Synthesis, structural characterization and in vitro biological screening of some homoleptic copper(II) complexes with substituted guanidines

European Journal of Medicinal Chemistry

Volumn 48, Issue , 2012, Pages 26-35

  Murtaza, Ghulam ^a   Rauf, Muhammad Khawar ^a   Badshah, Amin ^a   Ebihara, Masahiro ^c   Said, Muhammad ^a   Gielen, Marcel ^b   De Vos, Dick ^d   Dilshad, Erum ^a   Mirza, Bushra ^a  

^a QUAID I AZAM UNIVERSITY   (Pakistan)

^b VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

^c GIFU UNIVERSITY   (Japan)

^d TEVA Pharmachemie   (Netherlands)

Author keywords

Copper(II) complexes; Crystal structures; Cytotoxicity; Human cell lines; N,N ,N trisubstituted guanidines

Indexed keywords

BIS(N PHENYL N' CYCLOHEXYL N'' BENZOYLGUANIDINATO)COPPER; BIS(N,N' DIPHENYL N'' BENZOYLGUANIDINATO)COPPER; BIS[N PHENYL N' (1 NAPHTHYL) N'' BENZOYLGUANIDINATO]COPPER; BIS[N PHENYL N' (2,4 DICHLOROPHENYL) N'' BENZOYLGUANIDINATO]COPPER; BIS[N PHENYL N' (3,4 DICHLOROPHENYL) N'' BENZOYLGUANIDINATO]COPPER; BIS[N PHENYL N' (3,5 DICHLOROPHENYL) N'' BENZOYLGUANIDINATO]COPPER; BIS[N PHENYL N' (N BUTYL) N'' BENZOYLGUANIDINATO]COPPER; BIS[N PHENYL N' (SEC BUTYL) N'' BENZOYLGUANIDINATO]COPPER; CISPLATIN; COPPER COMPLEX; DOXORUBICIN; ETOPOSIDE; FLUOROURACIL; GUANIDINE DERIVATIVE; METHOTREXATE; N PHENYL N' (1 NAPHTHYL) N'' BENZOYLGUANIDINE; N PHENYL N' (2,4 DICHLOROPHENYL) N'' BENZOYLGUANIDINE; N PHENYL N' (3,4 DICHLOROPHENYL) N'' BENZOYLGUANIDINE; N PHENYL N' (3,5 DICHLOROPHENYL) N'' BENZOYLGUANIDINE; N PHENYL N' (N BUTYL) N'' BENZOYLGUANIDINE; N PHENYL N' (SEC BUTYL) N'' BENZOYLGUANIDINE; N PHENYL N' CYCLOHEXYL N'' BENZOYLGUANIDINE; N,N'' DIPHENYL N'' BENZOYLGUANIDINE; NITROGEN; OXYGEN; PACLITAXEL; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; ASSAY; ATOM; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; CYTOTOXICITY TEST; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; HUMAN; HUMAN CELL; MATHEMATICAL ANALYSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SUBSTITUTION REACTION; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; ARTEMIA; CELL LINE, TUMOR; CELL SURVIVAL; COPPER; GUANIDINES; HUMANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; X-RAY DIFFRACTION;

EID: 84856015579     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.11.029     Document Type: Article

References (63)

