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Merck

M4765

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

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

Sinónimos:

N-(Methoxysuccinyl)-L-alanyl-L-alanyl-L-prolyl-L-valine 4-nitroanilide, N-(Methoxysuccinyl)-Ala-Ala-Pro-Val 4-nitroanilide

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Fórmula empírica (notación de Hill):
C27H38N6O9
Número CAS:
70967-90-7
Peso molecular:
590.63
NACRES:
NA.32
PubChem Substance ID:
24896943
UNSPSC Code:
12352204
MDL number:
MFCD00077137
Beilstein/REAXYS Number:
6266359

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Nombre del producto

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.

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
0000511431
0000511431
0000502268
0000502268
0000455359

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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
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
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
Hanife Ataoglu et al.
Clinical oral implants research, 13(5), 470-476 (2002-11-28)
The aim of this study was to determine interleukin-1beta (IL-1beta), tumor necrosis factor-alpha (TNF-alpha) levels and neutrophil elastase (NE) activity in peri-implant crevicular fluid (PICF) of smoker and nonsmoker patients, and to investigate their relationships with clinical parameters. A total
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
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