ANA 12TrkB receptor antagonist CAS# 219766-25-3 |
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Quality Control & MSDS
3D structure
Package In Stock
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| Cas No. | 219766-25-3 | SDF | Download SDF |
| PubChem ID | 2799722 | Appearance | Powder |
| Formula | C22H21N3O3S | M.Wt | 407.49 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : 9.09 mg/mL (22.31 mM; Need ultrasonic) H2O : < 0.1 mg/mL (insoluble) | ||
| Chemical Name | N-[2-[(2-oxoazepan-3-yl)carbamoyl]phenyl]-1-benzothiophene-2-carboxamide | ||
| SMILES | C1CCNC(=O)C(C1)NC(=O)C2=CC=CC=C2NC(=O)C3=CC4=CC=CC=C4S3 | ||
| Standard InChIKey | TUSCYCAIGRVBMD-UHFFFAOYSA-N | ||
| Standard InChI | 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) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | TrkB receptor antagonist. Demonstrates a 2-site mode of action, preventing activation by BDNF non-competitively (IC50 values are 45.6 nM and 41.1 μM for the high and low affinity sites respectively). Displays no effect on TrkA and TrkC in an assay of neurite outgrowth. Demonstrates antidepressant properties. |
ANA 12 Dilution Calculator
ANA 12 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.454 mL | 12.2702 mL | 24.5405 mL | 49.081 mL | 61.3512 mL |
| 5 mM | 0.4908 mL | 2.454 mL | 4.9081 mL | 9.8162 mL | 12.2702 mL |
| 10 mM | 0.2454 mL | 1.227 mL | 2.454 mL | 4.9081 mL | 6.1351 mL |
| 50 mM | 0.0491 mL | 0.2454 mL | 0.4908 mL | 0.9816 mL | 1.227 mL |
| 100 mM | 0.0245 mL | 0.1227 mL | 0.2454 mL | 0.4908 mL | 0.6135 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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ANA 12 is a potent and selective antagonist of TrkB with IC50 values of 45.6 nM and 41.1 μM for the high and low affinity sites, respectively [1].
Tropomyosin-related kinase B (TrkB) is a receptor for brain-derived neurotrophic factor (BDNF) and neurotrophin-4/5 (NT-4/5) and activates 3 major signaling pathways involving phospholipase C-γ, PI3K and MAPK. The BDNF/TrkB signaling plays an important role in drug addiction, depression and anxiety [1].
ANA 12 is a potent and selective TrkB antagonist. ANA-12 bound to the extracellular low-affinity site of TrkB with Kd value of 12 μM in a dose-dependent way. And ANA-12 bound to the high-affinity site with Kd value of 10 nM. Also, ANA-12 bound to TrkB in a noncompetitive mechanism. In the TrkB-expressing cells, ANA-12 (10 nM) effectively inhibited BDNF-induced neurite outgrowth and completely abolished the effects of BDNF at 10-100 μM [1].
In the mice brain, ANA-12 (0.5 mg/kg) inhibited endogenous TrkB activity by 25% 4 hours later. Also, ANA-12 showed antidepressant and anxiolytic activities [1].
Reference:
[1]. Cazorla M, Prémont J, Mann A, et al. Identification of a low-molecular weight TrkB antagonist with anxiolytic and antidepressant activity in mice. J Clin Invest, 2011, 121(5): 1846-1857.
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Comparison of ketamine, 7,8-dihydroxyflavone, and ANA-12 antidepressant effects in the social defeat stress model of depression.[Pubmed:26337614]
Psychopharmacology (Berl). 2015 Dec;232(23):4325-35.
RATIONALE: Brain-derived neurotrophic factor (BDNF) and signaling at its receptor, tropomyosin-related kinase B (TrkB), are implicated in the rapid and long-lasting antidepressant effects of ketamine. Moreover, a TrkB agonist, 7,8-dihydroxyflavone (7,8-DHF), and/or TrkB antagonist, ANA-12, shows antidepressant effects in animal models of depression. OBJECTIVE: The objective of this study is to compare the influence of ketamine, 7,8-DHF, and ANA-12 on antidepressant activity in the social defeat stress model. RESULTS: In the tail suspension and forced swimming tests, ketamine, 7,8-DHF, or ANA-12 markedly attenuated the increased immobility time in depressed mice compared with the vehicle-treated group. In the sucrose preference test, all drugs significantly improved the reduced preference in depressed mice at both 1 and 3 days after a single dose. Antidepressant effect of ketamine, but not 7,8-DHF or ANA-12, was still detectable 7 days after a single dose. Western blot analyses showed that ketamine, but not 7,8-DHF or ANA-12, markedly attenuated reduced levels of BDNF and postsynaptic density protein 95 (PSD-95) in the prefrontal cortex (PFC), dentate gyrus (DG), and CA3 of the hippocampus in depressed mice 8 days after a single dose. Furthermore, ketamine markedly increased reduced levels of GluA1 in the PFC and DG of depressed mice. In contrast, ketamine showed no effect against increased levels of BDNF, PSD-95, and GluA1 observed in the nucleus accumbens of depressed mice. CONCLUSIONS: Compared with 7,8-DHF and ANA-12, ketamine is a longer-lasting antidepressant in the social defeat stress model, and synaptogenesis may be required for the mechanisms that promote sustained antidepressant effects of ketamine.
Identification of a low-molecular weight TrkB antagonist with anxiolytic and antidepressant activity in mice.[Pubmed:21505263]
J Clin Invest. 2011 May;121(5):1846-57.
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 to develop. Using a combination of structure-based in silico screening and high-capacity functional assays in recombinant and neuronal cells, we identified a low-molecular weight TrkB ligand (ANA-12) that prevented activation of the receptor by BDNF with a high potency. ANA-12 showed direct and selective binding to TrkB and inhibited processes downstream of TrkB without altering TrkA and TrkC functions. KIRA-ELISA analysis demonstrated that systemic administration of ANA-12 to adult mice decreased TrkB activity in the brain without affecting neuronal survival. Mice administered ANA-12 demonstrated reduced anxiety- and depression-related behaviors on a variety of tests predictive of anxiolytic and antidepressant properties in humans. This study demonstrates that structure-based virtual screening strategy can be an efficient method for discovering potent TrkB-selective ligands that are active in vivo. We further propose that 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.
