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Key Documents

SML0358

Sigma-Aldrich

AA74-1

≥98% (HPLC)

Synonym(s):

[4-(4-Hydroxy-2,6-dimethylheptan-4-yl)-2H-1,2,3-triazol-2-yl](pyrrolidin-1-yl)methanone, [4-[1-Hydroxy-3-methyl-1-(2-methylpropyl)butyl]-2H-1,2,3-triazol-2-yl]-1-pyrrolidinylmethanone

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About This Item

Empirical Formula (Hill Notation):
C16H28N4O2
CAS Number:
Molecular Weight:
308.42
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

film

color

colorless

solubility

DMSO: >15 mg/mL

storage temp.

2-8°C

SMILES string

CC(C)CC(O)(CC(C)C)c1cnn(n1)C(=O)N2CCCC2

InChI

1S/C16H28N4O2/c1-12(2)9-16(22,10-13(3)4)14-11-17-20(18-14)15(21)19-7-5-6-8-19/h11-13,22H,5-10H2,1-4H3

InChI key

GXBVPGCIMCIASQ-UHFFFAOYSA-N

Biochem/physiol Actions

AA74-1 is an extremely potent and selective inhibitor of the serine hydrolase acyl-peptide hydrolase (APEH) with an IC50 of 5 nM in mouse T-cell proteomes. AA74-1 potently blocked the activity of its target serine hydrolase, APEH, in mice in vivo without significantly affecting other enzymes. The APEH inhibition caused accumulation of N-acetylated proteins and stimulated cellular proliferation in T cells.

The APEH gene is deleted in some cancers, in which it has been proposed to serve as a potential tumor suppressor, and is involved in the degradation of oligomeric amyloid-beta which could make it a new target for therapy aimed at reducing neurodegeneration in Alzheimer′s disease. AA74-1 is the first selective tool for studying APEH activity.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Rubayet Elahi et al.
mSphere, 4(3) (2019-05-10)
The human malaria parasite Plasmodium falciparum causes disease as it replicates within the host's erythrocytes. We have found that an erythrocyte serine hydrolase, acylpeptide hydrolase (APEH), accumulates within developing asexual parasites. Internalization of APEH was associated with a proteolytic event

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