New ruthenium(II) complexes with N-alkylphenothiazines: Synthesis, structure, in vivo activity as free radical scavengers and in vitro cytotoxicity

European Journal of Medicinal Chemistry

Volumn 45, Issue 9, 2010, Pages 3669-3676

  Krstić, Milena ^a   Sovilj, Sofija P ^b   Grgurić Ipka, Sanja ^b   Radosavljević Evans, Ivana ^c   Borozan, Sunica ^a   Santibanez, Juan Francisco ^d   Kocić, Jelena ^d  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c DURHAM UNIVERSITY   (United Kingdom)

^d UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Antioxidant enzymes; Cytotoxicity; N alkylphenothiazines; Ruthenium complexes; Single crystal X ray diffraction

Indexed keywords

(CP.H)[RUCL3(DMSO)3] C2H5OH; (TF.H2)[RUCL3(DMSO)3]CL 0.5C2H5OH; (TR.H)[RUCL3(DMSO)3] 0.5C2H5OH; CATALASE; MALONALDEHYDE; NITRITE; RUTHENIUM COMPLEX; SCAVENGER; SUPEROXIDE DISMUTASE; THIORIDAZINE; TRIFLUOPERAZINE; UNCLASSIFIED DRUG;

ADENOCARCINOMA; ANIMAL CELL; ARTICLE; BLOOD; BREAST CARCINOMA; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN MCF 7; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ERYTHROCYTE LEVEL; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; INFRARED SPECTROMETRY; MYELOMA CELL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

ANIMALS; ANTINEOPLASTIC AGENTS; CATALASE; CELL LINE, TUMOR; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; FREE RADICAL SCAVENGERS; FREE RADICALS; HUMANS; MALE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PHENOTHIAZINES; RATS; RUTHENIUM; SUPEROXIDE DISMUTASE;

EID: 77955560077     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.05.013     Document Type: Article

References (68)

