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Key Documents

SML3144

Sigma-Aldrich

delta-Secretase inhibitor, CP11

≥95% (HPLC)

Synonym(s):

δ-Secretase inhibitor 11, δ-Secretase inhibitor, compound 11, δ-Secretase inhibitor, compound 11A, 7-(4-Morpholinyl)-2,1,3-benzoxadiazol-4-amine, 7-(Morpholin-4-yl)-2,1,3-benzoxadiazol-4-amine, 7-Morpholin-4-yl-benzo[1,2,5]oxadiazol-4-ylamine, CP11, CPA, delta-Secretase inhibitor, compound 11

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About This Item

Empirical Formula (Hill Notation):
C10H12N4O2
CAS Number:
842964-18-5
Molecular Weight:
220.23
MDL number:
MFCD03422529
UNSPSC Code:
12352200
NACRES:
NA.28

Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

, Faint Brown to dark red

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

N3(CCOCC3)c1c2n[o]nc2c(cc1)N

InChI

1S/C10H12N4O2/c11-7-1-2-8(10-9(7)12-16-13-10)14-3-5-15-6-4-14/h1-2H,3-6,11H2

InChI key

LWCSTSZSZFUHAT-UHFFFAOYSA-N

Biochem/physiol Actions

Compound 11 (CP11) is an orally active and brain-penetrant delta-secretase (δ-secretase; AEP) inhibitor that selectively blocks AEP (IC50 = 710 nM) but not other related cysteine proteases (Caspase-3/-8 IC50 = 31.86/86.71 μM, Cathepsin-S/-L IC50 >200 μM) via a dual active site-directed and allosteric mode of inhibition. CP11 inhibits Pala cellular AEP activity in cultures (IC50 = 800 nM) and improves cognitive functions in murine models of Alzheimer′s disease (AD) in vivo (10 mg/kg tau P301S or 5xFAD mice via daily p.o.) by reducing tau and APP cleavage, ameliorating synapse loss and augmenting long-term potentiation.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H302,H311

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000187269
0000187267
0000182497

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Ju Wang et al.
Translational neurodegeneration, 10(1), 12-12 (2021-04-02)
Currently, there is no cure for Alzheimer's disease (AD). Therapeutics that can modify the early stage of AD are urgently needed. Recent studies have shown that the pathogenesis of AD is closely regulated by an endo/lysosomal asparaginyl endopeptidase (AEP). Inhibition
Zhentao Zhang et al.
Nature communications, 8, 14740-14740 (2017-03-28)
δ-secretase, also known as asparagine endopeptidase (AEP) or legumain, is a lysosomal cysteine protease that cleaves both amyloid precursor protein (APP) and tau, mediating the amyloid-β and tau pathology in Alzheimer's disease (AD). Here we report the therapeutic effect of
Guiqin Chen et al.
Science advances, 7(16) (2021-04-18)
Netrin-1, a family member of laminin-related secreted proteins, mediates axon guidance and cell migration during neural development. T835M mutation in netrin receptor UNC5C predisposes to the late-onset Alzheimer's disease (AD) and increases neuronal cell death. However, it remains unclear how

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