
Z-DEVD-AFC | 1135416-11-3
Catalog Number | A18-0043 |
Category | Fluorescent Enzyme Substrates |
Molecular Formula | C36H38F3N5O14 |
Molecular Weight | 821.7 |
Catalog Number | Size | Price | Quantity |
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A18-0043 | -- | $-- |
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Product Introduction
Z-DEVD-AFC is a fluorogenic substrate for caspase-3. It is cleaved by caspase-3 to release the fluorescent moiety 7-amino-7-trifluoromethylcoumarin (AFC), which can be used to quantify caspase-3 activity.
Chemical Information |
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Synonyms | Caspase-3 Fluorogenic Substrate IV; (5S,8S,11S,14S)-8-(2-carboxyethyl)-5-(carboxymethyl)-11-isopropyl-3,6,9,12-tetraoxo-14-((2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl)carbamoyl)-1-phenyl-2-oxa-4,7,10,13-tetraazahexadecan-16-oic acid |
Purity | ≥95% |
IUPAC Name | (4S)-5-[[(2S)-1-[[(2S)-3-carboxy-1-oxo-1-[[2-oxo-4-(trifluoromethyl)chromen-7-yl]amino]propan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-[[(2S)-3-carboxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]-5-oxopentanoic acid |
Canonical SMILES | CC(C)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(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)OCC3=CC=CC=C3 |
InChI | InChI=1S/C36H38F3N5O14/c1-17(2)30(34(55)42-23(14-27(47)48)32(53)40-19-8-9-20-21(36(37,38)39)13-29(51)58-25(20)12-19)44-31(52)22(10-11-26(45)46)41-33(54)24(15-28(49)50)43-35(56)57-16-18-6-4-3-5-7-18/h3-9,12-13,17,22-24,30H,10-11,14-16H2,1-2H3,(H,40,53)(H,41,54)(H,42,55)(H,43,56)(H,44,52)(H,45,46)(H,47,48)(H,49,50)/t22-,23-,24-,30-/m0/s1 |
InChI Key | JEPURZRNABGOCW-CQUCHYGKSA-N |
- Product Specification
- Application
Storage | Store at -20°C |
Z-DEVD-AFC is a synthetic fluorogenic substrate specifically designed for the quantification of caspase-3 activity. It comprises a peptide sequence (Z-Asp-Glu-Val-Asp) linked to a fluorescent reporter molecule, 7-amino-4-trifluoromethylcoumarin (AFC). Upon cleavage by active caspase-3, AFC is released, generating a fluorescent signal that can be measured by a fluorometer. This process is indicative of apoptosis, as caspase-3 is a key executioner enzyme in the apoptotic pathway. Z-DEVD-AFC is thus instrumental in studying cellular processes that lead to programmed cell death.
One key application of Z-DEVD-AFC is in the assessment of apoptosis in cancer research. By measuring caspase-3 activity, researchers can evaluate the efficacy of anti-cancer drugs that aim to induce cell death in tumor cells. This substrate allows for the quantification of apoptotic cells in response to treatment, providing essential data for understanding how these therapies can effectively kill cancer cells. This application is vital for the development of novel therapeutics targeting apoptosis pathways.
Another application of Z-DEVD-AFC is in neuroscience. Apoptosis is a critical process in neurodegenerative diseases such as Alzheimer’s and Parkinson’s disease. By assessing caspase-3 activity through Z-DEVD-AFC, scientists can investigate neuronal cell death mechanisms, thereby gaining insights into disease progression and identification of potential therapeutic targets. This substrate thus serves as a valuable tool in understanding complex brain disorders and developing intervention strategies.
Z-DEVD-AFC is also employed in immunology, where understanding apoptosis aids in discerning immune function and dysfunction. Caspase-3 activity measurement helps in evaluating how immune cells respond to various stimuli and the regulation of immune responses. This application is crucial for studying autoimmune diseases, where inappropriate cell death can contribute to disease pathology, and for developing treatments aimed at modulating immune cell apoptosis.
Lastly, Z-DEVD-AFC finds significant application in toxicology studies. It is used to determine the cytotoxic effects of various compounds, such as environmental toxins, pharmaceutical drugs, and other chemicals, by evaluating induced apoptosis in exposed cells. This is critical for safety assessments and regulatory decisions, ensuring that substances do not pose harmful risks to human health. The utilization of Z-DEVD-AFC in toxicology provides essential insights into the mechanisms of toxicity and cellular responses to different chemical stresses.
Computed Properties | |
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XLogP3 | 1.1 |
Hydrogen Bond Donor Count | 8 |
Hydrogen Bond Acceptor Count | 17 |
Rotatable Bond Count | 20 |
Exact Mass | 821.23673539 g/mol |
Monoisotopic Mass | 821.23673539 g/mol |
Topological Polar Surface Area | 293Ų |
Heavy Atom Count | 58 |
Formal Charge | 0 |
Complexity | 1600 |
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 |
Literatures
PMID | Publication Date | Title | Journal |
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11598139 | 2001-12-14 | Characterization of fortilin, a novel antiapoptotic protein | The Journal of biological chemistry |
9696873 | 1998-09-01 | Caspase activation and specific cleavage of substrates after coxsackievirus B3-induced cytopathic effect in HeLa cells | Journal of virology |
9185777 | 1997-06-01 | Processing/activation of CPP32-like proteases is involved in transforming growth factor beta1-induced apoptosis in rat hepatocytes | Hepatology (Baltimore, Md.) |
Patents
Publication Number | Title | Priority Date |
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US-2004260094-A1 | Quinoline derivatives as caspase-3 inhibitor, preparation for producing the same and pharmaceutical composition comprising the same | 2002-04-30 |
US-7009053-B2 | Quinoline derivatives as caspase-3 inhibitor, preparation for producing the same and pharmaceutical composition comprising the same | 2002-04-30 |
US-2001010814-A1 | Adenoviral vector encoding pro-apoptotic bax gene and uses thereof | 1998-08-24 |
Applications of Fluorescent Probes & Dyes
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