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MedKoo Cat#: 510340 | Name: ANA-12
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

ANA-12 is aTrkB receptor antagonist. ANA-12 showed direct and selective binding to TrkB and inhibited processes downstream of TrkB without altering TrkA and TrkC functions. 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. 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.

Chemical Structure

ANA-12
ANA-12
CAS#219766-25-3

Theoretical Analysis

MedKoo Cat#: 510340

Name: ANA-12

CAS#: 219766-25-3

Chemical Formula: C22H21N3O3S

Exact Mass: 407.1304

Molecular Weight: 407.49

Elemental Analysis: C, 64.85; H, 5.19; N, 10.31; O, 11.78; S, 7.87

Price and Availability

Size Price Availability Quantity
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 450.00 Ready to ship
100mg USD 650.00 Ready to ship
200mg USD 950.00 Ready to ship
500mg USD 1,650.00 Ready to ship
1g USD 2,250.00 2 Weeks
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No Data
Synonym
ANA12; ANA 12; ANA-12.
IUPAC/Chemical Name
N-(2-((2-oxoazepan-3-yl)carbamoyl)phenyl)benzo[b]thiophene-2-carboxamide
InChi Key
TUSCYCAIGRVBMD-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(C1=CC2=CC=CC=C2S1)NC3=CC=CC=C3C(NC4C(NCCCC4)=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
        
