 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C33H37NO17 |
| Molecular Weight | 719.64 |
| Exact Mass | 719.206 |
| Elemental Analysis | C, 55.08; H, 5.18; N, 1.95; O, 37.79 |
| CAS # | 1884557-85-0 |
| Related CAS # | Daunorubicin hydrochloride;23541-50-6;Daunorubicin;20830-81-3 |
| PubChem CID | 9961878 |
| Appearance | Solid powder |
| Hydrogen Bond Donor Count | 9 |
| Hydrogen Bond Acceptor Count | 18 |
| Rotatable Bond Count | 9 |
| Heavy Atom Count | 51 |
| Complexity | 1190 |
| Defined Atom Stereocenter Count | 6 |
| 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)N)O.C(C(=O)O)C(CC(=O)O)(C(=O)O)O |
| InChi Key | VNTHYLVDGVBPOU-QQYBVWGSSA-N |
| InChi Code | InChI=1S/C27H29NO10.C6H8O7/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t10-,14-,16-,17-,22+,27-;/m0./s1 |
| Chemical Name | (8S,10S)-8-acetyl-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione 2-hydroxypropane-1,2,3-tricarboxylate |
| Synonyms | Daunoxome |
| 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 | Daunorubicins/Doxorubicins; Topoisomerase II |
| ln Vitro | In Ehrlich ascites tumor cells, both sensitive and resistant, daunorubicin citrate (0-256 μg/mL, 30 minutes) suppresses DNA and RNA production [2]. In Molt-4 and L3.6 cells, daunorubicin citrate (7 nM-1.9 μM, 72 hours) demonstrates chemosensitivity [3][4]. Induction of necrosis and apoptosis in L3.6 cells is achieved by daunorubicin citrate (0.4 μM) for 48 hours. Induction of ROS generation in L3.6 cells is achieved by daunorubicin citrate (0.4 μM) for 120 minutes (2). K562 cells, a myeloid cell line, undergo autophagy in response to daunorubicin citrate (2 μM) for a 24-hour period [6]. |
| ln Vivo | Rats administered daunorubicin citrate (intravenous injection, 3 mg/kg, three times, 48 hours apart) develop nephrotoxicity and cardiotoxicity [5]. In mice, sister chromatid exchange is induced by intraperitoneal injection of daunorubicin citrate at a dose of 10 mg/kg [7]. |
| Enzyme Assay | Daunorubicin inhibits of both DNA and RNA syntheses in HeLa cells over a concentration range of 0.2 through 2 μM. |
| Cell Assay |
Cell viability assay[3][4] Cell Types: Molt-4 cells (human T lymphocytic leukemia cell line), L3.6 cells (metastatic human pancreatic cell line) Tested Concentrations: 7 nM-1.9 μM Incubation Duration: 72 hrs (hours) Experimental Results: Inhibited cell viability with IC50 values of 40 nM (Molt-4) and 400 nM (L3.6). Apoptosis analysis [4] Cell Types: L3.6 Cell Tested Concentrations: 0.4 μM Incubation Duration: 24 h, 48 h Experimental Results: 24 h induced necrosis without apoptosis, 48 h induced apoptosis and extensive necrosis reaction. Western Blot Analysis [6] Cell Types: K562 cells Tested Concentrations: 2 μM Incubation Duration: 24 h Experimental Results: LC3-I was converted into LC3-II, accompanied by a significant increase in LC3 expression level. |
| Animal Protocol |
Animal/Disease Models: Male SD (SD (Sprague-Dawley)) rat [5] Doses: 3 mg/kg Route of Administration: intravenous (iv) (iv)injection, 3 times, 48 hrs (hrs (hours)) apart. Experimental Results: It resulted in a significant increase in MDA (malondialdehyde) levels in renal tissue and a significant decrease in total GPx activity. Urinary protein excretion, serum creatinine, and BUN levels increased. |
| References |
[1]. Activity of topoisomerase inhibitors daunorubicin, idarubicin, and aclarubicin in the Drosophila Somatic Mutation and Recombination Test. Environ Mol Mutagen. 2004;43(4):250-7. [2]. Inhibition of DNA and RNA synthesis by daunorubicin in sensitive and resistant Ehrlich ascites tumor cells in vitro. Cancer Res. 1972 Jun;32(6):1307-14. [3]. Melanin inhibits cytotoxic effects of Doxorubicin and Daunorubicin in MOLT 4 cells. Pigment Cell Res. 2003 Aug;16(4):351-4. [4]. An effective in vitro antitumor response against human pancreatic carcinoma with paclitaxel and Daunorubicin by induction of both necrosis and apoptosis. Anticancer Res. 2004 Sep-Oct;24(5A):2617-26. h. [5]. Telmisartan prevents the progression of renal injury in daunorubicin rats with the alteration of angiotensin II and endothelin-1 receptor expression associated with its PPAR-γ agonist actions. Toxicology. 2011 Jan 11;279(1-3):91-9. [6]. MiR-15a-5p Confers Chemoresistance in Acute Myeloid Leukemia by Inhibiting Autophagy Induced by Daunorubicin. Int J Mol Sci. 2021 May 13;22(10):5153. [7]. Doxorubicin suppresses chondrocyte differentiation by stimulating ROS production. Eur J Pharm Sci. 2021 Dec 1;167:106013. |
| Additional Infomation | Daunorubicin Citrate is a semi-synthetic anthracycline glycoside antibiotic obtained from Streptomyces with antineoplastic activity. Daunorubicin citrate intercalates DNA, which leads to inhibition of DNA and RNA synthesis, and consequently blocks cell division and results in apoptosis. This anti-tumor antibiotic is most active in the S phase of cell division. Daunorubicin is indicated in the treatment of a wide variety of cancers including acute non-lymphocytic leukemia, non-Hodgkin lymphomas, Ewing's sarcoma, Wilms' tumor, and chronic myelocytic leukemia. (NCI05) |
Solubility Data
| Solubility (In Vitro) | DMSO: > 10 mM |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.3896 mL | 6.9479 mL | 13.8958 mL | |
| 5 mM | 0.2779 mL | 1.3896 mL | 2.7792 mL | |
| 10 mM | 0.1390 mL | 0.6948 mL | 1.3896 mL |