5227-58-7Relevant academic research and scientific papers
Redox-activated, hypoxia-selective DNA cleavage by quinoxaline 1,4-di-N-oxide
Ganley, Brian,Chowdhury, Goutam,Bhansali, Jennifer,Daniels,Gates, Kent S.
, p. 2395 - 2401 (2007/10/03)
Quinoxaline 1,4-dioxide (4) is the historical prototype for modern heterocyclic N-oxide antitumor agen s such as 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine, 1) and 3-amino-2-quinoxalinecarbonitrile 1,4-dioxide (11). 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 characerized using in vitro assays. The hypoxia-selective DNA-cleaving properties of 4 reported here may provide a chemical basis for understanding the cytotoxic and mutagenic activities of various quinoxaline 1,4-dioxide antibiotics. Copyright
