SML0209
ANA-12
≥98% (HPLC), TrkB antagonist, powder
Synonym(s):
N-[2-[[(Hexahydro-2-oxo-1H-azepin-3-yl)amino]carbonyl]phenyl]-benzo[b]thiophene-2-carboxamide
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About This Item
Empirical Formula (Hill Notation):
C22H21N3O3S
CAS Number:
Molecular Weight:
407.49
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
ANA-12, ≥98% (HPLC)
Quality Level
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
Application
ANA-12 was used to inhibit TrkB in primary mouse cortical neurons and primary rat hippocampal cultures.
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.
TrkB antagonist that possesses potent anxiolytic-like and antidepressant-like activities in mice
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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A Montalbano et al.
Hippocampus, 23(10), 879-889 (2013-05-16)
Long-term potentiation (LTP) is accompanied by increased spine density and dimensions triggered by signaling cascades involving activation of the neurotrophin brain-derived neurotrophic factor (BDNF) and cytoskeleton remodeling. Chemically-induced long-term potentiation (c-LTP) is a widely used cellular model of plasticity, whose
Shi-Meng Zhou et al.
Neuroreport, 28(5), 259-267 (2017-02-28)
Cucurbitacin IIa (CuIIa) is the major active component of the Helmseya amabilis root and is known to have antiviral and anti-inflammatory effects. In this study, we examined the antidepressant-like effects of CuIIa in a mouse model of chronic unpredictable mild
Maxime Cazorla et al.
The Journal of clinical investigation, 121(5), 1846-1857 (2011-04-21)
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. However, therapeutic compounds that interact with TrkB receptors have been difficult