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565772

Sigma-Aldrich

γ-Secretase Inhibitor XI - CAS 62252-26-0 - Calbiochem

Synonym(s):

7-Amino-4-chloro-3-methoxyisocoumarin, JLK6

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Assay

≥97% (HPLC)

form

solid

color

yellow

solubility

DMSO: 5 mg/mL

General description

A non-peptidic, cell-permeable, active site-directed, irreversible serine protease inhibitor that belongs to the class of isocoumarin analogs. Acts as a potent and selective inhibitor of γ-secretase and blocks the production of both amyloid-β 40 (Aβ40) and 42 (Aβ42) in HEK293 cells (70-80% inhibition at 100 μM concentration) expressing wild-type and Swedish-mutant β-amyloid precursor protein (βAPP). Does not exhibit any significant effect on either the processing or mΔEnotch-1 or the endoproteolysis of presenilins.

Application

The γ-Secretase Inhibitor XI controls the biological activity of γ-Secretase. This small molecule/inhibitor is primarily used for Neuroscience applications.

Biochem/physiol Actions

γ-secretase and blocks the production of both Aβ40 and Aβ42 in HEK293 cells expressing wild-type and Swedish-mutant β-amyloid precursor protein (APP)
Target IC50:< 100 μM against γ-secretase and blocks the production of both amyloid-β40 (Aβ40) and Aβ42 in HEK293 cells expressing wild-type and Swedish-mutant β-amyloid precursor protein (APP)

Physical form

t1/2 = 200 min in 100 μM HEPES, 500 μM NaCl, and 10% DMSO, pH 7.5.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 weeks at -20°C. This product is not stable in aqueous solution, hence, dilute in aqueous solution right prior to use (t½ at 25°C = 3.3 h in 100 mM HEPE

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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J E Kerrigan et al.
Journal of medicinal chemistry, 38(3), 544-552 (1995-02-03)
A series of 3-alkoxy-7-amino-4-chloroisocoumarins with various 3-alkoxy substituents have been prepared and evaluated as inhibitors of human leukocyte elastase (HLE). In addition, a new series of acyl, urea, and carbamate derivatives of 7-amino-4-chloro-3-methoxyisocoumarin (1), 7-amino-4-chloro-3-propoxyisocoumarin (3), and 7-amino-4-chloro-3-(2-bromoethoxy)isocoumarin (6) have
A Petit et al.
Nature cell biology, 3(5), 507-511 (2001-05-02)
We have designed new non-peptidic potential inhibitors of gamma-secretase and examined their ability to prevent production of amyloid-beta 40 (Abeta40) and Abeta42 by human cells expressing wild-type and Swedish-mutant beta-amyloid precursor protein (betaAPP). Here we identify three such agents that
J W Harper et al.
Biochemistry, 24(25), 7200-7213 (1985-12-03)
The time-dependent inactivation of several serine proteases including human leukocyte elastase, cathepsin G, rat mast cell proteases I and II, and human skin chymase by a number of 3-alkoxy-4-chloroisocoumarins, 3-alkoxy-4-chloro-7-nitroisocoumarins, and 3-alkoxy-7-amino-4-chloroisocoumarins at pH 7.5 and the inactivation of several
Amyloid-lowering isocoumarins are not direct inhibitors of gamma-secretase.
William P Esler et al.
Nature cell biology, 4(5), E110-E111 (2002-05-04)
K Nagata et al.
The Journal of biological chemistry, 269(37), 23290-23295 (1994-09-16)
We previously reported that activated platelets stimulated neutrophils and monocytes to produce superoxide anion (O2-) through the interaction between P-selectin and its carbohydrate ligand, sialyl Lewis X (sLeX) (Nagata, K., Tsuji, T., Todoroki, N., Katagiri, Y., Tanoue, K., Yamazaki, H.

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