Disease relevance of Daunosamine

• Methyl daunosamine inhibited the replication of herpes simplex virus type 1 in a dose-dependent manner [1].
• Cloning and characterization of the Streptomyces peucetius dnrQS genes encoding a daunosamine biosynthesis enzyme and a glycosyl transferase involved in daunorubicin biosynthesis [2].
• The excess DNR toxicity seen for PKH67-labeled K562S appears to be drug related, since it is not seen with vincristine, and may be due to the daunosamine sugar moiety present in DNR [3].

High impact information on Daunosamine

• Role of daunosamine and hydroxyacetyl side chain in reaction with iron and lipid peroxidation by anthracyclines [4].
• The plasma concentration v time curves of (7d)-aglycones showed a second peak between two and 12 hours after injection, suggesting an enterohepatic circulation for metabolites lacking the daunosamine sugar moiety [5].
• Acetylation of the amine on the daunosamine moeity of adriamycin did not preclude the formation of a ferric complex but resulted in total loss of inhibitory activity [6].
• The growth of the host Vero cells was not affected by daunosamine levels that had significant antiviral activity (2.5 mM) but was inhibited by concentrations of 5 mM or greater [1].
• Methyl daunosamine appears to be unique among the sugars with antiviral activity because at antiviral concentrations it did not inhibit the glycosylation of macromolecules [1].

Biological context of Daunosamine

• This structure-activity relationship study showed that the substitution of the daunosamine for the disaccharide moiety dramatically reduced the cytotoxic potency of the drug in the 4-methoxy series (daunorubicin analogs) [7].
• Finally, from a comparison of pertinent site binding constants, approximate free energy contributions to sequence specific DNA interaction, due to C9-OH on the aglycone and -NH3+ on daunosamine, are estimated not to exceed 2 kcal/mol [8].
• Although these genes were believed to be necessary for the synthesis of the deoxyaminosugar, daunosamine, a constituent of daunorubicin, the dnrM gene contains a frameshift in the DNA sequence that causes the premature termination of translation [9].
• The obtained results indicated that introduction of the amidino group into the daunosamine moiety of anthracycline molecules appears to overcome the drug resistance of cancer cells [10].
• Cytotoxicity, cellular uptake and DNA damage by daunorubicin and its new analogues with modified daunosamine moiety [11].

Associations of Daunosamine with other chemical compounds

• The discrepancy between recovery of drug fluorescence and 14C was due to the production of nonfluorescent hippuric acid (benzoylglycine) and N-benzyl daunosamine as a consequence of hepatic and renal drug metabolism [12].
• Stereocontrolled routes to cis-hydroxyamino sugars, Part VII: Synthesis of daunosamine and ristosamine [13].
• Accordingly, only phenol hydroxyl ionization constants could be determined in these experiments, but a crude estimate of daunosamine pKa was obtained in a fluorometric titration [14].

Analytical, diagnostic and therapeutic context of Daunosamine

• In contrast with an early literature report [Sturgeon, R.J. & Schulman, S.G. J. Pharm. Sci. 66, 958-961; 1977] the perturbation from amino group ionization on daunosamine sugar was found to be negligible in our spectrophotometric titrations [14].

References