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Ac-VDVAD-AFC | CAS 210344-94-8
| Catalog Number | A18-0012 |
| Category | Fluorescent Enzyme Substrates |
| Molecular Formula | C33H41F3N6O12 |
| Molecular Weight | 770.7 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
Ac-VDVAD-AFC is a fluorogenic substrate whose amino acids VDVAD have been shown to be a preferred cleavage site for caspase-2. Caspase activity can be quantified by fluorescent detection of free AFC (7-amino-4-trifluoromethylcoumarin), which is excited at 400 nm and emits at 505 nm.
Chemical Information
Product Specification
Application
Computed Properties
Patents
| Synonyms | N-Acetyl-Val-Asp-Val-Ala-Asp-7-amino-4-Trifluoromethylcoumarin; N-acetyl-L-valyl-L-α-aspartyl-L-valyl-L-alanyl-N-[2-oxo-4-(trifluoromethyl)-2H-1-benzopyran-7-yl]-L-α-asparagine |
| Purity | ≥95% |
| IUPAC Name | (3S)-3-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-methylbutanoyl]amino]-3-carboxypropanoyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]-4-oxo-4-[[2-oxo-4-(trifluoromethyl)chromen-7-yl]amino]butanoic acid |
| Canonical SMILES | CC(C)C(C(=O)NC(CC(=O)O)C(=O)NC(C(C)C)C(=O)NC(C)C(=O)NC(CC(=O)O)C(=O)NC1=CC2=C(C=C1)C(=CC(=O)O2)C(F)(F)F)NC(=O)C |
| InChI | InChI=1S/C33H41F3N6O12/c1-13(2)26(38-16(6)43)32(53)41-21(12-24(46)47)30(51)42-27(14(3)4)31(52)37-15(5)28(49)40-20(11-23(44)45)29(50)39-17-7-8-18-19(33(34,35)36)10-25(48)54-22(18)9-17/h7-10,13-15,20-21,26-27H,11-12H2,1-6H3,(H,37,52)(H,38,43)(H,39,50)(H,40,49)(H,41,53)(H,42,51)(H,44,45)(H,46,47) |
| InChIKey | BKQMJQIAIFEZJR-OIOUIRQFSA-N |
| Appearance | Solid Powder |
| Excitation | 400 nm |
| Emission | 505 nm |
| Storage | Store at -20°C |
Ac-VDVAD-AFC is a specialized fluorogenic substrate commonly used in biochemical assays to study the activity of caspase-2, a critical enzyme involved in apoptosis. The substrate contains a specific sequence of amino acids, VDVAD, which is the preferred cleavage site for caspase-2. Upon enzymatic cleavage by caspase-2, the substrate releases 7-amino-4-trifluoromethylcoumarin (AFC), a fluorescent molecule that can be detected and quantified due to its distinct excitation at 400 nm and emission at 505 nm. This unique property makes Ac-VDVAD-AFC a valuable tool in the detailed study of apoptotic processes where caspase-2 activity is crucial.
One key application of Ac-VDVAD-AFC is its use in apoptosis research. Apoptosis, or programmed cell death, is an essential cellular process in both health and disease. The ability to measure caspase-2 activity allows researchers to gain insights into the mechanisms regulating apoptosis. By using Ac-VDVAD-AFC in cell assays, scientists can quantify changes in caspase-2 activity, thus elucidating its role in various cellular contexts and disease states, such as cancer or neurodegenerative disorders, where apoptosis is dysregulated.
Another pivotal application is in drug discovery and development. Ac-VDVAD-AFC can be employed in high-throughput screening to identify potential drug candidates that can modulate caspase-2 activity. By observing changes in AFC fluorescence, researchers can evaluate the efficacy of compounds to either inhibit or activate caspase-2, leading to potential therapeutic strategies for diseases where apoptosis modulation acts as a promising treatment avenue. This makes it immensely useful for pharmaceutical research targeting apoptosis-related pathways.
In addition to apoptosis and drug discovery, Ac-VDVAD-AFC serves as a critical tool in toxicological studies. Researchers can assess the cytotoxic effects of various substances by measuring caspase-2 activity triggered in response to the compounds. By employing Ac-VDVAD-AFC, it becomes feasible to quantify and compare the apoptotic response of cells to different toxic agents, providing valuable data for environmental safety assessments and regulatory standards concerning chemical exposure.
Finally, Ac-VDVAD-AFC is invaluable in fundamental research exploring the molecular mechanisms of caspase-2 itself. Scientists leverage this substrate to dissect the biochemical pathways caspase-2 is involved in, including its substrates and cofactors. Such studies offer critical insights into its structure-function relationships and its integration with other apoptotic pathways, contributing to a deeper understanding of cellular homeostasis and dysfunction. By providing a measurable way to assess caspase-2 activity, Ac-VDVAD-AFC supports broad-ranging inquiries from basic biology to clinical applications.
| XLogP3 | 0.4 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 15 |
| Rotatable Bond Count | 17 |
| Exact Mass | 770.27345525 g/mol |
| Monoisotopic Mass | 770.27345525 g/mol |
| Topological Polar Surface Area | 276Ų |
| Heavy Atom Count | 54 |
| Formal Charge | 0 |
| Complexity | 1520 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 5 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
| Publication Number | Title | Priority Date |
|---|---|---|
| US-2013096050-A1 | Highly active polypeptides and methods of making and using the same | 2010-04-22 |
| US-2018193422-A1 | Highly active polypeptides and methods of making and using the same | 2010-04-22 |
| US-9782454-B2 | Highly active polypeptides and methods of making and using the same | 2010-04-22 |
| US-10772934-B2 | Highly active polypeptides and methods of making and using the same | 2010-04-22 |
| US-2021205415-A1 | Highly active polypeptides and methods of making and using the same | 2010-04-22 |
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