Biological target:
ANA-12 is a TrkB antagonist with IC50s of 45.6 nM and 41.1 μM for the high and low affinity sites, respectively.
In vitro activity:
To evaluate the effects of TrkB inhibition on MB cell viability, this study exposed the cells to varying concentrations of ANA-12 (5, 10, 20, or 30 µM) for different time periods (24, 48, or 72 h). A dose-dependent reduction of cell viability was observed in both cell lines, and increasing effects were observed with longer exposure ANA-12 (Figure 1 A). Fifty percent inhibition of growth (IC50) was calculated for ANA-12 considering different exposure times, ranging from 23.99 to 17.42 µM in UW228 cells and 24.83 to 14.74 in D283 cells (Figure 1B). Moreover, changes in cell viability were accompanied by alterations in cell morphology characteristic of cell death features in both cell lines, and differentiation in UW228 cells (Figure 1C). Reference: Front Pharmacol. 2019; 10: 698. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6606946/
In vivo activity:
After this study further blocked the BDNF/TrkB-CREB signalling pathway with an inhibitor (ANA-12), the degree of rat spinal cord oedema and BSCB permeability increased significantly, and the intercellular connection widened, suggesting severe destruction of the BSCB structure, accompanied by poor motor function scores. Furthermore, the increased expression of TJ and AJ proteins (p120-Catenin, β-Catenin, Occludin, Claudin-5, and ZO-1) mediated by TT was effectively suppressed by the inhibitor. These results prove that TT-mediated BSCB protection is mediated by the BDNF/TrkB-CREB signalling pathway (Fig. 7). Reference: Neurochem Int. 2021 Feb;143:104945. https://pubmed.ncbi.nlm.nih.gov/33359781/
Solvent mg/mL mM comments
Solubility
DMSO 14.8 36.34
DMF 5.0 12.27
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 407.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Thomaz A, Pinheiro KV, Souza BK, Gregianin L, Brunetto AL, Brunetto AT, de Farias CB, Jaeger MDC, Ramaswamy V, Nör C, Taylor MD, Roesler R. Antitumor Activities and Cellular Changes Induced by TrkB Inhibition in Medulloblastoma. Front Pharmacol. 2019 Jun 26;10:698. doi: 10.3389/fphar.2019.00698. PMID: 31297057; PMCID: PMC6606946. 2. Heinen TE, Dos Santos RP, da Rocha A, Dos Santos MP, Lopez PL, Silva Filho MA, Souza BK, Rivero LF, Becker RG, Gregianin LJ, Brunetto AL, Brunetto AT, de Farias CB, Roesler R. Trk inhibition reduces cell proliferation and potentiates the effects of chemotherapeutic agents in Ewing sarcoma. Oncotarget. 2016 Jun 7;7(23):34860-80. doi: 10.18632/oncotarget.8992. PMID: 27145455; PMCID: PMC5085195. 3. Ying X, Xie Q, Yu X, Li S, Wu Q, Chen X, Yue J, Zhou K, Tu W, Jiang S. Water treadmill training protects the integrity of the blood-spinal cord barrier following SCI via the BDNF/TrkB-CREB signalling pathway. Neurochem Int. 2021 Feb;143:104945. doi: 10.1016/j.neuint.2020.104945. Epub 2020 Dec 24. PMID: 33359781. 4. Gross KS, Alf RL, Polzin TR, Frick KM. 17β-estradiol activation of dorsal hippocampal TrkB is independent of increased mature BDNF expression and is required for enhanced memory consolidation in female mice. Psychoneuroendocrinology. 2021 Mar;125:105110. doi: 10.1016/j.psyneuen.2020.105110. Epub 2020 Dec 15. PMID: 33352471; PMCID: PMC7904635.
In vitro protocol:
1. Thomaz A, Pinheiro KV, Souza BK, Gregianin L, Brunetto AL, Brunetto AT, de Farias CB, Jaeger MDC, Ramaswamy V, Nör C, Taylor MD, Roesler R. Antitumor Activities and Cellular Changes Induced by TrkB Inhibition in Medulloblastoma. Front Pharmacol. 2019 Jun 26;10:698. doi: 10.3389/fphar.2019.00698. PMID: 31297057; PMCID: PMC6606946. 2. Heinen TE, Dos Santos RP, da Rocha A, Dos Santos MP, Lopez PL, Silva Filho MA, Souza BK, Rivero LF, Becker RG, Gregianin LJ, Brunetto AL, Brunetto AT, de Farias CB, Roesler R. Trk inhibition reduces cell proliferation and potentiates the effects of chemotherapeutic agents in Ewing sarcoma. Oncotarget. 2016 Jun 7;7(23):34860-80. doi: 10.18632/oncotarget.8992. PMID: 27145455; PMCID: PMC5085195.
In vivo protocol:
1. Ying X, Xie Q, Yu X, Li S, Wu Q, Chen X, Yue J, Zhou K, Tu W, Jiang S. Water treadmill training protects the integrity of the blood-spinal cord barrier following SCI via the BDNF/TrkB-CREB signalling pathway. Neurochem Int. 2021 Feb;143:104945. doi: 10.1016/j.neuint.2020.104945. Epub 2020 Dec 24. PMID: 33359781. 2. Gross KS, Alf RL, Polzin TR, Frick KM. 17β-estradiol activation of dorsal hippocampal TrkB is independent of increased mature BDNF expression and is required for enhanced memory consolidation in female mice. Psychoneuroendocrinology. 2021 Mar;125:105110. doi: 10.1016/j.psyneuen.2020.105110. Epub 2020 Dec 15. PMID: 33352471; PMCID: PMC7904635.
1: Tillu DV, Hassler SN, Burgos-Vega CC, Quinn TL, Sorge RE, Dussor G, Boitano S, Vagner J, Price TJ. Protease activated receptor 2 (PAR2) activation is sufficient to induce the transition to a chronic pain state. Pain. 2015 Feb 12. [Epub ahead of print] PubMed PMID: 25734998. 2: Dalton JE, Glover AC, Hoodless L, Lim EK, Beattie L, Kirby A, Kaye PM. The neurotrophic receptor Ntrk2 directs lymphoid tissue neovascularization during Leishmania donovani infection. PLoS Pathog. 2015 Feb 24;11(2):e1004681. doi: 10.1371/journal.ppat.1004681. eCollection 2015 Feb. PubMed PMID: 25710496; PubMed Central PMCID: PMC4339582. 3: Zhang JC, Wu J, Fujita Y, Yao W, Ren Q, Yang C, Li SX, Shirayama Y, Hashimoto K. Antidepressant Effects of TrkB Ligands on Depression-Like Behavior and Dendritic Changes in Mice After Inflammation. Int J Neuropsychopharmacol. 2014 Oct 31;18(4). pii: pyu077. doi: 10.1093/ijnp/pyu077. PubMed PMID: 25628381. 4: Kishi T, Hirooka Y, Nagayama T, Isegawa K, Katsuki M, Takesue K, Sunagawa K. Calorie Restriction Improves Cognitive Decline via Up-Regulation of Brain-Derived Neurotrophic Factor. Int Heart J. 2015 Jan 21;56(1):110-5. doi: 10.1536/ihj.14-168. Epub 2014 Dec 11. PubMed PMID: 25503654. 5: Fan D, Li J, Zheng B, Hua L, Zuo Z. Enriched Environment Attenuates Surgery-Induced Impairment of Learning, Memory, and Neurogenesis Possibly by Preserving BDNF Expression. Mol Neurobiol. 2014 Nov 29. [Epub ahead of print] PubMed PMID: 25432890. 6: Li PC, Jiao Y, Ding J, Chen YC, Cui Y, Qian C, Yang XY, Ju SH, Yao HH, Teng GJ. Cystamine Improves Functional Recovery via Axon Remodeling and Neuroprotection after Stroke in Mice. CNS Neurosci Ther. 2015 Mar;21(3):231-40. doi: 10.1111/cns.12343. Epub 2014 Nov 27. PubMed PMID: 25430473. 7: Liang DY, Sun Y, Shi XY, Sahbaie P, Clark JD. Epigenetic regulation of spinal cord gene expression controls opioid-induced hyperalgesia. Mol Pain. 2014 Sep 12;10:59. doi: 10.1186/1744-8069-10-59. PubMed PMID: 25217253; PubMed Central PMCID: PMC4171542. 8: Chen W, Walwyn W, Ennes HS, Kim H, McRoberts JA, Marvizón JC. BDNF released during neuropathic pain potentiates NMDA receptors in primary afferent terminals. Eur J Neurosci. 2014 May;39(9):1439-54. doi: 10.1111/ejn.12516. Epub 2014 Mar 11. PubMed PMID: 24611998; PubMed Central PMCID: PMC4122572. 9: Leggio GM, Camillieri G, Platania CB, Castorina A, Marrazzo G, Torrisi SA, Nona CN, D'Agata V, Nobrega J, Stark H, Bucolo C, Le Foll B, Drago F, Salomone S. Dopamine D3 receptor is necessary for ethanol consumption: an approach with buspirone. Neuropsychopharmacology. 2014 Jul;39(8):2017-28. doi: 10.1038/npp.2014.51. Epub 2014 Mar 3. PubMed PMID: 24584330; PubMed Central PMCID: PMC4059912. 10: Greenberg GD, Laman-Maharg A, Campi KL, Voigt H, Orr VN, Schaal L, Trainor BC. Sex differences in stress-induced social withdrawal: role of brain derived neurotrophic factor in the bed nucleus of the stria terminalis. Front Behav Neurosci. 2014 Jan 9;7:223. doi: 10.3389/fnbeh.2013.00223. eCollection 2014. PubMed PMID: 24409132; PubMed Central PMCID: PMC3885825.

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