Mixed-valence Cu(II)/Cu(I) complex of quinolone ciprofloxacin isolated by a hydrothermal reaction in the presence of l-histidine: Comparison of biological activities of various copper-ciprofloxacin compounds

Journal of Inorganic Biochemistry

Volumn 99, Issue 2, 2005, Pages 432-442

  Drevenšek, Petra ^a   Zupančič, Tatjana ^a   Pihlar, Boris ^a   Jerala, Roman ^b   Kolitsch, Uwe ^c   Plaper, Andreja ^d   Turel, Iztok ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^c UNIVERSITY OF VIENNA   (Austria)

^d KRKA D D   (Slovenia)

Author keywords

Biological activity (antibacterial, DNA gyrase, DNA cleavage); Ciprofloxacin; Electrochemistry (DPP, CV); l Histidine; Mixed valence Cu(I) Cu(II) complex

Indexed keywords

CHLORIDE; CIPROFLOXACIN; COPPER COMPLEX; DNA TOPOISOMERASE (ATP HYDROLYSING); HISTIDINE; OXYGEN; PHENANTHROLINE; QUINOLONE;

ANTIBACTERIAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; ATOMIC PARTICLE; COMPLEX FORMATION; DIFFERENTIAL PULSE POLAROGRAPHY; DNA CLEAVAGE; DRUG ACTIVITY; ENZYME INHIBITION; MEASUREMENT; MOLECULE; POTENTIOMETRY; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; CIPROFLOXACIN; COPPER; CRYSTALLOGRAPHY, X-RAY; DNA GYRASE; DNA, SUPERHELICAL; ELECTROCHEMISTRY; ENZYME INHIBITORS; HISTIDINE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; POLAROGRAPHY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 11144267302     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2004.10.018     Document Type: Article

References (71)

