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SML0063

Sigma-Aldrich

Q-VD-OPh hydrate

≥95% (HPLC)

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:
1435786-01-8
Molecular Weight:
513.49 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329825128
NACRES:
NA.77

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Combined inhibition of BET proteins and class I HDACs synergistically induces apoptosis in urothelial carcinoma cell lines
Holscher A S, et al.
Clinical epigenetics, 10(1) (2018)
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)
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
Ifeanyi Jude Ezeonwumelu et al.
International journal of molecular sciences, 23(23) (2022-12-12)
HIV latent infection may be associated with disrupted viral RNA sensing, interferon (IFN) signaling, and/or IFN stimulating genes (ISG) activation. Here, we evaluated the use of compounds selectively targeting at the inhibitor of nuclear factor-κB (IκB) kinase (IKK) complex subunits
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)
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