QVD-OPH
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MedKoo CAT#: 526845

CAS#: 1135695-98-5

Description: QVD-OPH, also known as Quinoline-Val-Asp-Difluorophenoxymethylketone, is a broad spectrum caspase inhibitor with potent antiapoptotic properties. Q-VD-OPh prevents neonatal stroke in P7 rat: a role for gender. Q-VD-OPh has anti-leukemia effects and can interact with vitamin D analogs to increase HPK1 signaling in AML cells. Q-VD-OPh reduces trauma-induced apoptosis and improves the recovery of hind-limb function in rats after spinal cord injury.

Chemical Structure

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QVD-OPH
CAS# 1135695-98-5
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 526845
Name: QVD-OPH
CAS#: 1135695-98-5
Chemical Formula: C26H25F2N3O6
Exact Mass: 513.17
Molecular Weight: 513.600
Elemental Analysis: C, 60.82; H, 4.91; F, 7.40; N, 8.18; O, 18.69

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2850 Ready to ship
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Synonym: QVD-OPH; Q-VD-OPH; Quinoline-Val-Asp-Difluorophenoxymethylketone. quinoline-val-asp(OMe)-CH2-OPH.

IUPAC/Chemical Name: (3S)-5-(2,6-difluorophenoxy)-3-[[(2S)-3-methyl-1-oxo-2-[(2-quinolinylcarbonyl)amino]butyl]amino]-4-oxo-pentanoic acid

InChi Key: OOBJCYKITXPCNS-REWPJTCUSA-N

InChi Code: InChI=1S/C26H25F2N3O6/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)/t20-,23-/m0/s1

SMILES Code: O=C(O)C[C@H](NC([C@@H](NC(C1=NC2=CC=CC=C2C=C1)=O)C(C)C)=O)C(COC3=C(F)C=CC=C3F)=O

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Inhibits caspase 7 with an IC50 of 48 nM and 25-400 nM for other caspases including caspase 1, 3, 8, 9, 10, and 12.
In vitro activity: Simultaneous addition of Q-VD-OPh at <50 nM concentration was sufficient to fully inhibit caspase-3 and -7 activity which was assessed using the fluorogenic substrateAc-DEVD-AFC (Fig. 1). Anti-caspase-3 immunoblots (Fig. 3) showed that Q-VD-OPh binds to the large caspase-3 subunit andeven prevents the procaspase-3 processing. The active caspase-3 isproduced by proteolytic cleavage of the proenzyme (32 kDa) atAsp175 into the 12 kDa subunit and a 20 kDa fragment andsubsequent two-step autoprocessing of the latter fragment into themature 17 kDa subunit [Fernandes-Alnemri et al., 1996; Han et al.,1997]. The antibody we used detects an epitope within the 17 kDasubunit which contains the reactive cysteine. Covalent binding ofthe inhibitor Q-VD-OPh to the cysteine results in a very slight shift (about 0.3 kDa) of the detected band to the higher MW. As shown inFigure 3, Q-VD-OPh also prevents the autoprocessing of the 20 and18.5 kDa fragments into the 17 kDa subunit. Moreover, at 10 mMconcentration, Q-VD-OPh inhibits the protease responsible for theinitial procaspase3 cleavage (possibly one of the initiator caspases orgranzyme B). Reference: J Cell Biochem. 2011 Nov;112(11):3334-42. https://onlinelibrary.wiley.com/doi/abs/10.1002/jcb.23263
In vivo activity: Analysis of 12 month-old TgCRND8 mice, which represent an early-onset animal model for AD, indicated the activation of caspase-7 as well as the cleavage of tau and the amyloid precursor protein (APP). Having established that TgCRND8 mice represent a suitable model system to target caspases therapeutically, a prophylactic study was initiated utilizing Q-VD-OPh. Three month-old TgCRND8 mice were injected intraperitoneally three times a week for three months with 10 mg/kg Q-VD-OPh and compared to control mice injected with vehicle. Although there was no apparent effect on extracellular Abeta deposition, chronic treatment with Q-VD-OPh did prevent caspase-7 activation and limited the pathological changes associated with tau, including caspase cleavage. These preliminary findings suggest that further studies examining the utility of Q-VD-OPh as a potential therapeutic compound for the treatment of AD are warranted. Reference: Int J Clin Exp Med. 2009 Nov 5;2(4):300-8. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2802048/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 100.0 194.75
Ethanol 100.0 194.75

