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Synthesis, DNA-binding and cleavage studies of macrocyclic copper(II) complexes

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Abstract

Two macrocyclic copper(II) complexes, [CuL1](ClO4)2 (L1 = 2,6,9,13-tetraparacyclophane, a Schiff base) and [CuL2]Cl2 [L2 = 3,10-bis(2-benzyl)-1,3,5,8,10,13-hexaazacyclotetradecane] have been prepared and characterized by elemental analysis, u.v.–vis., i.r. and mass spectra. Absorption, fluorescence, circular dichroic spectra and viscosity experiments have been carried out on the interaction of the two complexes with calf thymus CT DNA. The results suggest that both complexes can bind to CT DNA by intercalation via the aromatic moiety ring in the macrocycle into the base pairs of DNA. [CuL1](ClO4)2 binds to CT DNA more strongly than [CuL2]Cl2. The position of the aromatic ring in the macrocycle plays an important role in deciding the extent of binding of the complexes to DNA. Significantly, the complexes have been found to be single-strand DNA cleavers in the presence of H2O2 or/and 2-mercaptoethanol.

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References

  1. P.J. Dardlier, R.E. Holmlin and J.K. Barton, Science, 274, 1465 (1997).

    Google Scholar 

  2. J.K. Barton, Science, 223, 727 (1986).

    Google Scholar 

  3. P.B. Dervan, Science, 232, 464 (1986).

    Google Scholar 

  4. D.B. Hall, R.E. Holmlin and J. K. Barton, Nature, 382, 731 (1996).

    Google Scholar 

  5. J.K. Barton, A.T. Danishefsky and J.M. Goldberg, J. Am. Chem. Soc., 106, 2172 (1984).

    Google Scholar 

  6. M.V. Keek and S.J. Lippard, J. Am. Chem. Soc., 114, 3386 (1992).

    Google Scholar 

  7. A.E. Friedman, J.C. Chambron, J.P. Sauvage, N.J. Turro and J.K. Barton, J. Am. Chem. Soc., 114, 5919 (1992).

    Google Scholar 

  8. P. Lincoln and B. Norden, Chem. Commun., 2145 (1996).

  9. R.P. Hertzberg and P.B. Dervan, J. Am. Chem. Soc., 104, 313 (1982).

    Google Scholar 

  10. R.M. Hartshorn and J.K. Barton, J. Am. Chem. Soc., 112, 4960 (1990).

    Google Scholar 

  11. N.B. Thornton and K.S. Schanze, Inorg. Chem., 32, 4994 (1993).

    Google Scholar 

  12. H.Q. Liu, T.C. Cheung and C.M. Che, Chem. Commun., 1039 (1996).

  13. K.E. Erkkila, D.T. Odom and J.K. Barton, Chem. Rev., 99, 2777 (1999).

    Google Scholar 

  14. B.A. Jackson, U.Y. Alekseyev and J.K. Barton, Biochemistry, 38, 4655 (1999).

    Google Scholar 

  15. Y. Xiong and L.-N. Ji, Coord. Chem. Rev., 185 (1999).

  16. X.-H. Zou, B.-H. Ye, H. Li, J.-L. Liu, Y. Xiong and L.-N. Ji, J. Chem. Soc., Dalton Trans., 1423 (1999).

  17. G. Yang, J.-Z. Wu, L. Wang, L.-N. Ji and X. Tian, J. Inorg. Biochem., 66, 141 (1997).

    Google Scholar 

  18. Q.-L. Zhang, J.-G. Liu, H. Chao, G.-Q. Xue and L.-N. Ji, J. Inorg. Biochem., 83, 49 (2001).

    Google Scholar 

  19. J.-G. Liu, B.-H. Ye, Q.-L. Zhang, X.-H. Zou, Q.-X. Zhen, X. Tian and L.-N. Ji, Biol. Inorg. Chem., 5, 119 (2000).

    Google Scholar 

  20. D.S. Sigman, Biochemistry, 29, 9097 (1990).

    Google Scholar 

  21. A.S. Sitlani, E.C. Long, A.M. Pyle and J.K. Barton, J. Am. Chem. Soc., 114, 2303 (1992).

    Google Scholar 

  22. D.S. Sigman, D.R. Graham, V.D. Aurora and A.M. Stern,J. Biol Chem., 254, 12269 (1979).

    Google Scholar 

  23. C.-L. Liu, J.-Y. Zhou, Q.-X. Li, L.-J. Wang, Z.-R. Liao and H.-B. Xu, J. Inorg. Biochem., 75, 233 (1999).

    Google Scholar 

  24. D.K. Chand, H.J. Schneider, J.A. Aguilar, F. Escarti, E. Garcia-Esspara and S.V. Luis, Inorg. Chim. Acta, 316, 71 (2001).