1. V. Milacic, D. Chen, L. Ronconi, R. Kristin, L. Piwowar, D. Fregona, and Q.P. Dou Cancer Res. 66 21 2006 10478 10486
2. M. Gielen, and E.R.T. Tiekink Metallotherapeutic Drugs and Metal-based Diagnostic Agents 2005 John Wiley and Sons Chichester
3. I. Kostova Anti-Cancer Agents Med. Chem. 6 2006 19 32
4. L. Ronconi, L. Giovagnini, and C. Marzano Inorg. Chem. 44 2005 1867 1881
5. L. Ronconi, C. Marzano, and P. Zanello J. Med. Chem. 49 2006 1648 1657
6. M.F. Ahmad, D. Singh, A. Taiyab, T. Ramakrishna, B. Raman, and C.M. Rao J. Mol. Biol. 382 2008 812 824
7. M.E. Letelier, A.M. Lepe, M. Faundez, J. Salazar, R. Marin, P. Aracena, and H. Speisky Chem. Biol. Interact 151 2005 71 82
8. H.W. Kuo, S.F. Chen, C.C. Wu, D.R. Chen, and J.H. Lee Biol. Trace Elem. Res. 89 2002 1 11
9. M.M. Eatock, A. Schatzlein, and S.B. Kaye Cancer Treat. Rev. 26 2000 191 204
10. E.J. Margalioth, J.G. Schenker, and M. Chevion Cancer 52 1983 868 872
11. S. Brem Cancer Control 6 1999 436 458
12. J. Liu, H. Zhang, C. Chen, H. Deng, T. Lu, and L. Ji Dalton Trans. 1 2003 114 119
13. T.A. Khan, S. Naseem, S.N. Khan, A.U. Khan, and M. Shakir Spectrochim. Acta A 73 2009 622 629
14. R. Nagane, M. Chikira, M. Oumi, H. Shindo, and W.E. Antholine J. Inorg. Biochem. 78 2000 243 249
15. P. Gomez-Saiz, R. Gil-Garcia, M.A. Maestro, J.L. Pizarro, M.I. Arriortua, L. Lezama, T. Rojo, M. Gonzalez-Alvarez, J. Borras, and J. Garcia-Tojal J. Inorg. Biochem. 102 2008 1910 1920
16. P.R. Reddy, K.S. Rao, and B. Satyanarayana Tetrahedron Lett. 47 2006 7311 7315
17. F. Arjmand, B. Mohani, and S. Ahmad Eur. J. Med. Chem. 40 2005 1103 1110
18. A.P. Singh, N.K. Kaushik, A.K. Verma, G. Hundal, and R. Gupta Eur. J. Med. Chem. 44 2009 1607 1614
19. X. Qiao, Z.Y. Ma, C.Z. Xie, F. Xue, Y.W. Zhang, J.Y. Xu, Z.Y. Qiang, J.S. Lou, G.J. Chen, and S.P. Yan J. Inorg. Biochem. 105 2011 728 737
20. G.J. Chen, X. Qiao, P.Q. Qiao, G.J. Xu, J.Y. Xu, J.L. Tian, W. Gu, X. Liu, and S.P. Yan J. Inorg. Biochem. 105 2011 119 126
21. R.G.S. Berlinck, and M.H. Kossuga Nat. Prod. Rep. 22 2005 516 550
22. R.G.S. Berlinck Nat. Prod. Rep. 19 2002 617 649
23. R.G.S. Berlinck Nat. Prod. Rep. 13 1996 377 409
24. R.G.S. Berlinck Nat. Prod. Rep. 16 1999 339 365
25. P.M. Fresneda, S. Delgado, A. Francesch, I. Manzanares, C. Cuevas, and P. Molina J. Med. Chem. 49 2006 1217 1221
26. P.J. Hajduk, S. Boyd, D. Nettesheim, V. Nienaber, J. Severin, R. Smith, D. Davidson, T. Rockway, and S.W. Fesik J. Med. Chem. 43 2000 3862 3866
27. D.M. Evens, K. Sloanstakleff, M. Arvan, and D.P. Guyton Clin. Exp. Metastasis 16 1998 353 357
28. J. Jankun, R.W. Keck, E. Skrzypczak-Jankun, and R. Swierca Cancer Res. 57 1997 559 563
29. J. Chern, Y. Leu, S. Wang, R. Jou, S. Hsu, Y. Liaw, and H. Lin Med. Chem. 40 1997 2276 2286
30. Z. Brzozowski, F. Saczewski, and M. Gdaniec Eur. J. Med. Chem. 37 2002 285 293
31. A.V. Dolzhenko, B.J. Tan, A.V. Dolzhenko, G.N.C. Chiu, and W.K. Chui J. Fluorine Chem. 129 2008 429 434
32. K. Ohara, M. Smietana, A. Restouin, S. Mollard, J. Borg, Y. Collette, and J. Vasseur J. Med. Chem. 50 2007 6465 6475
33. J.H. Chan, and B. Roth J. Med. Chem. 34 1991 550 555
