| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Ca2+-activated Cl- currents[1]
Anthracene-9-carboxylic acid targets Ca2+-activated chloride channels (CaCCs), including TMEM16A (ANO1) and TMEM16B (ANO2), as well as muscle-type CLC chloride channels (CLC-0 and CLC-1) from the intracellular side. It acts as a chloride current blocker with a moderate to strong inhibitory action on PKA-activated cardiac ICl. It also has been used to block and identify Ca2+-activated Cl- currents in diverse cell types. Its mechanism involves blocking Cl- transport by binding to the channel pore. |
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| ln Vitro |
In HEK 293T cells, anthracene-9-carboxylic acid blocks outward currents in a voltage-dependent manner and inhibits a greater proportion of the current as depolarization increases[1]. In HEK 293T, anthracene-9-carboxylic acid causes a lengthening of the deactivation kinetics and a substantial potentiation of tail currents measured at -100 mV following depolarizing voltages[1]. The maximum outward Cl-current at +70 mV (21±10%) is somewhat inhibited by anthracene-9-carboxylic acid (500 μM) in rabbit pulmonary artery smooth muscle cells, whereas the amplitude of the instantaneous inward relaxation at -80 mV is increased by 321±34%[2].
In vitro, Anthracene-9-carboxylic acid is a Cl- transport inhibitor with a moderate to strong inhibitory action on PKA-activated cardiac ICl. It has been investigated for its extracellular effects on TMEM16B/anoctamin2 Ca2+-activated chloride channels using the whole-cell patch-clamp technique. It blocks CaCCs in diverse smooth muscle cells, epithelial cells, and salivary gland cells. It is a well-established tool for electrophysiological studies of chloride channel function. |
| ln Vivo |
In vivo, Anthracene-9-carboxylic acid has been examined for its protective effects against myocardial ischemia-reperfusion damage. The chloride channel blockers anthracene-9-carboxylic acid (9-AC) and SITS exert protective effects against myocardial ischemia-reperfusion damage in animal models. By blocking chloride channels, 9-AC may reduce cellular swelling, prevent arrhythmias, and limit infarct size following ischemia-reperfusion injury. The compound may also be used to study the role of CaCCs in smooth muscle contraction.
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| Enzyme Assay |
The specific protocol for assessing chloride channel inhibition uses the whole-cell patch-clamp technique. HEK-293T cells expressing TMEM16B (ANO2) or TMEM16A (ANO1) are used. The external solution contains (in mM): 140 NaCl, 2 CaCl2, 1 MgCl2, 10 HEPES, 10 glucose (pH 7.4). Pipettes (3-5 Momega) are filled with internal solution containing (in mM): 130 CsCl, 1 MgCl2, 0.5 EGTA, 10 HEPES, 2 Mg-ATP (pH 7.2). Anthracene-9-carboxylic acid is dissolved in DMSO (100 mM stock) and diluted to final concentrations of 0.1-1000 uM in the external solution. After establishing the whole-cell configuration, voltage-ramp or step protocols are applied to activate chloride currents. The reduction in current amplitude in the presence of 9-AC is recorded, and the IC50 is calculated from concentration-response curves.
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| Cell Assay |
For in vitro cellular assays, primary human bronchial epithelial cells or immortalized cell lines (e.g., Calu-3) are grown on permeable supports (Transwell inserts) to form polarized monolayers. Short-circuit current (Isc) measurements are performed in Ussing chambers. Anthracene-9-carboxylic acid is added to the apical or basolateral side at concentrations of 10-1000 uM. The reduction in Isc, which reflects chloride secretion, is measured. The compound's ability to block Ca2+-activated Cl- secretion can be assessed after stimulation with ionomycin (1 uM) or ATP (100 uM). Amiloride-sensitive sodium transport and CFTR-mediated Cl- transport are used as controls to assess selectivity.
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| Animal Protocol |
An in vivo protocol for evaluating myocardial protection uses a rat model of ischemia-reperfusion injury. Male Sprague-Dawley rats (250-300 g) are anesthetized and subjected to left anterior descending (LAD) coronary artery occlusion for 30 minutes, followed by 120 minutes of reperfusion. Anthracene-9-carboxylic acid is dissolved in a suitable vehicle (e.g., 0.1% DMSO in saline) and administered as an intravenous bolus (1-10 mg/kg) 5 minutes before the onset of ischemia. Infarct size is measured by TTC (2,3,5-triphenyltetrazolium chloride) staining at the end of the reperfusion period. Cardiac troponin I levels are measured from plasma samples. Arrhythmias are monitored by continuous ECG recording. The compound is expected to reduce infarct size and decrease the incidence of ventricular arrhythmias.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
9-Anthracoic acid is a known metabolite of 9-anthraaldehyde in the human body. Detailed pharmacokinetic data for Anthracene-9-carboxylic acid is not available. As a carboxylic acid, it is expected to have low oral bioavailability and is typically administered intravenously for in vivo studies due to its low water solubility. The compound is poorly soluble in water but soluble in ethanol and DMSO. Standard PK studies would involve IV administration to rats at 1-10 mg/kg, followed by plasma sampling and HPLC-UV analysis to determine T1/2, Cmax, and AUC. Plasma protein binding is expected to be high due to its lipophilic anthracene ring system. |
| Toxicity/Toxicokinetics |
Anthracene-9-carboxylic acid is classified as a hazardous chemical. GHS hazard statement H301: Toxic if swallowed. Intraperitoneal LD50 in mice is 750 mg/kg. It may cause irritation of the digestive tract, respiratory tract irritation, skin irritation, and serious eye irritation. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Appropriate personal protective equipment (PPE) including gloves, goggles, and masks should be worn when handling this chemical. The toxicological properties of this substance have not been fully investigated.
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| References |
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| Additional Infomation |
9-Anthraquinone is anthraquinone with a carboxyl substituent at the 9-position.
Anthracene-9-carboxylic acid (9-AC) is a research-grade chemical and is not approved for clinical use. Its molecular formula is C15H10O2 with a molecular weight of 222.24 and a purity of >98%. It is an anthracene derivative that functions as a chloride current blocker, primarily targeting Ca2+-activated chloride channels (CaCCs). It has been utilized to investigate CaCCs in smooth muscle cells, epithelial cells, and salivary gland cells. The compound is stored at -20degC and is soluble in DMSO. It is a valuable tool in electrophysiological studies and research focused on cellular ion transport mechanisms. |
| Molecular Formula |
C15H10O2
|
|---|---|
| Molecular Weight |
222.24
|
| Exact Mass |
222.068
|
| CAS # |
723-62-6
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| Related CAS # |
Anthracene-9-carboxylic acid-d9;1219803-78-7
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| PubChem CID |
2201
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
467.5±14.0 °C at 760 mmHg
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| Melting Point |
213-217 °C(lit.)
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| Flash Point |
206.1±14.8 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.743
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| LogP |
4.36
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| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
17
|
| Complexity |
277
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| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1=CC=C2C(=C1)C=C3C=CC=CC3=C2C(=O)O
|
| InChi Key |
XGWFJBFNAQHLEF-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C15H10O2/c16-15(17)14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9H,(H,16,17)
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| Chemical Name |
anthracene-9-carboxylic acid
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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: 125 mg/mL (562.46 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4996 mL | 22.4982 mL | 44.9964 mL | |
| 5 mM | 0.8999 mL | 4.4996 mL | 8.9993 mL | |
| 10 mM | 0.4500 mL | 2.2498 mL | 4.4996 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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