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Novel Cu(II) complexes of bithiazole: structure and biological study

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Abstract

The reaction of copper(II) bromide with 2,2′-dimethyl-4,4′-bithiazole (dm4bt) affords a dimer complex, [{CuBr(dm4bt)}2(µ-Br)2] (1), in CH3OH/CH3CN; and a monomer complex, [Cu(dm4bt)Br2(DMSO)] (2), in DMSO. Monomer copper(II) complex [Cu(4bt)Br2(DMSO)] (3) also resulted from the treatment of the copper salt with 4,4′-bithiazole (4bt) in DMSO. The complexes were characterized by elemental analysis, IR, UV and X-ray crystallography. The interaction of monomeric complexes 2 and 3 with calf thymus DNA (CT DNA) has been explored by using absorption, emission and thermal denaturation, where they exhibit high interaction ability with CT DNA, with intrinsic binding constants K b of 1.58 × 105 and 1.24 × 105 M−1 at 298 K, for complexes 2 and 3, respectively. Furthermore, the intermolecular interaction between the mentioned copper complexes and bovine serum albumin (BSA) under imitated physiological conditions was investigated using UV–Vis and fluorescence. Tryptophan-quenching experiment illustrated that both complexes strongly bind BSA, with dynamic quenching constants of about 1 × 105 M−1 s−1 at 298 K, and a single class of binding site for the complexes on BSA.

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References

  1. B. Rosenberg, L. Vancamp, J.E. Trosko, V.H. Mansour, Nature 222, 358 (1969)

    Article  Google Scholar 

  2. M. Reithofer, M. Galanksi, A. Roller, B.K. Keppler, Eur. J. Inorg. Chem. 13, 2612 (2006)

    Article  Google Scholar 

  3. E. Wong, C.M. Giandomenico, Chem. Rev. 99, 2451 (1999)

    Article  CAS  Google Scholar 

  4. C.A. Rabik, M.E. Dolan, Cancer Treat. Rev. 33, 9 (2007)

    Article  CAS  Google Scholar 

  5. P.J. O’Dwyer, J.P. Stevenson, S.W. Johnson, Drugs 59, 19 (2000)

    Article  Google Scholar 

  6. M.F. Primik, G. Mühlgassner, M.A. Jakupec, O. Zava, P.J. Dyson, V.B. Arion, B.K. Keppler, Inorg. Chem. 49, 302 (2010)

    Article  CAS  Google Scholar 

  7. P. Shi, M. Lin, J. Zhu, Y. Zhang, Q. Jiang, J. Biochem. Mol. Toxicol. 23, 259 (2009)

    Article  Google Scholar 

  8. S. Zhang, C. Tu, X. Wang, Z. Yang, J. Zhang, L. Lin, J. Ding, Z. Guo, Eur. J. Inorg. Chem. 20, 4028 (2004)

    Article  Google Scholar 

  9. S. Kida, Y. Nishida, M. Sakamoto, Bull. Chem. Soc. Jpn. 46, 2428 (1973)

    Article  CAS  Google Scholar 

  10. J.S. Lazo, B.A. Chabner, Bleomycin, in Cancer Chemotherapy and Biotherapy: Principles and Practice, ed. by B.A. Chabner, D.L. Longo (Lippincott-Raven Publishers, New York, 1996), pp. 379–394

    Google Scholar 

  11. J. Chen, J. Stubbe, Nat. Rev. Cancer 5, 102 (2005)

    Article  CAS  Google Scholar 

  12. A. Abedi, N. Safari, V. Amani, S. Tavajohi, S.N. Ostad, Inorg. Chim. Acta 376, 679 (2011)

    Article  CAS  Google Scholar 

  13. Z. Mehri-Lighvan, A. Abedi, M. Bordar, Polyhedron 42, 153 (2012)

    Article  Google Scholar 

  14. B. Notash, V. Amani, N. Safari, S.N. Ostad, A. Abedi, M. Zare Dehnavi, Dalton Trans. 42, 6852 (2013)

    Article  CAS  Google Scholar 

  15. H. Erlenmeyer, H. Ueberwasser, Helv. Chim. Acta 22, 938 (1939)

    Article  CAS  Google Scholar 

  16. H.R. Khavasi, A. Abedi, V. Amani, B. Notash, N. Safari, Polyhedron 27, 1848 (2008)

    Article  CAS  Google Scholar 

  17. G.M. Sheldrick, SHELXTL (Version 5.1), Structure Determination Software Suite (Bruker AXS, Madison, Wisconsin, USA, 1998)

