Metal complexes of thiosemicarbazones for imaging and therapy

Inorganica Chimica Acta

Volumn 389, Issue , 2012, Pages 3-15

  Dilworth, Jonathan R ^a   Hueting, Rebekka ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Complexes; Imaging; Review; Therapy; Thiosemicarbazones

Indexed keywords

AMINES; IMAGING TECHNIQUES; METAL COMPLEXES; PHENOLS; REVIEWS; SINGLE PHOTON EMISSION COMPUTED TOMOGRAPHY; SYNTHESIS (CHEMICAL);

CO-ORDINATION CHEMISTRIES; COMPLEXES; DONOR ATOMS; SPECT IMAGING; TETRADENTATE; THERAPY; THIOSEMICARBAZONES;

LIGANDS;

EID: 84861583035     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2012.02.019     Document Type: Review

References (137)

1. M.W. Bishop, J. Chatt, J.R. Dilworth, G. Kaufman, S. Kim, and J. Zubieta J. Chem. Soc., Chem. Commun. 1977 70
2. K.A. Jensen, and Z. Anorg Allg. Chem. 221 1934 11
3. K.A. Jensen, and Z. Anorg Allg. Chem. 221 1934 6
4. E. Jouad, G. Larcher, M. Allain, A. Riou, G. Bouet, M. Khan, and X. Do Thanh J. Inorg. Biochem. 86 2001 565
5. M. Campbell Coord. Chem. Rev. 15 1975 279
6. T. Lobana, R. Sharma, G. Bawa, and S. Khanna Coord. Chem. Rev. 253 2009 977
7. P.S. Donnelly Dalton Trans. 40 2011 999
8. D. West, A. Liberta, S. Padhye, R. Chikate, P. Sonawane, A. Kumbhar, and R. Yerande Coord. Chem. Rev. 123 1993 49
9. S. Turk, C. Shipman, and J. Drach J. Gen. Virol. 67 1986 1625
10. N. Ryabova, V. Ponomarev, V. Zelentsov, V. Shipilov, and L. Atovmyan J. Struct. Chem. 22 1981 234
11. N. Gomez, D. Santos, R. Vazquez, L. Suescun, A. Mombru, M. Vermeulen, L. Finkielsztein, C. Shayo, A. Moglioni, D. Gambino, and C. Davio ChemMedChem 6 2011 1485
12. D.S. Raja, G. Paramaguru, N.S.P. Bhuvanesh, J.H. Reibenspies, R. Renganathan, and K. Natarajan Dalton Trans. 40 2011 4548
13. J.-Z. Lu, Y.-F. Du, H.-W. Guo, J. Jiang, X.-D. Zeng, and L.-Q. Zang J. Coord. Chem. 64 2011 1229
14. K.O.S. Ferraz, G.M.M. Cardoso, C.M. Bertollo, E.M. Souza-Fagundes, N. Speziali, C.L. Zani, I.C. Mendes, M.A. Gomes, and H. Beraldo Polyhedron 30 2011 315
15. G. Pelosi, F. Bisceglie, F. Bignami, P. Ronzi, P. Schiavone, M.C. Re, C. Casoli, and E. Pilotti J. Med. Chem. 53 2010 8765
16. J.A. Lessa, I.C. Mendes, P.R.O. da Silva, M.A. Soares, R.G. dos Santos, N.L. Speziali, N.C. Romeiro, E.J. Barreiro, and H. Beraldo Eur. J. Med. Chem. 45 2010 5671
17. J.G. da Silva, L.S. Azzolini, S.M.S.V. Wardell, J.L. Wardell, and H. Beraldo Polyhedron 28 2009 2301
18. I.C. Mendes, M.A. Soares, R.G. dos Santos, C. Pinheiro, and H. Beraldo Eur. J. Med. Chem. 44 2009 1870
19. D. Kovala-Demertzi, A. Papageorgiou, L. Papathanasis, A. Alexandratos, P. Dalezis, J.R. Miller, and M.A. Demertzis Eur. J. Med. Chem. 44 2009 1296
20. R. Mahajan, K. Vohra, P. Arora, R. Sharma, and T. Lobana J. Coord. Chem. 63 2010 1220
21. N. Saha, A. Seal, R. Butcher, and N. Saha J. Ind. Chem. Soc. 78 2001 601
22. N. Saha, A. Saha, R. Butcher, S. Chaudhuri, and N. Saha Inorg. Chim. Act. 339 2002 348
23. A.R. Cowley, J.R. Dilworth, P.S. Donnelly, and J. Woollard-Shore Dalton Trans. 2003 748