1. J.E.F. Reynolds Martindale - The Extra Pharmacopeia 30th ed. 1993 The Pharmaceutical Press London 145 147
2. P. Ball V.T. Andriole The Quinolones 2000 Academic Press San Diego, CA 1 31
3. G. Sheehan, and N.S.Y. Chew A.R. Ronald D.E. Low Fluoroquinolone Antibiotics 2003 Birkhauser Basel, Switzerland 1 10
4. I. Turel Coord. Chem. Rev. 232 2002 27 47 and the references therein
5. L.-J. Ming Med. Res. Rev. 23 2003 697 762
6. G.J. Brewer Curr. Opin. Chem. Biol. 7 2003 207 212
7. P. Drevenšek, I. Turel, and N. Poklar Ulrih J. Inorg. Biochem. 96 2003 407 415
8. P. Drevenšek, A. Golobič, I. Turel, N. Poklar, and K. Sepčič Acta Chim. Slov. 49 2002 857 870
9. P. Drevenšek, I. Leban, I. Turel, G. Giester, and E. Tillmanns Acta Crystallogr. C 59 2003 m376 m378
10. Z.F. Chen, R.G. Xiong, J.L. Zuo, Z. Guo, X.Z. You, and H.K. Fun J. Chem. Soc., Dalton Trans. 2000 4013 4014
11. Z.F. Chen, R.G. Xiong, J. Zhang, X.T. Chen, Z.L. Xue, and X.Z. You Inorg. Chem. 40 2001 4075 4077
12. Z.-R. Qu, H. Zhao, L.-X. Xing, X.-S. Wang, Z.F. Chen, Z. Yu, R.G. Xiong, and X.-Z. You Eur. J. Inorg. Chem. 2003 2920 2923
13. Z.F. Chen, H. Liang, H.-M. Hu, Y. Li, R.G. Xiong, and X.-Z. You Inorg. Chem. Commun. 6 2003 241 243
14. I. Turel, I. Leban, and N. Bukovec J. Inorg. Biochem. 56 1994 273 282
15. N. Osheroff Biochim. Biophy. Acta 1400 1998 1 2
16. T.D. Gootz, and N. Osheroff D.C. Hooper J.S. Wolfson Quinolone Antimicrobial Agents 1993 American Society for Microbiology Washington DC 139 160
17. L.L. Shen, and A.G. Pernet Proc. Natl. Acad. Sci. USA 82 1985 307 311
18. C. Sissi, M. Andreolli, V. Cecchetti, A. Fravolini, B. Gatto, and M. Palumbo Bioorg. Med. Chem. 6 1998 1555 1561
19. C. Sissi, E. Perdona, E. Domenici, A. Feriani, A.J. Howells, A. Maxwell, and M. Palumbo J. Mol. Biol. 31 2001 195 203
20. G.-S. Son, J.-A. Yeo, J.-M. Kim, S.K. Kim, H.R. Moon, and W. Nam Biophy. Chem. 74 1998 225 236
21. G. Palu, S. Valisena, G. Ciarocchi, B. Gatto, and M. Palumbo Proc. Natl. Acad. Sci. USA 89 1992 9671 9675
22. V.G. Vaidyanthan, and B.U. Nair J. Inorg. Biochem. 93 2003 271 276
23. G. Pratviel, J. Bernadou, and B. Meunier Angew. Chem. Int. Ed. Engl. 34 1995 746 769
24. Z. Otwinowski, and W. Minor Methods Enzymol. 276 1997 307 326
25. G.M. Sheldrick shelx 97, Programs for Crystal Structure Analysis 1998 University of Göttingen Göttingen, Germany
26. Performance Standards for Antimicrobial Disk Susceptibility Tests, fifth ed., Approved standard: NCCLS document M2-A5, vol. 13, No. 24, 940 West Valley Road, Suite 1400, Wayne, Pennsylvania 19087, 1993
27. B. Evertson Acta Crystallogr. B 25 1969 30 41
28. N. Camerman, J.K. Fawcett, T.P.A. Kruck, B. Sarkar, and A. Camerman J. Am. Chem. Soc. 1978 2690 2693
29. P. Deschamps, P.K. Kulkarni, and B. Sarkar Inorg. Chem. 43 2004 3338 3340
30. A. García-Raso, P.M. Deyá, and J.M. Saá J. Org. Chem. 1986 4285 4287
31. E.R. Stadtman, and B.S. Berlett J. Biol. Chem. 1991 17201 17211
32. K. Uchida, and S. Kawakishi J. Biol. Chem. 1994 2405 2410
33. C.D. Smith, J.M. Carney, P.E. Starke-Reed, C.N. Oliver, E.R. Stadtman, R.A. Floyd, and W.R. Markesbery Proc. Natl. Acad. Sci. USA 88 2001 10540 10543
34. C.N. Oliver, B.-W. Ahn, E.J. Moerman, S. Goldstein, and E.R. Stadtman J. Biol. Chem. 262 1987 5488 5491
35. J.R. Requena, D. Groth, G. Legname, E.R. Stadtman, S.B. Prusiner, and R.L. Levine Proc. Natl. Acad. Sci. USA 98 2001 7170 7175
