Physicochemical Properties
| Molecular Formula | C21H23N3O9 |
| Molecular Weight | 461.42202 |
| Exact Mass | 461.143 |
| CAS # | 79541-46-1 |
| PubChem CID | 133219 |
| Appearance | Typically exists as solid at room temperature |
| Melting Point | 168-170°C dec. |
| LogP | 2.1 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 33 |
| Complexity | 699 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2OC3C(C(C(C(O3)CO)O)O)O)O)O)N=[N+]=[N-] |
| InChi Key | AXCDEMZKQHNYNE-QNDFHXLGSA-N |
| InChi Code | InChI=1S/C21H23N3O9/c22-24-23-11-4-1-10(2-5-11)3-6-13(27)17-14(28)7-12(26)8-15(17)32-21-20(31)19(30)18(29)16(9-25)33-21/h1-2,4-5,7-8,16,18-21,25-26,28-31H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1 |
| Chemical Name | 3-(4-azidophenyl)-1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]propan-1-one |
| Synonyms | 4-Azidophlorizin; 4-Azidophlorhizin; 79541-46-1; DTXSID70229761; 2'-O-(beta-D-Glucopyranosyl)-4-azidophloretin; 1-Propanone, 3-(4-azidophenyl)-1-(2-(beta-D-glucopyranosyloxy)-4,6-dihydroxyphenyl)-; DTXCID20152252; 3-(4-azidophenyl)-1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]propan-1-one; |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| Targets |
Glucose transporter in brush - border membranes [1] |
| ln Vitro |
- High - affinity binding: 4 - Azidophlorizin showed high - affinity binding to the glucose transporter in brush - border membranes. It competitively inhibited the uptake of [³H] - glucose in brush - border membrane vesicles, with a dissociation constant (Kd) in the low - micromolar range. The binding was specific, as it could be displaced by unlabeled phlorizin and other glucose transport inhibitors [1] - Photoaffinity labeling: Upon irradiation with ultraviolet light, 4 - Azidophlorizin covalently labeled a protein component of the glucose transporter complex in brush - border membranes. The labeled protein had a molecular weight of approximately 55 kDa, which was identified as a subunit of the glucose transporter [1] |
| Enzyme Assay |
- Binding assay: Brush - border membrane vesicles were prepared from rabbit small intestine. The vesicles were incubated with different concentrations of 4 - Azidophlorizin and [³H] - glucose at 25°C for 10 minutes. Then, the vesicles were rapidly filtered through glass - fiber filters, and the radioactivity on the filters was measured to determine the binding of 4 - Azidophlorizin to the glucose transporter. Scatchard analysis was used to calculate the dissociation constant (Kd) [1] - Photoaffinity labeling assay: Brush - border membrane vesicles were incubated with 4 - Azidophlorizin in the dark. After incubation, the samples were irradiated with ultraviolet light for 10 minutes at 0°C. Then, the membrane proteins were solubilized with SDS - PAGE sample buffer, separated by SDS - PAGE, and transferred to a nitrocellulose membrane. The labeled protein was detected by autoradiography [1] |
| References | [1]. 4-Azidophlorizin, a high affinity probe and photoaffinity label for the glucose transporter in brush border membranes. Biochim Biophys Acta. 1982 Jun 14;688(2):547-56. |
| Additional Infomation |
- Function mechanism: 4 - Azidophlorizin acts as a high - affinity probe and photoaffinity label for the glucose transporter in brush - border membranes. It can bind to the glucose transporter specifically and be covalently linked to the transporter protein under ultraviolet light, which is helpful for the identification and characterization of the glucose transporter [1] |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1672 mL | 10.8361 mL | 21.6722 mL | |
| 5 mM | 0.4334 mL | 2.1672 mL | 4.3344 mL | |
| 10 mM | 0.2167 mL | 1.0836 mL | 2.1672 mL |