Physicochemical Properties
| Molecular Formula | C18H14N2O3 |
| Molecular Weight | 306.321 |
| Exact Mass | 306.1 |
| Elemental Analysis | C, 70.58; H, 4.61; N, 9.15; O, 15.67 |
| CAS # | 133550-49-9 |
| Related CAS # | 133550-49-9 |
| PubChem CID | 1838043 |
| Appearance | Light yellow to yellow solid powder |
| Melting Point | 215 °C |
| LogP | 2.659 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 23 |
| Complexity | 536 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(/C(/C#N)=C\C1C=CC(=C(C=1)O)O)N1C2C=CC=CC=2CC1 |
| InChi Key | MYKCTDWWIWGLHW-NTEUORMPSA-N |
| InChi Code | InChI=1S/C18H14N2O3/c19-11-14(9-12-5-6-16(21)17(22)10-12)18(23)20-8-7-13-3-1-2-4-15(13)20/h1-6,9-10,21-22H,7-8H2/b14-9+ |
| Chemical Name | (E)-2-(2,3-dihydroindole-1-carbonyl)-3-(3,4-dihydroxyphenyl)prop-2-enenitrile |
| Synonyms | Tyrphostin AG-528; Tyrphostin AG528; AG-528; AG 528; AG528; Tyrphostin B-66; Tyrphostin B66; Tyrphostin-B66; Tyrphostin AG 528 |
| 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 | EGFR (IC50 = 4.9 μM); ErbB2 (IC50 = 2.1 μM) |
| ln Vitro | For the first time, Density Functional Theory (DFT) calculations in solvent water have been used to examine the relationship between the drug Tyrphostin AG528 and CNT(6,6-6) nanotube in this work. The complex stability of CNT(6,6-6)/Tyrphostin AG528 is largely dependent on intermolecular hydrogen bonds that form between the molecule Tyrphostin AG528's active position and the hydrogen atoms of the nanotube. The effects of Tyrphostin AG528's non-bonded interaction with the CNT(6,6-6) nanotube on the molecule's electrical characteristics, chemical shift tensors, and natural charge have also been identified. Tyrphostin AG528 is a molecule that donates electrons, and the CNT(6,6-6) nanotube acts as an electron acceptor at the complex CNT(6,6-6)/Tyrphostin AG528[2], according to the natural bond orbital (NBO) analysis. |
| References |
[1]. Tyrphostin Tumor Growth Inhibitors of EGFR and ErbB2 Tyrosine Kinase. J Chem Crystallogr. 2007, 37, 679–683. [2]. Investigation of Adsorption Tyrphostin AG528 Anticancer Drug Upon the CNT(6,6-6) Nanotube: A DFT Study. Curr Mol Med. 2019;19(2):91-104. |
Solubility Data
| Solubility (In Vitro) |
DMSO: 25~61 mg/mL (81.6~199.1 mM) Water: ˂1 mg/mL Ethanol: ~5 mg/mL (~16.3 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.16 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 25.0 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: ≥ 2.5 mg/mL (8.16 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 25.0 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2646 mL | 16.3228 mL | 32.6456 mL | |
| 5 mM | 0.6529 mL | 3.2646 mL | 6.5291 mL | |
| 10 mM | 0.3265 mL | 1.6323 mL | 3.2646 mL |