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Merck

M4765

Sigma-Aldrich

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-4-nitroanilid

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

Synonym(e):

N-(Methoxysuccinyl)-L-alanyl-L-alanyl-L-prolyl-L-valin-4-nitroanilid

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About This Item

Empirische Formel (Hill-System):
C27H38N6O9
CAS-Nummer:
Molekulargewicht:
590.63
Beilstein:
6266359
MDL-Nummer:
UNSPSC-Code:
12352204
PubChem Substanz-ID:
NACRES:
NA.32
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Produktbezeichnung

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-4-nitroanilid, elastase substrate

Qualitätsniveau

Assay

≥98% (HPLC)

Form

powder

Löslichkeit

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

Lagertemp.

−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

InChIKey

VLVGCNNWNUERRZ-OSAZLGQLSA-N

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Anwendung

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. Wirkung

Human leukocyte elastase (HLE) is a serine proteinase associated with inflammation and tissue degradation.[4] 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,[5] 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.

Substrate

Substrate for human leukocyte elastase.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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S C Wright et al.
Cancer research, 58(23), 5570-5576 (1998-12-16)
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Tickle I, et al.
Chemical Society Reviews, 33, 558-565 (2004)
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
Hanh H Nguyen et al.
Proceedings of the National Academy of Sciences of the United States of America, 105(50), 19750-19755 (2008-12-10)
Indole-3-carbinol (I3C), a naturally occurring component of Brassica vegetables, such as broccoli, cabbage, and Brussels sprouts, induces a G(1) cell-cycle arrest of human breast cancer cells, although the direct cellular targets that mediate this process are unknown. Treatment of highly

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