XR 5944 | CAS# 343247-32-5 | DNA Binding Agent

MedKoo Cat#: 341465 | Name: XR 5944

Description:

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

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.

Chemical Structure

XR 5944

CAS#343247-32-5

Theoretical Analysis

MedKoo Cat#: 341465

Name: XR 5944

CAS#: 343247-32-5

Chemical Formula: C34H34N8O2

Exact Mass: 586.2805

Molecular Weight: 586.70

Elemental Analysis: C, 69.61; H, 5.84; N, 19.10; O, 5.45

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

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

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).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 586.70 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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.