Synthesis, cytotoxic and antibacterial studies of p-benzyl-substituted NHC-silver(I) acetate compounds derived from 4,5-di-p-diisopropylphenyl- or 4,5-di-p-chlorophenyl-1H-imidazole

Journal of Organometallic Chemistry

Volumn 749, Issue , 2014, Pages 88-99

  Streciwilk, Wojciech ^a   Cassidy, Jennifer ^a   Hackenberg, Frauke ^a   Müller Bunz, Helge ^a   Paradisi, Francesca ^a   Tacke, Matthias ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Anticancer drugs; Caki 1; Escherichia coli; MCF 7; N Heterocyclic carbene silver complex; Staphylococcus aureus

Indexed keywords

ANTICANCER DRUG; CAKI-1; MCF-7; N-HETEROCYCLIC; STAPHYLOCOCCUS AUREUS;

ALKYLATION; BACTERIA; CELL CULTURE; CELLS; ESCHERICHIA COLI; ORGANIC COMPOUNDS; VOLATILE FATTY ACIDS; X RAY DIFFRACTION;

SILVER COMPOUNDS;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; NEGIBACTERIA; POSIBACTERIA; STAPHYLOCOCCUS AUREUS;

EID: 84885336864     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2013.09.033     Document Type: Article

References (45)

