Bisantrene | CAS#78186-34-2 | DNA intercalator

MedKoo Cat#: 127414 | Name: Bisantrene

Description:

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

Bisantrene, aslo known as CL-216942 and NSC 337766, is topoisomerase II poisons and DNA intercalators. It may be used as model compounds to study P-glycoprotein-mediated multiple drug resistance (MDR1). Bisantrene may be used as a Rac1 inhibitor. Bisantrene intercalates with and disrupts the configuration of DNA, resulting in DNA single-strand breaks, DNA-protein crosslinking, and inhibition of DNA replication. This agent is similar to doxorubicin in activity, but unlike doxorubicin, does not exhibit cardiotoxicity.

Chemical Structure

Bisantrene

CAS#78186-34-2 (free base)

Theoretical Analysis

MedKoo Cat#: 127414

Name: Bisantrene

CAS#: 78186-34-2 (free base)

Chemical Formula: C22H22N8

Exact Mass: 398.1967

Molecular Weight: 398.47

Elemental Analysis: C, 66.31; H, 5.57; N, 28.12

Price and Availability

Size	Price	Availability
25mg	USD 450.00	2 Weeks
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
1g	USD 4,250.00	2 Weeks

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Related CAS #

71439-68-4 (2HCl) 97910-18-4 (4HCl) 97910-19-5 (nitrate) 97910-20-8 (sulfate) 101218-44-4 (acetate) 78186-34-2 (free base)

Synonym

Bisantrenum; Bisantrene; CL-216942; CL216942; CL 216942; NSC-337766; NSC337766; NSC 337766

IUPAC/Chemical Name

9,10-bis((E)-(2-(4,5-dihydro-1H-imidazol-2-yl)hydrazineylidene)methyl)anthracene

InChi Key

NJSMWLQOCQIOPE-OCHFTUDZSA-N

InChi Code

InChI=1S/C22H22N8/c1-2-6-16-15(5-1)19(13-27-29-21-23-9-10-24-21)17-7-3-4-8-18(17)20(16)14-28-30-22-25-11-12-26-22/h1-8,13-14H,9-12H2,(H2,23,24,29)(H2,25,26,30)/b27-13+,28-14+

