XR 5944

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

MedKoo CAT#: 341465

CAS#: 343247-32-5

Description: XR 5944 is a potent DNA binding agent which stabilizes topoisomerase-dependent cleavage, thereby demonstrating exceptional efficacy against a number of murine and human tumor models.


Price and Availability

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XR 5944 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#: 341465
Name: XR 5944
CAS#: 343247-32-5
Chemical Formula: C34H34N8O2
Exact Mass: 586.2805
Molecular Weight: 586.7
Elemental Analysis: C, 69.61; H, 5.84; N, 19.10; O, 5.45


Synonym: XR 5944; XR-5944; XR5944 ; MLN 944; MLN-944; MLN944

IUPAC/Chemical Name: N,N'-(1,2-Ethanediylbis(imino-2,1-ethanediyl))bis(9-methyl-1-phenazinecarboxamide)

InChi Key: SFOADSRLCHRTKT-UHFFFAOYSA-N

InChi Code: InChI=1S/C34H34N8O2/c1-21-7-3-11-25-29(21)41-31-23(9-5-13-27(31)39-25)33(43)37-19-17-35-15-16-36-18-20-38-34(44)24-10-6-14-28-32(24)42-30-22(2)8-4-12-26(30)40-28/h3-14,35-36H,15-20H2,1-2H3,(H,37,43)(H,38,44)

SMILES Code: O=C(C1=CC=CC2=NC3=CC=CC(C)=C3N=C21)NCCNCCNCCNC(C4=CC=CC5=NC6=CC=CC(C)=C6N=C54)=O


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

Shelf Life:
>2 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


References

1: Lin C, Yang D. DNA Recognition by a Novel Bis-Intercalator, Potent Anticancer Drug XR5944. Curr Top Med Chem. 2015;15(14):1385-97. Review. PubMed PMID: 25866279; PubMed Central PMCID: PMC4772870.

2: Lin C, Mathad RI, Zhang Z, Sidell N, Yang D. Solution structure of a 2:1 complex of anticancer drug XR5944 with TFF1 estrogen response element: insights into DNA recognition by a bis-intercalator. Nucleic Acids Res. 2014 May;42(9):6012-24. doi: 10.1093/nar/gku219. Epub 2014 Apr 7. PubMed PMID: 24711371; PubMed Central PMCID: PMC4027214.

3: Moorthy NS, Pratheepa V, Ramos MJ, Vasconcelos V, Fernandes PA. Fused aryl-phenazines: scaffold for the development of bioactive molecules. Curr Drug Targets. 2014;15(7):681-8. Review. PubMed PMID: 24499398.

4: Sidell N, Mathad RI, Shu FJ, Zhang Z, Kallen CB, Yang D. Intercalation of XR5944 with the estrogen response element is modulated by the tri-nucleotide spacer sequence between half-sites. J Steroid Biochem Mol Biol. 2011 Apr;124(3-5):121-7. doi: 10.1016/j.jsbmb.2011.02.003. Epub 2011 Feb 17. PubMed PMID: 21333738; PubMed Central PMCID: PMC3072055.

5: Wolf SJ, Wakelin LP, He Z, Stewart BW, Catchpoole DR. In vitro assessment of novel transcription inhibitors and topoisomerase poisons in rhabdomyosarcoma cell lines. Cancer Chemother Pharmacol. 2009 Nov;64(6):1059-69. doi: 10.1007/s00280-009-0962-4. Epub 2009 Mar 10. PubMed PMID: 19277661.

6: Jobson AG, Willmore E, Tilby MJ, Mistry P, Charlton P, Austin CA. Effect of phenazine compounds XR11576 and XR5944 on DNA topoisomerases. Cancer Chemother Pharmacol. 2009 Apr;63(5):889-901. doi: 10.1007/s00280-008-0812-9. Epub 2008 Aug 5. PubMed PMID: 18679685.

7: Verborg W, Thomas H, Bissett D, Waterfall J, Steiner J, Cooper M, Rankin EM. First-into-man phase I and pharmacokinetic study of XR5944.14, a novel agent with a unique mechanism of action. Br J Cancer. 2007 Oct 8;97(7):844-50. Epub 2007 Sep 11. PubMed PMID: 17848959; PubMed Central PMCID: PMC2360398.

8: Punchihewa C, De Alba A, Sidell N, Yang D. XR5944: A potent inhibitor of estrogen receptors. Mol Cancer Ther. 2007 Jan;6(1):213-9. Epub 2007 Jan 11. PubMed PMID: 17218634.

9: Lewis LJ, Mistry P, Charlton PA, Thomas H, Coley HM. Mode of action of the novel phenazine anticancer agents XR11576 and XR5944. Anticancer Drugs. 2007 Feb;18(2):139-48. PubMed PMID: 17159600.

10: Harris SM, Scott JA, Brown JL, Charlton PA, Mistry P. Preclinical anti-tumor activity of XR5944 in combination with carboplatin or doxorubicin in non-small-cell lung carcinoma. Anticancer Drugs. 2005 Oct;16(9):945-51. PubMed PMID: 16162971.

11: Harris SM, Mistry P, Freathy C, Brown JL, Charlton PA. Antitumour activity of XR5944 in vitro and in vivo in combination with 5-fluorouracil and irinotecan in colon cancer cell lines. Br J Cancer. 2005 Feb 28;92(4):722-8. PubMed PMID: 15700035; PubMed Central PMCID: PMC2361868.

12: Di Nicolantonio F, Knight LA, Whitehouse PA, Mercer SJ, Sharma S, Charlton PA, Norris D, Cree IA. The ex vivo characterization of XR5944 (MLN944) against a panel of human clinical tumor samples. Mol Cancer Ther. 2004 Dec;3(12):1631-7. PubMed PMID: 15634657.

13: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Jul-Aug;26(6):473-503. PubMed PMID: 15349141.

14: Sappal DS, McClendon AK, Fleming JA, Thoroddsen V, Connolly K, Reimer C, Blackman RK, Bulawa CE, Osheroff N, Charlton P, Rudolph-Owen LA. Biological characterization of MLN944: a potent DNA binding agent. Mol Cancer Ther. 2004 Jan;3(1):47-58. PubMed PMID: 14749475.

15: Stewart AJ, Mistry P, Dangerfield W, Bootle D, Baker M, Kofler B, Okiji S, Baguley BC, Denny WA, Charlton PA. Antitumor activity of XR5944, a novel and potent topoisomerase poison. Anticancer Drugs. 2001 Apr;12(4):359-67. PubMed PMID: 11335793.