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SML0031

Sigma-Aldrich

DBeQ

≥98% (HPLC)

Synonym(s):

JRF 12, N2,N4-dibenzylquinazoline-2,4-diamine

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About This Item

Empirical Formula (Hill Notation):
C22H20N4
CAS Number:
177355-84-9
Molecular Weight:
340.42
MDL number:
MFCD03691820
UNSPSC Code:
12352200
PubChem Substance ID:
329825101
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: ≥20 mg/mL

storage temp.

room temp

SMILES string

C(Nc1nc(NCc2ccccc2)c3ccccc3n1)c4ccccc4

InChI

1S/C22H20N4/c1-3-9-17(10-4-1)15-23-21-19-13-7-8-14-20(19)25-22(26-21)24-16-18-11-5-2-6-12-18/h1-14H,15-16H2,(H2,23,24,25,26)

InChI key

QAIMUUJJAJBPCL-UHFFFAOYSA-N

Application

HeLa cells were treated with DBeQ and the effects on in vivo ubiquitination and protein dislocation were studied by live cell imaging.

Biochem/physiol Actions

DBeQ is a potent and specific inhibitor of ATPase p97, an integral component of the ubiquitin-fusion degradation (UFD) pathway. DBeQ inhibits the degradation of ubiquitinated proteins, the endoplasmic reticulum-associated degradation pathway, and autophagosome maturation. The compound also potently inhibits cellular proliferation and induces caspase 3/7 activity and apoptosis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Ainoa Figuerola-Conchas et al.
ACS chemical biology, 15(1), 243-253 (2019-12-04)
VCP/p97 belongs to the AAA+ ATPase family and has an essential role in several cellular processes ranging from cell division to protein homeostasis. Compounds targeting p97 inhibit the main ATPase domain and cause cell death. Here, using PNA-encoded chemical libraries
Holger W Auner et al.
PloS one, 8(9), e74415-e74415 (2013-09-27)
Inhibition of the proteasome is a widely used strategy for treating multiple myeloma that takes advantage of the heavy secretory load that multiple myeloma cells (MMCs) have to deal with. Resistance of MMCs to proteasome inhibition has been linked to
Ajit Tiwari et al.
Scientific reports, 6, 38681-38681 (2016-12-09)
Caveolin-1 (Cav1) drives the formation of flask-shaped membrane invaginations known as caveolae that participate in signaling, clathrin-independent endocytosis and mechanotransduction. Overexpression or mutations of Cav1 can lead to its mistrafficking, including its accumulation in a perinuclear compartment previously identified as
Stephanie L Moon et al.
The Journal of cell biology, 219(8) (2020-06-11)
Stress granules are dynamic assemblies of proteins and nontranslating RNAs that form when translation is inhibited in response to diverse stresses. Defects in ubiquitin-proteasome system factors including valosin-containing protein (VCP) and the proteasome impact the kinetics of stress granule induction
Sandra Loaiza et al.
Biomaterials, 183, 102-113 (2018-08-29)
Cellular function depends on the maintenance of protein homeostasis (proteostasis) by regulated protein degradation. Chronic dysregulation of proteostasis is associated with neurodegenerative and age-related diseases, and drugs targeting components of the protein degradation apparatus are increasingly used in cancer therapies.
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