SML1995
Capzimin dimer
≥96% (HPLC)
Synonym(s):
8,8′-Disulfanediylbis(N-(2-(thiazol-2-yl)ethyl)quinoline-3-carboxamide)
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About This Item
Empirical Formula (Hill Notation):
C30H24N6O2S4
CAS Number:
Molecular Weight:
628.81
UNSPSC Code:
12352200
NACRES:
NA.77
Recommended Products
assay
≥96% (HPLC)
form
powder
storage condition
desiccated
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
2-8°C
SMILES string
O=C(NCCC1=NC=CS1)C2=CC3=CC=CC(SSC4=C(N=CC(C(NCCC5=NC=CS5)=O)=C6)C6=CC=C4)=C3N=C2
Biochem/physiol Actions
Capzimin can be used as a therapeutic for cancer treatment.
Capzimin dimer is the stable precursor form of capzimin. Capzimin is a selective inhibitor of proteasome isopeptidase Rpn11, a proteasomal deubiquitinase that is part of the proteosome 19S regulatory particle subunit that removes the polyubiquitin chain from substrates in preparation for degradation. Capzimin was shown to have an IC50 value of 340 nM and have selectivity over related enzymes with 80-fold selectivity for Rpn11 over Csn5, ten-fold over AMSH and six-fold over BRCC36. It stabilized proteasome substrates that would otherwise have been degraded, induced an unfolded protein response, and blocked the proliferation of cancer cells, including some that had become resistant to bortezomib. Capzimin dimer will be quickly reduced to capzimin by glutathione in cell-based systems; DTT should be added to in vitro assays to reduce the disulfide.
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
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Jing Li et al.
Nature chemical biology, 13(5), 486-493 (2017-03-01)
The proteasome is a vital cellular machine that maintains protein homeostasis, which is of particular importance in multiple myeloma and possibly other cancers. Targeting of proteasome 20S peptidase activity with bortezomib and carfilzomib has been widely used to treat myeloma.
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