 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C27H30N2O9 |
| Molecular Weight | 526.5351 |
| Exact Mass | 526.2 |
| CAS # | 72983-78-9 |
| Related CAS # | 5-Iminodaunorubicin hydrochloride;67324-99-6 |
| PubChem CID | 72400 |
| Appearance | Solid powder |
| LogP | 1.4 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 38 |
| Complexity | 963 |
| Defined Atom Stereocenter Count | 6 |
| SMILES | CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=N)C(=CC=C5)OC)O)(C(=O)C)O)N)O |
| InChi Key | BLLIIPIJZPKUEG-HPTNQIKVSA-N |
| InChi Code | InChI=1S/C27H30N2O9/c1-10-23(31)14(28)7-17(37-10)38-16-9-27(35,11(2)30)8-13-19(16)26(34)20-21(25(13)33)24(32)12-5-4-6-15(36-3)18(12)22(20)29/h4-6,10,14,16-17,23,29,31,33-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,23+,27-/m0/s1 |
| Chemical Name | (8S,10S)-8-acetyl-10-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,8,11-trihydroxy-12-imino-1-methoxy-9,10-dihydro-7H-tetracen-5-one |
| Synonyms | 5-Iminodaunorubicin |
| 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
| ln Vitro | 5-Iminodaunorubicin causes protein-concealed DNA strand breaks in murine leukemia L1210 cells. Apposed single-strand breaks, or double-strand breaks, may be the source of many 5-iminodaunorubicin breaks[2]. |
| ln Vivo | 5-Iminodaunorubicin (5-ID; 1–16 mg/kg) therapy widens the QRS complex, raises the voltage of the R- and S-waves, and lengthens the Q alpha T interval in rats. Additionally, 5-Iminodaunorubicin suppresses the quinone redox cycle. 5-Iminodaunorubicin exhibits reduced cardiotoxicity [1]. |
| References |
[1]. R A Jensen, et al. Electrocardiographic and transmembrane potential effects of 5-iminodaunorubicin in the rat. Cancer Res. 1984 Sep;44(9):4030-9. [2]. L A Zwelling, et al. Cytotoxicity and DNA strand breaks by 5-iminodaunorubicin in mouse leukemia L1210 cells: comparison with adriamycin and 4'-(9-acridinylamino)methanesulfon-m-anisidide. Cancer Res. 1982 Jul;42(7):2687-91. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~189.9 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.75 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 (4.75 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 | 1.8992 mL | 9.4960 mL | 18.9919 mL | |
| 5 mM | 0.3798 mL | 1.8992 mL | 3.7984 mL | |
| 10 mM | 0.1899 mL | 0.9496 mL | 1.8992 mL |