Abstract
Daunomycin (NSC 82151, daunorubicin) (figure 1) and Adriamycin (NSC 123127, doxorubicin) are anthracycline anticancer antibiotics isolated from strains of Streptomyces peucetius. Both drugs are in current clinical use, the former being active mainly against acute lymphocytic leukaemia. Adriamycin has an exceptionally wide spectrum of antitumour activity (Goldin et al, 1981; Arcamone, 1981), having clinical applications in the treatment of a number of solid tumours as well as acute leukaemias. Both drugs produce severe dose-dependent cumulative cardiomyopathy in a high percentage of patients. Thus there has been continuing effort in many laboratories to develop analogues with reduced toxicity, and an improved spectrum of activity; to date well over 500 daunomycin derivatives have been examined. The supposition that DNA is the major cellular receptor for the drug’s action has provided rationalisations for many of these endeavours. (See Chapter 3 of this volume and the numerous reviews available for further information on the relationships between daunomycin modification, DNA binding and biological activity (Arcamone, 1978, 1981; Arlandini, Vigevani and Arcamone, 1980; Brown, 1978; Di Marco and Arcamone, 1975; Henry, 1976; Neidle, 1978, 1979).) This chapter is concerned with the interactions of the parent antibiotics with nucleic acids, an area which has undergone extensive development since it was last reviewed in detail (Neidle, 1978).
The molecular structures of daunomycin (R-H) and Adriamycin (R-OH).
This is a preview of subscription content, log in via an institution to check access.
Preview
Unable to display preview. Download preview PDF.
References
Angiuli, R., Foresti, E., Riva Di Sanserverino, L., Issacs, N. W., Kennard, O., Motherwell, W. D. S., Wampler, D. L. and Arcamone, F. (1971). Nature new Biol., 234, 78
Arcamone, F. (1978). In Topics in Antibiotic Chemistry, Vol. 2 (ed. P. G. Sammes), Ellis Horwood, Chichester, p. 89
Arcamone, F. (1981). In Doxorubicin, Anticancer Antibiotics, Academic Press, New York
Arcamone, F., Cassinelli, G., Franceshi, G., Orezzi, P. and Mondelli, R. (1968). Tetrahedron Lett., 30, 3353
Arlandini, E., Vigevani, A. and Arcamone, F. (1980). Farmaco, Sci., 35, 65
Arnott, S. (1981). In Topics in Nucleic Acid Structure (ed. S. Neidle), Macmillan Press, London, p. 65
Barthelemy-Clavey, V., Maurizot, J. -C, Dimicoli, J. C. and Sicard, P. (1974). FEBS Lett., 46, 5
Barthelemy-Clavey, V., Maurizot, J. -C. and Sicard, P. J. (1973). Biochimie, 55, 859
Berlin, V. and Haseltine, W. A. (1981). J. biol. Chem., 256, 4747
Berman, H. M., Neidle, S. and Stodola, R. K. (1978). Proc. natn. Acad. Sci. U. S. A., 72, 828
Brown, J. R., (1978). Prog. med. Chem., 15, 125
Brown, S. C, Kollman, P. A. and Weiner, P. K. (1982). Biochim. biophys. Acta, 717, 49
Byrn, S. R. and Dolch, G. D. (1978). J. pharm. Sci., 67, 688
Calendi, E., Di Marco, A., Reggiani, M., Scarpinato, B., and Valentini, L. (1965). Biochim. biophys. Acta. 103, 25
Center, M. S. (1979). Biochem. biophys. Res. Commun., 89, 1231
Chaires, J. B., Dattagupta, N. and Crothers, D. M. (1982a). Biochemistry, 21, 3933
Chaires, J. B., Dattagupta, N. and Crothers, D. M. (1982b). Biochemsitry, 21, 3927
