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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

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About This Item

Empirical Formula (Hill Notation):
C22H28Cl2N2 · 2HCl
CAS Number:
366-93-8
Molecular Weight:
464.30
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥95% (HPLC)
Form:
solid
Quality level:
100
Storage condition:
OK to freeze, desiccated (hygroscopic)
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Quality Level

100

description

RTECS - GU7025000

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

SMILES string

[Cl-].[Cl-].Clc1c(cccc1)CNCC2CCC(CC2)CNCc3c(cccc3)Cl.[H+].[H+]

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

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

Preparation Note

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

Disclaimer

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk

WGK 3

Certificates of Analysis (COA)

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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

Global Trade Item Number

SKUGTIN
190080-5MG04055977221336