Berubicin

Berubicin (RTA 744 free base) is a Doxorubicin (HY-15142A) analog that can cross the blood-brain barrier. Berubicin inhibits P-gp and MRP1-mediated efflux and suppresses glioblastoma multiforme (GBM) . Berubicin exerts toxic effects on leukemia cells by activating nuclear factor κB (NF-κB) and induces apoptosis in neuroblastoma cells. Berubicin can be used in the study of tumors related to the nervous system[1][2][3][4][5].

Product Specifications

CAS Number

[677017-23-1]

Product Name Alternative

RTA 744 (free base) ; WP 744 (free base) ; WP 769

UNSPSC

12352005

Target

Apoptosis; Caspase; NF-κB

Type

Reference compound

Related Pathways

Apoptosis; NF-κB

Applications

Cancer-programmed cell death

Field of Research

Cancer; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/berubicin.html

Purity

87.76

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

OC1=C2C([C@@]([H])(O[C@H]3C[C@H](N)[C@H](OCC4=CC=CC=C4)[C@H](C)O3)C[C@@](C(CO)=O)(O)C2)=C(O)C5=C1C(C6=CC=CC(OC)=C6C5=O)=O

Molecular Formula

C34H35NO11

Molecular Weight

633.64

References & Citations

[1]Kazerooni R, et al. Phase I clinical pharmacokinetics of RTA 744 (berubicin (B) ), a blood-brain barrier penetrating anthracycline active against high grade glioma, and evaluation of its 13-hydroxy metabolite, berubicinol (B-ol) [J]. Molecular Cancer Therapeutics, 2007, 6 (11_Supplement) : B101-B101.|[2]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. doi: 10.1016/j.jss.2004.05.017. PMID: 15555623.|[3]Faderl S, Estrov Z, Kantarjian HM, Harris D, Van Q, Fokt I, Przewloka T, Godlewski C, Woynarowski JM, Priebe W. WP744, a novel anthracycline with enhanced proapoptotic and antileukemic activity. Anticancer Res. 2001 Nov-Dec;21 (6A) :3777-84. PMID: 11911247.|[4]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.|[5]Silberman S, et al. RTID-03. DESIGN AND INITIATION OF PIVOTAL STUDIES FOR BERUBICIN, A NOVEL, POTENT TOPOISOMERASE II POISON FOR THE TREATMENT OF RECURRENT GLIOBLASTOMA MULTIFORME (GBM) . Neuro Oncol. 2021 Nov 12;23 (Suppl 6) :vi193.