B4563

Sigma-Aldrich

Bisantrene dihydrochloride

≥98% (HPLC)

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:
Molecular Weight:
471.39
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

solid

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.

Packaging

10, 50 mg in glass bottle

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

RIDADR

UN 2811 6.1 / PGIII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

S Yao et al.
Science in China. Series B, Chemistry, life sciences & earth sciences, 38(12), 1462-1472 (1995-12-01)
The binding of bisantrene to four DNA tetramers, d(CGCG)2, d(GCGC)2, d(CATG)2, and d(GTAC)2, was investigated by 1D and 2D NMR spectroscopy. Bisantrene is a well known anticancer drug and has been used clinically for years. DNA is believed to be...
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...
S Venitt et al.
Journal of medicinal chemistry, 41(19), 3748-3752 (1998-09-11)
Fifteen anthracene-9,10-dione ("anthraquinone") derivatives with (omega-aminoalkyl)carboxamido substituents at the 1-, 2-, 1,4-, or 2, 6-ring positions were tested for bacterial mutagenicity in reverse-mutation assays using Salmonella typhimurium frameshift strains TA1538, TA98, and TA97a, in the presence and absence of a...
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...
V I Salianov et al.
Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic], 35(1), 19-22 (1990-01-01)
The effect of anthrachinone and anthracene derivatives on linear and circular superstranded molecules of DNA in conditions of their condensation was studied. It was shown that the compounds formed strong intercalation complexes with the molecules of the linear and circular...

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