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

D. E. Graves, C. Pattaroni, B. S. Krishnan, J. M. Ostrander, Laurence Hurley, T. R. Krugh

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Abstract

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 animal 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).

Original languageEnglish (US)
Pages (from-to)8202-8209
Number of pages8
JournalJournal of Biological Chemistry
Volume259
Issue number13
StatePublished - 1984
Externally publishedYes

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Anthramycin
DNA Adducts
Protons
Magnetic Resonance Spectroscopy
Carbon
Nuclear magnetic resonance
Oligonucleotides
DNA
Oligodeoxyribonucleotides
Guanine
Biochemistry
Covalent bonds
Nuclear magnetic resonance spectroscopy
Animals
anthramycin-DNA

ASJC Scopus subject areas

  • Biochemistry

Cite this

The reaction of anthramycin with DNA. Proton and carbon nuclear magnetic resonance studies on the structure of the anthramycin-DNA adduct. / Graves, D. E.; Pattaroni, C.; Krishnan, B. S.; Ostrander, J. M.; Hurley, Laurence; Krugh, T. R.

In: Journal of Biological Chemistry, Vol. 259, No. 13, 1984, p. 8202-8209.

Research output: Contribution to journalArticle

Graves, D. E. ; Pattaroni, C. ; Krishnan, B. S. ; Ostrander, J. M. ; Hurley, Laurence ; Krugh, T. R. / The reaction of anthramycin with DNA. Proton and carbon nuclear magnetic resonance studies on the structure of the anthramycin-DNA adduct. In: Journal of Biological Chemistry. 1984 ; Vol. 259, No. 13. pp. 8202-8209.
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