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Antiviral API
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Q-VD-OPH
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| Category | Human immunodeficiency Virus (HIV) |
| CAS | 1135695-98-5 |
| Description | QVD-OPH, also known as Quinoline-Val-Asp-Difluorophenoxymethylketone, is a selective, brain and cell permeable, highly potent and irreversible inhibitor of caspase-3 (IC50 = 25nm), caspase-1 (IC50 = 50nM), caspase-8 (IC50 = 100nM) and caspase-9 (IC50 = 430nM). It can be 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. |
Product Information
| Synonyms | Q-VD-OPH; Quinoline-Val-Asp-Difluorophenoxymethylketone; quinoline-val-asp(OMe)-CH2-OPH |
| IUPAC Name | (3S)-5-(2,6-difluorophenoxy)-3-[[(2S)-3-methyl-2-(quinoline-2-carbonylamino)butanoyl]amino]-4-oxopentanoic acid |
| Molecular Weight | 513.8 |
| Molecular Formula | C26H25F2N3O6 |
| Canonical SMILES | CC(C)C(C(=O)NC(CC(=O)O)C(=O)COC1=C(C=CC=C1F)F)NC(=O)C2=NC3=CC=CC=C3C=C2 |
| InChI | 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 |
| InChIKey | OOBJCYKITXPCNS-REWPJTCUSA-N |
| Boiling Point | 808.9±65.0°C(Predicted) |
| Flash Point | 443.0±34.3 °C |
| Purity | >98% |
| Density | 1.346±0.06 g/cm3 |
| Solubility | Soluble in DMSO |
| Appearance | White to Off-white Solid Powder |
| Storage | Store at -20°C |
| Complexity | 818 |
| Exact Mass | 513.17114185 |
| Index Of Refraction | 1.591 |
| In Vitro | Q-VD-OPh is a potent inhibitor of Caspase-7 with an IC50 of 48 nM utilizing a cell-free assay consisting of human recombinant Caspase-7, Q-VD-OPh, and the substrate AMC-DEVD-pNa. Q-VD-OPh fully inhibits Caspase-3 and -7 activity at 0.05 μM. Caspase-8 is also inhibited at low Q-VD-OPh concentrations. The cleavage of PARP-1 is fully prevented at 10 μM Q-VD-OPh. DNA fragmentation and disruption of the cell membrane functionality are both prevented at 2 μM Q-VD-OPh. Q-VD-OPh is significantly more effective in preventing Apoptosis than the widely used inhibitors, ZVAD-fmk and Boc-D-fmk, and is also equally effective in preventing Apoptosis mediated by the three major apoptotic pathways, Caspase 9/3, Caspase 8/10, and Caspase12. Q-VD-OPh is not toxic to cells even at extremely high concentrations. QVD is also able to increase the expression of differentiation markers in acute myeloid leukemia (AmL) blasts. QVD alone or combined with VDDs increases differentiation and HPK1-cJun signaling in AmL cell context-dependent manner. |
| In Vivo | Chronic treatment with Q-VD-OPh prevents Caspase-7 activation and limits the pathological changes associated with tau, including Caspase cleavage. Q-VD-OPh could be a potential therapeutic compound for the treatment of Alzheimer's disease. |
| PSA | 138.18000 |
| Target | Caspase; HIV |
| Vapor Pressure | 0.0±3.0 mmHg at 25°C |
| XLogP3-AA | 3.7 |