SMILES Code

C1(/C=N/NC2=NCCN2)=C3C=CC=CC3=C(C4=C1C=CC=C4)/C=N/NC5=NCCN5

Appearance

To be determined

Purity

>95% (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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 398.47 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: Valdez BC, Yuan B, Murray D, Nieto Y, Popat U, Andersson BS. Enhanced cytotoxicity of bisantrene when combined with venetoclax, panobinostat, decitabine and olaparib in acute myeloid leukemia cells. Leuk Lymphoma. 2022 Jul;63(7):1634-1644. doi: 10.1080/10428194.2022.2042689. Epub 2022 Feb 20. PMID: 35188042. 2: Canaani J, Danylesko I, Shemtov N, Zlotnick M, Lozinsky K, Benjamini O, Yerushalmi R, Nagar M, Dor C, Shimoni A, Avigdor A, Nagler A. A phase II study of bisantrene in patients with relapsed/refractory acute myeloid leukemia. Eur J Haematol. 2021 Feb;106(2):260-266. doi: 10.1111/ejh.13544. Epub 2020 Nov 21. PMID: 33159365. 3: Dorr RT, Peng YM, Alberts DS. Bisantrene solubility and skin toxicity studies: efficacy of sodium bicarbonate as a local ulceration antidote. Invest New Drugs. 1984;2(4):351-7. doi: 10.1007/BF00171585. PMID: 6096286. 4: Spadea A, Petti MC, Aloespiriti MA, Avvisati G, De Gregoris C, Fazi P, Latagliata R, Amadori S, Mandelli F. Bisantrene in relapsed and refractory acute myelogenous leukemia. Leuk Lymphoma. 1993 Feb;9(3):217-20. doi: 10.3109/10428199309147373. PMID: 8471980. 5: Cowan JD, Neidhart J, McClure S, Coltman CA Jr, Gumbart C, Martino S, Hutchins LF, Stephens RL, Vaughan CB, Osborne CK. Randomized trial of doxorubicin, bisantrene, and mitoxantrone in advanced breast cancer: a Southwest Oncology Group study. J Natl Cancer Inst. 1991 Aug 7;83(15):1077-84. doi: 10.1093/jnci/83.15.1077. PMID: 1875415. 6: Coltman CA Jr, Osborne CK. Bisantrene, biological and clinical effects. Cancer Treat Rev. 1984 Dec;11(4):285-8. doi: 10.1016/0305-7372(84)90024-0. PMID: 6534510. 7: Polverini PJ, Novak RF. Inhibition of angiogenesis by the antineoplastic agents mitoxantrone and bisantrene. Biochem Biophys Res Commun. 1986 Nov 14;140(3):901-7. doi: 10.1016/0006-291x(86)90720-5. PMID: 2430572. 8: Rybak ME, Badstubner B, Griffin T. The effects of bisantrene on human platelets. Invest New Drugs. 1986;4(2):119-25. doi: 10.1007/BF00194590. PMID: 3015826. 9: Artman M, Roloff JS, Olson RD, Parrish MD. Depression of cardiac function by bisantrene. South Med J. 1985 Dec;78(12):1517-8. doi: 10.1097/00007611-198512000-00029. PMID: 3865379. 10: Myers JW, Von Hoff DD, Kuhn JG, Osborne CK, Sandbach JF, Pocelinko R. Anaphylactoid reactions associated with bisantrene infusions. Invest New Drugs. 1983;1(1):85-8. doi: 10.1007/BF00180195. PMID: 6678858. 11: Yap HY, Yap BS, Blumenschein GR, Barnes BC, Schell FC, Bodey GP. Bisantrene, an active new drug in the treatment of metastatic breast cancer. Cancer Res. 1983 Mar;43(3):1402-4. PMID: 6825109. 12: Vogelzang NJ, Lanzotti VJ, Muntean B, Blough RR. Bisantrene in advanced, hormone-resistant carcinoma of the prostate: an Illinois Cancer Council phase II study. Invest New Drugs. 1990 Aug;8(3):313-5. doi: 10.1007/BF00171845. PMID: 2272771. 13: Folini M, Pivetta C, Zagotto G, De Marco C, Palumbo M, Zaffaroni N, Sissi C. Remarkable interference with telomeric function by a G-quadruplex selective bisantrene regioisomer. Biochem Pharmacol. 2010 Jun 15;79(12):1781-90. doi: 10.1016/j.bcp.2010.02.018. Epub 2010 Mar 3. PMID: 20206144. 14: Buck M, Kovach JS. Blood and tissue concentrations of Bisantrene measured by a simple fluorometric assay. Cancer Chemother Pharmacol. 1985;15(1):40-3. doi: 10.1007/BF00257292. PMID: 4006048. 15: Alberts DS, Mason-Liddil N, Green SJ, Cowan JD, Fletcher WS, Neilan B, Guy JT, Epstein RB. Phase II evaluation of bisantrene hydrochloride in refractory malignant melanoma. A Southwest Oncology Group Study. Invest New Drugs. 1987;5(3):289-92. doi: 10.1007/BF00175300. PMID: 3667164. 16: Miller TP, Jones SE, Alberts DS, Mackel C. Phase II trial of bisantrene in patients with intermediate and high grade diffuse non-Hodgkin's lymphomas. Invest New Drugs. 1984;2(1):75-7. doi: 10.1007/BF00173790. PMID: 6469502. 17: Forastiere AA, Perry MC, Hughes AK, Wood WC. Bisantrene (NSC 337766) (CL 216,942) in advanced breast cancer. A cancer and leukemia group B study. Cancer Chemother Pharmacol. 1984;13(3):226-9. doi: 10.1007/BF00269035. PMID: 6488443. 18: Miller TP, Ahmann FR, Mackel C, Greenberg BR, Alberts DS. Phase II trial of bisantrene in non-small cell lung cancer. Invest New Drugs. 1985;3(4):393-5. doi: 10.1007/BF00170764. PMID: 4086247. 19: Zhang XP, Ritke MK, Yalowich JC, Slovak ML, Ho JP, Collins KI, Annable T, Arceci RJ, Durr FE, Greenberger LM. P-glycoprotein mediates profound resistance to bisantrene. Oncol Res. 1994;6(7):291-301. PMID: 7865904.