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Merck

B4563

Sigma-Aldrich

Bisantrene dihydrochloride

≥98% (HPLC)

Sinónimos:

Bis((4,5-dihydro-1H-imidazol-2-yl)hydrazone)-9,10-anthracenedicarboxaldehyde dihydrochloride, NSC 337766

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About This Item

Fórmula empírica (notación de Hill):
C22H22N8 ·2HCl
Número de CAS:
Peso molecular:
471.39
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77

Ensayo

≥98% (HPLC)

Formulario

solid

condiciones de almacenamiento

desiccated

solubilidad

deionized water: 8 mg/mL

temp. de almacenamiento

room temp

cadena SMILES

Cl.Cl.C1CN=C(N1)N\N=C\c2c3ccccc3c(\C=N\NC4=NCCN4)c5ccccc25

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+;;

Clave InChI

KINULKKPVJYRON-PVNXHVEDSA-N

Aplicación

Bisantrene (NSC 337766), and its derivatives are 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.

Acciones bioquímicas o fisiológicas

Bisantrene dihydrochloride is an antineoplastic agent, MDR1 substrate, DNA intercalator and topoisomerase II poison
Bisantrene dihydrochloride is an antineoplastic agent, MDR1 substrate, DNA intercalator, and topoisomerase II poison. Cancer cells that develop resistance to bisantrene tend to overexpress P-glycoprotein. Bisantrene can be used to select for P-glycoprotein-mediated multiple drug resistance. The data suggest that bisantrene is an excellent substrate for P-glycoprotein.
Bisantrene is an anthracene bishydrazone derivative, which has antitumor activity.

Pictogramas

Exclamation markEnvironment

Palabra de señalización

Warning

Frases de peligro

Consejos de prudencia

Clasificaciones de peligro

Acute Tox. 4 Oral - Aquatic Acute 1

Código de clase de almacenamiento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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G Zagotto et al.
Bioorganic & medicinal chemistry letters, 8(2), 121-126 (1999-01-01)
New bisantrene analogues were synthesized, bearing one or two 4,5-dihydro-1H-imidazol-2-yl hydrazone side chains at positions 1,4 or 9 of the anthracene ring system. A 10-azabioisostere was also prepared. The position of substituents in structurally isomeric drugs modulates topoisomerase II poisoning
G M Mills et al.
American journal of clinical oncology, 12(6), 507-510 (1989-12-01)
Twenty-nine patients with heavily pretreated acute leukemia in relapse were treated with bisantrene (maximum dose 120 mg/m2/day x 5) in a phase II study. Twenty-seven of the 29 patients were evaluable for response, receiving a total of 53 courses of
I Aksentijevich et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 2(6), 973-980 (1996-06-01)
In this work, we demonstrate a protective effect conferred by the human multidrug resistance gene (MDR1) to populations of the murine hematopoietic system against the toxic effects of bisantrene, a novel intercalating cytotoxic agent under investigation as an anticancer agent.
T Leblanc et al.
Medical and pediatric oncology, 22(2), 119-124 (1994-01-01)
Bisantrene is an anthracene derivative which has demonstrated activity in acute myeloblastic leukemia (AML) and in lymphoma. The present study was designed to assess the reinduction rate and toxicity of bisantrene (250 mg/m2/d x 5) associated with aracytine (100 mg/m2
G Capranico et al.
The Journal of biological chemistry, 273(21), 12732-12739 (1998-05-28)
To identify structural determinants for the sequence-specific recognition of covalent topoisomerase II-DNA complexes by anti-cancer drugs, we investigated a number of bisantrene congeners, including a 10-azabioisoster, bearing one or two 4, 5-dihydro-1H-imidazol-2-yl hydrazone side chains at positions 1, 4, or

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