Comparison of DNA sequence selectivity of anthracycline antibiotics and their 3′-hydroxylated analogs

Chemico-Biological Interactions

Volumn 100, Issue 2, 1996, Pages 165-176

  Jollès, Béatrice ^a,b   Laigle, Alain ^a,b   Priebe, Waldemar ^c   Garnier Suillerot, Ariette ^a,b  

^a SORBONNE UNIVERSITÉ   (France)

^b UNIVERSITÉ PARIS 13   (France)

^c UNIVERSITY OF TEXAS   (United States)

Author keywords

Anthracycline; DNA sequence selectivity; Dnase I footprinting; Hydroxyanthracycline

Indexed keywords

3' DEAMINO 3' HYDROXYDAUNORUBICIN; 3' DEAMINO 3' HYDROXYDOXORUBICIN; 3' DEAMINO 3' HYDROXYIDARUBICIN; ANTHRACYCLINE ANTIBIOTIC AGENT; ANTHRACYCLINE DERIVATIVE; DAUNORUBICIN; DAUNOSAMINE; DEOXYRIBONUCLEASE I; DNA FRAGMENT; DOXORUBICIN; IDARUBICIN; INTERCALATING AGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DNA BINDING; DNA FOOTPRINTING; DNA SEQUENCE; DRUG SELECTIVITY; DRUG SPECIFICITY; STRUCTURE ACTIVITY RELATION;

ANTIBIOTICS, ANTINEOPLASTIC; BASE COMPOSITION; BASE SEQUENCE; DAUNORUBICIN; DEOXYRIBONUCLEASE I; DNA; DNA FOOTPRINTING; DOXORUBICIN; IDARUBICIN; INTERCALATING AGENTS; KINETICS; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE;

EID: 0029997741     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/0009-2797(96)03697-6     Document Type: Article

References (27)

