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M0398

Sigma-Aldrich

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone

elastase inhibitor, powder, ≥98% (TLC)

Synonym(s):

N-(Methoxysuccinyl)-L-alanyl-L-alanyl-L-prolyl-L-valine chloromethylketone

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About This Item

Empirical Formula (Hill Notation):
C22H35ClN4O7
CAS Number:
65144-34-5
Molecular Weight:
502.99
Beilstein:
6167019
MDL number:
MFCD00077136
UNSPSC Code:
12352202
PubChem Substance ID:
24896552
NACRES:
NA.77

product name

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone, elastase inhibitor

Assay

≥98% (TLC)

form

powder

mp

159 °C

solubility

methanol: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)CCl

InChI

1S/C22H35ClN4O7/c1-12(2)19(16(28)11-23)26-21(32)15-7-6-10-27(15)22(33)14(4)25-20(31)13(3)24-17(29)8-9-18(30)34-5/h12-15,19H,6-11H2,1-5H3,(H,24,29)(H,25,31)(H,26,32)/t13-,14-,15-,19-/m0/s1

InChI key

PJGDFLJMBAYGGC-XLPNERPQSA-N

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General description

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone is a tetrapeptide, cell-permeable and non-cytotoxic inhibitor.

Application

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone has been used as an elastase specific inhibitor.

Biochem/physiol Actions

N-(Methoxysuccinyl)-Ala-Ala-Pro-Val-chloromethyl ketone acts as a competitive inhibitor of human leukocyte elastase (HLE).
Irreversible inhibitor of human leukocyte and neutrophil elastase.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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P S Hiemstra et al.
Immunobiology, 182(2), 117-126 (1991-03-01)
The role of elastase and proteinase inhibitors in polymorphonuclear leukocyte(PMN)-mediated injury to human umbilical cord venous endothelial cells (HUVEC) was investigated. Both purified human neutrophil elastase and PMN that were stimulated with serum-treated zymosan (STZ) induced detachment, but not lysis
B O Anderson et al.
Surgery, 108(2), 262-267 (1990-08-01)
Neutrophils have been implicated in multiple models of end-organ injury. The purposes of this study were to determine whether (1) a sublethal septic insult promotes lung neutrophil accumulation, (2) this pulmonary neutrophil accumulation is reversible, (3) these accumulated neutrophils can
A Molla et al.
Journal of virology, 67(8), 4688-4695 (1993-08-01)
A polyprotein cleavage assay has been developed to assay the proteolytic activities in vitro of the 2A proteinases encoded by poliovirus and human rhinovirus 14, which are representative members of the Enterovirus and Rhinovirus genera of picornaviruses, respectively. The elastase-specific
D S Fletcher et al.
The American review of respiratory disease, 141(3), 672-677 (1990-03-01)
A pharmacokinetic model is described for testing of polymorphonuclear leukocyte (PMN) elastase inhibitors administered by intratracheal or aerosol dosing of hamsters. Acute lung injury, measured as hemorrhage occurring within hours after intratracheal instillation of human PMN elastase, correlated directly with
Elastin governs the mechanical response of medial collateral ligament under shear and transverse tensile loading
Henninger HB, et al.
Acta Biomaterialia, 25, 304-312 (2015)
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