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| Targets |
Carubicin's primary mechanism of action involves intercalation into DNA and inhibition of topoisomerase II. Intercalation is the process by which the planar anthracycline ring system inserts itself between adjacent DNA base pairs, causing structural distortion and inhibition of DNA and RNA synthesis. The inhibition of topoisomerase II prevents the enzyme from repairing DNA breaks and managing DNA supercoiling, which are essential for DNA replication. This combination of actions leads to DNA damage and apoptosis.
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| ln Vitro |
Carubicin hydrochloride is an effective inhibitor of VHL-defective (VHL−/−) CCRCC (clear cell renal cell carcinoma) cell proliferation. It also induces apoptosis by a mechanism that is independent of p53 or hypoxia-inducible factor HIF2. This suggests that it may be particularly effective in cancers with certain genetic backgrounds, such as those with VHL mutations, which are common in renal cell carcinoma. Its in vitro potency is demonstrated by its ability to inhibit cell growth in a variety of cancer cell lines.
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| ln Vivo |
Carubicin is used in the treatment of bladder cancer, often administered intravesically. This route of administration is designed to deliver a high concentration of the drug directly to the tumor site while reducing systemic exposure and associated side effects, such as cardiotoxicity, which is a well-known complication of other anthracyclines like doxorubicin. Its use in this context highlights its value as a potent anticancer agent with a profile that may allow for targeted local therapy.
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| Enzyme Assay |
The in vitro activity of Carubicin hydrochloride is typically assessed using cell viability and proliferation assays. In a standard protocol, cancer cells (e.g., VHL-defective CCRCC cells) are seeded in 96-well plates and treated with increasing concentrations of Carubicin for a specified period (e.g., 48-72 hours). Cell viability is then measured using a colorimetric assay, such as MTT or CCK-8, which measures metabolic activity. The half-maximal inhibitory concentration (IC50) is then calculated.
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| Cell Assay |
The in vitro cellular activity of Carubicin HCl is evaluated in a panel of cancer cell lines. Cells are seeded in multi-well plates and allowed to adhere. They are then treated with serial dilutions of Carubicin hydrochloride. After an incubation period, the effect on cell proliferation is measured. For apoptosis studies, cells are treated with the compound and then stained with Annexin V and propidium iodide, followed by flow cytometry analysis to quantify apoptotic and necrotic cells.
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| Animal Protocol |
The in vivo efficacy of Carubicin is evaluated in animal models of cancer, such as xenograft models in immunodeficient mice. In these models, human tumor cells are implanted subcutaneously. Once tumors are established, the animals are treated with Carubicin via the appropriate route (e.g., intravenous or intraperitoneal). Tumor growth is monitored by caliper measurements, and tumor weights are assessed at the end of the study. These studies are crucial for determining the in vivo antitumor activity and therapeutic index of the compound.
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| ADME/Pharmacokinetics |
Carubicin hydrochloride has a molecular weight of 549.95 and is soluble in DMSO at 62.5 mg/mL. Detailed pharmacokinetic data for Carubicin is typical of anthracyclines, which are known for their extensive tissue distribution and metabolism. However, specific parameters for Carubicin HCl are not standardly reported. Given its use in intravesical therapy, its systemic absorption is designed to be minimal to reduce side effects, a key advantage over other anthracyclines.
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| Toxicity/Toxicokinetics |
Carubicin, like other anthracyclines, is a highly toxic compound. Its primary dose-limiting toxicity is myelosuppression and cardiotoxicity. However, it is considered to have enhanced stability and reduced cardiotoxicity compared to other anthracyclines, which makes it a valuable alternative in oncology. The compound is described as a "very toxic anthracycline-type antineoplastic", indicating that it is a potent agent that requires careful handling and administration under controlled conditions.
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| References |
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| Additional Infomation |
Carubicin hydrochloride is the hydrochloride salt of the anthracycline antitumor antibiotic Carubicin. Carubicin can intercalate into DNA and inhibit topoisomerase II, thereby inhibiting DNA replication and ultimately interfering with RNA and protein synthesis. It is a highly toxic anthracycline antitumor drug, associated with daunorubicin, extracted from Carubicin (Actinomadura carminata).
Carubicin hydrochloride is also known as carminomycin hydrochloride. It is a DNA intercalator and topoisomerase II inhibitor primarily used in the treatment of bladder cancer. Its enhanced stability and reduced cardiotoxicity profile compared to other anthracyclines make it a valuable alternative in oncology. As a research compound, it is not widely used outside of specialized cancer research and clinical settings, but it represents an important class of chemotherapeutic agents. |
| Molecular Formula |
C26H28CLNO10
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|---|---|
| Molecular Weight |
549.957
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| Exact Mass |
549.14
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| Elemental Analysis |
C, 56.78; H, 5.13; Cl, 6.45; N, 2.55; O, 29.09
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| CAS # |
52794-97-5
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| Related CAS # |
Carubicin;50935-04-1
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| PubChem CID |
11570269
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| Appearance |
Brown to red solid powder
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| Density |
1.63g/cm3
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| Boiling Point |
750.6ºC at 760mmHg
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| Flash Point |
407.7ºC
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| LogP |
2.228
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| Hydrogen Bond Donor Count |
7
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
38
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| Complexity |
944
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| Defined Atom Stereocenter Count |
6
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| SMILES |
CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)O)O)(C(=O)C)O)N)O.Cl
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| InChi Key |
WYVYEIZFAUXWKW-SHUUXQFMSA-N
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| InChi Code |
InChI=1S/C26H27NO10/c1-9-21(30)13(27)6-16(36-9)37-15-8-26(35,10(2)28)7-12-18(15)25(34)20-19(23(12)32)22(31)11-4-3-5-14(29)17(11)24(20)33/h3-5,9,13,15-16,21,29-30,32,34-35H,6-8,27H2,1-2H3/t9-,13-,15-,16-,21+,26-/m0/s1
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| Chemical Name |
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-4,6,9,11-tetrahydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
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| Synonyms |
Karminomycin hydrochloride; Carubicin HCl; Carubicin hydrochloride; NSC 275649
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ~62.5 mg/mL (~113.7 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.78 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 20.8 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: ≥ 2.08 mg/mL (3.78 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 20.8 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 | 1.8183 mL | 9.0916 mL | 18.1831 mL | |
| 5 mM | 0.3637 mL | 1.8183 mL | 3.6366 mL | |
| 10 mM | 0.1818 mL | 0.9092 mL | 1.8183 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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