190080

AY 9944

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

• Synonym(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
• Empirical Formula (Hill Notation): C₂₂H₂₈Cl₂N₂ · 2HCl
• CAS Number: 366-93-8
• Molecular Weight: 464.30
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥95% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; desiccated (hygroscopic)
• color: white
• solubility: DMSO: 20 mg/mL; water: 20 mg/mL
• shipped in: ambient
• storage temp.: 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
• InChI key: NRVIEWRSGDDWHP-UHFFFAOYSA-N

Description

General description

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.

Biochem/physiol Actions

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

Packaging

Packaged under inert gas

Warning

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.

Other Notes

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.

Legal Information

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

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3