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Berubicin HCl (RTA-774; WP-769), an anthracycline derivative, is a novel and potent DNA intercalator and antineoplastic agent. Acting by intercalating into DNA and interrupting the activity of topoisomerase II, leading to the inhibition of DNA replication and repair, and RNA and protein synthesis. Unlike other anthracycline derivatives, Berubicin is able to cross the blood-brain barrier (BBB).
| ln Vitro |
K562 cell activity is inhibited by WP 769 hydrochloride, with an IC50 value of 0.18 mg/mL[1]. A 24-hour exposure to WP 769 Hydrochloride (0-100 µM) inhibits the absorption of the thymic circuit guideline by KBM-5 cells [2]. In KBM-5 cells, WP 769 hydrochloride (1 µM; 15 min) activates NF-κB via the p50 and p65 NF-κB subunits [2]. In a dose-dependent manner, WP 769 Hydrochloride (0-100 µM; 72 h) inhibits the Jurkat and RIP buffer cell viability experiment [2].
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| Cell Assay |
Cell viability assay [3]
Cell Types: SH-SY5Y cells. Tested Concentrations: 0.1, 1 and 10 µM. Incubation Duration: 0, 1, 2, 3, 4 and 5 days. Experimental Results: Cell viability was inhibited in a dose-dependent manner. Apoptosis analysis [3] Cell Types: SH-SY5Y cells. Tested Concentrations: 50, 500 and 2000 nM. Incubation Duration: 48 hrs (hours). Experimental Results: Promote cell apoptosis. Western Blot Analysis[3] Cell Types: SH-SY5Y cells. Tested Concentrations: 0, 0.1, 1.0 or 10 µM. Incubation Duration: 0, 0.5, 1, 2, 4, 6, 8, 12 or 24 hrs (hours). Experimental Results: Casp 3 and Casp 9 are activated. p53 and NF-κB expression increased. IκBα expression is diminished. |
| References |
[1]. Faderl S, et al. WP744, a novel anthracycline with enhanced proapoptotic and antileukemic activity. Anticancer Res. 2001 Nov-Dec;21(6A):3777-84.
[2]. Ashikawa K, et al. Evidence that activation of nuclear factor-kappaB is essential for the cytotoxic effects of doxorubicin and its analogues. Biochem Pharmacol. 2004 Jan 15;67(2):353-64. [3]. Wu J, Harris NL, Inge TH. Nuclear factor-kappa B and apoptosis inducing factor activation by doxorubicin analog WP744 in SH-SY5Y neuroblastoma cells. J Surg Res. 2004 Dec;122(2):231-9. |
| Additional Infomation |
RTA 744 is a novel anthracycline derivative that crosses the blood-brain barrier and shows significant potential for the treatment of primary and metastatic brain cancers. Anthracyclines are one of the most broadly used and effective classes of cancer therapies; however, they are not used to treat brain cancers because current therapies do not cross the blood-brain barrier.
Berubicin Hydrochloride is the hydrochloride salt of the anthracycline derivative berubicin with potential antineoplastic activity. Berubicin intercalates into DNA and interrupts topoisomerase II activity, resulting in the inhibition of DNA replication and repair, and RNA and protein synthesis. Unlike other anthracycline derivatives, this agent crosses the blood-brain barrier (BBB). Drug Indication Investigated for use/treatment in brain cancer. Mechanism of Action RTA 744 is a substance being studied in the treatment of adult brain tumors. RTA 744 crosses the blood-brain barrier and blocks an enzyme needed for cancer growth. RTA 744 is a type of topoisomerase inhibitor. Also called topoisomerase II inhibitor RTA 744. |
| Exact Mass |
669.198
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|---|---|
| CAS # |
293736-67-1
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| Related CAS # |
677017-23-1;293736-67-1 (HCl);
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| PubChem CID |
9874591
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
3.728
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
47
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| Complexity |
1130
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| Defined Atom Stereocenter Count |
6
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| 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)CO)O)N)OCC6=CC=CC=C6.Cl
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| InChi Key |
GPMIHHFZKBVWAZ-LMMKTYIZSA-N
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| InChi Code |
InChI=1S/C34H35NO11.ClH/c1-16-33(44-15-17-7-4-3-5-8-17)20(35)11-24(45-16)46-22-13-34(42,23(37)14-36)12-19-26(22)32(41)28-27(30(19)39)29(38)18-9-6-10-21(43-2)25(18)31(28)40;/h3-10,16,20,22,24,33,36,39,41-42H,11-15,35H2,1-2H3;1H/t16-,20-,22-,24-,33+,34-;/m0./s1
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| Chemical Name |
(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
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| Synonyms |
WP-769 Berubicin HCl RTA-744 RTA774 WP 769RTA 744 WP769
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT04915404 | TERMINATED | Drug: Berubicin Hydrochloride | Recurrent Glioblastoma Multiforme | WPD Pharmaceuticals Sp. z o.o. | 2022-12-07 | Phase 1 Phase 2 |
| NCT04762069 | ACTIVE, NOT RECRUITING | Drug: Berubicin Drug: Lomustine |
Glioblastoma Multiforme, Adult | CNS Pharmaceuticals, Inc | 2021-05-18 | Phase 2 |
| NCT05082493 | WITHDRAWN | Drug: Berubicin Hydrochloride | High Grade Glioma | WPD Pharmaceuticals Sp. z o.o | 2023-12 | Phase 1 |
| NCT00538343 | TERMINATED | Drug: berubicin hydrochloride (RTA 744) | Brain Metastases | Reata, a wholly owned subsidiary of Biogen | 2007-10-31 | Phase 2 |
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