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Research ArticleArticle

DNA Binding Studies on Several New Anthracycline Antitumor Antibiotics II. The Importance of the Carbomethoxy-group at Position-10 of the Class II Anthracycline Molecule

VIRGIL H. DUVERNAY JR., JONATHAN A. PACHTER and STANLEY T. CROOKE
Molecular Pharmacology September 1979, 16 (2) 623-632;
VIRGIL H. DUVERNAY JR.
The Bristol-Baylor Laboratory, Department of Pharmacology, Baylor College of Medicine, Houston, Texas 77030
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JONATHAN A. PACHTER
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STANLEY T. CROOKE
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Abstract

The DNA binding characteristics of the new anthracycline antitumor antibiotics, marcellomycin and rudolfomycin, were compared with those of their respective 10-descarbomethoxy analogues. The fluorescence spectra were determined and the fluorescence quenching effects caused by interactions with the four natural DNAs—calf thymus DNA, salmon sperm DNA, Clostridium perfringens DNA and Micrococcus luteus DNA—were characterized. Binding parameters were determined by Scatchard analyses of results obtained by titrating anthracycline fluorescence with increasing concentrations of DNA. Removal of the carbomethoxy-group from position 10 of marcellomycin or rudolfomycin caused a significant reduction in DNA binding ability for all four DNAs studied. These results are correlated with a marked decrease in antitumor activity, and nucleolar RNA synthesis inhibitory activity, as previously reported, and thus confirm earlier studies indicating that one subcellular target of anthracycline antitumor action is nucleolar preribosomal RNA synthesis. Additionally, the correlation between DNA binding ability and antitumor activity provides further evidence of the mechanism of action of Class II anthracyclines.

ACKNOWLEDGMENTS The authors thank Dr. Archie Prestayko for valuable discussions regarding this and other work from our laboratory and Dr. Harris Busch for his continued guidance and support. We thank Dr. C. H. Huang for helpful discussions regarding the interpretation of results. We also thank Drs. T. H. Sawyer and J. E. Strong for reviewing the manuscript. We are indebted to Ms. Linda Whiteman and Ms. Sandra Muckelroy for typing and manuscript preparation.

  • Copyright © 1979 by Academic Press, Inc.

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Molecular Pharmacology
Vol. 16, Issue 2
1 Sep 1979
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Research ArticleArticle

DNA Binding Studies on Several New Anthracycline Antitumor Antibiotics II. The Importance of the Carbomethoxy-group at Position-10 of the Class II Anthracycline Molecule

VIRGIL H. DUVERNAY, JONATHAN A. PACHTER and STANLEY T. CROOKE
Molecular Pharmacology September 1, 1979, 16 (2) 623-632;

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Research ArticleArticle

DNA Binding Studies on Several New Anthracycline Antitumor Antibiotics II. The Importance of the Carbomethoxy-group at Position-10 of the Class II Anthracycline Molecule

VIRGIL H. DUVERNAY, JONATHAN A. PACHTER and STANLEY T. CROOKE
Molecular Pharmacology September 1, 1979, 16 (2) 623-632;
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