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Ac-LEHD-AFC | CAS 210345-03-2
| Catalog Number | A18-0001 |
| Category | Fluorescent Enzyme Substrates |
| Molecular Formula | C33H38F3N7O11 |
| Molecular Weight | 765.69 |
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Product Introduction
Ac-LEHD-AFC is a fluorogenic substrate that features a peptide sequence conjugated to 7-amino-4-trifluoromethylcoumarin (AFC), a widely recognized fluorophore. Upon enzymatic cleavage by caspase family proteases, the non-fluorescent substrate releases the highly fluorescent AFC, allowing for the detection and quantification of protease activity in biochemical assays. This compound is commonly utilized in apoptosis research, where it supports the monitoring of caspase activation through its distinct excitation and emission properties.
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Synonyms | N-acetyl-L-leucyl-L-α-glutamyl-L-histidyl-N-[2-oxo-4-(trifluoromethyl)-2H-1-benzopyran-7-yl]-L-α-asparagine; N-Acetyl-Leu-Glu-His-Asp-7-amino-4-Trifluoromethylcoumarin; Caspase-9 substrate; L-α-Asparagine, N-acetyl-L-leucyl-L-α-glutamyl-L-histidyl-N-[2-oxo-4-(trifluoromethyl)-2H-1-benzopyran-7-yl]-; (4S,7S,10S,13S)-10-((1H-imidazol-5-yl)methyl)-7-(2-carboxyethyl)-4-isobutyl-2,5,8,11-tetraoxo-13-((2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl)carbamoyl)-3,6,9,12-tetraazapentadecan-15-oic acid |
| Purity | ≥95% |
| IUPAC Name | (4S)-4-[[(2S)-2-acetamido-4-methylpentanoyl]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(C)CC(C(=O)NC(CCC(=O)O)C(=O)NC(CC1=CN=CN1)C(=O)NC(CC(=O)O)C(=O)NC2=CC3=C(C=C2)C(=CC(=O)O3)C(F)(F)F)NC(=O)C |
| InChI | InChI=1S/C33H38F3N7O11/c1-15(2)8-22(39-16(3)44)31(52)41-21(6-7-26(45)46)29(50)42-23(9-18-13-37-14-38-18)32(53)43-24(12-27(47)48)30(51)40-17-4-5-19-20(33(34,35)36)11-28(49)54-25(19)10-17/h4-5,10-11,13-15,21-24H,6-9,12H2,1-3H3,(H,37,38)(H,39,44)(H,40,51)(H,41,52)(H,42,50)(H,43,53)(H,45,46)(H,47,48) |
| InChIKey | HULKIXRFKRCRHD-ZJZGAYNASA-N |
| Solubility | Soluble in DMF, DMSO |
| Density | 1.457±0.06 g/cm3 (Predicted) |
| Appearance | Slightly Yellow Powder |
| Boiling Point | 1211.9±65.0°C (Predicted) |
Product Specification
| Excitation | 400 nm |
| Emission | 505 nm |
| Storage | Store at -20°C |
Application
Ac-LEHD-AFC is a synthetic peptide substrate commonly used in biochemical research. Here are some key applications of Ac-LEHD-AFC:
Apoptosis Research: Ac-LEHD-AFC is frequently used to monitor caspase-9 activity, a key enzyme involved in apoptotic pathways. By quantifying the fluorescence released upon cleavage of the substrate, researchers can assess the degree of apoptosis in cell samples. This helps in understanding the mechanisms of cell death and in screening potential anti-cancer drugs.
Enzyme Kinetics: This substrate is ideal for studying the kinetic properties of caspase-9. By performing enzyme assays with Ac-LEHD-AFC, scientists can determine parameters such as Km and Vmax, which are crucial for characterizing enzyme activity. These studies provide fundamental insights into enzyme function and regulation.
Drug Screening: Ac-LEHD-AFC is used in high-throughput screening assays to identify inhibitors of caspase-9. By observing the reduction in fluorescence, researchers can identify compounds that effectively block caspase-9 activity. This application is important for discovering new therapeutics for diseases where apoptosis plays a key role.
Toxicology Studies: In toxicology, Ac-LEHD-AFC is employed to evaluate the cytotoxic effects of various compounds and environmental agents. By measuring caspase-9 activation, researchers can infer the potential of a substance to induce apoptosis in target cells. This information is vital for risk assessment and regulatory compliance.
Computed Properties
| XLogP3 | 0.2 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 15 |
| Rotatable Bond Count | 18 |
| Exact Mass | 765.25813954 g/mol |
| Monoisotopic Mass | 765.25813954 g/mol |
| Topological Polar Surface Area | 275Ų |
| Heavy Atom Count | 54 |
| Formal Charge | 0 |
| Complexity | 1480 |
| 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 |
|---|---|---|
| US-2016058847-A1 | IS100- A Highly Effective Enzyme Principle For Use In Dermal Therapeutics, And For Health And Beauty | 2014-09-03 |
| WO-2004100888-A2 | N-thiolated azetidinones and anti-cancer use thereof | 2003-05-06 |
| US-2004167115-A1 | Methods for preventing and treating cancer using N-thiolated beta-lactam compounds and analogs thereof | 2002-05-06 |
| US-2006160787-A1 | Methods for preventing and treating cancer using N-thiolated beta-lactam compounds and analogs thereof | 2002-05-06 |
| US-7026472-B2 | Methods for preventing and treating cancer using N-thiolated β-lactam compounds and analogs thereof | 2002-05-06 |
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