Interaction of the C14-OH group of adriamycin with DNA phosphate as spectroscopically evidenced.
Monitoring the band of the antisymmetric stretching vibration of the backbone PO-2 group in DNA-anthracycline complexes demonstrates an extraordinary wavenumber shift for the adriamycin complex compared to that of daunomycin. The structures of both anthracyclines, however, are very closely related and differ only by a surplus hydroxyl group of adriamycin in the C14 position. The wavenumber shift observed for the DNA-adriamycin complex is unequivocally attributed to an additional linkage of the C14-OH of adriamycin to the phosphate group of DNA. Thus, several of the hypothetical structural models for the DNA-adriamycin complex for which a hydrogen bond between the C14 hydroxyl of the drug and DNA phosphate was postulated (S. Neidle, Cancer Treatment Rep. 61, 928 (1977); G. J. Quigley et. al., Proc. Natl. Acad. Sci. USA 77, 7204 (1980)) get the first clear-cut experimental evidence.
Pohle
W
W
Academy of Sciences of the GDR, Department of Biophysical Chemistry, Jena.
Flemming
J
J
D000818:Animals; D004247:DNA; D004317:Doxorubicin; D006860:Hydrogen Bonding; D007700:Kinetics; D008297:Male; D010710:Phosphates; D012474:Salmon; D013055:Spectrophotometry, Infrared; D013094:Spermatozoa
D010710:Phosphates; D004317:Doxorubicin; D004247:DNA