34. S. Cunha, M.B. Costa, H.B. Napolitano, C. Lauriucci, and I. Vecanto Tetrahedron 57 2001 1671 1675
35. U. Schröder, L. Beyer, R. Richter, J. Angulo-Cornejo, M. Castillo-Montoya, and M. Lino-Pacheco Inorg. Chim. Acta 353 2003 59 67
36. J. Binoy, C. James, I.H. Joe, and V.S. Jayakumar J. Mol. Str. 784 2006 32 46
37. S. Herres, A.J. Heuwing, U. Flörke, J. Schneider, and G. Henkel Inorg. Chim. Acta 358 2005 1089 1095
38. Atta-ur-Rahman Nuclear Magnetic Resonance Spectroscopy 1989 National Academy of Higher Education Pakistan 23-24
39. D.A. Powell, P.D. Ramsden, and R.A. Batey J. Org. Chem. 68 2003 2300 2309
40. G. Murtaza, M. Said, M.K. Rauf, M. Ebihara, and A. Badshah Acta Cryst E63 2007 o4664
41. G. Murtaza, Hanif-ur-Rehman, M.K. Rauf, M. Ebihara, and A. Badshah Acta Cryst E65 2009 o343
42. G. Murtaza, M. Ebihara, M. Said, M.K. Rauf, and S. Anwar Acta Cryst E65 2009 o2297 o2298
43. J. García-Tojal, A. García-Orad, J.L. Serra, J.L. Pizarro, L. Lezama, M.I. Arriortua, and T. Rojo J. Inorg. Biochem. 75 1999 45 54
44. J.L. McLaughlin, and L.L. Rogers Drug Inf. J. 32 1998 513 524
45. J.S. Metcalf, J. Lindsay, K.A. Beatie, S. Birmingham, M.L. Saker, A.K. Torokne, and G.A. Codd Toxicon 40 2002 1115 1120
46. M.F. Primik, S. Göschl, M.A. Jacupek, A. Roller, B.K. Keppler, and V.B. Arion Inorg. Chem. 49 2010 11084 11095
47. A. Kellett, M. O'Connor, M. McCann, M. McNamara, P. Lynch, G. Rosair, V. McKee, B. Greaven, M. Walsh, S. McClean, A. Foltyn, D. O'Shea, O. Howe, and M. Devereux Dalton Trans. 40 2011 1024 1027
48. N. Dixit, R.K. Koiri, B.K. Mauya, S.K. Trgun, C. Höbartner, and L. Mishra J. Inorg. Biochem. 105 2011 256 267
49. S. Kashanian, M.M. Khodaei, H. Roshanfekr, N. Shahabadi, A. Rezvani, and G. Mansouri DNA Cell Biol. 30 5 2011 287 296
50. Y. Zhang, J. Jiang, and Y. Chen Polymer 40 1999 6189 6198
51. R. Lakhan, B.P. Sharma, and B.N. Shukla Il Farmaco 55 2000 331 337
52. E. Rodriguez-Fernandez, J.L. Manzano, J.J. Benito, R. Hermosa, E. Monte, and J.J. Criado J. Inorg. Biochem. 99 2005 1558 1572
53. Atta-ur-Rahman, M.I. Choudhary, and W.J. Thomesen Bioassay Techniques for Drug Development 2001 Harwood Academic Publishers Amsterdam 9-25
54. S.E. Blondelle, E. Crooks, J.M. Ostresh, and R.A. Houghten Antimicrob. Agents Chemother. 43 1999 106 114
55. A. Altomare, M.C. Burla, M. Camalli, G.L. Cascarano, C. Giacovazzo, A. Gaugliardi, A.G.G. Moliterni, G. Polidori, and R. Spagna J. Appl. Crystallogr. 32 1999 115 119
56. G.M. Sheldrick SHELXL97 1997 University of Gottingen Germany
57. S. Inayatullah, R. Irum, A. Rehman, M.F. Chaudhary, and B. Mirza Pharm. Biol. 45 2007 397 403
58. Y.P. Keepers, P.E. Pizao, G.J. Peters, J. van Ark-Otte, B. Winograd, and H.M. Pinedo Eur. J. Cancer 27 1991 897 900
59. N. Katsaros, and A. Anagnostopoulou Crit. Rev. Oncol. Hematol. 42 2002 297 308
60. M.R. Boyd Cancer Principles Pract. Oncol. 3 1989 1 12
61. B. Kivack, T. Mert, and H. Tansel Turk. J. Biol. 26 2001 197 200
62. R. Carran, A. Maran, J.M. Montero, L. Fernadozlago, and A. Dominguez Plants Med. Phyto. 21 1987 195 204
63. B.L. Lu, S.G. Zhang, and Y.H. Zhang Acta Pharm. Sin. 15 1980 118 123