24. E.A. Enyedy, M.F. Primik, C.R. Kowol, V.B. Arion, T. Kiss, and B.K. Keppler Dalton Trans. 40 2011 5895
25. C. Kowol, R. Berger, R. Eichinger, A. Roller, M. Jakupec, P. Schmidt, V. Arion, and B. Keppler J. Med. Chem. 50 2007 1254
26. S. Abram, C. MaichleMossmer, and U. Abram Polyhedron 17 1998 131
27. J. Grewe, A. Hagenbach, B. Stromburg, R. Alberto, E. Vazquez-Lopez, U. Abram, and Z. Anorg Allg. Chem. 629 2003 303
28. L. Liu, W. Shi, X. Chen, Y. Chen, and P. Cheng Synth. React. Inorg. Met.-Org. Chem. 36 2006 549
29. P. Jansson, P. Sharpe, P. Bernhardt, and D. Richardson J. Med. Chem. 53 2010 5759
30. V. Philip, V. Suni, M. Kurup, and M. Nethaji Polyhedron 24 2005 1133
31. C. Kowol, E. Reisner, I. Chiorescu, V. Arion, M. Galanski, D. Deubel, and B. Keppler Inorg. Chem. 47 2008 11032
32. A. Kumbhar, S. Padhye, D. West, and A. Liberta Trans. Met. Chem. 17 1992 247
33. R. Brockman, J. Thomson, and H. Skipper Canc. Res. 2 1955 7
34. R. Brockman, J. Thomson, M. Bell, and H. Skipper Canc. Res. 16 1956 167
35. Y. Yu, D. Kalinowski, Z. Kovacevic, A. Siafakas, P. Jansson, C. Stefani, D. Lovejoy, P. Sharpe, P. Bernhardt, and D. Richardson J. Med. Chem. 52 2009 5271
36. C. Kowol, R. Trondl, P. Heffeter, V. Arion, M. Jakupec, A. Roller, M. Galanski, W. Berger, and B. Keppler J. Med. Chem. 52 2009 5032
37. B. Booth, K. Agrawal, E. Moore, and A. Sartorelli Canc. Res. 34 1974 1308
38. J. Easmon, G. Purstinger, G. Heinisch, T. Roth, H. Fiebig, W. Holzer, W. Jager, M. Jenny, and J. Hofmann J. Med. Chem. 44 2001 2164
39. C.R. Kowol, R. Eichinger, M.A. Jakupec, M. Galanski, V.B. Arion, and B.K. Keppler J. Inorg. Biochem. 101 2007 1946
40. B. Zeglis, V. Divilov, and J. Lewis J. Med. Chem. 54 2011 2391
41. J. Shao, B. Zhou, B. Chu, and Y. Yen Curr. Canc. Drug Targ. 6 2006 409
42. W. Antholine, J. Knight, H. Whelan, and D. Petering Mol. Pharm. 13 1977 89
43. M. Liu, T. Lin, P. Penketh, and A. Sartorelli J. Med. Chem. 38 1995 4234
44. R. Finch, M. Liu, A. Cory, J. Cory, and A. Sartorelli Adv. Enzyme Regul. 39 1999 3
45. K. Lee, J. Noveroske, and B. Almassian Int. J. Toxicol. 19 2000 85
46. S. Wadler, D. Makower, C. Clairmont, P. Lambert, K. Fehn, and M. Sznol J. Clin. Oncol. 22 2004 1553
47. C. Barker, W. Burgan, D. Carter, K. Camphausen, and P. Tofilon Int. J. Rad. Oncol. Biol. Phys. 63 2005 S170
48. A. Alvero, W. Chen, A. Sartorelli, P. Schwartz, T. Rutherford, and G. Mor J. Soc. Gynecol. Investig. 13 2006 145
49. M. Mackenzie, D. Saltman, H. Hirte, J. Low, C. Johnson, G. Pond, and M. Moore Invest. New Drugs 25 2007 553
50. B. Choi, D. Alberti, W. Schelman, J. Kolesar, J. Thomas, R. Marnocha, J. Eickhoff, S. Ivy, G. Wilding, and K. Holen Canc. Chem. Pharm. 66 2010 973
51. A. Popovic-Bijelic, C.R. Kowol, M.E.S. Lind, J.H. Luo, F. Himo, E.A. Enyedy, V.B. Anion, and A. Graslund J. Inorg. Biochem. 105 2011 1422
52. J. Kolesar, R. Brundage, M. Pomplun, D. Alberti, K. Holen, A. Traynor, P. Ivy, and G. Wilding Canc. Chem. Pharm. 67 2011 393
53. D. Atieh, M. Modiano, L. Shriberg, L. Brafman, M. Szno, and L. Vahdat J. Clin. Oncol. 22 2004 92S
