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B4563

Sigma-Aldrich

Bisantrene dihydrochloride

≥98% (HPLC)

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Synonym(s):
Bis((4,5-dihydro-1H-imidazol-2-yl)hydrazone)-9,10-anthracenedicarboxaldehyde dihydrochloride, NSC 337766
Empirical Formula (Hill Notation):
C22H22N8 ·2HCl
CAS Number:
78186-34-2
Molecular Weight:
471.39
MDL number:
MFCD01743164
UNSPSC Code:
12352200
PubChem Substance ID:
329773240
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

solubility

deionized water: 8 mg/mL

storage temp.

room temp

SMILES string

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+;;

InChI key

KINULKKPVJYRON-PVNXHVEDSA-N

Application

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.

Biochem/physiol Actions

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.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H400

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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.
P Tosi et al.
Haematologica, 74(6), 555-558 (1989-11-01)
The antileukemic activity of Bisantrene, a new anthracene derivative, has been evaluated in a phase II clinical study in 10 patients affected by refractory or primary relapsed ANLL. The patients received an induction course consisting of 250 mg/m2/day for 7
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
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
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