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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

Quality Level

200

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

Regulatory Information

常规特殊物品

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC6872
BCCC2076
BCBZ5601
BCBZ3273
BCBW8775

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V S Carl et al.
Immunopharmacology, 33(1-3), 325-329 (1996-06-01)
Bradykinin (BK) is a potent inflammatory mediator, which can release other inflammatory mediators by interacting with bradykinin B1 and B2 receptors. The role of kinins in regulating human PMN elastase release was studied. BK induced elastase release 5-fold over basal
Takeshi Kawamura et al.
Microbiology and immunology, 46(3), 225-230 (2002-05-15)
Carboxypeptidase R (EC 3.4.17.20; CPR) is an unstable basic carboxypeptidase found in fresh serum in addition to carboxypeptidase N (CPN) which is a stable enzyme. CPR in fresh serum is generated from its zymogen (proCPR) during coagulation by trypsin-like enzymes
E J Bates et al.
Journal of leukocyte biology, 54(6), 590-598 (1993-12-01)
Previously published work has indicated that polyunsaturated fatty acids (PUFA) may enhance neutrophil-mediated damage to host tissues. We have found that endothelial detachment was significantly increased by neutrophils pretreated with docosahexaenoic (22:6, n-3) and arachidonic (20:4, n-6) acids at 10-40
R M Senior et al.
The Journal of clinical investigation, 69(2), 384-393 (1982-02-01)
As an approach to facilitating the understanding of proteinases associated with monocytes we have studied U-937 monocytelike cells. Elastase activity was identified in U-937 cell extracts and compared to monocyte elastase activity, neutrophil elastase, and the elastase activity from a
L A Smedly et al.
The Journal of clinical investigation, 77(4), 1233-1243 (1986-04-01)
The neutrophil has been implicated as an important mediator of vascular injury, especially after endotoxemia. This study examines neutrophil-mediated injury to human microvascular endothelial cells in vitro. We found that neutrophils stimulated by formyl-methionyl-leucyl-phenylalanine (FMLP), the complement fragment C5a, or
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