Courseille, C, Busetta, B., Geoffre, S. and Hospital, M. (1979). Acta crystallogr., B35, 764
Di Marco, A. (1975). Cancer Chemotherapy Rep., 6, 91
Di Marco, A. and Arcamone, F. (1915). Arnz. Forschung, 25, 368
Fritzsche, H., Triebel, H., Chaires, J. B., Dattagupta, N. and Crothers, D. M. (1982). Biochemistry, 21, 3940
Gabbay, E. J., Grier, D., Fingerle, R. E., Reiner, R., Levy, R., Pearce, S. W. and Wilson, W. D. (1976). Biochemistry, 15, 2062
Gale, E. F., Cundliffe, E., Reynolds, P. E., Richmond, M. H. and Waring, M. J. (1981). The Molecular Basis of Antibiotic Action 2nd edn John Wiley, London
Garner, A. and Fox, B. W. (1981). Chem. -biol. Interactions, 36, 189
Goldin, A., Venditti, J. M., MacDonald, J. S., Muggian, F. M., Henny, J. E. and deVitta, V. T. Jr. (1981). Eur. J. Cancer, 17, 129
Grant, M. and Phillips, D. R. (1979). Molec. Pharmac, 16, 357
Gray, P. J. and Phillips, D. R. (1976). Eur. J. Cancer, 12, 237
Henry, D. W. (1976). Am. chem. Soc. Symp. Ser., 30, 15
Huang, Y. M. and Phillips, D. R. (1977). Biophys. Chem., 6, 363
Islam, S. A. and Neidle, S. (1983). Acta crystallogr., B39, 114
Iwamoto, R. H., Lim, P. and Bhacca, N. S. (1968). Tetrahedron Lett., 3891
Jain, S. C., Tsai, C. C. and Sobell, H. M. (1977). J. molec. Biol., 114, 317
Kersten, W., Kersten, H. and Szybalski, W. (1966). Biochemistry, 5, 236
Krugh, T. R. and Reinhardt, C. G. (1975). J. molec. Biol., 97, 133
Krugh, T. R., Winkle, S. A. and Graves, D. E. (1981). Biochem. biophys. Res. Commun., 98, 317
Lee, Y. C. and Byfield, J. E. (1976). J. natn. Cancer Inst., 57, 221
Lown, J. W. and Chen, H. -H. (1981). Can. J. Chem., 59, 3212
Malhotra, D. and Hopfinger, A. J. (1980). Nucleic Acids Res., 8, 5289
Martin, S. R. (1980). Biopolymers, 19, 713
Meriwether, W. D. and Bachur, N. R. (1972). Cancer Res., 32, 1137
Nakata, Y. and Hopfinger, A. J. (1980a). FEBS Lett., 117, 259
Nakata, Y. and Hopfinger, A. J. (1980b). Biochem. biophys. Res. Commun., 95, 583
Neidle, S. (1977). Cancer Treat. Rep., 61, 928
Neidle, S. (1978). In Topics in Antibiotic Chemistry, Vol. 2 (ed. P. G. Sammes), Ellis Horwood, Chichester, p. 230
Neidle, S. (1979). Prog. med. Chem., 16, 151
Neidle, S. (1981). In Topics in Nucleic Acid Structure (ed. S. Neidle), Macmillan Press, London, p. 177
Neidle, S., Achari, A., Taylor, G. L., Berman, H. M., Carrell, H. L., Glusker, J. P. and Stallings, W. C. (1977). Nature, Lond., 269, 304
Neidle, S. and Taylor, G. (1977). Biochim. biophys. Acta., 479, 450
Neidle, S. and Taylor, G. (1979). FEBSLett., 107, 348
Noël, G., Peterson, C, Trouet, A. and Tulkens, P. (1978). Eur. J. Cancer, 14, 363
Nuss, M. E., James, T. L., Apple, M. A. and Kollman, P. A. (1980). Biochim. biophys. Acta., 609, 136
Patel, D. J. (1979a). Biopolymers, 18, 553
Patel, D. J. (1919b). Acc. Chem., Res., 12, 118
Patel, D. J. and Canuel, L. L. (1977). Proc. natn. Acad. Sci. U. S. A., 74, 2624
Patel, D. J. and Canuel, L. L. (1978). Eur. J. Biochem., 90, 247
Patel, D. J., Kozlowski, S. A. and Rice, J. A. (1981). Proc. natn. Acad. Sci. U. S. A., 78, 3333
Phillips, D. R., Di Marco, A. and Zunino, F. (1978). Eur. J. Biochem., 85, 487
Phillips, D. R. and Roberts, G. C. K. (1980). Biochemistry, 19, 4795
Pigram, W. J., Fuller, W. and Hamilton, L. D. (1972). Nature new Biol., 235, 17
