Redox-activated, hypoxia-selective DNA cleavage by quinoxaline 1,4-di-N-oxide
摘要:
Quinoxaline 1,4-dioxide () is the historical prototype for modern heterocyclic -oxide antitumor agents such as 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine, ) and 3-amino-2-quinoxalinecarbonitrile 1,4-dioxide (). Early experiments in bacterial cell lines suggested that enzymatic, single-electron reduction of quinoxaline 1,4-dioxides under low-oxygen (hypoxic) conditions leads to DNA damage. Here the ability of quinoxaline 1,4-dioxide to cleave DNA has been explicitly characterized using in vitro assays. The hypoxia-selective DNA-cleaving properties of reported here may provide a chemical basis for understanding the cytotoxic and mutagenic activities of various quinoxaline 1,4-dioxide antibiotics.The hypoxia-selective DNA-cleaving properties of quinoxaline 1,4-dioxide reported here may provide a chemical basis for understanding the cytotoxic and mutagenic activities of this compound as well as and other substituted quinoxaline 1,4-dioxide antibiotics.
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DOI:
10.1016/S0968-0896(01)00163-8
被引量:
年份:
2001
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