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Structural Constraints in the Binding of Drugs to DNA

  • Conference paper
Drug Receptor Interactions in Antimicrobial Chemotherapy

Part of the book series: Topics in Infectious Diseases ((TIDIS,volume 1))

Abstract

Drugs which interact with DNA so as to impair its function as a template for nucleic acid synthesis are used in the chemotherapy of so wide a range of infectious and malignant diseases that it is hard to over-estimate their importance in present-day medical practice. In the treatment of such conditions as malaria, trypanosomiasis, schistosomiasis and various forms of cancer they occupy a central place, in some instances providing virtually the only means of effective chemotherapy. Even among the great number of compounds which are currently under active investigation as potentially useful antiviral agents there are many whose action derives from their ability to react with nucleic acids. Small wonder, then, that this topic has been the subject of numerous reviews in recent years (see, for example, Newton, 1970; Goldberg & Friedman, 1971; Waring, 1972; Corcoran & Hahn, 1974).

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References

  • BAMFORD, D.G., D.F. BIGGS, M. DAVIS & E.W. PARNELL: Neuromuscular blocking properties of stereoisomeric androstane-3,17-bisquaternary ammonium salts. Brit. J. Pharmacol. Chemother. 30, 194–202 (1967)

    CAS  Google Scholar 

  • BAUER, W. & J. VINOGRAD: The interaction of closed circular DNA with intercalative dyes. I. The superhelix density of SV40 DNA in the presence and absence of dye. J. Mol. Biol. 33, 141–171 (1968)

    Article  PubMed  CAS  Google Scholar 

  • BROOKES, P.: Reaction of alkylating agents with nucleic acids. In ‘Chemotherapy of Cancer’ (ed. P.A. PLATTNER), Elsevier, Amsterdam, pp 32–43 (1964)

    Google Scholar 

  • CHANDRA, P., A. DI MARCO, F. ZUNINO, A.M. CASAZZA, D. GERICKE, F. GIULIANI, C. SORANZO, R. THORBECK, A. GÓTZ, F. ARCAMONE & M. GHIONE: Influence of some antitumor antibiotics on viral neoplasia. Naturwissenschaften 59, 448–455 (1972)

    Article  PubMed  CAS  Google Scholar 

  • COHEN, P., R.C. CHIN & C. KIDSON: Interactions of hormonal steroids with nucleic acids. II. Structural and thermodynamic aspects of binding. Biochemistry 8, 3603–3609 (1969)

    Article  PubMed  CAS  Google Scholar 

  • COHEN, S.N. & K.L. YIELDING: Spectrophotometric studies of the interaction of chloroquine with DNA. J. Biol. Chem. 240, 3123–3131 (1965)

    PubMed  CAS  Google Scholar 

  • CORCORAN, J.W. & F.E. HAHN (eds.): Antibiotics. III. Mechanism of Action of Antimicrobial and Antitumor Agents. Springer-Verlag, Berlin-Heidelberg-New York (1974).

    Google Scholar 

  • CRAWFORD, L.V. & M.J. WARING: Supercoiling of polyoma virus DNA measured by its interaction with ethidium bromide. J. Mol. Biol. 25, 23–30 (1967)

    Article  PubMed  CAS  Google Scholar 

  • DAVIS, M., E.W. PARNELL & J. ROSENBAUM: Steroid amines. Part IV. 3,17-Diaminoandrostane derivatives. J. Chem. Soc. (C) 1967, 1045–1052

    Google Scholar 

  • FULLER, W. & M.J. WARING: A molecular model for the interaction of ethidium bromide with DNA. Ber. Bunsenges. Physik. Chem. 68, 805–808 (1964)

    CAS  Google Scholar 

  • GOLDBERG, I.H. & P.A. FRIEDMAN: Antibiotics and ‘nucleic acids. Ann. Rev. Biochem. 40, 775–810 (1971)

    Article  PubMed  CAS  Google Scholar 

  • HAHN, F.E. (ed.): Antimalarials and nucleic acids. Progress in Molecular and Sub-Cellular Biology 2, 69–133 (1971)

    Google Scholar 

  • HIRSCHBERG, E.: Thiaxanthenones: Miracil D and hycanthone. In ‘Antibiotics. III. Mechanism of Action of Antimicrobial and Antitumor Agents’ (eds. J.W. CORCORAN & F.E. HAHN ), Springer-Verlag, Berlin-Heidelberg-New York (1974).