1. L.X. Cubeddu, I.S. Hoffman, N.T. Fuenmayor, and A.L. Finn New Engl. J. Med. 322 1990 810 816
2. J. Reedijk Chem. Commun. 1996 801 806
3. I. Ott, and R. Gust Anticancer Agents Med. Chem. 7 2007 95 110
4. M. Skander, P. Retailleau, B. Bourrié, L. Schio, P. Mailliet, and A. Marinetti J. Med. Chem. 53 2010 2146 2154
5. M. Viciano, E. Mas-Marzá, M. Sanaú, and E. Peris Organometallics 25 2006 3063 3069
6. A.J. Arduengo, R.L. Harlow, and M. Kline J. Am. Chem. Soc. 113 1991 361 363
7. M.L. Teyssot, A.S. Jarrousse, M. Manin, A. Chevry, S. Roche, F. Norre, C. Beaudoin, L. Morel, D. Boyer, R. Mahiou, and A. Gautier Dalton Trans. 2009 6894 6902
8. R. Durmaz, H. Kücükbay, E. Cetinkaya, and B. Cetinkaya Turk. J. Med. Sci. 27 1997 59 61
9. A. Krüger, and M. Albrecht Aust. J. Chem. 64 2011 1113 1117
10. L. Kaps, B. Biersack, H. Müller-Bunz, K. Mahal, J. Münzner, M. Tacke, T. Mueller, and R. Schobert J. Inorg. Biochem. 106 2012 52 58
11. R. Rubbiani, E. Schuh, A. Meyer, J. Lemke, J. Wimberg, N. Metzler-Nolte, F. Meyer, F. Mohr, and I. Ott Med. Chem. Commun. 4 2013 942 948
12. M.L. Teyssot, A.S. Jarrousse, A. Chevry, A. Haze, C. Beaudoin, M. Manin, S.P. Nolan, S. Díez-González, L. Morel, and A. Gautier Chem. Eur. J. 15 2009 314 318
13. L. Oehninger, M. Stefanopoulou, H. Alborzinia, J. Schur, S. Ludewig, K. Namikawa, A. Muñoz-Castro, W. Köster, K. Baumann, S. Wölfl, W.S. Sheldrick, and I. Ott Dalton Trans. 42 2013 1657 1666
14. S. Patil, J. Claffey, A. Deally, B. Gleeson, M. Hogan, L.M. Menéndez Méndez, H. Müller-Bunz, F. Paradisi, and M. Tacke Eur. J. Inorg. Chem. 2010 1020 1031
15. S. Patil, A. Deally, B. Gleeson, H. Müller-Bunz, F. Paradisi, and M. Tacke Appl. Organomet. Chem. 24 2010 781 793
16. S. Patil, K. Dietrich, A. Deally, B. Gleeson, H. Müller-Bunz, F. Paradisi, and M. Tacke Helv. Chim. Acta 93 2010 2347 2364
17. S. Patil, A. Deally, B. Gleeson, F. Hackenberg, H. Müller-Bunz, F. Paradisi, M. Tacke, and Z. Allg Anorg. Chem. 637 2011 386 396
18. S. Patil, and M. Tacke M. Melník, P. Segla, M. Tatarko, Insights into Coordination, Bioinorganic and Applied Inorganic Chemistry 2011 Press of Slovak University of Technology Bratislava 555 565
19. S. Patil, A. Deally, F. Hackenberg, L. Kaps, H. Müller-Bunz, R. Schobert, and M. Tacke Helv. Chim. Acta 94 2011 1551 1562
20. S. Patil, A. Deally, B. Gleeson, H. Müller-Bunz, F. Paradisi, and M. Tacke Metallomics 3 2011 74 88
21. I. Fichtner, D. Behrens, J. Cinatl Jr., M. Michaelis, L.C. Sanders, R. Hilger, B.N. Kennedy, A.L. Reynolds, F. Hackenberg, G. Lally, Susan Quinn, I. McRae, and M. Tacke Lett. Drug Des. Disc. 9 2012 815 822
22. B. Cetinkaya, I. Ozemir, B. Binbasioglu, R. Durmaz, and S. Gunal Arzneim.-Forsch./Drug Res. 49 1999 538 540
23. K.M. Hindi, M.J. Panzner, C.A. Tessier, C.L. Cannon, and W.J. Youngs Chem. Rev. 109 2009 3859 3884
24. W. Liu, and R. Gust Chem. Soc. Rev. 42 2013 755 773
25. L. Oehninger, R. Rubbiani, and I. Ott Dalton Trans. 42 2013 3269 3284
26. A. Melaiye, Z. Sun, K. Hindi, A. Milsted, D. Ely, D.H. Reneker, C.A. Tessier, and W.J. Youngs J. Am. Chem. Soc. 127 2005 2285 2291
27. A. Melaiye, R.S. Simons, A. Milsted, F. Pingitore, C. Wesdemiotis, C.A. Tessier, and W.J. Youngs J. Med. Chem. 47 2004 973 977
28. C.L. Cannon, L.A. Hogue, R.K. Vajravelu, G.H. Capps, A. Ibricevic, K.M. Hindi, A. Kascatan-Nebioglu, M.J. Walter, S.L. Brody, and W.J. Youngs Antimicrob. Agents Chemother. 53 2009 3285 3293
29. S. Ray, R. Mohan, J.K. Singh, M.K. Samantaray, M.M. Shaikh, D. Panda, and P. Ghosh J. Am. Chem. Soc. 129 2007 15042 15053
30. H. Zhu, X. Zhang, X. Liu, X. Wang, G. Liu, A. Usman, and H. Fun Inorg. Chem. Commun. 6 2003 1113 1116
31. J. Liu, P. Galetis, A. Farr, L. Maharaj, H. Samarasinha, A. McGechan, B. Baguley, R. Bowen, S. Berners-Price, and M. McKeage J. Inorg. Biochem. 102 2008 303 310
32. D.A. Medvetz, K.M. Hindi, M.J. Panzner, A.J. Ditto, Y.H. Yun, and W.J. Youngs Metal-Based Drugs 2008 Article ID 384010, 7 pages http://dx.doi.org/10. 1155/2008/384010
33. F. Hackenberg, A. Deally, G. Lally, S. Malenke, H. Müller-Bunz, F. Paradisi, S. Patil, D. Quaglia, and M. Tacke Int. J. Inorg. Chem. 2012 121540 http://dx.doi.org/10.1155/2012/121540
34. F. Hackenberg, G. Lally, H. Müller-Bunz, F. Paradisi, D. Quaglia, W. Streciwilk, and M. Tacke J. Organomet. Chem. 717 2012 123 134
35. F. Hackenberg, G. Lally, H. Müller-Bunz, F. Paradisi, D. Quaglia, W. Streciwilk, and M. Tacke Inorg. Chim. Acta 395 2013 135 144
36. R.C. Clarke, and J.S. Reid Acta Crystallogr. A51 1995 887 897
37. G.M. Sheldrick Acta Crystallogr. A64 2008 112 122
38. A.L. Spek J. Appl. Crystallogr. 36 2003 7 13
39. M. Böesler Chem. Ber. 14 1881 323 330
40. W. Liu, K. Bensdorf, M. Proetto, U. Abram, A. Hagenbach, and R. Gust J. Med. Chem. 24 2011 8605 8615
41. A. Bondi, H.E. Spaulding, E.D. Smith, and C.C. Dietz Am. J. Med. Sci. 213 1947 221 225
42. S.E. Luria Bacteriol. Rev. 11 1947 1 40
43. T. Mosmann J. Immunol. Methods 65 1983 55 63
44. T.R. Sharpe, S.C. Cherkofsky, W.E. Hewes, D.H. Smith, W.A. Gregory, S.B. Haber, M.R. Leadbetter, and J.G. Whitney J. Med. Chem. 28 1985 1188 1194
45. K.M. Hindi, T.J. Siliciano, S. Durmus, M.J. Panzner, D.A. Medvetz, D.V. Reddy, L.A. Hogue, C.E. Hovis, J.K. Hillard, R.J. Mallet, C.A. Tessier, C.L. Cannon, and W.J. Youngs J. Med. Chem. 51 2008 1577 1583