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SML1314

Sigma-Aldrich

SAG dihydrochloride

≥98% (HPLC), lyophilized solid, smoothened (Smo) agonist

Synonym(s):

3-Chloro-N-[trans-4-(methylamino)cyclohexyl]-N-[[3-(4-pyridinyl)phenyl]methyl]-benzo[b]thiophene-2-carboxamide dihydrochloride, Smoothened Agonist

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About This Item

Empirical Formula (Hill Notation):
C28H28ClN3OS · 2HCl
CAS Number:
912545-86-9
Molecular Weight:
562.98
UNSPSC Code:
51111800
PubChem Substance ID:
329825779
NACRES:
NA.77

product name

SAG dihydrochloride, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

lyophilized solid

storage condition

desiccated

color

white to beige

solubility

H2O: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C(C1=C(Cl)C2=C(C=CC=C2)S1)N([C@@]3([H])CC[C@@](NC)([H])CC3)CC4=CC(C5=CC=NC=C5)=CC=C4

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

Application

Smoothened agonist (SAG) dihydrochloride has been used as a sonic hedgehog (SHH) pathway agonist:
  • to study its effects on mouse hippocampal cells
  • to determine its effects on the mitochondrial network in zebrafish embryo
  • to study its effects on murine embryonic fibroblasts

Biochem/physiol Actions

SAG is a potent and cell-permeable smoothened (Smo) agonist that activates Hedgehog pathway and counteracts Cyclopamine inhibition of Smo.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H413

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 4

Storage Class Code

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

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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Michaela Prochazkova et al.
Development (Cambridge, England), 144(12), 2212-2221 (2017-05-17)
The patterning of repeated structures is a major theme in developmental biology, and the inter-relationship between spacing and size of such structures is an unresolved issue. Fungiform papillae are repeated epithelial structures that house taste buds on the anterior tongue.
Alp Ozgun et al.
Materials today. Bio, 25, 100992-100992 (2024-02-19)
Modern in vitro technologies for preclinical research, including organ-on-a-chip, organoids- and assembloid-based systems, have rapidly emerged as pivotal tools for elucidating disease mechanisms and assessing the efficacy of putative therapeutics. In this context, advanced in vitro models of Parkinson's Disease
Lina Zhu et al.
PeerJ, 10, e13381-e13381 (2022-05-10)
Smoothened (SMO) protein is a member of the G protein-coupled receptor (GPCR) family that is involved in the Hedgehog (Hh) signaling pathway. It is a putative target for treating various cancers, including medulloblastoma and basal cell carcinoma (BCC). Characterizing membrane
Suping Qin et al.
Behavioural brain research, 367, 91-100 (2019-04-04)
Obesity induces hippocampal neuronal apoptosis and leads to cognitive function deficits. Sonic hedgehog (SHH) signaling is crucial during nervous system development and is neuroprotective in many neurologic diseases. This study assessed the role of SHH signaling in the cognitive deficits
Friederike Hantel et al.
Journal of cell science, 135(9) (2022-05-12)
Cilia are evolutionarily conserved organelles that orchestrate a variety of signal transduction pathways, such as sonic hedgehog (SHH) signaling, during embryonic development. Our recent studies have shown that loss of GID ubiquitin ligase function results in aberrant AMP-activated protein kinase
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