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Synthesis, spectroscopic characterization, thermal stability and biological studies of mixed ligand complexes of gemifloxacin drug and 2,2′-bipyridine with some transition metals

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Abstract

The mixed ligand Zn(II), Zr(IV), Pd(II), Ce(IV), Th(IV), and U(VI) complexes of gemifloxacin and N-donor 2,2′-bipyridine have been prepared. These complexes have been characterized by elemental, infrared (IR), ultraviolet–visible (UV–Vis), 1H nuclear magnetic resonance (NMR), mass spectroscopy, thermal, molar conductance and magnetic susceptibility analyses. The infrared spectra indicate that gemifloxacin acts as a bidentate deprotonated ligand bound to the metal through the pyridone oxygen and one carboxylate oxygen, whereas the 2,2′-bipyridine coordinates through the two nitrogen atoms. The central metal in each complex is six-coordinate and a slightly distorted octahedral geometry is proposed. The calculated bond length and force constant, F(U=O), in the uranyl complex are 1.751 Å and 641.04 N m−1, respectively. The thermodynamic parameters are calculated from the thermal analysis curves using the Coats–Redfern and Horowitz–Metzger methods. The antibacterial and antifungal activities of the ligand, metal salt and metal complexes have been tested. The data show that the complexes exhibit significant action against some of the four bacterial species but no effect on two species of fungi compared with gemifloxacin. The antitumor activity of the ligands and their complexes has been evaluated against breast (MCF-7) and colon (HCT-116) cancer cells.

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References

  1. I. Turel, Coord. Chem. Rev. 232, 27–47 (2002)

    Article  CAS  Google Scholar 

  2. V.T. Andriole, The quinolones: prospects, in The Quinolones, 3rd edn., ed. by V.T. Andriole (Academic, San Diego, 2000), pp. 477–495

    Chapter  Google Scholar 

  3. J. Kuhlmann, H.G. Schaefer, D. Beermann, Clinical pharmacology, in Quinolone Antibacterials, Handbook of Experimental Pharmacology, vol. 127, ed. by J. Kuhlmann, A. Dalhoff, H.-J. Zeile (Springer, Berlin, 1998), pp. 339–406

  4. D.M. Johnson, R.N. Jones, M.E. Erwin, Diagn. Microbiol. Infect. Dis. 33, 87–91 (1999)

    Article  CAS  Google Scholar 

  5. R. Grossman, J. Rotschafer, J. Tan, Am. J. Med. 118, 29–38 (2005)

    Article  Google Scholar 

  6. R.N. Patel, N. Singh, K.K. Shukla, V.L.N. Gundla, U.K. Chauhan, Spectrochim. Acta, Part A 63, 21–26 (2006)

    Article  CAS  Google Scholar 

  7. B. Viossat, J. Daran, G. Savouret, G. Morgant, F.T. Greenaway, N. Dung, V.A. Pham-Tran, J.R.J. Sorenson, J. Inorg. Biochem. 96, 375–385 (2003)

    Article  CAS  Google Scholar 

  8. F. Dimiza, A.N. Papadopoulos, V. Tangoulis, V. Psycharis, C.P. Raptopoulou, D.P. Kessissoglou, G. Psomas, Dalton Trans. 39, 4517–4528 (2010)

    Article  CAS  Google Scholar 

  9. I. Turel, A. Golobic, A. Klavzar, B. Pihlar, P. Buglyo, E. Tolis, D. Rehder, K. Sepcic, J. Inorg. Biochem. 95, 199–207 (2003)

    Article  CAS  Google Scholar 

  10. M.P. Lopez-Gresa, R. Ortiz, L. Perello, J. Latorre, M. Liu-Gonzalez, S. Garcia-Granda, M. Perez-Priede, E. Canton, J. Inorg. Biochem. 92, 65–74 (2002)

    Article  CAS  Google Scholar 

  11. E.K. Efthimiadou, M.E. Katsarou, A. Karaliota, G. Psomas, J. Inorg. Biochem. 102, 910–920 (2008)

    Article  CAS  Google Scholar 

  12. E.K. Efthimiadou, H. Thomadaki, Y. Sanakis, C.P. Raptopoulou, N. Katsaros, A. Scorilas, A. Karaliota, G. Psomas, J. Inorg. Biochem. 101, 64–73 (2007)

