Physicochemical Properties
| Molecular Formula | C28H34O14 |
| Molecular Weight | 594.5612 |
| Exact Mass | 594.194 |
| CAS # | 14259-47-3 |
| PubChem CID | 16760075 |
| Appearance | White to yellow solid |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 896.6±65.0 °C at 760 mmHg |
| Melting Point | 211-213ºC |
| Flash Point | 295.3±27.8 °C |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| Index of Refraction | 1.678 |
| LogP | 2.72 |
| Hydrogen Bond Donor Count | 7 |
| Hydrogen Bond Acceptor Count | 14 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 42 |
| Complexity | 900 |
| Defined Atom Stereocenter Count | 11 |
| SMILES | O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[C@@]1([H])[C@@]([H])([C@@]([H])([C@]([H])([C@]([H])(C([H])([H])[H])O1)O[H])O[H])O[H])O[H])O[H])O[H])OC1=C([H])C(=C2C(C([H])([H])[C@@]([H])(C3C([H])=C([H])C(=C([H])C=3[H])OC([H])([H])[H])OC2=C1[H])=O)O[H] |
| InChi Key | RMCRQBAILCLJGU-HIBKWJPLSA-N |
| InChi Code | InChI=1S/C28H34O14/c1-11-21(31)23(33)25(35)27(39-11)38-10-19-22(32)24(34)26(36)28(42-19)40-14-7-15(29)20-16(30)9-17(41-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-8,11,17,19,21-29,31-36H,9-10H2,1-2H3/t11-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1 |
| Chemical Name | (2S)-5-hydroxy-2-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-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
| Targets | N-Myc; RKIP |
| ln Vitro | Human non-small cell lung cancer cells cannot proliferate when didymin (1–20 μM) is applied for 48 hours [1]. A549 and H460 cells undergo apoptosis when exposed to didymin (10–20 μM) for 12–48 hours, but cell cycle division is unaffected [1]. |
| ln Vivo | Didymin (6 mg/kg/day; i.p.; once daily for 28 days) delays tumor growth in nude mice [1]. |
| Enzyme Assay |
N-Myc promoter-reporter assay[2] CHLA-90 and SMS-KCNR cells were cultured as adherent monolayers in a 96-well plate at a density of 2 × 104 cells per well. The Firefly luciferase reporter construct (0.4 ug, pEB-Luc-N-Myc), kindly gifted by Prof William L Carroll, M.D., New York University Medical Center, NY, was co-transfected with 100 ng of Renilla luciferase construct (thymidine kinase promoter-driven Renilla luciferase; pTK-RL) by Lipofectamine Reagent according to the manufacturer's instructions (Invitrogen, Carlsbad, CA). After 24 h of incubation, transfected cells were treated with 50 μM of Didymin. At 24 h post-treatment, promoter activity was measured as luciferase activity by mixing cells with 50 μl of passive lysis buffer followed by 15 min of shaking at room temperature. On a luminometer plate, 20 μl of the lysate was then mixed with 100 μl of luciferase assay reagent followed by 100 μl of Stop N' Glo Buffer. Luciferase activity was then determined as a ratio of Firefly to Renilla luciferase. Renilla luciferase activity was thus used as an internal control. |
| Cell Assay |
Cell proliferation assay [1] Cell Types: A549 and H460 cells Tested Concentrations: 1μM, 5μM, 10μM, 20μM Incubation Duration: 48h Experimental Results: Inhibition of cell proliferation of human non-small cell lung cancer cells. Apoptosis analysis [1] Cell Types: A549 and H460 cells Tested Concentrations: 10 μM, 20 μM Incubation Duration: 12 h, 24 h, 48 h Experimental Results: Induced apoptosis of A549 and H460 cells without affecting cell cycle distribution. |
| Animal Protocol |
Animal/Disease Models: Male nude mouse [6 weeks old; 28 days old]. BALB/cA-nu (nu/nu)] injection of A549 cells [1] Doses: 6 mg/kg/day Route of Administration: intraperitoneal (ip) injection; one time/day for 28 days Experimental Results: Inhibited tumor growth in nude mice. |
| References |
[1]. Didymin, a dietary flavonoid glycoside from citrus fruits, induces Fas-mediated apoptotic pathway in human non-small-cell lung cancer cells in vitro and in vivo. Lung Cancer. 2010 Jun;68(3):366-74. [2]. Didymin induces apoptosis by inhibiting N-Myc and upregulating RKIP in neuroblastoma. Cancer Prev Res (Phila). 2012 Mar;5(3):473-83. |
| Additional Infomation |
Didymin is a member of flavonoids and a glycoside. Didymin has been reported in Citrus reticulata, Cyclotrichium niveum, and other organisms with data available. See also: Tangerine peel (part of). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~250 mg/mL (~420.48 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.17 mg/mL (3.65 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 21.7 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: ≥ 2.17 mg/mL (3.65 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 21.7 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: ≥ 2.17 mg/mL (3.65 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 21.7 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 | 1.6819 mL | 8.4096 mL | 16.8192 mL | |
| 5 mM | 0.3364 mL | 1.6819 mL | 3.3638 mL | |
| 10 mM | 0.1682 mL | 0.8410 mL | 1.6819 mL |