    Google Scholar 

  25. C.J. Burrows and S.E. Rokita, Acc. Chem. Res.,27, 295 (1994).

    Google Scholar 

  26. X.Y. Chen, S.E. Rokita and C.J. Burrows, J. Am. Chem. Soc., 113, 5884 (1991).

    Google Scholar 

  27. X.Y. Chen, S.E. Rokita and C.J. Burrows, J. Am. Chem. Soc., 114, 322 (1992).

    Google Scholar 

  28. J.G. Muller, R.P. Hickerson, R.J. Perez and C.J. Burrows, J. Am. Chem. Soc., 119, 1501 (1997).

    Google Scholar 

  29. S. Satyanarayana, J.C. Daborusak and J.B. Chaires, Biochemistry, 32, 2573 (1993).

    Google Scholar 

  30. H.C. Shih, N. Tang, C.J. Burrows and S.E. Rokita, J. Am. Chem. Soc., 120, 3284 (1998).

    Google Scholar 

  31. J. Liu, T.-B. Lu, H. Li, Q.-L. Zhang, L.-N. Ji, T.-X. Zhang. L.-H. Qu and H. Zhou, Transition Met. Chem., in press.

  32. J. Liu, T.-X. Zhang, T.-B. Lu, L.-H. Qu, H. Zhou and L.-N. Ji, J. Inorg. Biochem., in press.

  33. J. Liu, C.-H. Chen, H. Zhang, H. Deng, H. Li, L.-H. Qu, H. Zhou, T.-B. Lu and L.-N. Ji, J. Chem. Soc., Dalton Trans., submitted.

  34. J. Marmur, J. Mol. Biol., 3, 208 (1961).

    Google Scholar 

  35. M.E. Reichmann, S.A. Rice, C.A. Thomas and P. Doty, J. Am. Chem. Soc., 76, 3047 (1954).

    Google Scholar 

  36. D. Chen and A.E. Matell, Tetrahedron, 47, 6895 (1991).

    Google Scholar 

  37. S.A. Tysoe, R.J. Morgan, A.D. Baker and T.C. Strekas, J. Phys. Chem., 97, 1707 (1993).

    Google Scholar 

  38. T.M. Kelly, A.B. Tossi, D.J. McConnell and T.C. Strekas, Nucleic Acids Res., 13, 6017 (1985).

    Google Scholar 

  39. M. Sethuraman and P. Mallayan, Inorg. Chem., 37, 693 (1998).

    Google Scholar 

  40. K.A. Meadows, F. Liu, J. Sou and B.P. McMillin, Inorg. Chem., 32, 2919 (1993).

    Google Scholar 

  41. B.C. Baguley and M. LeBret, Biochemistry, 23, 937 (1984).

    Google Scholar 

  42. J.R. Lakowicz and G. Webber, Biochemistry, 12, 4161 (1973).

    Google Scholar 

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Authors and Affiliations

  1. State Key Laboratory of Optoelectronic Materials and Technologies, School of Chemistry and Chemical Engineering, Zhongshan University, Guangzhou, 510275, P.R. China

    Jie Liu, Tong-Bu Lu, Hong Deng & Liang-Nian Ji

  2. The Key Laboratory of Gene Engineering of Ministry of Education, School of Life Sciences, Zhongshan University, Guangzhou, 510275, P.R. China

    Liang-Hu Qu & Hui Zhou

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  1. Jie Liu
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  2. Tong-Bu Lu
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  3. Hong Deng
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  4. Liang-Nian Ji
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  5. Liang-Hu Qu
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  6. Hui Zhou
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Liu, J., Lu, TB., Deng, H. et al. Synthesis, DNA-binding and cleavage studies of macrocyclic copper(II) complexes. Transition Metal Chemistry 28, 116–121 (2003). https://doi.org/10.1023/A:1022543601034

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