1. F. Arcamone, Doxorubicin: anticancer antibiotics, in: S.T. Crooke and S.D. Reich (Eds.), Medicinal Chemistry 17, Academic Press, New York, 1981, pp 265-278.
2. T.R. Tritton and G. Yee, The anticancer adriamycin can be actively cytotoxic without entering cells, Science 217 (1982) 248-250.
3. K.M. Tewey, T.C Rowe, L. Yang, B.D. Halligan and L.F. Liu, Adriamycin-induced DNA damage mediated by mammalian DNA topoisomerase II, Science, 226 (1984) 466-468.
4. A.H.J. Wang, G. Ughetto, G.J. Quigley and A. Rich, Interactions between an anthracycline antibiotic and DNA: molecular structure of daunomycin complexed to d(CpGpTpApCpG) at 1.2-Å resolution, Biochemistry, 26 (1987) 1152-1163.
5. M.H. Moore, W.N. Junter, B. Langlois d'Estaintot and O. Kennard, DNA-drug interactions. The crystal structure of d(CGATCG) complexed with daunomycin, J. Mol. Biol., 206 (1989) 693-705.
6. K.X. Chen, N. Gresh and B. Pullman, A theoretical investigation on the sequence selective binding of daunomycin to double-stranded polynucleotides, J. Biomol. Struct. Dyn., 3 (1985) 445-466.
7. J.B. Chaires, K.R. Fox, J.E. Herrera, M. Britt and M.J. Waring, Site and sequence specificity of the daunomycin-DNA interaction, Biochemistry, 26 (1987) 8227-8236.
8. J.B. Chaires, J.E. Herrera and M.J. Waring, Preferential binding of daunomycin to 5′A/T CG and 5′ A/T GC sequences revealed by footprinting titration experiments, Biochemistry, 29 (1990) 6145-6153.
9. H. Trist and D.R. Phillips, In vitro transcription analysis of the role of flanking sequence on the DNA sequence specificity of adriamycin, Nucl. Acids Res., 17 (1989) 3673-3687.
10. C. Cullinane and D.R. Phillips, Induction of stable transcriptional blockage sites by adriamycin: GpC specificity of apparent adriamycin-DNA adducts and dependence on iron (III) ions, Biochemistry 29 (1990) 5638-5646.
11. D.R. Phillips, R.J. White and C. Cullinane, DNA sequence-specific adducts of adriamycin and mitomycin C, FEBS Lett., 246 (1989) 233-240.
12. A. Skorobogaty, R.J. White, D.R. Phillips and J.A. Reiss, The 5′-CA DNA-sequence preference of daunomycin, FEBS Lett., 227 (1988) 103-106.
13. W. Priebe, N.T. Van, T.G. Burke and R. Perez-Soler, Removal of the basis center from doxorubicin partially overcomes multidrug resistance and decreases cardiotoxicity, Anti-Cancer Drugs, 4 (1993) 37-48.
14. W. Priebe and R. Perez-Soler, Design and tumour targeting of anthracyclines able to overcome multidrug resistance: a double advantage approach, Pharmacol. Ther., 60 (1993) 215-234.
15. Y. Zou, Y.H. Ling, N.T. Van, W. Priebe and R. Perez-Soler, Antitumor activity of free and liposome entrapped annamycin, a lipophilic anthracycline antibiotic with non-cross-resistance properties, Cancer Res., 54 (1994) 1479-1484.
16. J.B. Chaires, W. Priebe, D.E. Graves and T.G. Burke, Dissection of the free energy of anthracycline antibiotic binding to DNA: electrostatic contributions, J. Am. Chem. Soc., 115 (1993) 5360-5364.
17. E. Solary, Y.H. Ling, R. Perez-Soler, W. Priebe and Y. Pommier, Hydroxyrubicin, a deaminated derivative of doxorubicin, inhibits mammalian DNA topoisomerase II and partially circumvents multidrug resistance, Int. J. Cancer, 58 (1994) 85-94.
18. G. Capranico, R. Supino, N. Binaschi, L. Capolongo, M. Grandi, A. Suarato and F. Zunino, Influence of structural modifications at the 3′ and 4′ positions of doxorubicin on the drug ability to trap topoisomerase II and to overcome multidrug resistance, Mol. Pharmacol., 45 (1994) 908-915.
19. J.B. Chaires, N. Dattagupta and D.M. Crothers, Self-association of daunomycin, Biochemistry, 21 (1982) 3927-3932.
20. K.R. Fox and M.J. Waring, DNA structural variations produced by actinomycin and distamycin are revealed by DNAase I footprinting, Nucl. Acids Res., 12 (1984) 9271-9285.
21. J. Sambrook, E.F. Fritsch and T. Maniatis, DNA sequencing, in: Molecular Cloning: a Laboratory Manual, 2nd Edn., Cold Spring Harbor Laboratory, Cold Spring Harbor, NY, 1989, pp. 13.0-13.104.
22. I. Brukner, V. Jurukovski and A. Savic, Sequence-dependent structural variations of DNA revealed by DNase I, Nucl. Acids Res., 18, (1990) 891-894.
23. 2 complex in solution: intercalation and sequence specificity of drug binding at the tetranucleotide duplex level, Proc. Natl. Acad. Sci. USA, 73 (1976) 3343-3347.
24. P.E. Pjura, K. Grzeskowiak and R.E. Dickerson, Binding of Hoechst 33258 to the minor groove of B-DNA, J. Mol. Biol., 197 (1987) 257-271.
25. A. Pullman and B. Pullman, Structural factors involved in the binding of netropsin and distamycin A to nucleic acids, Stud. Biophys., 86 (1981) 95-102.
26. C.J. Roche, D. Berkowitz, G.A. Sulikowski, S.J. Danishefsky and D.M. Crothers, Binding affinity and site selectivity of daunomycin analogues, Biochemistry, 33 (1994) 936-942.
27. E. Friche, P. Buhl Jensen, H. Roed, T. Skovsgaard and N.I. Nissen, In vitro circumvention of anthracycline resistance in Ehrlich ascites tumour by anthracycline analogues, Biochem. Pharmacol., 39 (1990) 1721-1726.