Reference

Superoxide radical reactions with anthracycline antibiotics

Superoxide radical reactions with anthracycline antibiotics. Nakazawa, Hiroyuki; Andrews, Paul A.; Callery, Patrick S.; Bachur, Nicholas R. (Lab. Med. Chem. Pharmacol., NCI, Bethesda, MD 20205, USA). Biochem. Pharmacol., 34(4), 481-90 (English) 1985. CODEN: BCPCA6. ISSN: 0006-2952. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology) The reaction of superoxide with daunorubicin (I) [20830-81-3] or its aglycons in the aprotic solvents di-Me sulfoxide and DMF was studied. This interaction generated the blue anthracycline phenolate anion as monitored by UV-visilble spectrometry and mol. O as detd. by a modified Clark-type O electrode. The visible spectrum of the phenolate anion (lmax604, 652 nm) was subject to considerable shifts dependent on the size of the cation present. The phenolate anion could be further oxidized by mol. O to generate the C-6, C-11 (B-ring) semiquinone as detected by a weak ESR spectrometry signal. These results raise the possibility that similar reactions of superoxide with anthracyclines in vivo may play a role in the antitumor activity and/or the etiol. of the toxic side effects of this class of drugs.

Mechanism of daunorubicin interaction with DNA

Mechanism of daunorubicin interaction with DNA. Brikenshtein, V. Kh.; Baranov, E. P. (Res. Inst. Biol. Test. Chem. Compd., Kupavna, USSR). Antibiot. Med. Biotekhnol., 30(2), 90-6 (Russian) 1985. CODEN: AMBIEH. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology) The kinetics of binding of daunorubicin [20830-81-3] and its aglycon daunomycinone [21794-55-8] with DNA were studied. Formation of the complex of daunorubicin with DNA involved 2 stages. At the first stage the antibiotic aglycon intercalated between the DNA base-pairs, and at the second stage the resulting complex was addnl. stabilized due to interaction of the pos. charged amino sugar residue of the antibiotic with the neg. charged DNA phosphates. The formation of the complex of daunomycinone with DNA involved one stage. Estn. of the consts. characterizing the above reactions is presented.