
Ac-WEHD-AFC | CAS 210344-99-3
| Catalog Number | A18-0009 |
| Category | Fluorescent Enzyme Substrates |
| Molecular Formula | C38H37F3N8O11 |
| Molecular Weight | 838.7 |
| Catalog Number | Size | Price | Quantity |
|---|---|---|---|
| A18-0009 | 50 mg | $498 | |
| A18-0009 | 1 g | $1998 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
Ac-WEHD-AFC is a fluorogenic probe that features the 7-amino-4-trifluoromethylcoumarin (AFC) fluorophore, known for its blue-green fluorescence upon enzymatic cleavage. This compound is often utilized in caspase activity assays, where it functions as a substrate that releases the fluorescent AFC moiety upon proteolytic processing, enabling the real-time monitoring of enzyme kinetics. The acetylated peptide sequence Ac-WEHD serves as a recognition site for specific caspases, making this probe a valuable tool in apoptosis research and biochemical pathway elucidation.
Chemical Information
Product Specification
Application
QC Data
Computed Properties
Patents
Chemical Information
| Synonyms | Caspase 1 (ICE) Substrate 3f; fluorogenic, Ac-WEHD-AFC; N-Acetyl-L-tryptophyl-L-alpha-glutamyl-L-histidyl-N-[2-oxo-4-(trifluoromethyl)-2H-1-benzopyran-7-yl]-L-alpha-asparagine; N-Acetyl-Trp-Glu-His-Asp-7-amido-4-trifluoromethylcoumarin trifluoroacetate salt |
| Purity | ≥97% by HPLC |
| IUPAC Name | (4S)-4-[[(2S)-2-acetamido-3-(1H-indol-3-yl)propanoyl]amino]-5-[[(2S)-1-[[(2S)-3-carboxy-1-oxo-1-[[2-oxo-4-(trifluoromethyl)chromen-7-yl]amino]propan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid |
| SMILES | CC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCC(=O)O)C(=O)NC(CC3=CN=CN3)C(=O)NC(CC(=O)O)C(=O)NC4=CC5=C(C=C4)C(=CC(=O)O5)C(F)(F)F |
| InChI | InChI=1S/C38H37F3N8O11/c1-18(50)45-27(10-19-15-43-25-5-3-2-4-22(19)25)36(58)47-26(8-9-31(51)52)34(56)48-28(11-21-16-42-17-44-21)37(59)49-29(14-32(53)54)35(57)46-20-6-7-23-24(38(39,40)41)13-33(55)60-30(23)12-20/h2-7,12-13,15-17,26-29,43H,8-11,14H2,1H3,(H,42,44)(H,45,50)(H,46,57)(H,47,58)(H,48,56)(H,49,59)(H,51,52)(H,53,54)/t26-,27-,28-,29-/m0/s1 |
| InChIKey | NEGOLAGPKZGIKJ-DZUOILHNSA-N |
| Density | 1.528±0.06 g/cm3(Predicted) |
| Appearance | White to yellow Solid |
| Boiling Point | 1351.5±65.0°C(Predicted) |
Product Specification
| Excitation | 400 nm |
| Emission | 505 nm |
| Storage | Store at -20°C |
Application
Ac-WEHD-AFC is a highly specialized fluorogenic substrate designed to facilitate the study of group I caspases, specifically caspase-1, -4, and -5. These caspases play crucial roles in the inflammatory response and apoptosis, making them significant targets in the study of numerous diseases. The unique aspect of Ac-WEHD-AFC is its ability to provide a measurable fluorescent signal when cleaved by these caspases. When this substrate is cleaved, it releases 7-amino-4-trifluoromethylcoumarin (AFC), a compound that can be excited at a wavelength of 400 nm and emits fluorescence at 505 nm, allowing researchers to quantify caspase activity with high precision and sensitivity.
The first key application of Ac-WEHD-AFC is in drug discovery, particularly in developing new anti-inflammatory drugs. By enabling precise measurement of caspase activity, researchers can screen potential inhibitors that might reduce unwanted inflammation, a common pathway in a variety of chronic diseases. With continued research, such screening processes could lead to significant breakthroughs in the treatment of conditions like arthritis, asthma, and inflammatory bowel disease by identifying compounds that modulate caspase activity effectively.
Secondly, Ac-WEHD-AFC is instrumental in cancer research, where understanding the mechanisms of apoptosis is crucial. Some cancers evade cell death by manipulating apoptotic pathways, and caspases are central to these processes. Using Ac-WEHD-AFC, scientists can investigate how different cancer cells regulate caspase activity, identify which apoptotic pathways are disrupted, and develop targeted therapies that reactivate these pathways to induce cancer cell death, providing a potential approach to overcome chemoresistance.
Furthermore, Ac-WEHD-AFC is applied in neurodegenerative disease studies. Neurodegenerative diseases, such as Alzheimer’s and Parkinson’s, have been linked to caspase-mediated neuroinflammation and cell death. By using Ac-WEHD-AFC, researchers can explore these pathways in detail, helping to unravel the complex biochemical processes that lead to neuronal damage. This knowledge could aid the discovery of new therapeutic strategies aimed at reducing neuronal loss and preserving cognitive function.
Lastly, Ac-WEHD-AFC is valuable in virology, where caspase activity can influence viral replication and the host’s immune response. Certain viruses exploit caspase pathways to facilitate their replication or evade the immune system. By using Ac-WEHD-AFC in virological studies, researchers can elucidate the interaction between viral components and host cell apoptosis machinery, potentially leading to the development of antiviral drugs that enhance the immune response or prevent viral replication by targeting these pathways.
QC Data
Computed Properties
| XLogP3 | 0.6 |
| Hydrogen Bond Donor Count | 9 |
| Hydrogen Bond Acceptor Count | 15 |
| Rotatable Bond Count | 18 |
| Exact Mass | 838.25338851 g/mol |
| Monoisotopic Mass | 838.25338851 g/mol |
| Topological Polar Surface Area | 291Ų |
| Heavy Atom Count | 60 |
| Formal Charge | 0 |
| Complexity | 1680 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| EP-3884941-A1 | Inflammasome inhibitors and use thereof | 2020-03-26 |
| US-2019038602-A1 | Granzyme b inhibitor formulations and methods for the treatment of burns | 2016-02-03 |
| US-10537652-B2 | Cyclic urea compounds as granzyme B inhibitors | 2014-08-01 |
| US-2017015705-A1 | Pyrrole compounds as granzyme b inhibitors | 2014-08-01 |
| US-2020062803-A1 | Azaindoline compounds as granzyme b inhibitors | 2014-08-01 |
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