  18. Bruker, Software Package (Version 2.0-1) (Bruker AXS Inc., Madison, Wisconsin, USA, 2005)

  19. G.M. Sheldrick, SHELXTL, v.5.10, Structure Determination Software Suite (Bruker AXS, Madison, Wisconsin, USA, 1998)

  20. G.M. Sheldrick, Acta Crystallogr. A 64, 112 (2008)

    Article  CAS  Google Scholar 

  21. L.J. Farrugia, J. Appl. Cryst. 32, 837 (1999)

    Article  CAS  Google Scholar 

  22. Mercury 1.4.1, Copyright Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, UK, (2001–2005)

  23. J. Marmur, J. Mol. Biol. 3, 585 (1961)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  25. R. Al-Hashemi, N. Safari, S. Amani, V. Amani, A. Abedi, H.R. Khavasi, S.W. Ng, J. Coord. Chem. 63, 3207 (2010)

    Article  CAS  Google Scholar 

  26. A. Abedi, V. Amani, R. Boča, L. Dlháň, H.R. Khavasi, N. Safari, Inorg. Chim. Acta 395, 58 (2013)

    Article  CAS  Google Scholar 

  27. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds Part B: Application in Coordination, Organometallic and Bioinorganic Chemistry (Wiley, New York, 2009)

    Google Scholar 

  28. L.A. Morris, M. Jaspars, J.J. Kettenes-van den Bosch, K. Versluis, A.J.R. Heck, S.M. Kelly, N.C. Price, Tetrahedron 57, 3185 (2001)

