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M4765

Sigma-Aldrich

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

elastase substrate

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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
Beilstein:
6266359
MDL number:
MFCD00077137
UNSPSC Code:
12352204
PubChem Substance ID:
24896943
NACRES:
NA.32

Quality Level

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

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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.

Substrates

Substrate for human leukocyte elastase.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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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
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
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
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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