An agonist of Smoothened
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SAG

Item No. 11914

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-chloro-N-[trans-4-(methylamino)cyclohexyl]-N-[[3-(4-pyridinyl)phenyl]methyl]-benzo[b]thiophene-2-carboxamide
CAS Number
912545-86-9
Synonyms
  • Smoothened Agonist
Molecular Formula
C28H28ClN3OS
Formula Weight
490.1
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
230 nm
SMILES
O=C(C(SC1=CC=CC=C21)=C2Cl)N([C@@H]3CC[C@@H](NC)CC3)CC4=CC(C5=CC=NC=C5)=CC=C4
InChi Code
InChI=1S/C28H28ClN3OS/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/t22-,23-
InChi Key
VFSUUTYAEQOIMW-YHBQERECSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $29

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    5 mg

    $101

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    10 mg

    $129

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    50 mg

    $429

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    Product Description

    Smoothened agonist (SAG) is a chlorobenzothiophene-containing compound which acts as a SMO agonist (EC50 = 3 nM) but inhibits hedgehog signaling at high concentrations (>1 μM).1 It directly binds to SMO and can block SMO inhibition by cyclopamine.1 Binding of SAG alters the conformation of SMO, leading to its accumulation in cilia and activation of gene transcription.2,3,4 At 15-240 nM, SAG prevents the neurotoxic effects of glucocorticoids without interfering with the beneficial effects of glucocorticoids on lung maturation.5 At higher concentrations (0.4 mM), SAG improves the conversion of human induced pluripotent stem cells to the neural lineage.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, J.K., Taipale, J., Young, K.E., et al. Small molecule modulation of smoothened activity. Proc. Natl. Acad. Sci. USA 99(22), 14071-14076 (2002).

    2. Frank-Kamenetsky, M., Zhang, X.M., Bottega, S., et al. Small-molecule modulators of Hedgehog signaling: Identification and characterization of smoothened agonists and antagonists. J. Biol. 1(2), 10 (2002).

    3. Yang, H., Xiang, J., Wang, N., et al. Converse conformational control of smoothened activity by structurally related small molecules. The Journal of Biological Chemisty 284(31), 20876-20884 (2009).

    4. Rohatgi, R., Milenkovic, L., Corcoran, R.B., et al. Hedgehog signal transduction by smoothened: Pharmacologic evidence for a 2-step activation process. Proc. Natl. Acad. Sci. USA 106(9), 3196-3201 (2009).

    5. Heine, V.M., Griveau, A., Chapin, C., et al. A small-molecule smoothened agonist prevents glucocorticoid-induced neonatal cerebellar injury. Sci. Transl. Med. 3(105), 1-9 (2011).

    6. Mak, S.K., Huang, Y.A., Iranmanesh, S., et al. Small molecules greatly improve conversion of human-induced pluripotent stem cells to the neuronal lineage. Stem Cells Int. 2012, (2012).