| Size | Price | |
|---|---|---|
| 2g | ||
| 5g | ||
| Other Sizes |
Purity: ≥98%
| Targets |
Human carbonic anhydrase I (CA I) – Kd = 7.14 μM [1]
Human carbonic anhydrase II (CA II) – Kd = 1.79 μM [1] Human carbonic anhydrase VI (CA VI) – Kd = 14.0 μM [1] Human carbonic anhydrase VII (CA VII) – Kd = 6.67 μM [1] Human carbonic anhydrase XII (CA XII) – Kd = 12.5 μM [1] Human carbonic anhydrase XIII (CA XIII) – Kd = 10.0 μM [1] |
|---|---|
| ln Vitro |
In a previous study, a series of N-aryl-β-alanine- and diazo-derivatives of benzenesulfonamide were designed, synthesized, and their binding affinities to carbonic anhydrases (CA) I, II, VI, VII, XII, and XIII was investigated by the use of isothermal titration calorimetry and fluorescent thermal shift assay. The results indicated that 4-substituted diazobenzenesulfonamides were found to be most potent CA binders among the synthesized derivatives. In addition, the majority of the N-aryl-β-alanine derivatives had better affinity for CA II while diazobenzenesulfonamides showed nanomolar affinities towards CA I isozyme. Moreover, the X-ray crystallographic data showed the binding modes of both derivative groups.
In vitro binding affinity of benzenesulfonamide to six human carbonic anhydrase isoforms (I, II, VI, VII, XII, XIII) was determined. The dissociation constants (Kd) were: CA I = 7.14 μM, CA II = 1.79 μM, CA VI = 14.0 μM, CA VII = 6.67 μM, CA XII = 12.5 μM, CA XIII = 10.0 μM. (Table 1) [1] |
| ln Vivo |
In the rat CPE model, the most potnet benzenesulfonamide indole derivative at 10 mg/kg in the MC/TW formulation displayed oral efficacy. Moreover, this compound, when administered in another preferred, minimal formulation in the same in vivo model, demonstrated superior oral efficacy to the lead phenylmethane sulfonamide WAY-196025 orally administered in a lipid-based formulation. In addition, this benzenesulfonamide indole derivative was also orally efficacious at 1 mg/kg by attenuating both LAR and the associated AHR to aerosolized carbachol in naturally sensitized sheep, which had been challenged through the airways with A. suum antigen.
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| Enzyme Assay |
Fluorescent thermal shift assay (FTSA): Experiments were performed in a Corbett Rotor‑Gene 6000 RT‑PCR instrument using blue channel (excitation 365±20 nm, detection 460±15 nm). Sample volume 20 μL contained 5–10 μM protein, 0–200 μM ligand (benzenesulfonamide as one of the compounds), 50 μM solvatochromic dye ANS (8‑anilino‑1‑naphthalene sulfonate), and 50 mM sodium phosphate buffer with 100 mM NaCl at pH 7.0, final DMSO concentration 2%. Samples were heated at constant rate of 1 °C/min. Data analysis was performed as described previously [43]. [1]
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| Animal Protocol |
10 mg/kg; oral Rats
|
| References |
Molecules.2014 Oct 28;19(11):17356-80;Bioorg Med Chem.2008 Feb 1;16(3):1345-58.
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| Additional Infomation |
Benzenesulfonamide is a sulfonamide compound. Sulfonamides are a class of compounds containing a sulfonamide group linked to a benzene ring via a sulfur bond. Many benzenesulfonamide derivatives are drugs (e.g., bosentan; sulfapyridine; sulfadiazine; celecoxib) because their sulfonamide moiety can target a variety of enzymes (e.g., carbonic anhydrase; acetylcholinesterase; butyrylcholinesterase; cyclooxygenase 2).
Benzenesulfonamide (BSA) was used as a control compound in this study. Its binding affinities were compared with those of synthesized N‑aryl‑β‑alanine derivatives and diazobenzenesulfonamides. The Kd values for CA II (1.79 μM) and other isoforms are reported. The data are consistent with known inhibition constants from literature (references [33,34] cited), though discrepancies due to different assay conditions (temperature, pH) are noted. [1] |
| Molecular Formula |
C6H7NO2S
|
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|---|---|---|
| Molecular Weight |
157.19
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|
| Exact Mass |
157.019
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| CAS # |
98-10-2
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| Related CAS # |
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| PubChem CID |
7370
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|
| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
299.1±23.0 °C at 760 mmHg
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|
| Melting Point |
149-152 °C(lit.)
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| Flash Point |
134.7±22.6 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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|
| Index of Refraction |
1.584
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|
| LogP |
0.62
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| Hydrogen Bond Donor Count |
1
|
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
10
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| Complexity |
186
|
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
KHBQMWCZKVMBLN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H7NO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)
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| Chemical Name |
benzenesulfonamide
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| Synonyms |
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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 |
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| 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) |
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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 | 6.3617 mL | 31.8086 mL | 63.6173 mL | |
| 5 mM | 1.2723 mL | 6.3617 mL | 12.7235 mL | |
| 10 mM | 0.6362 mL | 3.1809 mL | 6.3617 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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