Berubicin HCl

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 200490

CAS#: 293736-67-1 (HCl salt)

Description: 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).


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Berubicin, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200490
Name: Berubicin HCl
CAS#: 293736-67-1 (HCl salt)
Chemical Formula: C34H36ClNO11
Exact Mass:
Molecular Weight: 670.1
Elemental Analysis: C, 60.94; H, 5.41; Cl, 5.29; N, 2.09; O, 26.26


Synonym: RTA-744; RTA 744; RTA774; WP 769; WP769; WP-769; Berubicin HCl.

IUPAC/Chemical 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 hydrochloride

InChi Key: GPMIHHFZKBVWAZ-LMMKTYIZSA-N

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

SMILES Code: O=C1C2=C(O)C(C[C@](C(CO)=O)(O)C[C@@H]3O[C@H]4C[C@H](N)[C@H](OCC5=CC=CC=C5)[C@H](C)O4)=C3C(O)=C2C(C6=C1C=CC=C6OC)=O.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Related:
293736-67-1 (Berubicin HCl salt)
677017-23-1(Berubicin free base).

Berubicin belongs to a novel class of anthracycline derivatives that cross the blood-brain barrier and show significant potential for the treatment of primary and secondary brain cancers. While other drugs in this class (for example, doxorubicin) are some of the most broadly used and effective cancer therapies, they do not cross the blood-brain barrier and are not effective in treating brain tumors. These compounds are potent inhibitors of topoisomerase II, a DNA repair enzyme. Overexpression of topo II has been identified as an indicator of aggressive cell proliferation and a negative prognostic indicator in patients with primary brain cancers. Topo II inhibition is likely to be effective in combination with temozolomide, the current standard therapy in glioblastoma.   see http://www.reatapharma.com/pip_rta744.asp .
 
 


References

1. Wang, Yaolin; Wang, Yan; Liu, Ming; Bishop, Walter Robert; Seidel-Dugan, Cynthia. Anti-IGF-1 receptor antibody combined with chemotherapeutic agent, antitumor agent, radiotherapy or surgery for treating or preventing colorectal cancer. PCT Int. Appl. (2009), 52pp. CODEN: PIXXD2 WO 2009142810 A2 20091126 CAN 151:569615 AN 2009:1470605

2. Wang, Yaolin; Wang, Yan; Lu, Brian Der-Hua; Liu, Ming; Seidel-Dugan, Cynthia; Yao, Siu-Long. Sequential administration of chemotherapeutic agents and anti-(insulin-like growth factor 1 receptor) for treatment of cancer. PCT Int. Appl. (2009), 104 pp. CODEN: PIXXD2 WO 2009137378 A2 20091112 CAN 151:521177 AN 2009:1395230

3. Zabudkin, Alexander; Matvienko, Victor; Matveev, Alexey; Itkin, Aleksandr. Process of aralkylation of the 4'-hydroxyl group in anthracyclins. PCT Int. Appl. (2009), 14pp.; Chemical Indexing Equivalent to 151:124315 (US). CODEN: PIXXD2 WO 2009088618 A1 20090716 CAN 151:148572 AN 2009:859254

4. Zabudkin, Alexander F.; Matvienko, Victor; Matveev, Alexey; Itkin, Aleksandr M. Process of aralkylation of the 4'-hydroxyl group in anthracyclins. U.S. Pat. Appl. Publ. (2009), 5 pp., Chemical Indexing Equivalent to 151:148572 (WO). CODEN: USXXCO US 2009176974 A1 20090709 CAN 151:124315 AN 2009:829056

5. Wang, Yan; Wang, Yaolin; Levitan, Diane; Seidel-Dugan, Cynthia; Liu, Ming; Ding, Wei. Gene expression biomarkers for detecting IGF1R inhibitor-resistant or -sensitive cancers and uses in anti-IGF1R antibody combination chemotherapy. PCT Int. Appl. (2009), 165pp. CODEN: PIXXD2 WO 2009079587 A2 20090625 CAN 151:116583 AN 2009:769153

6. Ramachandra, Sumant; Bishop, Robert Walter; Masat, Linda; Huang, Chao Bai; Takeuchi, Toshihiko; Kantak, Seema. Human anti-VEGF antibodies and conjugates for treatment of angiogenesis conditions. PCT Int. Appl. (2009), 195pp. CODEN: PIXXD2 WO 2009055343 A2 20090430 CAN 150:492909 AN 2009:519479

7. Wang, Yan; Pachter, Jonathan A.; Hailey, Judith Anne; Brams, Peter; Williams, Denise; Srinivasan, Mohan; Feingersh, Mary Diane. Anti-insulin-like growth factor 1 receptor therapy. PCT Int. Appl. (2009), 129pp. CODEN: PIXXD2 WO 2009005673 A1 20090108 CAN 150:119716 AN 2009:25215

8. Wang, Yan; Zong, Chen; Seidel-Dugan, Cynthia; Wang, Yaolin; Yao, Siu-Long; Lu, Brian Der-Hua; Ladha, Mohamed H. Methods of treating cancer using IGF1R inhibitors. PCT Int. Appl. (2008), 103pp. CODEN: PIXXD2 WO 2008076278 A2 20080626 CAN 149:102715 AN 2008:771165

9. Szeja, Wieslaw. Method of producing anthracycline glycoside derivatives via regioselective alkylation reaction as prodrug antibacterial and antitumor agents. PCT Int. Appl. (2008), 35pp. CODEN: PIXXD2 WO 2008029294 A2 20080313 CAN 148:331949 AN 2008:322136

10. Wang, Yan. Blood levels of insulin-like growth factor-binding protein 2 as a marker for monitoring the effectiveness of inhibitors of insulin-like growth factor I receptors in cancer therapy. PCT Int. Appl. (2008), 133pp. CODEN: PIXXD2 WO 2008005469 A2 20080110 CAN 148:135980 AN 2008:43490