective, ATP-competetive inhibitor of AAA ATPase p97, also called valosine containing protein (VCP). The IC50 for p97 inhibition is 110 nM. ML240 rapidly induces activity of Caspases 3 and 7, leading to apoptosis. ML240 has potent antiproliferative activity towards NCI-60 cancer cell lines.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Specific mutations in the D1?D2 linker region of VCP/p97 enhance ATPase activity and confer resistance to VCP inhibitors.
Bastola P, et al.
Cell Death & Disease, 3, 17065-17065 (2017)
Feng Wang et al.
ChemMedChem, 15(8), 685-694 (2020-03-13)
A major challenge of targeted cancer therapy is the selection for drug-resistant mutations in tumor cells leading to loss of treatment effectiveness. p97/VCP is central regulator of protein homeostasis and a promising anticancer target because of its vital role in
Pratikkumar H Vekaria et al.
Leukemia, 33(7), 1675-1686 (2019-01-22)
p97 is an ATPase that works in concert with histone deacetylase 6 (HDAC6), to facilitate the degradation of misfolded proteins by autophagosomes. p97 has also been implicated in DNA repair and maintaining genomic stability. In this study, we determined the
Jasmine Harley et al.
Brain communications, 3(3), fcab166-fcab166 (2021-08-17)
RNA binding proteins have been shown to play a key role in the pathogenesis of amyotrophic lateral sclerosis (ALS). Mutations in valosin-containing protein (VCP/p97) cause ALS and exhibit the hallmark nuclear-to-cytoplasmic mislocalization of RNA binding proteins (RBPs). However, the mechanism
Xiaojun Wu et al.
Cell chemical biology, 27(5), 571-585 (2020-04-04)
Interferon-induced transmembrane protein 3 (IFITM3) is a key interferon effector that broadly prevents infection by diverse viruses. However, the cellular factors that control IFITM3 homeostasis and antiviral activity have not been fully elucidated. Using site-specific photo-crosslinking and quantitative proteomic analysis
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