    Article  CAS  Google Scholar 

  13. M.E. Katsarou, E.K. Efthimiadou, G. Psomas, A. Karaliota, D. Vourloumis, J. Med. Chem. 51, 470–478 (2008)

    Article  CAS  Google Scholar 

  14. E.K. Efthimiadou, Y. Sanakis, M. Katsarou, C.P. Raptopoulou, A. Karaliota, N. Katsaros, G. Psomas, J. Inorg. Biochem. 100, 1378–1388 (2006)

    Article  CAS  Google Scholar 

  15. G. Psomas, C.P. Raptopoulou, L. Iordanidis, C. Dendrinou-Samara, V. Tangoulis, D.P. Kessissoglou, Inorg. Chem. 39, 3042–3048 (2000)

    Article  CAS  Google Scholar 

  16. C. Dendrinou-Samara, G. Psomas, C.P. Raptopoulou, D.P. Kessissoglou, J. Inorg. Biochem. 83, 7–16 (2001)

    Article  CAS  Google Scholar 

  17. D.J. Beecher, A.C. Wong, Appl. Environ. Microbiol. 60, 1646–1651 (1994)

    CAS  Google Scholar 

  18. E. Fallik, J. Klein, S. Grinberg, E. Lomaniee, S. Lurie, A. Lalazar, Plant Dis. 77, 985–988 (1993)

    Article  Google Scholar 

  19. T.A. Yousef, O.A. El-Gammal, S.F. Ahmed, G.M. Abu El-Reash, Spectrochim. Acta, Part A 135, 690–703 (2015)

    Article  CAS  Google Scholar 

  20. Y. Saintigny, R.J. Monnat Jr, Sci. Aging Knowl. Environ. 13, 1–10 (2004)

    Google Scholar 

  21. T. Mosmann, J. Immunol. Methods 65, 55–63 (1983)

    Article  CAS  Google Scholar 

  22. K. Saotome, H. Morita, M. Umeda, Toxicol. In Vitro 3, 317–321 (1989)

    Article  CAS  Google Scholar 

  23. A.P. Wilson, in Cytotoxicity and Viability Assays in Animal Cell Culture: A Practical Approach, vol. 1, 3rd edn., ed. by J.R.W. Masters (Oxford University Press, Oxford, 2000)

  24. M.S. Refat, Spectrochim. Acta, Part A 68, 1393–1405 (2007)

    Article  Google Scholar 

  25. G.B. Deacon, R.J. Phillips, Coord. Chem. Rev. 33, 227–250 (1980)

    Article  CAS  Google Scholar 

  26. S.A. Sadeek, W.H. EL-Shwiniy, J. Mol. Struct. 977, 243–253 (2010)

    Article  CAS  Google Scholar 

  27. K. Nakamoto, P.J. McCarthy, S. FuJiwara, Y. Shimura, J. Fujita, C.R. Hare, Y. Saito, Spectroscopy and Structure of Metal Chelate Compounds (Wiley, New York, 1968)

    Google Scholar 

  28. R.M. Silverstein, G.C. Bassler, T.C. Morril, Spectroscopic Identification of Organic Compounds, 5th edn. (Wiley, New York, 1991)

    Google Scholar 

  29. W.M.I. Hassan, M.A. Badawy, G.G. Mohamed, H. Moustafa, S. Elramly, Spectrochim. Acta, Part A 111, 169–177 (2013)

    Article  CAS  Google Scholar 

  30. W.H. Mahmoud, G.G. Mohamed, M.M.I. El-Dessouky, J. Mol. Struct. 1082, 12–22 (2015)

    Article  CAS  Google Scholar 

  31. W.H. Mahmoud, G.G. Mohamed, M.M.I. El-Dessouky, Spectrochim. Acta, Part A 122, 598–608 (2014)

    Article  CAS  Google Scholar 

  32. D. Zhong, Z. Chen, Y. Liu, X. Luo, C. Barta, H. Liang, J. Coord. Chem. 63, 3146–3154 (2010)

    Article  CAS  Google Scholar 

  33. Y. Najajreh, J.M. Perez, C. Navarro-Ranninger, D. Gibson, J. Med. Chem. 45, 5189–5195 (2002)

    Article  CAS  Google Scholar 

  34. P.A. Nguewa, M.A. Fuertes, S. Iborra, Y. Najajeh, D. Gibson, E. Matínez, C. Alonso, J.M. Pérez, J. Inorg. Biochem. 99, 727–736 (2005)

