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SML0209 Sigma-Aldrich

ANA-12

≥98% (HPLC)

Synonym: N-[2-[[(Hexahydro-2-oxo-1H-azepin-3-yl)amino]carbonyl]phenyl]-benzo[b]thiophene-2-carboxamide

  • CAS Number 219766-25-3

  • Empirical Formula (Hill Notation) C22H21N3O3S

  • Molecular Weight 407.49

  •  MDL number MFCD00117444

  •  PubChem Substance ID 329825231

  •  NACRES NA.77

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Properties

Related Categories AN-AZ, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
Quality Level   100
assay   ≥98% (HPLC)
form   powder
color   white to beige
solubility   DMSO: ≥5 mg/mL at 60 °C
storage temp.   2-8°C
SMILES string   O=C1NCCCCC1NC(=O)c2ccccc2NC(=O)c3cc4ccccc4s3
InChI   1S/C22H21N3O3S/c26-20(25-17-10-5-6-12-23-21(17)27)15-8-2-3-9-16(15)24-22(28)19-13-14-7-1-4-11-18(14)29-19/h1-4,7-9,11,13,17H,5-6,10,12H2,(H,23,27)(H,24,28)(H,25,26)
InChI key   TUSCYCAIGRVBMD-UHFFFAOYSA-N

Description

Application

ANA-12 was used to inhibit TrkB in primary mouse cortical neurons and primary rat hippocampal cultures.

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

The neurotrophin brain-derived neurotrophic factor (BDNF) and its receptor tropomyosin-related kinase B (TrkB) have emerged as key mediators in the pathophysiology of several mood disorders, including anxiety and depression. ANA-12 is a TrkB ligand that prevents activation of the receptor by BDNF with a high potency. It binds selectively to TrkB and inhibits processes downstream of TrkB without altering TrkA and TrkC functions. In adult mice model ANA-12 decreases TrkB activity in the brain without affecting neuronal survival. Mice dosed with ANA-12 show reduced anxiety- and depression related behaviors on a variety of tests predictive of anxiolytic and antidepressant properties in humans. ANA-12 may be a valuable tool for studying BDNF/TrkB signaling and may constitute a lead compound for developing the next generation of therapeutic agents for the treatment of mood disorders. There is also N-T19, which is less potent.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Cytokines & Growth Factors Research

Cytokines and growth factors (GF) are chemical messengers that mediate intracellular communication, thereby regulating cellular and nuclear functions. These chemical messengers bind cell surface rece...
Keywords: Biological processes, Cancer, Cell proliferation, Diseases, Growth factors, Ligands, Phosphorylations, Transcription, Transduction

Trk

The neurotrophins are a family of proteins that regulate cell survival, differentiation and growth in the vertebrate nervous system. Nerve growth factor (NGF), brain derived neurotrophic factor (BDNF...
Keywords: Alzheimer Disease, Apoptosis, Atomic absorption spectroscopy, Cancer, Catalysis, Central Nervous System, Gene expression, Growth factors, Ligands, Neurotransmitters, Phosphorylations, RNA immunoprecipitation, Schizophrenia, Transduction

Peer-Reviewed Papers
15

References

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