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B4563

Sigma-Aldrich

Bisantrene dihydrochloride

≥98% (HPLC)

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C22H22N8 ·2HCl
Número CAS:
78186-34-2
Peso molecular:
471.39
Número MDL:
MFCD01743164
Código UNSPSC:
12352200
ID de substância PubChem:
329773240
NACRES:
NA.77

Nível de qualidade

100

Ensaio

≥98% (HPLC)

forma

solid

condição de armazenamento

desiccated

solubilidade

deionized water: 8 mg/mL

temperatura de armazenamento

room temp

cadeia de caracteres 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+;;

chave InChI

KINULKKPVJYRON-PVNXHVEDSA-N

Aplicação

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.

Ações bioquímicas/fisiológicas

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
GHS07,GHS09

Palavra indicadora

Warning

Frases de perigo

H302,H400

Declarações de precaução

P273 - P301 + P312 + P330

Classificações de perigo

Acute Tox. 4 Oral - Aquatic Acute 1

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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G Capranico et al.
Journal of molecular biology, 235(4), 1218-1230 (1994-01-28)
To gain further knowledge of the molecular features of topoisomerase II inhibitors required for drug-receptor complex formation, we investigated the conformational drug determinants of the sequence specificities of drug-stimulated DNA cleavage by computer-aided molecular modeling techniques. DNA sequence specificities of
T P Wunz et al.
Journal of medicinal chemistry, 33(6), 1549-1553 (1990-06-01)
The relative DNA binding strengths of bisantrene and nine new analogues were measured by spectrophotometric titration and melt transition temperature (Tm) techniques. Data from the spectrophotometric titrations could not be fit by simple Scatchard plots. However, they were fit by
K C Murdock et al.
Journal of medicinal chemistry, 36(15), 2098-2101 (1993-07-23)
The selective phosphorylation of bisantrene (1) affords bis(phosphonoguanidinic acid) 6, a prodrug with enhanced aqueous solubility (as sodium salt 7) at physiological pH. Unlike 1, in a rat tail vein model, no precipitation was observed when bis(phosphonoguanidinic acid) 6 was
A Spadea et al.
Leukemia & lymphoma, 9(3), 217-220 (1993-02-01)
Because of the lack of standard treatment in refractory and relapsed acute myelogenous leukemia (AML) several new drugs have been employed alone to evaluate their efficacy in this peculiar category of patient. Bisantrene, a new anthracene bishydrazone derivative, has shown
G Visani et al.
Haematologica, 75(6), 527-531 (1990-11-01)
In vitro clonogenic assays may be useful for determining the sensitivity of leukemic cells to chemotherapeutic agents. We evaluated the antileukemic effect of Bisantrene (an anthracene derivative now undergoing phase II clinical trials in relapsed/resistant acute non lymphoid leukemias-ANLL) using
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