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Complexation of the antibiotic daunomycin with desoxytetraribonucleoside triphosphate 5’-d(CpGpCpG) in aqueous solution

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Abstract

This paper presents the results of our study of the complexation of the antibiotic daunomycin with desoxytetranucleotide 5’-d(CpGpCpG) in aqueous salt solution by one- and two-dimensional (2D-TOCSY and 2D-NOESY)1H NMR spectroscopy (500 MHz). The concentration and temperature dependences of the proton chemical shifts of molecules were measured and used to calculate the equilibrium reaction constants, the relative contents of different types of complex as functions of concentration and temperature, the limiting values of the proton chemical shifts of daunomycin in various complexes, and the thermodynamic parameters of complexation δH and δS. It is concluded that the triplet nucleotide sequences are the preferable sites at which daunomycin is attached. The binding of the second daunomycin molecule to both single-stranded and duplex forms of tetramer is markedly anticooperative. This is explained by the presence in the antibiotic of a positively charged amino sugar residue creating steric hindrances for the attachment of the second antibiotic molecule to the short tetranucleotide sequence. The most plausible spatial structure of the 1:2 complex of antibiotic with desoxytetranucleotide is constructed using the calculated values of the induced proton chemical shifts of daunomycin and 2D-NOE data.

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References

  1. F. Arcamone and S. Penco, in:Anthracyclines and Anthracenedione-Based Anticancer Agents, J. W. Lown (ed.), Elsevier, New York (1988), pp. 1–43.

    Google Scholar 

  2. F. Boulad and N. A. Kernan,Cancer Invest.,11, 543–553 (1993).

    Article  Google Scholar 

  3. S. Neidle and Z. Abraham,CRC Crit. Rev. Biochem.,17, 73–121 (1984).

    Article  CAS  Google Scholar 

  4. S. Neidle and M. R. Sanderson, in:Molecular Aspects of Anticancer Drug Action, S. Neidle and M. J. Waring (eds.), Verlag Chemie, Weinland (1983), pp. 35–57.

