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Key Documents

190080

Sigma-Aldrich

AY 9944

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

Synonyma:

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

Empirický vzorec (Hillův zápis):
C22H28Cl2N2 · 2HCl
Číslo CAS:
366-93-8
Molekulová hmotnost:
464.30
UNSPSC Code:
12352200
NACRES:
NA.77

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

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

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_germany

WGK 3

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