SML0063
Q-VD-OPh hydrate
≥95% (HPLC), powder, pan-caspase inhibitor
Synonym(s):
5-(2,6-Difluorophenoxy)-3-[[3-methyl-1-oxo-2-[(2-quinolinylcarbonyl)amino]butyl]amino]-4-oxo-pentanoic acid hydrate
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About This Item
Empirical Formula (Hill Notation):
C26H25F2N3O6 · xH2O
CAS Number:
Molecular Weight:
513.49 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Product Name
Q-VD-OPh hydrate, ≥95% (HPLC)
Quality Level
assay
≥95% (HPLC)
form
powder
storage condition
desiccated
color
white to light brown
solubility
DMSO: ≥14 mg/mL
shipped in
wet ice
storage temp.
−20°C
SMILES string
O=C(NC(C(C)C)C(NC(C(COC1=C(F)C=CC=C1F)=O)CC(O)=O)=O)C2=NC3=CC=CC=C3C=C2.[H]O[H]
InChI
1S/C26H25F2N3O6.H2O/c1-14(2)23(31-25(35)19-11-10-15-6-3-4-9-18(15)29-19)26(36)30-20(12-22(33)34)21(32)13-37-24-16(27)7-5-8-17(24)28;/h3-11,14,20,23H,12-13H2,1-2H3,(H,30,36)(H,31,35)(H,33,34);1H2/t20-,23-;/m0./s1
InChI key
ONOTWLLTFZMERH-WCRWPNQISA-N
Application
Q-VD-OPh hydrate has been used:
- as a pan-caspase inhibitor to prevent cell death in urothelial carcinoma cells (UCC)
- to induce canonical caspase-dependent apoptosis in UC cells
- to block caspase-3 and Poly (ADP-ribose) polymerase-1 (PARP-1)
- to study the protective role of EspZ effector protein against apoptosis and necrosis in human epithelial cells
Biochem/physiol Actions
Pan-caspase inhibitor.
Q-VD-OPh is a potent pan-caspase inhibitor that protects cells from capsase-dependent apoptosis. Q-VD-OPh has superior aqueous stability, cell permeability, and efficacy than FMK-based caspase inhibitors and displays no cytotoxic effects alone.
Features and Benefits
This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Caspases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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The cyanobacterial metabolite nocuolin A is a natural oxadiazine that triggers apoptosis in human cancer cells
Voracova K, et al.
PLoS ONE, 12(3), e0172850-e0172850 (2017)
Jennifer Lising Roxas et al.
Infection and immunity, 80(11), 3850-3857 (2012-08-22)
The diarrheagenic pathogen enteropathogenic Escherichia coli (EPEC) limits the death of infected enterocytes early in infection. A number of bacterial molecules and host signaling pathways contribute to the enhanced survival of EPEC-infected host cells. EspZ, a type III secreted effector
Inhibition of class I histone deacetylases 1 and 2 promotes urothelial carcinoma cell death by various mechanisms
Pinkerneil M, et al.
Molecular Cancer Therapeutics, 15(2), 299-312 (2016)