2-HBA, an analog of curcumin, is a potent inducer of NAD(P)H:quinone acceptor oxidoreductase 1 (NQO1) which can also activate caspase-3 and caspase-10.
Physicochemical Properties
| Molecular Formula | C17H14O3 |
| Molecular Weight | 266.29126 |
| Exact Mass | 266.094 |
| Elemental Analysis | C, 76.68; H, 5.30; O, 18.02 |
| CAS # | 131359-24-5 |
| Related CAS # | 131359-24-5 |
| PubChem CID | 5472867 |
| Appearance | Light yellow to yellow solid powder |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 495.5±40.0 °C at 760 mmHg |
| Flash Point | 267.6±23.8 °C |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.704 |
| LogP | 4.91 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 20 |
| Complexity | 338 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(/C=C/C1=CC=CC=C1O)/C=C/C2=CC=CC=C2O |
| InChi Key | RFRXIWQYSOIBDI-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C17H14O3/c1-2-14-16(13-5-3-4-6-15(13)20-14)17(19)11-7-9-12(18)10-8-11/h3-10,18H,2H2,1H3 |
| Chemical Name | (2-ethyl-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone |
| Synonyms | 2-HBA |
| 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 | Caspase-3; Caspase-10 |
| ln Vitro | The specific activities of NQO1 and glutathione reductase increase by 6 and 1.5 fold, respectively, when L1210 cells are exposed to 0.6 M 2-HBA (bis(2-hydroxy-benzylidene)acetone). Additionally, a 2.4-fold coordinate induction of the total cellular glutathione content occurs. In a more in-depth investigation, it was discovered that 2-HBA induces NQO1 in a concentration-dependent manner. Treatments with 2-HBA induce cell cycle arrest and apoptosis in L1210 wild type cells and their Y8 drug-resistant counterparts in a concentration-dependent manner. Caspase-3 and Caspase-10 can both be triggered by 2-HBA[1]. |
| Enzyme Assay | In 96-well plates, cells are grown for 24 hours before being exposed to 2-HBA (bis(2-hydroxybenzylidene)acetone) for either 24 or 48 hours, depending on whether glutathione levels are to be measured or the activities of enzymes. After the exposure time has passed, cells are collected by centrifugation (1500 g for 15 min at 4 °C), then cleaned with DPBS before being lysed in 0.08% digitonin. For protein analysis, an aliquot (25 μL) is used. Using the Prochaska test, NQO1 activity is evaluated[1]. |
| Cell Assay | After exposure to 2-HBA (bis(2-hydroxybenzylidene)acetone) for 24 h, duplicate aliquots of cells (1×106) are collected by centrifugation and washed with cold DPBS. The Annexin-V-FLUOS assay is used to determine apoptosis, and propidium iodide uptake is used to determine the necrotic fraction at the same time[1]. |
| References |
[1]. Bis(2-hydroxybenzylidene)acetone, a potent inducer of the phase 2 response, causes apoptosis in mouse leukemia cells through a p53-independent, caspase-mediated pathway. Cancer Lett. 2007 Jan 8;245(1-2):341-9. |
| Additional Infomation | See also: 1,5-Bis(2-hydroxyphenyl)penta-1,4-dien-3-one (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | DMSO: ~100 mg/mL (~375.5 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.39 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 (9.39 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 | 3.7553 mL | 18.7765 mL | 37.5530 mL | |
| 5 mM | 0.7511 mL | 3.7553 mL | 7.5106 mL | |
| 10 mM | 0.3755 mL | 1.8777 mL | 3.7553 mL |