Mitoxantrone, structure

Mitoxantrone Mitoxantrone, l,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl) amino) ethyl]amino]]-9,10-anthracendione (30.6.3), is structurally related to the antibiotic dox-orubicine. It is synthesized from danthron (1,8-dihydroxyanthraquinone), which when reacted with nitric acid, and then a mixture of sodium sulfide and thiosulfate in a base, is transformed to 1,4,5,8-tetrahydroxyanthraquinone (30.6.2). Reacting this with 2-amino-ethylaminoethanol in the presence of chloranyl (2,3,5,6-tetrachlorobenzoquinone-l,4) gives the desired mitoxantrone (30.6.3), [142-145],... 

Mitoxantrone (Novantrone) is a synthetic anthraquinone that is structurally and mechanistically related to the an-thracyclines. It intercalates with DNA and produces single-strand DNA breakage. It is cross-resistant with dox-... 

Figure 13.2 Structures of a doxorubicin, b mitoxantrone, c topotecan and d etoposide.

Piroxantronc is an anthrapyrazole structurally related to mitoxantrone in having two phenolic hydroxyls and side chains containing amino groups however, its quinone ring... 

J Blanz, K Mewes, G Ehninger, B Proksch, B Greger, D Waidelich, K-P Zeller. Isolation and structure elucidation of urinary metabolites of mitoxantrone. Cancer Res 51 3427, 1991. 

Daunorubicin, doxorubicin, epirubicin, idarubicin, and mitoxantrone are among the most important antitumor agents. They are derived from the fungus S. peucetius var. caesius. Idarubicin and epirubicin are analogs of the naturally produced anthracyclines, differing only slightly in chemical structure, but having somewhat distinct patterns of clinical activity. Daunorubicin and idarubicin have been used primarily in acute leukemias, whereas doxorubicin... 

The DNA molecule is the primary target of many antitumour agents. Small molecules, which bind to DNA by intercalation, require polycyclic systems in their structure for efficient binding. Because of the symmetrical arrangement of the helical double strand, symmetry is found in the structure of DNA ligands. Polycyclic systems bearing symmetrical polyamine side chains, such as mitoxantrone ... 

Medicinal chemistry SERRS has been used to detect the antitumour drug mitoxantrone and its interaction with DNA in situ. The adsorption of the drug complex onto a colloidal surface did not destroy or interfere with the native structure. Therefore, bonding information from the complex was extracted from the SERRS spectra. Selective detection on DNA at ultra-low detection by SERRS has been developed. 

FIGURE 3.23 The studied flavonoids (Putz et al., 2009b) (with basic structure of as no.O while the others are in the Table 3.29 characterized by associate QSAR data), covering the flavones, isoflavones, chalcones, flavonols and flavanones, as they assist the increase of mitoxantrone (MX) accumulation in BCRP-overexpressing MCF-7 MX 100 breast caner cells (Zhang et al., 2005)... 

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