Physicochemical Properties
| Molecular Formula | C41H44N2O20 |
| Molecular Weight | 884.797 |
| Exact Mass | 884.249 |
| CAS # | 290304-24-4 |
| PubChem CID | 74891316 |
| Appearance | Brown to wine solid powder |
| LogP | 0.811 |
| Hydrogen Bond Donor Count | 9 |
| Hydrogen Bond Acceptor Count | 20 |
| Rotatable Bond Count | 11 |
| Heavy Atom Count | 63 |
| Complexity | 1700 |
| Defined Atom Stereocenter Count | 11 |
| SMILES | C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)NC(=O)OCC6=CC(=C(C=C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O)[N+](=O)[O-])O |
| InChi Key | BOIXMGNMIWJAEW-LCTCPDETSA-N |
| InChi Code | InChI=1S/C41H44N2O20/c1-15-31(46)20(42-40(54)59-14-17-7-8-22(21(9-17)43(56)57)62-39-38(53)37(52)34(49)25(13-44)63-39)10-26(60-15)61-24-12-41(55,16(2)45)11-19-28(24)36(51)30-29(33(19)48)32(47)18-5-4-6-23(58-3)27(18)35(30)50/h4-9,15,20,24-26,31,34,37-39,44,46,48-49,51-53,55H,10-14H2,1-3H3,(H,42,54)/t15-,20-,24-,25+,26-,31+,34-,37-,38+,39+,41-/m0/s1 |
| Chemical Name | [3-nitro-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl N-[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]carbamate |
| Synonyms | Daun 02; Daun-02; Daun02 |
| 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 | It has been demonstrated that daun02, a prodrug that β-galactosidase converts to daunorubicin, lowers the calcium ion (Ca2+)-dependent action potential in neuroblastoma cells [1]. An inhibitor of topoisomerase is daunorubicin [2]. Daun02 is a good substrate for β-galactosidase (β-gal). For T47-D, Panc02, and MCF-7, respectively, the Daun02 concentrations that decreased cell viability by 50% (EC50) were 0.5 μM, 1.5 μM, and 3.5 μM [3]. |
| ln Vivo | Daun02 has a protein content of 8.6 μmol/min/mg and Km and Vmax values of 0.37 mM, making it a promising substrate for β-gal. While daunorubicin binds to plasma proteins at a rate of 94%, Daun02 binds at a rate of 79% at a concentration of 10-5 M [3]. |
| References |
[1]. Targeted disruption of cocaine-activated nucleus accumbens neurons prevents context-specific sensitization. Nat Neurosci. 2009 Aug;12(8):1069-73. [2]. Activity of topoisomerase inhibitors daunorubicin, idarubicin, and aclarubicin in the Drosophila Somatic Mutation and Recombination Test. Environ Mol Mutagen. 2004;43(4):250-7. [3]. Suicide gene therapy using E. coli beta-galactosidase.Cancer Chemother Pharmacol. Cancer Chemother Pharmacol. 2002 Jul;50(1):65-70. |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 100 mg/mL (~113.02 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.83 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.1302 mL | 5.6510 mL | 11.3020 mL | |
| 5 mM | 0.2260 mL | 1.1302 mL | 2.2604 mL | |
| 10 mM | 0.1130 mL | 0.5651 mL | 1.1302 mL |