Oligonucleotide and polynucleotide — drug complexes in solution as investigated by NMR

Krugh, Thomas R.

doi:10.1007/978-1-349-04691-1_9

Oligonucleotide and polynucleotide — drug complexes in solution as investigated by NMR

Thomas R. Krugh

Chapter

112 Accesses
6 Citations

Part of the book series: Topics in Molecular and Structural Biology ((TMSB))

Abstract

This chapter discusses the solution complexes of drugs with oligo and polynucleotides. Although concentrating on magnetic resonance results, it also alludes to selected experiments using fluorescence, circular dichroism, and visible absorption spectroscopies, with a view to illustrating the advantages (and frequently the necessity) of combining the optical spectroscopic data with magnetic resonance data. In brief, not only does optical spectroscopy provide an independent means of obtaining kinetic, thermodynamic and equilibrium data, but it also gives an important correlation between the results for the binding of the drugs to oligonucleotides (that is, model systems) and polynucleotides (the systems of biological interest). The drugs that will be used as primary examples are actinomycin D, ethidium bromide, daunorubicin (or adriamycin) and 9-aminoacridine; the chemical structures of these molecules are shown in figure 9.1. Actinomycin D has been extensively studied over the last 20 years and, as shown later in this chapter, the interaction of actinomycin D with deoxyoligonucleotides is continuing to provide valuable information towards the goal of obtaining a molecular and thermodynamic basis for the binding of the drug to DNA. There are a number of reviews on the history, synthesis, binding studies and description of models for the binding of the actinomycins to DNA (for example, Hollstein, 1974; Lackner, 1975; Meienhofer and Atherton, 1977; Sobell, 1973; Wells, 1971; and the many references therein).

This is a preview of subscription content, log in via an institution.

Chapter: USD 29.95; Price excludes VAT (USA)

eBook: USD 84.99; Price excludes VAT (USA)

Softcover Book: USD 109.99; Price excludes VAT (USA)

