677017-23-1
Chemical Structure
Berubicin
Synonym(s): RTA 744 free base; WP 744 free base; WP 769
- CAS No.: 677017-23-1
- Formula:C34H35NO11
- Molecular Weight:633.64
IUPAC Name: (8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
InChIKey: FIGNGSHKNAHTSH-JJMFXPFOSA-N
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
Biological Activity: 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].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Berubicin | 85.02% | 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. | ||||||||||||||||||||
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References
- [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. [Content Brief]
- [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. [Content Brief]
- [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.