    Article  CAS  Google Scholar 

  29. P.V. Bernhardt, P. Comba, D.P. Fairlie, L.R. Gahan, G.R. Hanson, L. Lötzbeyer, Chem. Eur. J. 8, 1527 (2002)

    Article  CAS  Google Scholar 

  30. T. Pintauer, J. Qiu, G. Kickelbick, K. Matyiaszewski, Inorg. Chem. 40, 2818 (2001)

    Article  CAS  Google Scholar 

  31. M. Ghosh, P. Biswas, U. Flörke, K. Nag, Inorg. Chem. 47, 281 (2008)

    Article  CAS  Google Scholar 

  32. A.W. Addison, T.N. Rao, J. Reedijk, J. Van Rijn, G.C. Verschoor, J. Chem. Soc. Dalton Trans. 7, 1349 (1984)

    Article  Google Scholar 

  33. S.Y. Shaban, F.W. Heinemann, R. van Eldik, Eur. J. Inorg. Chem. 21, 3111 (2009)

    Article  Google Scholar 

  34. C.-W. Lee, Z.-K. Chan, T.-R. Chen, J.-D. Chen, Inorg. Chim. Acta 348, 135 (2003)

    Article  CAS  Google Scholar 

  35. R. Al-Hashemi, N. Safari, A. Abedi, B. Notash, V. Amani, H.R. Khavasi, J. Coord. Chem. 62, 2909 (2009)

    Article  CAS  Google Scholar 

  36. M.-J. Oh, H.-J. Kim, S.K. Kang, S.-N. Choi, Y.-M. Lee, Acta Cryst. C64, m153 (2008)

    Google Scholar 

  37. R.D. Willett, G. Pon, C. Nagy, Inorg. Chem. 40, 4342 (2001)

    Article  CAS  Google Scholar 

  38. R. Buchtik, Z. Travnicek, J. Vanco, R. Herchel, Z. Dvorak, Dalton Trans. 40, 9404 (2011)

    Article  CAS  Google Scholar 

  39. E.C. Long, J.K. Barton, Acc. Chem. Res. 23, 271 (1990)

    Article  CAS  Google Scholar 

  40. Y.M. Song, Q. Wu, P.J. Yang, N.N. Luan, L.F. Wang, Y.M. Liu, J. Inorg. Biochem. 100, 1685 (2006)

    Article  CAS  Google Scholar 

  41. L.F. Tan, H. Chao, Y.F. Zhou, L.N. Ji, Polyhedron 26, 3029 (2007)

    Article  CAS  Google Scholar 

  42. L.F. Tan, X.H. Liu, H. Chao, L.N. Ji, J. Inorg. Biochem. 101, 56 (2007)

    Article  CAS  Google Scholar 

  43. Y.J. Liu, H. Chao, Y.X. Yuan, H.J. Yu, L.N. Ji, Inorg. Chim. Acta 359, 3807 (2006)

    Article  CAS  Google Scholar 

  44. R. Rohs, H. Sklenar, J. Biomol. Struct. Dyn. 21, 699 (2004)

    Article  CAS  Google Scholar 

  45. Z. Hu, C. Tong, Anal. Chim. Acta 587, 187 (2007)

    Article  CAS  Google Scholar 

  46. J.R. Lakowicz, Principles of Fluorescence Spectroscopy, 3rd edn. (Springer, New York, 2006)

    Book  Google Scholar 

  47. E. Tselepi-Kalouli, N. Katsaros, J. Inorg. Biochem. 37, 271 (1989)

    Article  CAS  Google Scholar 

  48. G.A. Neyhart, N. Grover, S.R. Smith, W.A. Kalsbeck, T.A. Fairly, M. Cory, H.H. Thorp, J. Am. Chem. Soc. 115, 4423 (1993)

    Article  CAS  Google Scholar 

  49. S. Arounaguiri, B.G. Maiya, Inorg. Chem. 35, 4267 (1996)

    Article  CAS  Google Scholar 

  50. M.J. Waring, J. Mol. Biol. 13, 269 (1965)

    Article  CAS  Google Scholar 

  51. D. Li, M. Zhu, C. Xu, B. Ji, Eur. J. Med. Chem. 46, 588 (2011)

    Article  CAS  Google Scholar 

  52. F. Samari, B. Hemmateenejad, M. Shamsipur, M. Rashidi, H. Samouei, Inorg. Chem. 51, 3454 (2012)

    Article  CAS  Google Scholar 

  53. X.W. Li, X.J. Li, Y.T. Li, Z.Y. Wu, C.W. Yan, J. Photochem. Photobiol. B Biol. 118, 22 (2013)

    Article  Google Scholar 

  54. J. Toneatto, G.A. Argüello, J. Inorg. Biochem. 105, 645 (2011)

    Article  CAS  Google Scholar 

  55. S.S. Bhat, A.A. Kumbhar, H. Heptullah, A.A. Khan, V.V. Gobre, S.P. Gejji, V.G. Puranik, Inorg. Chem. 50, 545 (2011)

    Article  CAS  Google Scholar 

  56. Y. Zhang, Z. Qi, D. Zheng, C. Li, Y. Liu, Biol. Trace Elem. Res. 130, 172 (2009)

    Article  CAS  Google Scholar 

  57. J.R. Lakowicz, G. Weber, Biochemistry 12, 4161 (1973)

    Article  CAS  Google Scholar 

  58. S. Deepa, A.K. Mishra, J. Pharm. Biomed. Anal. 38, 556 (2005)

    Article  CAS  Google Scholar 

  59. J. Min, X. Meng-Xia, Z. Dong, L. Yuan, L. Xiao-Yu, C. Xing, J. Mol. Struct. 692, 71 (2004)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This paper was supported by Islamic Azad University, North Tehran Branch, with many thanks.

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Authors and Affiliations

  1. Department of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, P.O. Box 19585-936, Iran

    Anita Abedi & Mina Yasan

  2. Department of Chemistry, Isfahan University of Technology, Isfahan, 84156/83111, Iran

    Zohreh Mehri-Lighvan

  3. Department of Chemistry, Shahid Beheshti Campus, Farhangian University, Tehran, Iran

    Vahid Amani

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  1. Anita Abedi
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Abedi, A., Mehri-Lighvan, Z., Yasan, M. et al. Novel Cu(II) complexes of bithiazole: structure and biological study. J IRAN CHEM SOC 14, 491–502 (2017). https://doi.org/10.1007/s13738-016-0997-5

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