    Google Scholar 

  • LERMAN, L.S.: Structural considerations in the interaction of DNA and acridines. J. Mol. Biol. 3, 18–30 (1961)

    Article  PubMed  CAS  Google Scholar 

  • LERMAN, L.S.: Acridine mutagens and DNA structure. J. Cell. and Comp. Physiol. 64, Suppl. 1, 1–18 (1964)

    Article  CAS  Google Scholar 

  • MOLINARI, G. & G.F. LATA: Interaction of steroids with some pyrimidine and purine derivatives. Arch. Biochem. Biophys. 96, 486–490 (1962)

    Article  PubMed  CAS  Google Scholar 

  • MÃœLLER, W., D.M. CROTHERS & M.J. WARING: A non-intercalating proflavine derivative. Eur. J. Biochem. 39, 223–234 (1973)

    Article  PubMed  Google Scholar 

  • MUNCK, A., J.F. SCOTT & L.L. ENGEL: The interaction of steroid hormones and coenzyme components. Biochim. Biophys. Acta 26, 397–407 (1957)

    Article  PubMed  CAS  Google Scholar 

  • NEWTON, B.A.: Chemotherapeutic compounds affecting DNA structure and function. Adv. Pharmacol. Chemother. 8, 149–184 (1970)

    Article  PubMed  CAS  Google Scholar 

  • NEWTON, B.A.: Berenil. In ‘Antibiotics. III. Mechanism of Action of Antimicrobial and Antitumor Agents’ (eds. J.W. CORCORAN & F.E. HAHN ), Springer-Verlag, Berlin-H idelberg-New York (1974).

    Google Scholar 

  • PAOLETTI, J. & J.B. LE PECQ: The change of the torsion of the DNA helix caused by intercalation. I. A discussion of the two different possibilities, winding or unwinding. Biochimie 53, 969–972 (1971)

    Article  PubMed  CAS  Google Scholar 

  • PIGRAM, W.J., W. FULLER & M.E. DAVIES: Unwinding the DNA helix by intercalation. J. Mol. Biol. 80, 361–365 (1973)

    Article  PubMed  CAS  Google Scholar 

  • PIGRAM, W.J., W. FULLER & L.D. HAMILTON: Stereochemistry of intercalation: interaction of daunomycin with DNA. Nature New Biol. 235, 17–19 (1972)

    Article  PubMed  CAS  Google Scholar 

  • REVET, B.M.J., M. SCHMIR & J. VINOGRAD: Direct determination of the superhelix density of closed circular DNA by viscometric titration. Nature New Biol. 229, 10–13 (1971)

    PubMed  CAS  Google Scholar 

  • SEAMAN, A. & M. WOODBINE: The antibacterial activity of phenanthridine compounds. Brit. J. Pharmacol. 9, 265–270 (1954)

    PubMed  CAS  Google Scholar 

  • SOBELL, H.M., S.C. JAIN, T.D. SAKORE & C.E. NORDMAN: Stereochemistry of actinomycinDNA binding. Nature New Biol. 231, 200–205 (1971)

    PubMed  CAS  Google Scholar 

  • SZYBALSKI, W. & V.N. IYER: The mitomycins and porfiromycins. In ‘Antibiotics. I. Mechanism of Action’ (eds. D. GOTTLIEB & P.D. SHAW), Springer-Verlag, BerlinHeidelberg-New York, pp 211–245 (1967).

