Bisantrene HCl | CAS#71439-68-4 | CAS#78186-34-2 | DNA intercalator

MedKoo Cat#: 206518 | Name: Bisantrene HCl

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 HCl

CAS#71439-68-4 (2HCl)

Theoretical Analysis

MedKoo Cat#: 206518

Name: Bisantrene HCl

CAS#: 71439-68-4 (2HCl)

Chemical Formula: C22H24Cl2N8

Exact Mass: 0.0000

Molecular Weight: 471.39

Elemental Analysis: C, 56.06; H, 5.13; Cl, 15.04; N, 23.77

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,650.00	2 Weeks
2g	USD 6,450.00	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

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

IUPAC/Chemical Name

9,10-bis((Z)-(2-(4,5-dihydro-1H-imidazol-2-yl)hydrazono)methyl)anthracene dihydrochloride

InChi Key

KINULKKPVJYRON-VCZQZRGZSA-N

InChi Code

InChI=1S/C22H22N8.2ClH/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);2*1H/b27-13-,28-14-;;

SMILES Code

[H]Cl.[H]Cl.C12=CC=CC=C1C(/C=N\NC3=NCCN3)=C4C=CC=CC4=C2/C=N\NC5=NCCN5

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

>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

Related: 78186-34-2 (Bisantrene 2HCl) 78186-34-2 (Bisantrene free base).

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 471.39 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: 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. PubMed PMID: 20206144. 2: Zagotto G, Oliva A, Guano F, Menta E, Capranico G, Palumbo M. Synthesis, DNA-damaging and cytotoxic properties of novel topoisomerase II-directed bisantrene analogues. Bioorg Med Chem Lett. 1998 Jan 20;8(2):121-6. PubMed PMID: 9871638. 3: Sissi C, Bolgan L, Moro S, Zagotto G, Bailly C, Menta E, Capranico G, Palumbo M. DNA-binding preferences of bisantrene analogues: relevance to the sequence specificity of drug-mediated topoisomerase II poisoning. Mol Pharmacol. 1998 Dec;54(6):1036-45. PubMed PMID: 9855632. 4: Capranico G, Guano F, Moro S, Zagotto G, Sissi C, Gatto B, Zunino F, Menta E, Palumbo M. 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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. PubMed PMID: 2272771. 17: Salianov VI, Evdokimov IuM, Palumbo M. [Study of the properties of condensed forms of the complexes of linear and supercoiled DNA with mitoxantrone and bisantrene]. Antibiot Khimioter. 1990 Jan;35(1):19-22. Russian. PubMed PMID: 2334240. 18: Mills GM, Dahlberg S, Cowan J, Neilan BA, Gumbart CH, Hussein K, Coltman CA Jr. Phase II evaluation of bisantrene in acute leukemia. A Southwest Oncology Group Study. Am J Clin Oncol. 1989 Dec;12(6):507-10. PubMed PMID: 2589232. 19: Tosi P, Visani G, Colombini R, Verlicchi F, Benfenati D, Cenacchi A, Russo D, Zuffa E, Papadopulu P, Tura S. Phase II study of bisantrene in relapsed/refractory acute non lymphoid leukemias (ANLL). Haematologica. 1989 Nov-Dec;74(6):555-8. PubMed PMID: 2628237. 20: Elliott JA, Wilson WD, Shea RG, Hartley JA, Reszka K, Lown JW. 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