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MeoSuc-Ala-Ala-Pro-Val-AMC | 72252-90-5
| Catalog Number | A18-0015 |
| Category | Fluorescent Enzyme Substrates |
| Molecular Formula | C31H41N5O9 |
| Molecular Weight | 627.7 |
| Catalog Number | Size | Price | Quantity |
|---|---|---|---|
| A18-0015 | -- | $-- |
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Product Introduction
MeOSuc-AAPV-AMC is a fluorogenic substrate for human leukocyte and porcine pancreatic elastase. The methoxy succinyl (MeO-Suc) peptide AAPV is hydrolyzed by these elastases but not by cathepsin G. The addition of 7-amino-4-methylcoumarin (AMC) generates a peptide of low fluorescence (excitation: 355-380 nm; emission 440-460 nm) that demonstrates a linear increase in fluorescence intensity in the presence of elastase.
Chemical Information |
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|---|---|
| Synonyms | MeOSuc-AAPV-AMC;I 1270; Methoxy Succinyl-Ala-Ala-Pro-Val-AMC; N-(4-methoxy-1,4-dioxobutyl)-L-alanyl-L-alanyl-L-prolyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-L-valinamide |
| Purity | ≥95% by HPLC |
| IUPAC Name | methyl 4-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S)-3-methyl-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-oxobutanoate |
| Canonical SMILES | CC1=CC(=O)OC2=C1C=CC(=C2)NC(=O)C(C(C)C)NC(=O)C3CCCN3C(=O)C(C)NC(=O)C(C)NC(=O)CCC(=O)OC |
| InChI | InChI=1S/C31H41N5O9/c1-16(2)27(30(42)34-20-9-10-21-17(3)14-26(39)45-23(21)15-20)35-29(41)22-8-7-13-36(22)31(43)19(5)33-28(40)18(4)32-24(37)11-12-25(38)44-6/h9-10,14-16,18-19,22,27H,7-8,11-13H2,1-6H3,(H,32,37)(H,33,40)(H,34,42)(H,35,41)/t18-,19-,22-,27-/m0/s1 |
| InChI Key | CMEUDEVBFFPSEI-NFHWZJRKSA-N |
| Solubility | Soluble in DMSO, DMF |
| Appearance | White to Off-white Powder |
- Product Specification
- Application
| Excitation | 355-380 nm |
| Emission | 440-460 nm |
| Storage | Store at -20°C |
MeoSuc-Ala-Ala-Pro-Val-AMC, a synthetic substrate commonly utilized in protease activity assays, offers versatile applications:
Protease Activity Assays: Widely deployed to assess the activity of serine proteases, notably elastase, in diverse samples, MeoSuc-Ala-Ala-Pro-Val-AMC serves as a crucial tool. Through the cleavage of this substrate, proteases liberate a fluorescent reporter, enabling precise quantification of enzyme activity. This method is essential for scrutinizing protease functionality in biological and clinical specimens, shedding light on intricate enzymatic processes.
Drug Screening: In the realm of drug discovery, MeoSuc-Ala-Ala-Pro-Val-AMC plays a pivotal role in screening for potential protease inhibitors. Compounds hindering the cleavage of this substrate are earmarked as prospective drugs for conditions marked by heightened protease activity, such as inflammation and cancer. The remarkable sensitivity of this assay substrate renders it ideal for high-throughput screening, facilitating the identification of novel therapeutic agents.
Enzyme Kinetics: Scientists leverage MeoSuc-Ala-Ala-Pro-Val-AMC to explore the kinetic properties of proteases. By monitoring the pace of substrate cleavage, researchers unveil critical enzyme parameters like Km and Vmax. This data is indispensable for unraveling enzyme mechanisms and regulatory attributes, contributing to a deeper comprehension of enzymatic actions and behaviors.
Protease Characterization: A valuable asset in delineating the specificity and potency of diverse proteases, MeoSuc-Ala-Ala-Pro-Val-AMC aids in characterizing these enzymes. Each protease exhibits distinct cleavage patterns on this substrate, offering valuable insights into their substrate preferences and catalytic efficiency. This analytical approach aids in elucidating the roles of proteases across various physiological and pathological processes, enriching our understanding of the intricate interplay of these enzymes in biological systems.
Computed Properties | |
|---|---|
| XLogP3 | 1 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 13 |
| Exact Mass | 627.29042790 g/mol |
| Monoisotopic Mass | 627.29042790 g/mol |
| Topological Polar Surface Area | 189Ų |
| Heavy Atom Count | 45 |
| Formal Charge | 0 |
| Complexity | 1200 |
| 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-3929209-A1 | Vasopressin-2 receptor antagonist peptides and uses thereof | 2020-06-24 |
| WO-2021102176-A2 | Polypeptide inhibitors of neutrophil elastase activity and uses thereof | 2019-11-21 |
| JP-2023502508-A | Polypeptide inhibitors of neutrophil elastase activity and uses thereof | 2019-11-21 |
| US-2022372111-A1 | Polypeptide inhibitors of neutrophil elastase activity and uses thereof | 2019-11-21 |
| WO-2020150751-A2 | Devices and methods for tissue and cell staining (ii) | 2019-01-15 |
Applications of Fluorescent Probes & Dyes
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