B4563
比生群二盐酸盐
≥98% (HPLC)
别名:
Bis((4,5-dihydro-1H-imidazol-2-yl)hydrazone)-9,10-anthracenedicarboxaldehyde dihydrochloride, NSC 337766
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关于此项目
经验公式（希尔记法）:
C22H22N8 ·2HCl
化学文摘社编号:
分子量:
471.39
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
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+;;
SMILES string
Cl.Cl.C1CN=C(N1)N\N=C\c2c3ccccc3c(\C=N\NC4=NCCN4)c5ccccc25
InChI key
KINULKKPVJYRON-PVNXHVEDSA-N
assay
≥98% (HPLC)
form
solid
storage condition
desiccated
solubility
deionized water: 8 mg/mL
storage temp.
room temp
Quality Level
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
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Aquatic Acute 1
存储类别
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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
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
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
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
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