Preparing Stock Solutions

The following data is based on the product molecular weight 513.60 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Kuželová K, Grebeňová D, Brodská B. Dose-dependent effects of the caspase inhibitor Q-VD-OPh on different apoptosis-related processes. J Cell Biochem. 2011 Nov;112(11):3334-42. doi: 10.1002/jcb.23263. PMID: 21751237. 2. Chen-Deutsch X, Kutner A, Harrison JS, Studzinski GP. The pan-caspase inhibitor Q-VD-OPh has anti-leukemia effects and can interact with vitamin D analogs to increase HPK1 signaling in AML cells. Leuk Res. 2012 Jul;36(7):884-8. doi: 10.1016/j.leukres.2012.03.023. Epub 2012 Apr 26. PMID: 22541691; PMCID: PMC3361643. 3. Rohn TT, Kokoulina P, Eaton CR, Poon WW. Caspase activation in transgenic mice with Alzheimer-like pathology: results from a pilot study utilizing the caspase inhibitor, Q-VD-OPh. Int J Clin Exp Med. 2009 Nov 5;2(4):300-8. PMID: 20057974; PMCID: PMC2802048. 4. Melnikov VY, Faubel S, Siegmund B, Lucia MS, Ljubanovic D, Edelstein CL. Neutrophil-independent mechanisms of caspase-1- and IL-18-mediated ischemic acute tubular necrosis in mice. J Clin Invest. 2002 Oct;110(8):1083-91. doi: 10.1172/JCI15623. PMID: 12393844; PMCID: PMC150794.
In vitro protocol: 1. Kuželová K, Grebeňová D, Brodská B. Dose-dependent effects of the caspase inhibitor Q-VD-OPh on different apoptosis-related processes. J Cell Biochem. 2011 Nov;112(11):3334-42. doi: 10.1002/jcb.23263. PMID: 21751237. 2. Chen-Deutsch X, Kutner A, Harrison JS, Studzinski GP. The pan-caspase inhibitor Q-VD-OPh has anti-leukemia effects and can interact with vitamin D analogs to increase HPK1 signaling in AML cells. Leuk Res. 2012 Jul;36(7):884-8. doi: 10.1016/j.leukres.2012.03.023. Epub 2012 Apr 26. PMID: 22541691; PMCID: PMC3361643.
In vivo protocol: 1. Rohn TT, Kokoulina P, Eaton CR, Poon WW. Caspase activation in transgenic mice with Alzheimer-like pathology: results from a pilot study utilizing the caspase inhibitor, Q-VD-OPh. Int J Clin Exp Med. 2009 Nov 5;2(4):300-8. PMID: 20057974; PMCID: PMC2802048. 2. Melnikov VY, Faubel S, Siegmund B, Lucia MS, Ljubanovic D, Edelstein CL. Neutrophil-independent mechanisms of caspase-1- and IL-18-mediated ischemic acute tubular necrosis in mice. J Clin Invest. 2002 Oct;110(8):1083-91. doi: 10.1172/JCI15623. PMID: 12393844; PMCID: PMC150794.

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1 Saunders TL, Windley SP, Gervinskas G, Balka KR, Rowe C, Lane R, Tailler M, Nguyen TN, Ramm G, Lazarou M, De Nardo D, Kile BT, McArthur K. Exposure of the inner mitochondrial membrane triggers apoptotic mitophagy. Cell Death Differ. 2024 Feb 23. doi: 10.1038/s41418-024-01260-2. Epub ahead of print. PMID: 38396150.

2. McArthur K, Whitehead LW, Heddleston JM, Li L, Padman BS, Oorschot V, Geoghegan ND, Chappaz S, Davidson S, San Chin H, Lane RM, Dramicanin M, Saunders TL, Sugiana C, Lessene R, Osellame LD, Chew TL, Dewson G, Lazarou M, Ramm G, Lessene G, Ryan MT, Rogers KL, van Delft MF, Kile BT. BAK/BAX macropores facilitate mitochondrial herniation and mtDNA efflux during apoptosis. Science. 2018 Feb 23;359(6378):eaao6047. doi: 10.1126/science.aao6047. PMID: 29472455.