Banoxantrone dihydrochloride

Names

[ Name ]:
Banoxantrone dihydrochloride

[Synonym ]:
Banoxantrone
1,4-Bis{[2-(dimethylamino)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione bis-N-oxide
1,4-Bis((2-(dimethylamino)ethyl)amino)-5,8-dihydroxy-9,10-anthracenedione N,N'-dioxide
1,4-bis{[2-(dimethylamino-N-oxide)ethyl]amino}-5,8-dihydroxyanthracene-9,10-dione
AQ4N
1,4-bis-{[2-(dimethylamino-N-oxide)ethyl]amino}-5,8-dihydroanthracene-9,10-dione
1,4-bis-(2-dimethylamino-ethylamino)-5,8-dihydroxy-anthraquinone-bis-N-oxide
Banoxantrone [INN:BAN]
UNII-W5H7E45YT3
1,4-Bis(2-(dimethylazinoyl)ethylamino)-5,8-dihydroxy-9,10-anthraquinone

Biological Activity

[Description]:

Banoxantrone (AQ4N), as a prototype hypoxia selective cytotoxin, can be reduced to AQ4, a potent topoisomerase II inhibitor. Banoxantrone selectively kills hypoxic cells via an iNOS-dependent mechanism. Banoxantrone shows a potent cytotoxicity and hypoxia-selective effect enhanced by radiation[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Immunology/Inflammation >> NO Synthase

[Target]

iNOS

[In Vitro]

Banoxantrone (20 μM; 90 min) 选择性诱导缺氧的 T50/80 肿瘤细胞发生损伤[1]。

[In Vivo]

Banoxantrone (200 mg/kg; 腹腔注射; 单剂量) 在 BDF 小鼠中显著抑制T50/80肿瘤，并诱导细胞损伤[1]。

[References]

[1]. Hejmadi MV, et al. DNA damage following combination of radiation with the bioreductive drug AQ4N: possible selective toxicity to oxic and hypoxic tumour cells. Br J Cancer. 1996 Feb;73(4):499-505.

[2]. Mehibel M, et al. Radiation enhances the therapeutic effect of Banoxantrone in hypoxic tumour cells with elevated levels of nitric oxide synthase. Oncol Rep. 2016 Apr;35(4):1925-32.

Chemical & Physical Properties

[ Molecular Formula ]:
C₂₂H₂₈N₄O₆

[ Molecular Weight ]:
444.48100

[ Exact Mass ]:
444.20100

[ PSA ]:
157.52000

[ LogP ]:
2.03320

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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