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2-Aminoethyl diphenylborinate (also known as 2-APB) is a novel, potent and cell-permeable inhibitor of IP3R. 2-Aminoethyl diphenylborinate also inhibits the store-operated Ca2+ (SOC) channel and activates some TRP channels (V1, V2 and V3).
| Targets |
IP3R/Inositol triphosphate receptor
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|---|---|
| ln Vitro |
2-Aminoethoxydiphenyl borate (2-APB) is used as a pharmacological tool because it antagonizes inositol 1,4,5-trisphosphate receptors and store-operated Ca(2+) (SOC) channels, and activates some TRP channels. Recently, we reported that 2-APB enhanced the increase in cytotoxic [Ca(2+)]i, resulting in cell death under external acidic conditions in rat pheochromocytoma cell line PC12. However, the molecular mechanism and functional role of the 2-APB-induced Ca(2+) influx in PC12 have not been clarified. In this study, to identify the possible target for the action of 2-APB we examined the pharmacological and molecular properties of [Ca(2+)]i and secretory responses to 2-APB under extracellular low pH conditions. 2-APB dose-dependently induced a [Ca(2+)]i increase and dopamine release, which were greatly enhanced by the external acidification (pH 6.5). [Ca(2+)]i and secretory responses to 2-APB at pH 6.5 were inhibited by the removal of extracellular Ca(2+) and SOC channel blockers such as SK&F96365, La(3+) and Gd(3+). PC12 expressed all SOC channel molecules, Orai 1, Orai 2 and Orai 3. When we used an siRNA system, downregulation of Orai 3, but not Orai 1 and Orai 2, attenuated both [Ca(2+)]i and secretory responses to 2-APB. These results suggest that 2-APB evokes external acid-dependent increases of [Ca(2+)]i and dopamine release in PC12 through the activation of Orai 3. The present results indicate that 2-APB may be a useful pharmacological tool for Orai channel-related signaling[3].
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| ln Vivo |
Autologous arterial blood injection into the cisterna magna caused vasospasm in rats. 2-APB (2-Aminoethyl diphenylborate) treatment increased the BA wall thickness and reduced the BA lumen diameter, inducing significant vascular changes. 2-APB also alleviated cell apoptosis at 24 hours after SAH.
Conclusion: In experimental SAH in rats, 2-APB treatment increased the BA wall thickness and reduced the BA lumen diameter, inducing significant vascular changes. 2-APB also alleviated cell apoptosis at 24 hours after SAH. Keywords: 2-Aminoethyl diphenylborate/2-APB; Ca(2+) channels; Cerebral vasospasm; Orai channels; Subarachnoid hemorrhage; TRP channels[2]. Mean superoxide dismutase, total antioxidant capacity and glutathione were significantly higher in the sham treated group than in the ischemia-perfusion group (p <0.05). Mean malondialdehyde and DNA fragmentation levels were significantly lower in the sham treated group than in the ischemia-reperfusion group (p <0.05). After 2-APB treatment superoxide dismutase, total antioxidant capacity and glutathione were significantly increased but malondialdehyde and DNA fragmentation levels were significantly decreased compared to the ischemia-reperfusion group (p <0.05). The number of TUNEL positive cells was significantly lower in the 2-APB treatment groups than in the ischemia-reperfusion group (p <0.05). Conclusions: In rats 2-APB reduced the oxidative stress and apoptosis caused by testicular ischemia-reperfusion injury. The testicular protective effect of 2-APB appears to be mediated through its antiapoptotic and antioxidative effects. Keywords: 2-aminoethoxydiphenyl borate; apoptosis; oxidative stress; reperfusion injury; testis. https://pubmed.ncbi.nlm.nih.gov/25444954/ |
| Cell Assay |
Dopamine-release experiments[3]
PC12 cells (1×10~5) were seeded in 24-well plates and cultured for 48 h. The medium was then removed, and the cells were washed with HEPES-buffered solution twice and preincubated in HEPES-buffered solution at 37 °C for 20 min. Then they were washed and treated with or without 2-APB in HEPES-buffered solution under each pH condition. Incubation was performed at room temperature for 2 min and then was stopped on ice. Sample solution was collected in a 1.5 mL tube and centrifuged. The supernatant was collected and prepared as supernatant assay solution containing 0.4 N perchloric acid (PCA) (Sup sol.). The cells remaining on the dish were extracted with 0.4 N PCA and prepared as a cell assay solution (Cell sol.). These preparations were performed on ice. |
| Animal Protocol |
In this study, researchers performed an experimental study using 32 Sprague-Dawley rats divided into 4 groups: sham group (n = 8), SAH group (n = 8), 2-APB group (SAH rats intraperitoneally administered with 0.5 mg/kg 2-APB; n = 8), and 2-APB-2 group (SAH rats intraperitoneally administered with 2 mg/kg 2-APB; n = 8). The rats were sacrificed after 24 hours, and superoxide dismutase, glutathione peroxidase, malondialdehyde, tumor necrosis factor-α, and interleukin-1β in the brain tissue and serum were measured. The histopathological investigation of brain tissue included measurement of the luminal diameter and wall thickness of the basilar artery (BA), and apoptotic cells in the hippocampus were counted after caspase staining.[2]
A total of 28 rats were randomly divided into 4 groups, including sham treated, ischemia-reperfusion, ischemia-reperfusion plus 2 mg/kg 2-APB and ischemia-reperfusion plus 4 mg/kg 2-APB. Testicular tissue superoxide dismutase, glutathione, malondialdehyde, total antioxidant capacity and DNA fragmentation levels were determined. Testicular tissue samples were examined by histopathology and TUNEL staining. https://pubmed.ncbi.nlm.nih.gov/25444954/ |
| Toxicity/Toxicokinetics |
mouse LD50 intravenous 56 mg/kg U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals., NX#01899
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| References |
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| Additional Infomation |
2-aminoethoxydiphenylborane is an organoboron compound that is diphenylborane in which the borane hydrogen is replaced by a 2-aminoethoxy group. It has a role as an IP3 receptor antagonist, a calcium channel blocker and a potassium channel opener. It is an organoboron compound and a primary amino compound.
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| Molecular Formula |
C14H16BNO
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|---|---|
| Molecular Weight |
225.09394
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| Exact Mass |
225.132
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| CAS # |
524-95-8
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| PubChem CID |
1598
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| Appearance |
White to off-white solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
325.3±34.0 °C at 760 mmHg
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| Melting Point |
192-194 °C(lit.)
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| Flash Point |
150.6±25.7 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.560
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| LogP |
3.48
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
17
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| Complexity |
182
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
BLZVCIGGICSWIG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H16BNO/c16-11-12-17-15(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10H,11-12,16H2
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| Chemical Name |
2-diphenylboranyloxyethanamine
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| Synonyms |
2-Aminoethyl diphenylborinate; 524-95-8; 2-APB; (2-Aminoethoxy)diphenylborane; 2-Aminoethoxydiphenylborane; 2-((Diphenylboryl)oxy)ethanamine; 2-Aminoethoxydiphenylborate; 2-aminoethoxydiphenyl borate;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~250 mg/mL (~1110.67 mM)
H2O : ~1.61 mg/mL (~7.15 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (9.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (9.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (9.24 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4427 mL | 22.2133 mL | 44.4267 mL | |
| 5 mM | 0.8885 mL | 4.4427 mL | 8.8853 mL | |
| 10 mM | 0.4443 mL | 2.2213 mL | 4.4427 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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