    Google Scholar 

  5. J. B. Chaires,Biopolymers,22, 4204–4211 (1983).

    CAS  Google Scholar 

  6. D. D. Newlin, K. J. Miller, and D. F. Pilch,ibid.,23, 139–158 (1984).

    Article  CAS  Google Scholar 

  7. K.-X. Chen, N. Gresh, and B. Pullman,J. Biomol. Struct. Dyn.,3, 445–466 (1985).

    CAS  Google Scholar 

  8. J. B. Chaires, N. Dattagupta, and D. M. Crothers,Biochemistry,21, 3933–3940 (1982).

    Article  CAS  Google Scholar 

  9. J. B. Chaires, K. R. Fox, J. E. Herrera, et al.,ibid.,27, 8227–8236 (1987).

    Article  Google Scholar 

  10. D. B. Davies, L. N. Djimant, and A. N. Veselkov,Nucleot. Nucleos.,13, 637–655 (1994).

    Article  CAS  Google Scholar 

  11. D. B. Davies and A. N. Veselkov,J. Chem. Soc., Faraday Trans.,92, 3545–3557 (1996).

    Article  CAS  Google Scholar 

  12. Y. M. Huang and D. R. Phillips,Biophys. Chem.,6, 363–368 (1977).

    Article  CAS  Google Scholar 

  13. J. B. Chaires,Biochemistry,21, 3927–3932 (1982).

    Article  CAS  Google Scholar 

  14. A. N. Veselkov, L. N. Djimant, P. A. Bolotin, et al.,Zh. Strukt. Khim.,37, 1243–1255 (1996).

    Google Scholar 

  15. P. Hore,J. Magn. Res.,55, 283–300 (1983).

    CAS  Google Scholar 

  16. R. J. Eaton, D. A. Veselkov, D. B. Davies, et al.,Khim. Fiz.,18, No. 3 (1999).

  17. A. N. Veselkov, D. B. Davies, L. N. Djimant, et al.,Biopolim. Kiet,7, 15–22 (1991).

    CAS  Google Scholar 

  18. S. M. Freier, D. P. Albergo, and D. H. Turner,Biopolymers,22, 1107–1131 (1983).

    Article  CAS  Google Scholar 

  19. G. J. Quigley, A. H.-J. Wang, G. Ughetto, et al.,Proc. Natl. Acad. Sci. USA,77, 7204–7208 (1980).

    Article  CAS  Google Scholar 

  20. A. H.-J. Wang, G. Ughetto, G. J. Quigley, and A. Rich,Biochemistry,26, 1152–1163 (1987).

    Article  CAS  Google Scholar 

  21. J. D. McGhee and P. H. Von Hippel,J. Mol. Biol,86, 463–489 (1974).

    Article  Google Scholar 

  22. T. W. Plumbridge and J. R. Brown,Biochim. Biophys. Acta,479, 441–449 (1977).

    CAS  Google Scholar 

  23. E. J. Gabbay, D. Grier, R. E. Fingerle, et al.,Biochemistry,15, 2062–2070 (1976).

    Article  CAS  Google Scholar 

  24. A. N. Veselkov, E. B. Moroshkina, O. I. Soboleva, and é. V. Frisman,Molek. Biol.,18, 481–487 (1984).

    CAS  Google Scholar 

  25. D. B. Davies, L. N. Djimant, and A. N. Veselkov,Nucleot. Nucleos.,13, 657–671 (1994).

    Article  CAS  Google Scholar 

  26. D. B. Davies, L. N. Djimant, S. F. Baranovsky, and A. N. Veselkov,Biopolymers,42, 285–295 (1997).

    Article  CAS  Google Scholar 

  27. J. B. Chaires,ibid.,24, 403–419 (1985).

    Article  CAS  Google Scholar 

  28. A. Delbarre, B. P. Roques, J. B. Le Pecq, et al.,Biophys. Chem.,4, 275–279 (1976).

    Article  CAS  Google Scholar 

  29. P. D. Ross and S. Subramanian,Biochemistry,20, 3096–3102 (1981).

    Article  CAS  Google Scholar 

  30. L. Marky, K. S. Blumenfeld, and K. J. Breslauer,Nucleic Acids Res.,11, 2857–2870 (1983).

    Article  CAS  Google Scholar 

  31. J. M. Sturtevant,Proc. Natl. Acad. Sci. USA,74, 2236–2240 (1977).

    Article  CAS  Google Scholar 

  32. R. E. Dickerson, H. R. Drew, B. H. Conner, et al.,Science,216, 475–485 (1982).

    Article  CAS  Google Scholar 

  33. M. T. Record Jr., C. F. Anderson, and T. M. Lohman,Quart. Rev. Biophys.,11, 103–178 (1978).

    CAS  Google Scholar 

  34. D. B. Davies, S. F. Baranovsky, and A. N. Veselkov,J. Chem. Soc., Faraday Trans.,93, 1559–1572 (1997).

    Article  CAS  Google Scholar 

  35. D. P. Remeta, C. P. Mudd, R. L. Berger, and K. J. Breslauer,Biochemistry,30, 9799–9809 (1991).

    Article  CAS  Google Scholar 

  36. A. N. Veselkov, L. N. Djimant, P. A. Bolotin, et al.,Molek. Biol.,29, 326–338 (1995).

    CAS  Google Scholar 

  37. C. Giessner-Piettre and B. Pullman,Quart. Rev. Biophys.,20, 113–172 (1987).

    Article  Google Scholar 

  38. V. I. Poltev and A. V. Teplukhin,Int. J. Quant. Chem.,35, 91–102 (1989).

    Article  CAS  Google Scholar 

  39. R. E. Dickerson,J. Biomol. Struct. Dyn.,6, 627–634 (1989).

    CAS  Google Scholar 

  40. S. Neidle and G. Taylor,Biochim. Biophys. Acta,478, 450–459 (1977).

    Google Scholar 

  41. M. S. Searle,Prog. NMR Spectrosc,25, 403–480 (1993).

    Article  CAS  Google Scholar 

  42. G. M. Blackburn and J. M. Gait,Nucleic Acids in Chemistry and Biology, Oxford University, Oxford (1990), pp. 297–336.

    Google Scholar 

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Authors and Affiliations

  1. Sevastopol State Technical University, Russia

    A. N. Veselkov, R. J. Eaton, S. F. Baranovskii, S. G. Osetrov, P. A. Bolotin, L. N. Djimant, V. I. Pahomov & D. B. Davies

  2. Berkbeck College, London University, UK

    A. N. Veselkov, R. J. Eaton, S. F. Baranovskii, S. G. Osetrov, P. A. Bolotin, L. N. Djimant, V. I. Pahomov & D. B. Davies

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  1. A. N. Veselkov
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  2. R. J. Eaton
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  3. S. F. Baranovskii
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  4. S. G. Osetrov
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  5. P. A. Bolotin
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  6. L. N. Djimant
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  7. V. I. Pahomov
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  8. D. B. Davies
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Translated fromZhurnal Strukturnoi Khimii, Vol.40, No. 2, pp. 276–286, March–April, 1999.

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Veselkov, A.N., Eaton, R.J., Baranovskii, S.F. et al. Complexation of the antibiotic daunomycin with desoxytetraribonucleoside triphosphate 5’-d(CpGpCpG) in aqueous solution. J Struct Chem 40, 230–238 (1999). https://doi.org/10.1007/BF02903651

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  • DOI: https://doi.org/10.1007/BF02903651

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