19-Hydroxybufalin is a bufadienolide and the 18-hydorxylated form of bufalin, which is a novel and potent inhibitor of steroid receptor coactivator 3 (SRC-3) with anticancer, anti-inflammatory and antinociceptive activity. It is a naturally occurring digoxin-like immunoreactive component isolated from the Chinese medicine Chan Su. It exerts anticancer activity by inducing cell death through the ROS-mediated RIP1/RIP3/PARP-1 pathways.
Physicochemical Properties
| Molecular Formula | C24H34O5 |
| Molecular Weight | 402.5238 |
| Exact Mass | 402.241 |
| CAS # | 39844-86-5 |
| PubChem CID | 101375811 |
| Appearance | White to off-white solid powder |
| Boiling Point | 601.7±55.0 °C |
| LogP | 3.214 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 29 |
| Complexity | 758 |
| Defined Atom Stereocenter Count | 8 |
| SMILES | C[C@]12CC[C@H]3[C@H]([C@]1(CC[C@@H]2C4=COC(=O)C=C4)O)CC[C@H]5[C@@]3(CC[C@@H](C5)O)CO |
| InChi Key | AXTYMYOHGWVSQN-KLAFWMLLSA-N |
| InChi Code | InChI=1S/C24H34O5/c1-22-9-7-19-20(4-3-16-12-17(26)6-10-23(16,19)14-25)24(22,28)11-8-18(22)15-2-5-21(27)29-13-15/h2,5,13,16-20,25-26,28H,3-4,6-12,14H2,1H3/t16-,17+,18-,19+,20-,22-,23-,24+/m1/s1 |
| Chemical Name | 5-[(3S,5R,8R,9S,10R,13R,14S,17R)-3,14-dihydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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
| References |
[1].Jiang L, et al. Bufalin induces cell cycle arrest and apoptosis in gallbladder carcinoma cells. Tumour Biol. 2014 Nov;35(11):10931-41. [2].Wu SH, et al. Bufalin induces cell death in human lung cancer cells through disruption of DNA damage response pathways. Am J Chin Med. 2014;42(3):729-42. [3].Rong X, et al. Bufalin, a bioactive component of the chinese medicine chansu, inhibits inflammation and invasion of human rheumatoid arthritis fibroblast-like synoviocytes. Inflammation. 2014 Aug;37(4):1050-8. [4].Yan S, et al. Bufalin enhances TRAIL-induced apoptosis by redistributing death receptors in lipid rafts in breast cancer cells. Anticancer Drugs. 2014 Jul;25(6):683-9. [5].Wen L, et al. Anti-inflammatory and antinociceptive activities of bufalin in rodents. Mediators Inflamm. 2014;2014:171839 |
| Additional Infomation | 19-Hydroxybufalin has been reported in Duttaphrynus melanostictus with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~248.43 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (6.21 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. 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 (6.21 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (6.21 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4843 mL | 12.4217 mL | 24.8435 mL | |
| 5 mM | 0.4969 mL | 2.4843 mL | 4.9687 mL | |
| 10 mM | 0.2484 mL | 1.2422 mL | 2.4843 mL |