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566660

Sigma-Aldrich

SAG

≥98% (HPLC), solid, smoothened agonist, Calbiochem®

Synonym(s):

Smoothened Agonist, SAG

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About This Item

Empirical Formula (Hill Notation):
C28H28ClN3OS · 2HCl · 2H2O
CAS Number:
364590-63-6
Molecular Weight:
599.01
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Smoothened Agonist, SAG, A cell-permeable Smoothened Agonist, SAG, CAS 364590-63-6, modulates the coupling of Smo with its downstream effector by interacting with the Smo heptahelical domain (KD = 59 nM).

Quality Level

100

Assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

light yellow

solubility

DMSO: 10 mg/mL
water: 25 mg/mL

shipped in

ambient

storage temp.

2-8°C

InChI

1S/C28H28ClN3OS.2ClH.H2O/c1-30-22-9-11-23(12-10-22)32(28(33)27-26(29)24-7-2-3-8-25(24)34-27)18-19-5-4-6-21(17-19)20-13-15-31-16-14-20;;;/h2-8,13-17,22-23,30H,9-12,18H2,1H3;2*1H;1H2

InChI key

IYXUQUYRWPGIQL-UHFFFAOYSA-N

General description

A cell-permeable Smoothened Agonist, SAG, CAS 364590-63-6, modulates the coupling of Smo with its downstream effector by interacting with the Smo heptahelical domain (KD = 59 nM).
A cell-permeable benzothiophene compound that modulates the coupling of Smo with its downstream effector by interacting with the Smo heptahelical domain (KD = 59 nM). Shown to induce Smo internalization. Shown to induce Hedgehog pathway activation (EC50 ∼3 nM in NIH 3T3-derived Shh-LIGHT2 cells) and counteracts Cyclopamine-KAAD (Cat. No. 239804) inhibition of Smo. Reported to act as an activator at low concentrations and as an inhibitor at very high concentrations.
A cell-permeable benzothiophene compound that modulates the coupling of Smo with its downstream effector by interacting with the Smo heptahelical domain (KD = 59 nM). Shown to induce Smo internalization. Shown to induce Hedgehog pathway activation (EC50 = ∼ 3 nM in NIH 3T3-derived Shh-LIGHT2 cells) and counteracts Cyclopamine-KAAD (Cat. No. 239804) inhibition of Smo. Reported to act as an activator at low concentrations and as an inhibitor at very high concentrations. A 10 mM (500 µg/86 µl) solution of Smoothened Agonist, SAG (Cat. No. 566661) in H2O is also available.

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Wang, J., et al. 2010. Proc. Natl. Acad. Sci. USA.107, 9323.
Meloni, A.R., et al. 2006. Mol. Cell. Biol.26, 7750.
Chen, W., et al. 2004. Science306, 2257.
Chen, J.K., et al. 2002. Proc. Natl. Acad. Sci. USA99, 14071.
Frank-Kamenetsky, M., et al. 2002. J. Biol.1, 10.

Legal Information

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The Journal of cell biology, 220(1) (2020-12-08)
Vertebrate Hedgehog signals are transduced through the primary cilium, a specialized lipid microdomain that is required for Smoothened activation. Cilia-associated sterol and oxysterol lipids bind to Smoothened to activate the Hedgehog pathway, but how ciliary lipids are regulated is incompletely
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