M4765

N-Methoxysuccinyl-Ala-Ala-Pro-Val p-nitroanilide

elastase substrate, chromogenic, ≥98% (HPLC), powder

• Synonym(s): N-(Methoxysuccinyl)-L-alanyl-L-alanyl-L-prolyl-L-valine 4-nitroanilide, N-(Methoxysuccinyl)-Ala-Ala-Pro-Val 4-nitroanilide
• Empirical Formula (Hill Notation): C₂₇H₃₈N₆O₉
• CAS Number: 70967-90-7
• Molecular Weight: 590.63
• NACRES: NA.32
• PubChem Substance ID: 24896943
• UNSPSC Code: 12352204
• MDL number: MFCD00077137
• Beilstein/REAXYS Number: 6266359

Properties

• Product Name: N-Methoxysuccinyl-Ala-Ala-Pro-Val p-nitroanilide, elastase substrate
• Quality Segment: 300
• assay: ≥98% (HPLC)
• form: powder
• solubility: DMF: soluble 25 mg/mL, clear, colorless to light yellow
• storage temp.: −20°C
• SMILES string: [H][C@]1(CCCN1C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)CCC(=O)OC)C(=O)N[C@@H](C(C)C)C(=O)Nc2ccc(cc2)[N+]([O-])=O
• InChI: 1S/C27H38N6O9/c1-15(2)23(26(38)30-18-8-10-19(11-9-18)33(40)41)31-25(37)20-7-6-14-32(20)27(39)17(4)29-24(36)16(3)28-21(34)12-13-22(35)42-5/h8-11,15-17,20,23H,6-7,12-14H2,1-5H3,(H,28,34)(H,29,36)(H,30,38)(H,31,37)/t16-,17-,20-,23-/m0/s1
• InChI key: VLVGCNNWNUERRZ-OSAZLGQLSA-N

Description

General description

Substrate for human leukocyte elastase.

Application

MeO-SucAAPVpNA has been used to measure neutrophil elastase activity:

• in response to zinc supplementation using human and mice neutrophils in vitro[1]
• to determine the functional properties of aged neutrophils to assess their role in supporting metastasis[2]
• to determine the anti-elastase action of Sclerocarya birrea (A. Rich.) Hochst[3]

Biochem/physiol Actions

Human leukocyte elastase (HLE) is a serine proteinase associated with inflammation and tissue degradation. It is one of the most destructive proteases and its role in the development of pulmonary emphysema has been investigated. This peptide is selectively hydrolyzed by HLE,[4] and other elastase of different species and cells. Cleavage of MeO-SucAPVVpNA by an elastase-like protease is critical for the synthesis of platelet-activating factor (PAF) induced by tumor necrosis factor-α (TNF-α) and interleukin-1α (IL-1α). The rate of enzymatic hydrolysis of the substrate is followed by the increase in absorbance due to the release of 4-nitroaniline. The absorbance is routinely measured at 400 nm or higher.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)