Plumbridge, T. W., Aarons, L. J. and Brown, J. R. (1978). J. pharm. Pharmac, 30, 69
Plumbridge, T. W. and Brown, J. R. (1977). Biochim. biophys. Acta., 479, 441
Plumbridge, T. W. and Brown, J. R. (1978). Biochem. Pharmac, 27, 1881
Plumbridge, T. W. and Brown, J. R. (1979). Biochim. biophys. Acta., 563, 181
Pohl, F. M. and Jovin, T. M. (1972). J. molec. Biol., 67, 375
Porumb, H. (1978). Prog, biophys. molec. Biol., 34, 175
Quigley, G. J., Wang, A. H. -J., Ughetto, G., van der Marel, G., van Boom, J. H. and Rich, A. (1980). Proc. natn. Acad. Sci. U. S. A., 77, 7204
Rich, A. Quigley, G. J. and Wang, A. H. -J. (1981). In Biomolecular Stereodynamics Vol. 1 (ed. R. H. Sarma), Adenine Press, New York, p. 25
Ross, W. E. and Bradley, M. O. (1981). Biochim. biophys. Acta., 654, 129
Ross, W. E., Glaubiger, D. and Kohn, K. W. (1979). Biochim. biophys. Acta, 562, 41
Ross, W. E., Glaubiger, D. L. and Kohn, K. W. (1978). Biochim biophys Acta., 519, 23
Sabeur, G., Genert, D. and Aubel-Sadron, G. (1979). Biochem. biophys. Res. Commun., 88, 722
Schneider, Y. -J., Baurain, R., Zenebergh, A. and Trouet, A. (1979). Cancer Chemother. Pharmac, 2, 7
Shafer, R. H. (1977). Biochem. Pharmac, 26, 1729
Shieh, H. -S., Berman, H. M., Dabrow, M. and Neidle, S. (1980). Nucleic Acids Res., 8, 85
Sinha, B. K. and Sik, R. H. (1980). Biochem. Pharmac, 29, 1867
Tsou, K. C. and Yip, K. F. (1976). Cancer Res., 36, 3367
Von Dreele, R. B. and Einck, J. J. (1977). Acta crystallogr., B33, 3283
Waldes, H. and Center, M. S. (1981). Biochem. biophy. Res. Commun., 98, 95
Wang, A. H. -J., Quigley, G. J., Kolpak, F. J., Crawford, J. L., van Boom, J. H., van der Marel, G. and Rich, A. (1980). Nature, Lond., 282, 680
Ward, D. C., Reich, E. and Goldberg, I. H. (1965). Science, 149, 1259
Waring, M. J. (1970). J. molec. Biol., 54, 247
Wiesehahn, G., Varga, J. M. and Hearst, J. E. (1981). Nature, Lond., 292, 467
Zunino, F. (1971). FEBS Lett., 18, 249
Zunino, F., Di Marco, A. and Zaccara, A. (1979). Chem. -biol. Interactions, 24, 217
Zunino, F., Di Marco, A., Zaccara, A. and Gambetta, R. A. (1980). Biochim. biophys. Acto., 607, 206
Zunino, F., Di Marco, A., Zaccara, A. and Luoni, G. (1974). Chem. -biol. Interactions, 9, 25
Zunino, F., Gambetta, R., Di Marco, A., Velcich, A., Zaccara, A., Quadrifoglio, F. and Crescenzi, V. (1977). Biochim. biophys. Acta, 476, 38
Zunino, F., Gambetta, R., Di Marco, A. and Zaccara, A. (1972). Biochim. biophys. Acta., 277, 489
Zwelling, L. A., Michaels, S., Erickson, L. C, Ungerleider, R. S., Nichols, M. and Kohn, K. W. (1981). Biochemistry, 20, 6553
Editor information
Editors and Affiliations
Copyright information
© 1983 The Contributors
About this chapter
Cite this chapter
Neidle, S., Sanderson, M.R. (1983). The Interactions of Daunomycin Adriamycin with Nucleic Acids. In: Neidle, S., Waring, M.J. (eds) Molecular Aspects of Anti-Cancer Drug Action. Topics in Molecular and Structural Biology. Palgrave, London. https://doi.org/10.1007/978-1-349-06010-8_2
Download citation
DOI: https://doi.org/10.1007/978-1-349-06010-8_2
Publisher Name: Palgrave, London
Print ISBN: 978-1-349-06012-2
Online ISBN: 978-1-349-06010-8
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)