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

References

Altona, C. and Sundaralingam, M. (1973). J. Am. chem. Soc., 95, 2333.
Article CAS Google Scholar
Anderson, J. A., Kuntz, G. P. P., Evans, H. H. and Swift, T. J. (1971). Biochemistry, 10, 4368.
Article CAS Google Scholar
Arcamone, F., Cassinelli, G., Franceschi, G., Penco, S., Pol, C., Redaelli, S. and Selva, A. (1972). In International Symposium on Adriamycin (ed. S. K. Carter et al), Springer-Verlag, New York, p. 9.
Chapter Google Scholar
Arison, B. H. and Hoogsteen, K. (1970). Biochemistry, 9, 3976.
Article CAS Google Scholar
Barbet, J., Roques, B. P., Combrisson, S. and Le Pecq, J.-B. (1976). Biochemistry, 15, 2542.
Article Google Scholar
Barbet, J., Roques, B. P. and Le Pecq, J.-B. (1975). C.r. hebd. Séanc. Acad. Sci., Paris, 281, 851.
CAS Google Scholar
Berman, H. M., Neidle, S. and Stodola, R. K. (1978). Proc. natn. Acad. Sci. U.S.A., 75, 828.
Article CAS Google Scholar
Borer, P. N., Kan, L. S. and Ts’o, P. O. P. (1975). Biochemistry, 14, 4847.
Article CAS Google Scholar
Canellakis, E. S., Shaw, Y. H., Hanners, W. E. and Schwartz, R. A. (1976). Biochim. biophys. Acta, 418, 277.
Article CAS Google Scholar
Capelle, N., Barbet, J., Dessen, P., Blanquet, S., Roques, B. P. and Le Pecq, J.-B. (1979). Biochemistry, 18, 3354.
Article CAS Google Scholar
Chan, S. I., Bangerter, B. W. and Peter, H. H. (1966). Proc. natn. Acad. Sci. U.S.A., 55, 720.
Article CAS Google Scholar
Chan, S. I. and Kreishman, G. P. (1970). J. Am. chem. Soc., 92, 1102.
Article CAS Google Scholar
Chiao, Y.-C. C. and Krugh, T. R. (1977). Biochemistry, 16, 747.
Article CAS Google Scholar
Chien, M., Grollman, A. P. and Horwitz, S. B. (1977). Biochemistry, 16, 3641.
Article CAS Google Scholar
Cohn, M. and Hughes, T. R. Jr. (1962). J. biol. Chem., 237, 176.
CAS Google Scholar
Davidson, M. W., Griggs, B. G., Lopp, I. G. and Wilson, W. D. (1977). Biochem. biophys. Acta., 479, 378.
CAS Google Scholar
Dervan, P. B. and Becker, M. M. (1978). J. Am. chem. Soc., 100, 1968.
Article CAS Google Scholar
Dimicoli, J.-L. and Helene, C. (1974). Biochemistry, 13, 714.
Article CAS Google Scholar
Dwek, R. A. (1973). In Nuclear Resonance in Biochemistry, Oxford University Press, London, pp. 48, 213.
Google Scholar
Dugas, H. (1977). Acct. Chem. Res., 10, 47.
Article CAS Google Scholar
Emsley, J. W., Feeny, J. and Sutcliffe, L. H. (1965). High Resolution Nuclear Magnetic Resonance Spectroscopy, Pergamon Press, New York.
Google Scholar
Ezra, F. S., Lee, C.-H., Kondo, N. S., Danyluk, S. S. and Sarma, R. H. (1977). Biochemistry, 16, 1977.
Article CAS Google Scholar
Gabbay, E. J., Adawadkar, P. D., Kapicak, L., Pearce, S. and Wilson, W. D. (1976). Biochemistry, 15, 152.
Article CAS Google Scholar
Gabbay, E. J., Scofield, R. E. and Baxter, C. S. (1973). J. Am. chem. Soc., 95, 7850.
Article CAS Google Scholar
Giessner-Prettre, C., Pullman, B., Borer, P. N., Kan, L.-S. and Ts’o, P. O. P. (1976). Biopolymers, 15, 2277.
Article CAS Google Scholar
Gorenstein, D. G. (1975). J. Am. chem. Soc., 97, 898.
Article CAS Google Scholar
Gorenstein, D. G., Findlay, J. B., Momii, R. K., Luxon, B. A. and Kar, D. (1976). Biochemistry, 15, 3796.
Article CAS Google Scholar
Gorenstein, D. G. and Kar, D. (1975). Biochem. biophys. Res. Commun., 65, 1073.
Article CAS Google Scholar
Gorenstein, D. G. and Luxon, B. A. (1979). Biochemistry, 18, 3796.
Article CAS Google Scholar
Heller, M. J., Tu, A. T. and Maciel, G. E. (1974). Biochemistry, 13, 1623.
Article CAS Google Scholar
Henry, D. W. (1976). In Cancer Chemotherapy (ed. A. C. Sârtorelli), vol. 15, American Chemical Society, Washington.
Chapter Google Scholar
Hong, S.-J. and Piette, L. H. (1976). Cancer Res., 36, 1159.
CAS Google Scholar
Hollstein, U. (1974). Chem. Rev., 74, 625.
Article CAS Google Scholar
Jain, S. C., Tsai, C.-C. and Sobell, H. M. (1977). J. molec. Biol., 114, 317.
Article CAS Google Scholar
James, T. L. (1975). Nuclear Magnetic Resonance in Biochemistry: Principles and Applications, Academic Press, New York.