    Google Scholar 

  • WAKELIN, L.P.G. & M.J. WARING: The unwinding of circular DNA by phenanthridinium drugs: Structure-activity relations for the intercalation reaction. Mol. Pharmacol. 10, 544–561 (1974)

    PubMed  CAS  Google Scholar 

  • WARING, M.J.: Complex formation between ethidium bromide and nucleic acids. J. Mol. Biol. 13, 269–282 (1965)

    Article  PubMed  CAS  Google Scholar 

  • WARING, M.J.: Variation of the supercoils in closed circular DNA by binding of antibiotics and drugs: Evidence for molecular models involving intercalation. J. Mol. Biol. 54, 247–279 (1970)

    Article  PubMed  CAS  Google Scholar 

  • WARING, M.J.: Inhibitors of nucleic acid synthesis. In ‘The Molecular Basis of Antibiotic Action’ (E.F. GALE, E. CUNDLIFFE, P.E. REYNOLDS, M.H. RICHMOND & M.J. WARING), Wiley, London, pp 173–277 (1972)

    Google Scholar 

  • WARING, M.J.: Studies with closed circular duplex DNA as a probe for conformational alterations. Studia Biophysica (Berlin) 40, 151–157 (1973a)

    CAS  Google Scholar 

  • WARING, M.J.: Interaction of indazole analogs of lucanthone and hycanthone with closed circular duplex DNA. J. Pharm. Exp. Ther. 186, 385–389 (1973b)

    CAS  Google Scholar 

  • WARING, M.J.: Ethidium and propidium. In ‘Antibiotics. III. Mechanism of Action of Antimicrobial and Antitumor Agents’ (eds. J.W. CORCORAN & F.E. HAHN ), Springer-Verlag, Berlin-Heidelberg-New York (1974a).

    Google Scholar 

  • WARING, M.J.: Stacking interactions. Chemistry and Industry, in press (1974b)

    Google Scholar 

  • WARING, M.J. & J.W. CHISHOLM: Uncoiling of bacteriophage PM2 DNA by binding of steroidal diamines. Biochim. Biophys. Acta 262, 18–23 (1972)

    PubMed  CAS  Google Scholar 

  • WEINSTEIN, I.B. & E. HIRSCHBERG: Mode of action of Miracil D. Progress in Molecular and Subcellular Biology 2, 232–246 (1971)

    Article  CAS  Google Scholar 

  • WELLS, R.D. & J.E. LARSON: Studies on the binding of actinomycin D to DNA and DNA model polymers. J. Mol. Biol. 49, 319–342 (1970)

    Article  PubMed  CAS  Google Scholar 

  • WOOLFE, G.: Trypanocidal action of phenanthridine compounds: Effect of changing the quaternary groups of known trypanocides. Brit. J. Pharmacol. 11, 330–333 (1956).

    PubMed  CAS  Google Scholar 

  • Trypanocidal action of phenanthridine compounds: Further 2,7-diamino phenanthridinium compounds. Brit. J. Pharmacol. 11, 334–338 (1956)

    Google Scholar 

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Authors
  1. Michael Waring
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Editor information

Editors and Affiliations

  1. Sandoz Forschungsinstitut Gesellschaft m. b. H., Vienna, Austria

    Jürgen Drews

  2. Walter Reed Army Medical Center, Washington, D.C., USA

    E. Hahn Ph. D.

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Waring, M. (1975). Structural Constraints in the Binding of Drugs to DNA. In: Drews, J., Hahn, E. (eds) Drug Receptor Interactions in Antimicrobial Chemotherapy. Topics in Infectious Diseases, vol 1. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8405-9_6

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  • DOI: https://doi.org/10.1007/978-3-7091-8405-9_6

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-8407-3

  • Online ISBN: 978-3-7091-8405-9

  • eBook Packages: Springer Book Archive

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