1. C.G. Hartinger, A. Casini, C. Dyhot, Y.O. Tsybin, L. Messori, and P.J. Dyson J. Inorg. Biochem. 12 2008 2136 2141
2. E. Alessio Chem. Rev. 104 2004 4203 4242
3. F. Wang, J.A. Xu, A. Habtemariam, J. Bella, and P.J. Sadler J. Am. Chem. Soc. 127 2005 17734 17743
4. D. Griffith, S. Cecco, E. Zagrando, A. Bergamo, G. Sava, and C.J. Marmion J. Biol. Inorg. Chem. 13 2008 511 520
5. V.B. Arion, E. Reisner, M. Fremuth, M.A. Jakupec, B.K. Keppler, V.Y. Kukushin, and A.J.L. Pombeiro Inorg. Chem. 42 2003 6024 6031
6. W. Kandioler, C.G. Hartinger, A.A. Nazarov, J. Kasser, R. John, M.A. Jakupec, V.B. Arion, P.J. Dyson, and B.K. Keppler J. Org. Chem. 694 2009 922 929
7. P.J. Dyson, and G. Sava Dalton Trans. 2006 1929 1933
8. S. Grgurić-ipka, C.R. Kowol, S.M. Valiahdi, R. Eichinger, M.A. Jakupec, A. Roller, S. Shova, V.B. Arion, and B.K. Keppler Eur. J. Inorg. Chem. 18 2007 2870 2878
9. C.A. Vock, W.H. Ang, C. Scolaro, A.D. Phillips, L. Lagopoulos, J. Juillerat-Jeanneret, G. Sava, R. Scopelliti, and P.J. Dyson J. Med. Chem. 50 2007 2166 2175
10. A. Dorcier, C.G. Hartinger, R. Scopelliti, R. Fish, B.K. Keppler, and P.J. Dyson J. Inorg. Biochem. 102 2008 1066 1076
11. M.J. Clarke, F. Zhu, and D.R. Frasca Chem. Rev. 99 1999 2511 2533
12. I. Bratsos, B. Serli, E. Zagrando, N. Katsaros, and E. Alessio Inorg. Chem. 46 2007 975 992
13. T.W. Hambley Dalton Trans. 2007 4929 4937
14. C.S. Allardyce, A. Dorcier, C. Scolaro, and P.J. Dyson Appl. Organomet. Chem. 19 2005 1 10
15. C.X. Zhang, and S.J. Lippard Curr. Opin. Chem. Biol. 7 2003 481 489
16. S. Kapitza, M. Pongratz, M.A. Jakupec, P. Heffeter, W. Berger, L. Lackinger, B.K. Keppler, and B. Marian J. Cancer Clin. Oncol. 131 2005 101 120
17. M.A. Jakupec, M. Galanski, V.B. Arion, C.G. Hartinger, and B.K. Keppler Dalton Trans. 2008 183 194
18. M.M.S. Paula, C.T. Pich, F. Petronilho, L.B. Drei, M. Rudnicki, M.R. Oliveira, J.C.F. Moreira, J.A.P. Henriques, C.V. Franco, and F.D. Pizzol Redox Rep. 10 2005 139 143
19. W.T. Schmid, S. Zorbas-Seifried, R.O. John, V.B. Arion, M.A. Jakupec, A. Roller, M. Galanski, I. Shiroscu, H. Zorbas, and B.K. Keppler Inorg. Chem. 46 2007 3645 3656
20. M.J. Clarke Coord. Chem. Rev. 232 2002 69 73
21. A.T. Hoye, J.E. Davore, and P. Vipf Acc. Chem. Res. 41 2008 87 97
22. V. Parikh, M.M. Khan, and S.P. Mahadik Jpn. Psychol. Res. 37 2003 43 51
23. S. Stajković, S.Z. Borozan, and G. Gadjanski-Omerović J. Serb. Chem. Soc. 74 2009 15 25
24. S. Ivanović, S. Borozan, M. Jezdimirović, N. Aleksić, M. Milovanović, M. Tomaević-Canović, and S. Djurdjević Acta Vet. 57 2007 329 340
25. M.E. Goetz, and A. Luch Cancer Lett. 266 2008 73 83
26. T.B. Creczynski-Pasa, V.R. Bonetti, A. Beirith, K. Ckless, M. Konzen, I. Seifriz, M.S. Paula, C.V. Franco, D.W. Filho, and J.B. Calixto J. Inorg. Biochem. 86 2001 587 594
27. E.G. Victor, F. Zanette, M.R. Aguiar, C.S. Aguiar, D.C. Cardoso, M.P. Cristiano, E.L. Streck, and M.M.S. Paula Chem. Biol. Interact. 170 2007 59 66
28. W.L.C. Almeida, D.N. Vitor, M.R.G. Pereira, D.S. De Sa, L.D.G. Alvarez, A.M. Pinheiro, S.L. Costa, M.F.D. Costa, Z.N. Da Rocha, and R.S. El-Bacha J. Chil. Chem. Soc. 52 2007 1240 1243
29. S.C. Mitchell Curr. Drug Targets 7 2006 1181 1189
30. T.A. Ban Prog. Neuropsychopharmacol. 30 2006 429 441
31. W.L. Wilson, L.L. Shane, and J.H. Moyer Antibiotic. Med. Clin. Ther. 6 1959 421 425
32. K.P. Bhargava, and O.M. Chandra Br. J. Pharmacol. Chemother. 21 1963 436 440