    Article  CAS  Google Scholar 

  35. L.H. Jones, Spectrochim. Acta, Part A 15, 409–411 (1959)

    Article  Google Scholar 

  36. S.P. Mcglynn, J.K. Smith, W.C. Neely, J. Chem. Phys. 35, 105–116 (1961)

    Article  CAS  Google Scholar 

  37. F.D. Rochon, R. Melanson, J.P. Macouet, F. Belanger-Gariepy, A.L. Beauchamp, Inorg. Chim. Acta 108, 17–21 (1985)

    Article  CAS  Google Scholar 

  38. T.G. Appleton, J.R. Hall, S.F. Ralph, Inorg. Chem. 24, 673–677 (1985)

    Article  CAS  Google Scholar 

  39. M.A. Bennett, G.B. Robertson, A. Rokicki, W.A. Wickramasinghe, J. Am. Chem. Soc. 110, 7098–7105 (1988)

    Article  CAS  Google Scholar 

  40. S.A. Sadeek, W.H. EL-Shwiniy, J. Mol. Struct. 981, 130–138 (2010)

    Article  CAS  Google Scholar 

  41. S.A. Sadeek, W.H. EL-Shwiniy, M.S. El-Attar, Spectrochim. Acta, Part A 84, 99–110 (2011)

    Article  CAS  Google Scholar 

  42. B. Macias, M.V. Villa, I. Rubio, A. Castineiras, J. Borras, J. Inorg. Biochem. 84, 163–170 (2001)

    Article  CAS  Google Scholar 

  43. A.L. Ringer, C.D. Sherrill, R.A. King, T.D. Crawford, Int. J. Quantum Chem. 108, 1137–1140 (2008)

    Article  CAS  Google Scholar 

  44. N.N. Greenwood, A. Earnshaw, Chemistry of the Elements, 2nd edn. (Butterworth-Heinemann, London, 1997), pp. 320–321

    Google Scholar 

  45. M.S. Refat, I.M. El-Deen, I. Grabchev, Z.M. Anwer, S. El-Ghol, Spectrochim. Acta, Part A 72, 772–782 (2009)

    Article  Google Scholar 

  46. S.A. Sadeek, W.H. EL-Shwiniy, W.A. Zordok, A.M. EL-Didamony, Spectrochim. Acta Part A 78, 854–867 (2011)

    Article  Google Scholar 

  47. S. Kawahara, Nippon. Rinsho 56, 3096–3099 (1998)

    CAS  Google Scholar 

  48. B. Macias, M. Martinez, A. Sanchez, A. Dominguez-Gil, Int. J. Pharm. 106, 229–235 (1994)

    Article  Google Scholar 

  49. S. Sagdinc, S. Bayarı, J. Mol. Struct. 691, 107–113 (2004)

    Article  CAS  Google Scholar 

  50. A.W. Coats, J.P. Redfern, Nature 201, 68–69 (1964)

    Article  CAS  Google Scholar 

  51. H.H. Horowitz, G. Metzger, Anal. Chem. 35, 1464–1468 (1963)

    Article  CAS  Google Scholar 

  52. S.H. Guzar, Q.H. Jin, Chem. Res. Chin. Univ. 24, 143–147 (2008)

    Article  CAS  Google Scholar 

  53. Z. Chohan, A. Munawar, C. Supuran, Met. Based Drugs 8, 137–143 (2001)

    Article  CAS  Google Scholar 

  54. W. Hanna, M. Moawad, Trans. Met. Chem. 26, 644–651 (2001)

    Article  CAS  Google Scholar 

  55. J. Iqbal, S. Tirmizi, F. Watto, M. Imran, M.H. Watto, S. Sharfuddin, S. Latif, Turk. J. Biol. 30, 1–4 (2006)

    CAS  Google Scholar 

  56. V. Singh, A. Katiyar, S. Singh, Bio Metals 21, 491–501 (2008)

    CAS  Google Scholar 

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Sadeek, S.A., Abd El-Hamid, S.M. & El-Shwiniy, W.H. Synthesis, spectroscopic characterization, thermal stability and biological studies of mixed ligand complexes of gemifloxacin drug and 2,2′-bipyridine with some transition metals. Res Chem Intermed 42, 3183–3208 (2016). https://doi.org/10.1007/s11164-015-2205-0

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