M4765

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

Name: N-Methoxysuccinyl-Ala-Ala-Pro-Val p-nitroanilide
Brand: SIGMA

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

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About This Item

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

Product Name

N-Methoxysuccinyl-Ala-Ala-Pro-Val p-nitroanilide, elastase substrate

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

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 key

VLVGCNNWNUERRZ-OSAZLGQLSA-N

assay

≥98% (HPLC)

form

powder

solubility

DMF: soluble 25 mg/mL, clear, colorless to light yellow

storage temp.

−20°C

Quality Level

300

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Application

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

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

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, 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.

General description

Substrate for human leukocyte elastase.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000511431

0000502268

0000455359

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Synthesis and in-vitro evaluation of novel low molecular weight thiocarbamates as inhibitors of human leukocyte elastase.

N P Rodis et al.

Journal of enzyme inhibition, 16(2), 95-105 (2001-05-09)

A series of novel low molecular weight thiocarbamate esters (1e-6e) were synthesized and evaluated as inhibitors of human leukocyte elastase (HLE). The thiocarbamate esters studied consist of a substituted primary or secondary aliphatic or aromatic amine and a 1-phenyl-1H-tetrazole-5-thiol (Table

Trappin-2/elafin modulate innate immune responses of human endometrial epithelial cells to PolyI:C.

Anna G Drannik et al.

PloS one, 7(4), e35866-e35866 (2012-05-01)

Upon viral recognition, innate and adaptive antiviral immune responses are initiated by genital epithelial cells (ECs) to eradicate or contain viral infection. Such responses, however, are often accompanied by inflammation that contributes to acquisition and progression of sexually transmitted infections

Bcl-2-mediated resistance to apoptosis is associated with glutathione-induced inhibition of AP24 activation of nuclear DNA fragmentation.

S C Wright et al.

Cancer research, 58(23), 5570-5576 (1998-12-16)

Studies on the mechanism of apoptosis in this laboratory support a model in which signal transduction involving caspase 3 leads to activation of a serine protease called Mr 24,000 apoptotic protease (AP24), which then induces internucleosomal DNA fragmentation in the

Interference of PR3-ANCA with the enzymatic activity of PR3: differences in patients during active disease or remission of Wegener's granulomatosis.

Y M van der Geld et al.

Clinical and experimental immunology, 129(3), 562-570 (2002-08-29)

Anti-neutrophil cytoplasmic antibodies (ANCA) against proteinase 3 (PR3) are strongly associated with Wegener's granulomatosis (WG) and are thought to be involved in its pathogenesis. Levels of PR3-ANCA do not always correspond to clinical disease activity. To investigate the relationship between

Sulfonated Nonsaccharide Heparin Mimetics Are Potent and Noncompetitive Inhibitors of Human Neutrophil Elastase.

Rami A Al-Horani et al.

ACS omega, 6(19), 12699-12710 (2021-06-01)

Human neutrophil elastase (HNE) is a serine protease that plays vital roles in inflammation, innate immune response, and tissue remodeling processes. HNE has been actively pursued as a drug target, particularly for the treatment of cardiopulmonary diseases. Although thousands of

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