36. S.R. Breeze, and S. Wang Inorg. Chem. 35 1996 3404 3408
37. M. Dunaj-Jurčo, G. Ondrejovič, and M. Melnik Coord. Chem. Rev. 83 1988 1 28
38. J. Kuzelka, S. Mukhopadhyay, B. Spingler, and S.J. Lippard Inorg. Chem. 43 2004 1751 1761
39. L.J. Farrugia J. Appl. Crystallogr. 30 1997 565
40. M.B. Robin, and P. Day Adv. Inorg. Radiochem. 10 1967 247 422
41. R.R. Conry, and K.D. Karlin R.B. King Encyclopedia of Inorganic Chemistry vol. 2 1994 Wiley Chichester, UK 829 840
42. L. Subramanian, and R. Hoffmann Inorg. Chem. 31 1992 1021 1029 and the references therein
43. C. Rensing, and G. Grass FEMS Microbiol. Rev. 27 2003 197 213
44. M. Solioz, and J.V. Stoyanov FEMS Microbiol. Rev. 27 2003 183 195
45. D.K. Saha, S. Padhye, C.E. Anson, and A.K. Powell Trans. Metal Chem. 28 2003 579 584
46. D.K. Saha, S. Padhye, C.E. Anson, and A.K. Powell Inorg. Chem. Commun. 5 2002 1022 1027
47. F.A. Cotton, and G. Wilkinson Advanced Inorganic Chemistry 1972 Interscience Publishers New York
48. H. Sigel, K.H. Scheller, and B. Prijs Inorg. Chim. Acta 66 1982 147 155 and the references therein
49. I. Turel, I. Leban, G. Klintschar, N. Bukovec, and S. Zalar J. Inorg. Biochem. 66 1997 77 82
50. I. Turel, L. Golič, P. Bukovec, and M. Gubina J. Inorg. Biochem. 71 1998 53 60
51. I. Turel, A. Golobič, A. Klavžar, B. Pihlar, P. Buglyó, E. Tolis, D. Rehder, and K. Sepčič J. Inorg. Biochem. 95 2003 199 207
52. L.A. Finney, and T.V. O'Halloran Science 300 2003 931 935
53. J.-Y. Fan, D. Sun, H. Yu, S.M. Kerwin, and L.H. Hurley J. Med. Chem. 38 1995 408 424
54. W.K. Pogozelski, and T.D. Tullius Chem. Rev. 98 1998 1089 1107
55. C.J. Burrows, and J.G. Muller Chem. Rev. 98 1998 1109 1151
56. D.S. Sigman, D.R. Graham, V. D'Aurora, and A.M. Stern J. Biol. Chem. 254 1979 2269 2272
57. D.M. Perrin, A. Mazumder, and D.S. Sigman Chem. Rev. 93 1993 2295 2316
58. T.B. Thederahn, M.D. Kuwabara, T.A. Larsen, and D.S. Sigman J. Am. Chem. Soc. 111 1989 4941 4946
59. T. Oyoshi, and H. Sugiyama J. Am. Chem. Soc. 122 2000 6313 6314
60. P.A.N. Reddy, B.K. Santra, M. Nethaji, and A.R. Chakravarty J. Inorg. Biochem. 98 2004 377 386 and the references therein
61. A. García-Raso, J.J. Fiol, B. Adrover, V. Moreno, I. Mata, E. Espinosa, and E. Molins J. Inorg. Biochem. 95 2003 77 86
62. N. Ramirez-Ramirez, G. Mendoza-Díaz, F. Gutíerrez-Corona, and M. Pedraza-Reyes J. Biol. Inorg. Chem. 3 1998 188 194
63. S. Dhar, P.A.N. Reddy, M. Nethaji, S. Mahadevan, M.K. Saha, and A.R. Chakravarty Inorg. Chem. 41 2002 3469 3476
64. E.S.G. Baron, R.H. De Meio, and F. Klemperer J. Biol. Chem. 112 1936 625 640
65. F. Haber, and J. Weiss Proc. R. Soc. Lond. Ser. A 147 1934 332 351
66. B. Macías, M.V. Villa, I. Rubio, A. Castiñeiras, and J. Borrás J. Inorg. Biochem. 84 2001 163 170
67. I.D. Vilfan, P. Drevenšek, I. Turel, and N. Poklar Ulrih Biochim. Biophy. Acta 1628 2003 111 122
68. L.E. Pope, and D.S. Sigman Proc. Natl. Acad. Sci. USA 81 1984 3 7
69. K. Yamamoto, and S. Kawanishi J. Biol. Chem. 264 1989 15435 15440 and the references therein
70. A. Sreedhara, J.D. Freed, and J.A. Cowan J. Am. Chem. Soc. 122 2000 8814 8824 and the references therein
71. M. Jeżowska-Bojczuk, W. Szczepanik, W. Leśniak, J. Ciesiołka, J. Wrzesiński, and W. Bal Eur. J. Biochem. 269 2002 5547 5556 and the references therein