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Chemical Compound Review

Daunosamine     (3S,4S,5S)-3-amino-4,5- dihydroxy-hexanal

Synonyms: AG-K-71346, CHEBI:32539, CTK4F8121, AR-1F1709, AR-1F1710, ...
 
 
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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

 

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

  1. Inhibition of herpes simplex virus replication by methyl daunosamine. Spivack, J.G., Prusoff, W.H., Tritton, T.R. Antimicrob. Agents Chemother. (1982) [Pubmed]
  2. Cloning and characterization of the Streptomyces peucetius dnrQS genes encoding a daunosamine biosynthesis enzyme and a glycosyl transferase involved in daunorubicin biosynthesis. Otten, S.L., Liu, X., Ferguson, J., Hutchinson, C.R. J. Bacteriol. (1995) [Pubmed]
  3. Optimization of PKH67 labeling conditions for proliferation monitoring in daunorubicin-treated leukemic cells. Barbier, M., Morjani, H., Muirhead, K.A., Ronot, X., Boutonnat, J. Oncol. Rep. (2005) [Pubmed]
  4. Role of daunosamine and hydroxyacetyl side chain in reaction with iron and lipid peroxidation by anthracyclines. Gianni, L., Viganò, L., Lanzi, C., Niggeler, M., Malatesta, V. J. Natl. Cancer Inst. (1988) [Pubmed]
  5. Pharmacokinetics and metabolism of epidoxorubicin and doxorubicin in humans. Mross, K., Maessen, P., van der Vijgh, W.J., Gall, H., Boven, E., Pinedo, H.M. J. Clin. Oncol. (1988) [Pubmed]
  6. The adriamycin-iron(III) complex is a potent inhibitor of protein kinase C. Hannun, Y.A., Foglesong, R.J., Bell, R.M. J. Biol. Chem. (1989) [Pubmed]
  7. Configurational requirements of the sugar moiety for the pharmacological activity of anthracycline disaccharides. Arcamone, F., Animati, F., Bigioni, M., Capranico, G., Caserini, C., Cipollone, A., De Cesare, M., Ettorre, A., Guano, F., Manzini, S., Monteagudo, E., Pratesi, G., Salvatore, C., Supino, R., Zunino, F. Biochem. Pharmacol. (1999) [Pubmed]
  8. Association of anthracyclines and synthetic hexanucleotides. Structural factors influencing sequence specificity. Rizzo, V., Battistini, C., Vigevani, A., Sacchi, N., Razzano, G., Arcamone, F., Garbesi, A., Colonna, F.P., Capobianco, M., Tondelli, L. J. Mol. Recognit. (1989) [Pubmed]
  9. The dnrM gene in Streptomyces peucetius contains a naturally occurring frameshift mutation that is suppressed by another locus outside of the daunorubicin-production gene cluster. Gallo, M.A., Ward, J., Hutchinson, C.R. Microbiology (Reading, Engl.) (1996) [Pubmed]
  10. Effect of structural modifications of anthracyclines on the ability to overcome drug resistance of cancer cells. Wasowska, M., Wietrzyk, J., Opolski, A., Oszczapowicz, J., Oszczapowicz, I. Anticancer Res. (2006) [Pubmed]
  11. Cytotoxicity, cellular uptake and DNA damage by daunorubicin and its new analogues with modified daunosamine moiety. Ciesielska, E., Studzian, K., Wasowska, M., Oszczapowicz, I., Szmigiero, L. Cell Biol. Toxicol. (2005) [Pubmed]
  12. Pharmacology of N-benzyladriamycin-14-valerate in the rat. Sweatman, T.W., Seshadri, R., Israel, M. Cancer Chemother. Pharmacol. (1999) [Pubmed]
  13. Stereocontrolled routes to cis-hydroxyamino sugars, Part VII: Synthesis of daunosamine and ristosamine. Pauls, H.W., Fraser-Reid, B. Carbohydr. Res. (1986) [Pubmed]
  14. Determination of phenolic ionization constants of anthracyclines with modified substitution pattern of anthraquinone chromophore. Razzano, G., Rizzo, V., Vigevani, A. Farmaco (1990) [Pubmed]
 
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