Disease relevance of NSC109351

• Microbial transformation of daunomycinone by Streptomyces aureofaciens B-96 [1].
• The cytotoxic effect of (7S)- and (7R)-O-epoxyalkyl derivatives of daunomycinone on leukemia P388 cells was followed in in vitro tests and their mutagenicity was determined by means of the bacterial SOS chromotest [2].

High impact information on NSC109351

• The daunomycin aglycone chromophore is oriented at right angles to the long dimension of the DNA base pairs and the cyclohexene ring rests in the minor groove [3].
• Daunomycin aglycone (10(-6) M), which lacks antitumor activity, had no significant effect on the Ca2+ -dependent action potential [4].
• The title compounds were prepared by Koenigs-Knorr condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]-alpha-D-glucopyranosyl bromide with daunomycinone or a side-chain protected adraimycinone, followed by selective hydrolysis of blocking groups [5].
• Semiquinone free radical formation by daunorubicin aglycone incorporated into the cellular membranes of intact Chinese hamster ovary cells [6].
• The results of a growth inhibition assay carried out on cells into which daunorubicin aglycone had been incorporated showed almost no effect on cell growth [6].

Chemical compound and disease context of NSC109351

• Baumycin-negative mutants of Streptomyces coeruleorubidus ME130-A4 do not convert daunomycinone to daunomycin and baumycins [7].
• The filtrate broth as well as mycelium of the new strain Streptomyces erythrochromogenes nov. sp. isolated from Saudi Arabian soil, produce the antitumor antibiotic daunomycin 1 and two anthracyclic derivatives: 7-deoxy 13-dihydrodaunomycinone 2 and 7-deoxy daunomycinone 4 [8].
• Aklanonic acid is an anthracyclinone-related pigment that was found to be an intermediate at an early stage of the biosynthesis of daunomycinone glycosides by Streptomyces griseus [9].

Biological context of NSC109351

• The cytotoxic assay show that seleno daunomycinone derivatives are much better inhibitory activity than thiodaunomycinone and the structure-activity relationship was discussed [10].
• Since microM concentrations of S12 and S13 are cytostatic and cytotoxic, but do not sufficiently inhibit RNA and protein syntheses to block their own ability to sustain the active process of apoptosis and DNA fragmentation, such 3'-halo daunomycinone glycosides might be valuable to develop new means of polychemotherapy [11].

Anatomical context of NSC109351

• This result indicates that in spite of significant daunorubicin aglycone-induced radical formation taking place directly in the cell membrane, little cell damage results [6].

Associations of NSC109351 with other chemical compounds

• A fraction of glycosides with a higher RF (0.4-0.7), isolated from strain 39-146, could be transformed to daunomycin by mild hydrolysis and to daunomycinone by total hydrolysis [12].

Gene context of NSC109351

• The antileukemic activities of the daunomycinone glycosides synthesized in our laboratories (compounds 4 and 7, code names S12 and S13, respectively) were characterized in L1210 cells in vitro [11].

References