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Key Documents

190080

Sigma-Aldrich

AY 9944

A cell-permeable amphiphilic diamine that blocks cholesterol biosynthesis and its esterification.

Synonyme(s) :

AY 9944, trans-1,4- bis(2-Chlorobenzylaminomethyl)cyclohexane, 2HCl, Shh Signaling Antagonist IV, trans-1,4-bis(2-Chlorobenzylaminomethyl)cyclohexane, 2HCl, Shh Signaling Antagonist IV

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About This Item

Formule empirique (notation de Hill):
C22H28Cl2N2 · 2HCl
Numéro CAS:
366-93-8
Poids moléculaire :
464.30
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥95% (HPLC)

Forme

solid

Fabricant/nom de marque

Calbiochem®

Conditions de stockage

OK to freeze
desiccated (hygroscopic)

Couleur

white

Solubilité

DMSO: 20 mg/mL
water: 20 mg/mL

Conditions d'expédition

ambient

Température de stockage

2-8°C

InChI

1S/C22H28Cl2N2.2ClH/c23-21-7-3-1-5-19(21)15-25-13-17-9-11-18(12-10-17)14-26-16-20-6-2-4-8-22(20)24;;/h1-8,17-18,25-26H,9-16H2;2*1H

Clé InChI

NRVIEWRSGDDWHP-UHFFFAOYSA-N

Description générale

A cell-permeable amphiphilic diamine that blocks cholesterol biosynthesis and its esterification. Specifically blocks 7-dehydrocholesterol reductase (Δ7-sterol reductase) activity with IC50= 13 nM. Important tool in Sonic Hedgehog signaling and teratogenicity studies. Also reported to induce a rapid and irreversible reduction in Acidic-Sphingomyelinase activity in fibroblasts.
A cell-permeable, amphiphilic diamine that acts as a potent inhibitor of cholesterol biosynthesis and esterification and exhibits teratogenic properties. Specifically blocks 7-dehydro-cholesterol reductase (Δ7-sterol reductase; DHC) activity with IC50= 13 nM. Reported to disrupt Sonic Hedgehog (Shh) signaling during embryogenesis in rats. Also reported to induce a rapid and irreversible reduction in acidic-sphingomyelinase activity in fibroblasts.

Actions biochimiques/physiologiques

Cell permeable: yes
Primary Target
7-dehydrocholesterol reductase (δ7-sterol reductase)
Product does not compete with ATP.
Reversible: no
Target IC50: 13 nM in blocking 7-dehydrocholesterol reductase (δ7-sterol reductase) activity

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Reconstitution

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Autres remarques

Gofflot, F., et al. 2001. Dev. Dyn.220, 99.
Cooper, M.K., et al. 1998. Science280, 1603.
Incardona, J.P., et al. 1998. Development125, 3553.
Moebius, F.F., et al. 1998. Proc. Natl. Acad. Sci. USA95, 1899.
Yoshida, Y. 1985. J. Biochem.98, 1669.
Kraml, M., et al. 1964. Biochem. Biophys. Res. Commun.15, 455.

Informations légales

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

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Consulter la Bibliothèque de documents

Qi Sun et al.
Communications biology, 6(1), 1108-1108 (2023-11-02)
Recent findings have shown that fatty acid metabolism is profoundly involved in ferroptosis. However, the role of cholesterol in this process remains incompletely understood. In this work, we show that modulating cholesterol levels changes vulnerability of cells to ferroptosis. Cholesterol

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