The reaction of anthramycin with DNA. Proton and carbon nuclear magnetic resonance studies on the structure of the anthramycin-DNA adduct

Nuclear magnetic resonance techniques are used to confirm the points of attachment of anthramycin to DNA. Using 13C NMR spectroscopy, the C-11 resonance of anthramycin is shown to undergo a 16-ppm upfield shift upon formation of a covalent bond with DNA, indicative of an aminal linkage at that posit...

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Bibliographic Details
Published in:The Journal of biological chemistry 1984-07, Vol.259 (13), p.8202-8209
Main Authors: Graves, D E, Pattaroni, C, Krishnan, B S, Ostrander, J M, Hurley, L H, Krugh, T R
Format: Article
Language:English
Subjects:
Animals
Anthramycin
Benzodiazepinones
Cattle
Chemical Phenomena
Chemistry
DNA
Magnetic Resonance Spectroscopy - methods
Nucleic Acid Conformation
Oligodeoxyribonucleotides
Oligonucleotides
Spectrophotometry, Ultraviolet
Thermodynamics
Thymus Gland
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Summary:Nuclear magnetic resonance techniques are used to confirm the points of attachment of anthramycin to DNA. Using 13C NMR spectroscopy, the C-11 resonance of anthramycin is shown to undergo a 16-ppm upfield shift upon formation of a covalent bond with DNA, indicative of an aminal linkage at that position. The site of attachment on the DNA is determined using the self-complementary oligodeoxyribonucleotide d-(ApTpGpCpApT) as a DNA model. Proton NMR, both in H2O and D2O solutions, provides a direct characterization of the anthramycin-oligonucleotide adduct. Upon covalent attachment to the duplex, a loss in the helical symmetry is observed, resulting in a doubling of several of the oligonucleotide resonances. Examination of the data confirms that the point of attachment of the anthramycin to the d-(ApTpGpCpApT) is at the guanine-NH2-position, consistent with the model proposed by Hurley and Petrusek (Hurley, L. H., and Petrusek, R. L. (1979) Nature (Lond.) 282, 529-531) and Petrusek et al. (Petrusek, R. L., Anderson, G. L., Garner, T. F., Fannin, Q. L., Kaplan, D. J., Zimmer, S. G., and Hurley, L. H. (1981) Biochemistry 20, 1111-1119).
ISSN:0021-9258
1083-351X
DOI:10.1016/S0021-9258(17)39714-4