Synthesis, DNA binding, and cytotoxicity of 1,4-bis(2-amino-ethylamino)anthraquinone–amino acid conjugates

The metabolic profile of mitoxantrone and its relation with mitoxantrone-induced cardiotoxicity

“…2), including the naphtoquinoxaline metabolite (metabolite 5) and a novel metabolite that was never described before (an acetoxy ester derivative, metabolite 3) ( Table 1). The maintenance of the chromophore group suggests that all these metabolites possibly maintain the ability to intercalate into DNA base pairs since the tricyclic planar structure is essential for MTX activity (Hsin et al 2008).…”

β-casein–based nanovehicles for oral delivery of chemotherapeutic drugs: drug-protein interactions and mitoxantrone loading capacity

“…15 Calculated log of the octanol-water partition coefficient (log P) values reported recently were: 1.099 16 and 0.24. 17 Based on dynamic light scattering (DLS), zeta potential, absorbance spectra, and tryptophan (Trp) emission quenching measurements, we have recently shown 6 that MX is associated to β-CN and that optimally, particles of 100 to 300 nm on average were obtainable when MX was entrapped in a 1 mg/mL β-CN solution and a molar ratio of 4:1 MX/β-CN. Moreover, relatively stable colloidal nanoparticles were formed up to a molar ratio of 6:1.…”

Asymmetric Enzymatic Glycosylation of Mitoxantrone

“…Removal of one ‘arm’ was also found to be detrimental and, while a number of symmetrical di-substituted MXT conjugates have been generated (including amino acid, 9 galactose, 10 netropsin 11 and protein 12 ), the symmetry of MXT has proven to be a significant barrier to regioselective modification. 9–12,13 Herein we report that an engineered glycosyltransferase variant (OleD ASP) 14 surprisingly leads to the regio- and stereoselective modification of one ‘arm’ of MXT, providing a single unique MXT-glucoside that retains notable anticancer activity. This study reveals one of the first reported single-step asymmetric MXT modification strategies and highlights the synthesis of one of the only reported MXT mono-glycosides to date.…”