Google Scholar
Kallenbach, N. R. and Berman, H. M. (1977). Q. Rev. Biophys., 10, 137.
Article CAS Google Scholar
Kearns, D. R. (1977). Ann. Rev. Biophys. Bioeng., 6, 477.
Article CAS Google Scholar
Kondo, N. S. and Danyluk, S. S. (1972). J. Am. chem. Soc., 94, 5121.
Article CAS Google Scholar
Kreishman, G. P., Chan, S. I. and Bauer, W. (1971). J. molec. Biol., 61, 45.
Article CAS Google Scholar
Krugh, T. R. (1972). Proc. natn. Acad. Sci. U.S.A., 69, 1911.
Article CAS Google Scholar
Krugh, T. R. (1974). In Molecular and Quantum Pharmacology (eds. E. D. Bergman and B. Pullman), Reidel, Dordrecht, Holland, p. 465.
Chapter Google Scholar
Krugh, T. R. (1976). In Spin Labeling: Theory and Applications (ed. L. J. Berlinger), Academic Press, New York, p. 339.
Chapter Google Scholar
Krugh, T. R., Hook III, J. W., Lin, S. and Chen, F.-M. (1979). In Stereodvnamics of Molecular Systems (ed. R. H. Sarma), Pergamon Press, New York, p. 423.
Chapter Google Scholar
Krugh, T. R., Mooberry, E. S. and Chiao, Y.-C. C. (1977). Biochemistry, 16, 740.
Article CAS Google Scholar
Krugh, T. R. and Neely, J. W. (1973a). Biochemistry, 12, 1775.
Article CAS Google Scholar
Krugh, T. R. and Neely, J. W. (1973b). Biochemistry, 12, 4418.
Article CAS Google Scholar
Krugh, T. R. and Nuss, M. E. (1979). In Biological Applications of Magnetic Resonance (ed. R. G. Shulman) Academic Press, New York, p. 113.
Google Scholar
Krugh, T. R. and Reinhardt, C. G. (1975). J. molec. Biol., 97, 133.
Article CAS Google Scholar
Krugh, T. R. and Schafer, W. E. (1975). J. Magn. Reson., 19, 99.
CAS Google Scholar
Krugh, T. R., Wittlin, F. N. and Cramer, S. P. (1975). Biopolymers, 14, 197.
Article CAS Google Scholar
Kuhlman, K. F., Charbeneau, N. J. and Mosher, C. W. (1978). Nuel. Acids Res., 5, 2629.
Article Google Scholar
Lackner, H. (1975). Angew. Chem. Intern. Ed., 14, 375.
Article CAS Google Scholar
Lee, C.-H. and Sarma, R. H. (1976a). Biochemistry, 15, 697.
Article CAS Google Scholar
Lee, C.-H. and Sarma, R. H. (1976b). J. Am. chem. Soc., 98, 3541.
Article CAS Google Scholar
Lee, C.-H. and Tinoco, I., Jr. (1978). Nature, Lond., 274, 609.
Google Scholar
Le Pecq, J.-B. (1971). In Methods of Biochemical Analysis (ed. D. Glick), vol. 20, Wiley, New York, p. 41.
Chapter Google Scholar
Le Pecq, J.-B., Yot, P. and Paoletti, C. (1964). C. r. hebd. Séanc. Acad. Sci., Paris, 259, 1786.
Google Scholar
Levy, G. C. and Nelson, G. L. (1972). Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, Wiley-Interscience, New York.
Google Scholar
Mariam, Y. H. and Wilson, W. D. (1979). Biochim. Biophys. Res. Commun., 88, 861.
Article CAS Google Scholar
Meienhofer, J. and Atherton, E. (1977). In Structure-Activity Relationships Among the Semisynthetic Antibiotics (ed. D. Perlman) Academic Press, New York, p. 427.
Google Scholar
Mildvan, A. S. and Cohn, M. (1970). Adv. Enzymol., 33, 1.
CAS Google Scholar
Müller, W. and Crothers, D. M. (1968). J. molec. Biol., 35, 251.
Article Google Scholar
Patel, D. J. (1974a). Biochemistry, 13, 2388.
Article CAS Google Scholar
Patel, D. J. (1974b). Biochemistry, 13, 2396.
Article CAS Google Scholar
Patel, D. J. (1976a). Biopolymers, 13, 533.
Article Google Scholar
Patel, D. J. (1976b). Biochim. biophys. Acta, 442, 98.
Article CAS Google Scholar
Patel, D. J. (1977a). Biopolymers, 16, 1635.
Article CAS Google Scholar
Patel, D. J. (1977b). Biopolymers, 16, 2739.
Article CAS Google Scholar
Patel, D. J. (1979). Acct. Chem. Res., 12, 118.
Article CAS Google Scholar
Patel, D. J. and Canuel, L. L. (1976). Proc. natn. Acad. Sci. U.S.A., 73, 3343.
Article CAS Google Scholar
Patel, D. J. and Canuel, L. L. (1977a). Biopolymers, 16, 857.
Article CAS Google Scholar
Patel, D. J. and Canuel, L. L. (1977b). Proc. natn. Acad. Sci. U.S.A., 74, 2624.
Article CAS Google Scholar
Patel, D. J. and Canuel, L. L. (1977c). Proc. natn. Acad. Sci. U.S.A. 74 5207.
Google Scholar
Patel, D. J. and Shen, C. (1978). Proc. natn. Acad. Sci. U.S.A., 75, 2553.
Article CAS Google Scholar
Piette, L. H. (1974). Fed. Proc., 33, 1371.
