Display options
Share it on

Bioinorg Chem Appl. 2007;53521. doi: 10.1155/2007/53521.

Characterization of copper(II) interactions with sinefungin, a nucleoside antibiotic: combined potentiometric, spectroscopic and DFT studies.

Bioinorganic chemistry and applications

Maria Jaworska, Piotr Lodowski, Ariel Mucha, Wojciech Szczepanik, Gianni Valensin, Massimo Cappannelli, MaƂgorzata Jezowska-Bojczuk

Affiliations

  1. Department of Theoretical Chemistry, Faculty of Mathematics, Physics and Chemistry, University of Silesia, 14 Bankowa St., 40-007 Katowice, Poland.

PMID: 18273386 PMCID: PMC2216065 DOI: 10.1155/2007/53521

Abstract

Interactions between sinefungin and copper(II) ions were investigated. Stoichiometry and stability constants of the metal-free system and two mononuclear complexes present in solution were determined on the basis of potentiometric data analysis. The results were compared to the Cu(II)-ornithine system due to structural similarities between both molecules. Combined spectroscopic and theoretical studies allowed for determination of coordination pattern for the Cu(II)-sinefungin complexes. At acidic pH, copper is bound in "glycine-like" coordination mode, identical with that of ornithine. This involves alpha-amino group and the carboxyl oxygen. At higher pH, a "bis-complex" is formed by two sinefungin molecules. The second ligand binds in equatorial position displacing two water molecules, what results in the stable {2N,2O} coordination. Both axial positions are supposed to be occupied by N1 nitrogen donors of adenine moiety, what is confirmed by DFT calculations. They interact indirectly with copper(II) through water molecules as the result of dominant syn conformation of purine.

References

  1. J Antibiot (Tokyo). 1973 Dec;26(12):752-6 - PubMed
  2. J Biol Chem. 1978 Jun 25;253(12):4075-7 - PubMed
  3. J Phys Chem B. 2006 Mar 9;110(9):4413-22 - PubMed
  4. Biochem J. 1998 Nov 15;336 ( Pt 1):1-17 - PubMed
  5. Biol Trace Elem Res. 1989 Jul-Sep;21:49-59 - PubMed
  6. Biochim Biophys Acta. 1997 Feb 27;1360(1):3-16 - PubMed
  7. J Pharm Sci. 1981 Feb;70(2):204-7 - PubMed
  8. Biochim Biophys Acta. 1978 Apr 6;473(3-4):241-93 - PubMed
  9. Crit Rev Oncol Hematol. 2002 Apr;42(1):57-64 - PubMed
  10. J Inorg Biochem. 2006 Feb;100(2):178-85 - PubMed
  11. J Biol Inorg Chem. 2004 Apr;9(3):365-73 - PubMed
  12. Biochem Biophys Res Commun. 1978 Nov 14;85(1):371-6 - PubMed
  13. J Inorg Biochem. 2005 Mar;99(3):737-46 - PubMed
  14. J Med Chem. 1977 Feb;20(2):249-53 - PubMed
  15. J Med Chem. 1985 Sep;28(9):1350-4 - PubMed
  16. Nucleic Acids Res. 1981 Nov 11;9(21):5811-23 - PubMed
  17. Chemistry. 2003 Feb 17;9(4):881-92 - PubMed
  18. Methods Enzymol. 1990;186:1-85 - PubMed
  19. J Biol Chem. 1958 Oct;233(4):907-14 - PubMed
  20. Eur J Biochem. 2002 Nov;269(22):5547-56 - PubMed
  21. Chem Soc Rev. 2005 Oct;34(10):875-900 - PubMed
  22. Biochem Biophys Res Commun. 2001 Jun 15;284(3):856-62 - PubMed
  23. Biochem J. 1998 Aug 1;333 ( Pt 3):519-25 - PubMed
  24. J Antibiot (Tokyo). 1973 Aug;26(8):466-70 - PubMed
  25. Eur J Biochem. 1987 Mar 2;163(2):353-63 - PubMed
  26. J Biol Chem. 1993 Feb 25;268(6):4099-105 - PubMed
  27. Phys Rev B Condens Matter. 1988 Jan 15;37(2):785-789 - PubMed
  28. J Med Chem. 1978 Jan;21(1):50-5 - PubMed
  29. J Antibiot (Tokyo). 1986 Feb;39(2):286-93 - PubMed
  30. J Comput Aided Mol Des. 2000 Feb;14(2):123-34 - PubMed
  31. Antimicrob Agents Chemother. 1993 Apr;37(4):889-92 - PubMed
  32. J Med Chem. 2002 Apr 25;45(9):1918-29 - PubMed
  33. J Biol Chem. 1997 Feb 7;272(6):3520-6 - PubMed
  34. Eur J Biochem. 1974 Jan 16;41(2):209-16 - PubMed
  35. Science. 1999 Apr 30;284(5415):805-8 - PubMed
  36. J Antibiot (Tokyo). 1984 Jun;37(6):670-2 - PubMed
  37. Pol J Pharmacol Pharm. 1987 May-Jun;39(3):219-27 - PubMed
  38. Chem Rev. 1999 Sep 8;99(9):2535-44 - PubMed
  39. J Inorg Biochem. 2007 Jul;101(7):1005-12 - PubMed
  40. Cancer Res. 1987 Jul 15;47(14):3650-5 - PubMed
  41. Eur J Biochem. 1989 Feb 1;179(2):451-8 - PubMed
  42. Biochem J. 1984 Mar 15;218(3):983-5 - PubMed

Publication Types