190080

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

Propriétés

• 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

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

Informations sur la sécurité

• Pictogrammes: GHS06
• Mention d'avertissement: Danger
• Mentions de danger: H301
• Conseils de prudence: P264 - P270 - P301 + P310 - P405 - P501
• 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