Q-VD-OPh hydrate Chemical Properties

Boiling point:

808.9±65.0 °C(Predicted)

Density 

1.346±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

-20°C

solubility 

DMSO: ≥14mg/mL

pka

3.92±0.19(Predicted)

form 

powder

color 

white to light brown

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.

InChIKey

OOBJCYKITXPCNS-REWPJTCUSA-N

SMILES

C(O)(=O)C[C@H](NC(=O)[C@@H](NC(C1C=CC2C(N=1)=CC=CC=2)=O)C(C)C)C(=O)COC1=C(F)C=CC=C1F

Safety Information

WGK Germany 

3

Q-VD-OPh hydrate Usage And Synthesis

Description

Q-VD-OPH is a broad-spectrum caspase inhibitor, blocking caspases-3, -7, -8, -9, -10, and -12 and inhibiting apoptosis when used at 10 μM. It more effectively inhibits apoptosis and is much less cytotoxic than Z-VAD-FMK and Boc-D-FMK . Q-VD-OPH can be used in vivo, where it has been shown to prevent ischemia-reperfusion injury-induced apoptosis. This compound, by broadly inhibiting caspases, also promotes the differentiation of leukemic blasts cells, suggesting an application in differentiation therapy of certain forms of cancer.

Uses

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

Uses

An inhibitor that is used in Alzheimer’s studies relating to caspase-6, the cysteinyl protease involved in neurodegenerative conditions. As well it is an intermediate in the formation of Palinavir, a potent HIV protease inhibitor.

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.

target

caspase-1

storage

+4°C

References

[1] T. M. CASERTA. Q-VD-OPh, a broad spectrum caspase inhibitor with potent antiapoptotic properties[J]. Apoptosis, 2003, 8 4: 345-352. DOI:10.1023/a:1024116916932
[2] JOHANN SEBASTIAN BRAUN . Protection from brain damage and bacterial infection in murine stroke by the novel caspase-inhibitor Q-VD-OPH[J]. Experimental Neurology, 2007, 206 2: Pages 183-191. DOI:10.1016/j.expneurol.2007.03.032
[3] ABDELHADI REBBAA. Caspase inhibition switches doxorubicin-induced apoptosis to senescence[J]. Oncogene, 2003, 22 18: 2805-2811. DOI:10.1038/sj.onc.1206366
[4] IVANA BULATOVIC. Sublethal caspase activation promotes generation of cardiomyocytes from embryonic stem cells.[J]. PLoS ONE, 2015: e0120176. DOI:10.1371/journal.pone.0120176
[5] LIANE JENNIFER BAILEY. Augmented trophoblast cell death in preeclampsia can proceed via ceramide-mediated necroptosis[J]. Cell Death & Disease, 2017, 8 2: e2590-e2590. DOI:10.1038/cddis.2016.483

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