33. T. Olivry, and R.S. Mueller Vet. Dermatol. 14 2003 121 146
34. C. Korth, B.C.H. May, F.E. Cohen, and S.B. Prusiner Proc. Natl. Acad. Sci. USA 98 2001 9836 9841
35. T.N. Bansode, J.V. Shelke, and V.G. Dongre Eur. J. Med. Chem. 44 2009 5094 5098
36. Z. Zhelev, H. Ohba, R. Bakalova, V. Hadjimitova, M. Ishikawa, Y. Shinohara, and Y. Baba Cancer Chemother. Pharmacol. 53 2004 267 275
37. N. Motohashi, M. Kawase, K. Satoh, and H. Sakagami Curr. Drug Targets 7 2006 1055 1066
38. J.J. Aaron, M.D.G. Seye, S. Trajkovska, and N. Motohashi Top. Heterocycl. Chem. 16 2009 153 231
39. R. Kroener, M.J. Heeg, and E. Deutsch Inorg. Chem. 27 1988 558 566
40. N.M.M. Gowda, R.K. Vallabhaneni, I. Gajula, and S. Ananda J. Mol. Struct. 407 1997 125 130
41. N.M.M. Gowda, H.L. Pacquette, D.H. Kim, and B. Jayaram J. Mol. Struct. 382 1996 129 135
42. B. Keshavan, P.G. Chandrashekara, and N.M.M. Gowda J. Mol. Struct. 553 2000 193 197
43. B. Keshavan, and K. Gowda J. Indian Chem. Soc. 78 2001 37 38
44. X. Zhang, Y. Xie, W. Yu, Q. Zhao, M. Jiang, and Y. Tian Inorg. Chem. 42 2003 3734 3737
45. S.E. Kidd, T.W. Hambley, A. Hever, M.J. Nelson, and J. Molnar J. Inorg. Biochem. 62 1996 171 181
46. L. Ma, J. Zhang, R. Cai, Z. Chen, L. Weng, and X. Zhou J. Org. Chem. 690 2005 4926 4932
47. W.J. Geary Coord. Chem. Rev. 7 1971 81 122
48. I. Bratsos, A. Bergamo, G. Sava, T. Gianferrara, E. Zangrando, and E. Alessio J. Inorg. Biochem. 102 2008 606 617
49. I.P. Evans, A. Spencer, and G. Wilkinson J. Chem. Soc. Dalton Trans. 1973 204 209
50. E. Alessio, G. Mestroni, G. Nardin, W.M. Attia, M. Calligaris, G. Sava, and S. Zorzet Inorg. Chem. 27 1988 4099 4106
51. S. Geremia, M. Calligaris, Y.N. Kukushkin, A.V. Zinchenko, and V.Y. Kukushkin J. Mol. Struct. 516 2000 49 56
52. F.H. Allen, and W.D.S. Motherwell Acta Crystall. Sec. B Struc. Sci. 58 2000 407 422
53. J.J.H. McDowell Acta Crystall. Sect. B Struct. Crystall. Cryst. Chem. 32 1976 5 10
54. S.P. Fricker, E. Slade, N.A. Powell, O.J. Vaughan, G.R. Henderson, B.A. Murrer, I.L. Megson, S.K. Bisland, and F.W. Flitney Br. J. Pharmacol. 122 1997 1441 1449
55. M. Valko, D. Leibfritz, J. Moncol, M.T.D. Cronin, M. Mazur, and J. Telser Int. J. Biochem. Cell Biol. 39 2007 44 84
56. D.A. Wink, and J.B. Michell Free Radic. Biol. Med. 25 1998 434 456
57. P. Heffeter, M. Pongratz, E. Steiner, P. Chiba, M.A. Jakupec, L. Elbling, B. Marian, W. Korner, F. Sevelda, M. Micksche, B.K. Kepler, and W. Berger J. Pharmacol. Exp. Ther. 312 2005 281 289
58. Scion Corp http://www.scioncorp.com June, 2007
59. G.M. Sheldrick SADABS 1998 University of Göttingen Germany
60. SAINT Plus, Release 6.22 1997-2001 Bruker Analytical Systems Madison, Wisconsin, USA
61. A. Altomare, G. Cascarano, G. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori, and M. Camalli J. Appl. Crystallogr. 27 1994 435
62. P.W. Betteridge, J.R. Carruthers, R.I. Cooper, K. Prout, and D.J. Watkin J. Appl. Cryst. 36 2003 1487
63. H. Aebi Meth. Enzymol. 1984 121 126
64. C.H. Beauchamp, and I. Fridovich Anal. Biochem. 44 1971 276 287
65. J. Stock, and T.L. Dormandy Br. J. Haematol. 20 1971 95 111
66. A.M. Salvati, and L. Tentori Meth. Enzymol. 76 1981 707 715
67. I. Guevara, J. Iwanejko, A. Dembinska-Kiec, J. Pankiewics, A. Wanat, and P. Anna Clin. Chim. Acta 274 1998 177 188
68. D. Bugarski, A. Krstić, S. Mojsilović, M. Vlaki, M. Petakov, G. Jović, N. Stojanović, and P. Milenković Exp. Biol. Med. 232 2006 156 163