SAG
| Code | Size | Price |
|---|
| AG-CR1-3506-M001 | 1 mg | £55.00 |
Quantity:
| AG-CR1-3506-M005 | 5 mg | £110.00 |
Quantity:
| AG-CR1-3506-M025 | 25 mg | £240.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
3-Chloro-N-[trans-4-(methylamino)cyclohexyl]-N-[3-(4-pyridinyl)benzyl]-1-benzothiophene-2-carboxamide
Appearance:
Off-white to light yellow powder.
CAS:
912545-86-9
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Protect from light.
InChi:
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-
InChiKey:
VFSUUTYAEQOIMW-YHBQERECSA-N
Long Description:
Chemical. CAS: 912545-86-9. Formula: C28H28ClN3OS. MW: 490.1. Cell permeable Sonic hedgehog (Shh) agonist. Cell permeable smoothened (Smo) agonist. Induces Sonic hedgehog (Shh) pathway activation and counteracts cyclopamine inhibition of Smo. Acts as an activator of Smo at low concentrations and as an inhibitor of Smo at very high concentrations. Potent activator of VEGF expression in vitro.
MDL:
MFCD22581513
Molecular Formula:
C28H28ClN3OS
Molecular Weight:
490.1
Package Type:
Vial
Product Description:
Cell permeable Sonic hedgehog (Shh) agonist. Cell permeable smoothened (Smo) agonist. Induces Sonic hedgehog (Shh) pathway activation and counteracts cyclopamine inhibition of Smo. Acts as an activator of Smo at low concentrations and as an inhibitor of Smo at very high concentrations. Potent activator of VEGF expression in vitro.
Purity:
>98% (NMR)
SMILES:
[H][C@@]1(CC[C@@]([H])(CC1)N(CC1=CC=CC(=C1)C1=CC=NC=C1)C(=O)C1=C(Cl)C2=CC=CC=C2S1)NC
Solubility Chemicals:
Soluble in DMSO. Sparingly soluble in water (acidification with HCl increases water solubility).
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C. Store solutions at -20°C in the dark.
References
Small-molecule modulators of Hedgehog signaling: identification and characterization of Smoothened agonists and antagonists: M. Frank-Kamenetsky, et al.; J. Biol. 1, 10 (2002) | Small molecule modulation of Smoothened activity: J.K. Chen, et al.; PNAS 99, 14071 (2002) | Activity-dependent internalization of smoothened mediated by beta-arrestin 2 and GRK2: W. Chen, et al.; Science 306, 2257 (2004) | Smoothened Signal Transduction is Promoted by G-Protein Coupled Receptor Kinase 2: A.R. Meloni et al.; Mol. Cell Biol. 26, 7550 (2006) | Oxysterols stimulate Sonic hedgehog signal transduction and proliferation of medulloblastoma cells: R.B. Corcoran & M.P. Scott; PNAS 103, 8408 (2006) | Identification and characterization of Hedgehog modulator properties after functional coupling of Smoothened to G15: C. Masdeu, et al.; BBRC 349, 471 (2006) | Wnt signaling stimulates transcriptional outcome of the Hedgehog pathway by stabilizing GLI1 mRNA: F.K. Noubissi, et al.; Cancer Res. 69, 8572 (2009) | Evidence for allosteric interactions of antagonist binding to the smoothened receptor: C.M. Rominger, et al.; J. Pharmacol. Exp. Ther. 329, 995 (2009) | Converse conformational control of smoothened activity by structurally related small molecules: H. Yang, et al.; J. Biol. Chem. 284, 20876 (2009) | Identification of a suppressive mechanism for Hedgehog signaling through a novel interaction of Gli with 14-3-3: Y. Asoaka, et al.; J. Biol. Chem. 285, 4185 (2010) | Smoothened agonist augments proliferation and survival of neural cells: O. Bragina, et al.; Neurosci. Lett. 482, 81 (2010) | Subregional specification of embryonic stem cell-derived ventral telencephalic tissues by timed and combinatory treatment with extrinsic signals: T. Danjo, et al.; J. Neurosci. 31, 1919 (2011) | Potent small molecule Hedgehog agonists induce VEGF expression in vitro: K. Seifert, et al.; Bioorg. Med. Chem. 20, 6465 (2012) | Synchronous firing patterns of induced pluripotent stem cell-derived cortical neurons depend on the network structure consisting of excitatory and inhibitory neurons: S. Iida, et al.; BBRC 501, 152 (2018) | Mitogen-activated kinase kinase kinase 1 inhibits hedgehog signaling and medulloblastoma growth through GLI1 phosphorylation: L. Antonucci, et al. Int. J. Oncol. 54, 505 (2018)