Google Scholar
Reed, G. H., Leigh, J. S. and Pearson, J. E. (1971). J. Chem. Phys., 55, 3311.
Article CAS Google Scholar
Reinhardt, C. G. and Krugh, T. R. (1977). Biochemistry, 16, 2890.
Article CAS Google Scholar
Reinhardt, C. G. and Krugh, T. R. (1978). Biochemistry, 17, 4845.
Article CAS Google Scholar
Reuben, J., Adawadkar, P. and Gabbay, E. J. (1976). Biophys. Struct. Mech., 2, 13.
Article CAS Google Scholar
Reuben, J., Baker, B. M. and Kallenbach, N. R. (1978). Biochemistry, 17, 2915.
Article CAS Google Scholar
Reuben, J. and Gabbay, E. J. (1975). Biochemist,y, 14, 1230.
Article CAS Google Scholar
Sakore, T. D., Jain, S. C., Tsai, C.-C. and Sobell, H. M. (1977). Proc. natn. Acad. Sci. U.S.A., 74, 188.
Article CAS Google Scholar
Salemink, P. J. M., Swarthof, T. and Hilbers, C. W. (1979). Biochemistry, 18, 3477.
Article CAS Google Scholar
Shulman, R. G. and Sternlicht, H. (1965). J. molec. Biol., 13, 952.
Article CAS Google Scholar
Shulman, R. G., Sternlicht, H. and Wyluda, B. J. (1965). J. Chem. Phys., 43, 3116.
Article CAS Google Scholar
Sinha, B., Cysyk, R. L., Millar, D. B. and Chignell, C. F. (1976). J. Med. Chem., 19, 994.
Article CAS Google Scholar
Sobell, H. M. (1973). Prog. Nucl. Acid Res. Mol. Biol., 13, 153.
Article CAS Google Scholar
Sobell, H. M. and Jain, S. C. (1972). J. molec. Biol., 68, 21.
Article CAS Google Scholar
Sobell, H. M., Jain, S. C., Sakore, T. D. and Nordman, C. E. (1971). Nature, Lond., 231, 200.
CAS Google Scholar
Sobell, H. M., Jain, S. C., Sakore, T. D., Reddy, B. S., Bhandary, K. K. and Seshadri (1980). In Proceedings International Symposium on Biomolecular Structure, Function and Evolution (ed. R. Srinivasan), Pergamon Press, New York.
Google Scholar
Sobell, H. M., Tsai, C.-C., Jain, S. C. and Gilbert, S. G. (1977). J. molec. Biol., 114, 333.
Article CAS Google Scholar
Stothers, J. B. (1972). Carbon-13 NMR Spectroscopy, Academic Press, New York.
Google Scholar
Swift, T. J. (1973). In NMR of Paramagnetic Molecules (eds. G. N. LaMar, W. Dew Horrocks, Jr. and R. H. Holm), Academic Press, New York, p. 53.
Chapter Google Scholar
Tsai, C.-C., Jain, S. C. and Sobell, H. M. (1977). J. molec. Biol., 114, 301.
Article CAS Google Scholar
Ts’o, P. O. P. (1974a). Basic Principles in Nucleic Acid Chemistry, vol. I, Academic Press, New York.
Google Scholar
Ts’o, P. O. P. (1974b). Basic Principles in Nucleic Acid Chemistry, vol. II, Academic Press, New York.
Google Scholar
Wakelin, L. P. G. and Waring, M. J. (1976). Biochem. J., 157, 721.
Article CAS Google Scholar
Wang, J. C. (1971). Biochim. biophys. Acta, 232, 246.
Article CAS Google Scholar
Waring. M. J. (1965). J. molec. Biol., 13, 269.
Article Google Scholar
Waring, M. J. (1970). J. molec. Biol., 54, 247.
Article CAS Google Scholar
Waring, M. J. and Wakelin, L. P. G. (1974). Nature, Lond., 252, 653.
Article CAS Google Scholar
Wartell, R. M., Larson, J. E. and Wells, R. D. (1974). J. Biol. Chem., 249, 6719.
CAS Google Scholar
Wehrli, F. W. and Wirthlin, T. (1976). Interpretation of Carbon-13 NMR Spectra, Heydon and Son, London.
Google Scholar
Wells, R. D. (1971). In Progress in Molecular and Subcellular Biology (ed. F. E. Hahn), vol. 2, Springer Verlag, New York, p. 21.
Google Scholar

Download references

Authors

Thomas R. Krugh
View author publications
You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

Department of Biophysics, University of London King’s College, UK
Stephen Neidle

Copyright information

About this chapter

Cite this chapter

Krugh, T.R. (1981). Oligonucleotide and polynucleotide — drug complexes in solution as investigated by NMR. In: Neidle, S. (eds) Topics in Nucleic Acid Structure. Topics in Molecular and Structural Biology. Palgrave Macmillan, London. https://doi.org/10.1007/978-1-349-04691-1_9

Download citation

DOI: https://doi.org/10.1007/978-1-349-04691-1_9
Publisher Name: Palgrave Macmillan, London
Print ISBN: 978-1-349-04693-5
Online ISBN: 978-1-349-04691-1
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)

Publish with us

Policies and ethics