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B4563 Sigma-Aldrich

Bisantrene dihydrochloride

≥98% (HPLC)

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

  • CAS Number 78186-34-2

  • Empirical Formula (Hill Notation) C22H22N8 ·2HCl

  • Molecular Weight 471.39

  •  MDL number MFCD01743164

  •  PubChem Substance ID 329773240

  •  NACRES NA.77

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Properties

Related Categories Apoptosis and Cell Cycle, B, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology,
Quality Level   100
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

Description

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.

Safety & Documentation

Safety Information

Symbol 
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

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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