54. S. Attia, J. Kolesar, M. Mahoney, H. Pitot, D. Laheru, J. Heun, W. Huang, J. Eickhoff, C. Erlichman, and K. Holen Invest. New Drugs 26 2008 369
55. J.M. Kolesar, K. Sachidanandam, W.R. Schelman, J. Eickhoff, K.D. Holen, A.M. Traynor, D.B. Alberti, J.P. Thomas, C.R. Chitambar, G. Wilding, and W.E. Antholine Exp. Ther. Med. 2 2011 119 123
56. I. Gojo, M. Tidwell, J. Greer, N. Takebe, K. Seiter, M. Pochron, B. Johnson, M. Sznol, and J. Karp Leuk. Res. 31 2007 1165
57. J. Karp, F. Giles, L. Gojo, L. Morris, J. Greer, B. Johnson, M. Thein, M. Sznol, and J. Low Leuk. Res. 32 2008 71
58. D. Kolinowski, and D. Richardson Pharmacol. Rev. 57 2005 547
59. J. Shao, B. Zhou, A. Di Bilio, L. Zhu, T. Wang, C. Qi, J. Shih, and Y. Yen Mol. Canc. Ther. 5 2006 586
60. C.R. Kowol, R. Trondl, V.B. Arion, M.A. Jakupec, I. Lichtscheidl, and B.K. Keppler Dalton Trans. 39 2010 704
61. C. Cooper, G. Lynagh, K. Hoyes, R. Hider, R. Cammack, and J. Porter J. Biol. Chem. 271 1996 20291
62. C. Austin, and K. Marsh BioEssays 20 1998 215
63. H. Huang, Q. Chen, X. Ku, L. Meng, L. Lin, X. Wang, C. Zhu, Y. Wang, Z. Chen, M. Li, H. Jiang, K. Chen, J. Ding, and H. Liu J. Med. Chem. 53 2010 3048
64. L. Wei, J. Easmon, R.K. Nagi, B.D. Muegge, L.A. Meyer, and J.S. Lewis J. Nucl. Med. 47 2006 2034
65. I. Hall, M. Miller, and D. West Editon edn. 4 1997 89
66. M.C. Miller, C.N. Stineman, J.R. Vance, D.X. West, and I.H. Hall Appl. Organomet. Chem. 13 1999 9
67. N. Le, and D. Richardson Blood 104 2004 2967
68. M.D. Hall, K.R. Brimacombe, M.S. Varonka, K.M. Pluchino, J.K. Monda, J. Li, M.J. Walsh, M.B. Boxer, T.H. Warren, H.M. Fales, and M.M. Gottesman J. Med. Chem. 54 2011 5878
69. C. Neuberg, and W. Neimann Chem. Ber. 35 1902 2054
70. G. Baehr, and Z. Anorg Allg. Chem. 268 1952 351
71. G. Baehr, and Z. Anorg Allg. Chem. 273 1953 325
72. G. Baehr, G. Schleitzer, and Z. Anorg Allg. Chem. 280 1955 161
73. M. Christlieb, and J.R. Dilworth Chem. Eur. J. 12 2006 6194
74. J. Lim, C. Mathias, and M. Green J. Med. Chem. 40 1997 132
75. M. Christlieb, H.S.R. Struthers, P.D. Bonnitcha, A.R. Cowley, and J.R. Dilworth Dalton Trans. 2007 5043
76. J.P. Holland, M.W. Jones, P.D. Bonnitcha, J.S. Lewis, and J.R. Dilworth New J. Chem. 33 2009 1845
77. S.R. Bayly, R.C. King, D.J. Honess, P.J. Barnard, H.M. Betts, J.P. Holland, R. Hueting, P.D. Bonnitcha, J.R. Dilworth, F.I. Aigbirhio, and M. Christlieb J. Nucl. Med. 49 2008 1862
78. B. Paterson, J. Karas, D. Scanlon, J. White, and P. Donnelly Inorg. Chem. 49 2010 1884
79. A. Diaz, I. Garcia, R. Cao, H. Beraldo, M. Salberg, D. West, L. Gonzalez, and E. Ochoa Polyhedron 16 1997 3549
80. Y. Kilany, H. Hamid, and S. Ashry Carbohydr. Res. (Editon edn.) 125 1984 77
81. A. Yokoyama, A. Yamada, Y. Arano, K. Horiuchi, K. Yamamoto, and K. Torizuka J. Nucl. Med. and Allied Sciences 26 1982 159
82. A. Yokoyama, H. Tanaka, A. Yamada, Y Arano, US Patent, 81-302563, 4444743, 1984.
83. K. Alexacou, A. Tenchiu, E. Chrysina, M. Charavgi, I. Kostas, S. Zographos, N. Oikonomakos, and D. Leonidas Bioorg. Med. Chem. 18 2010 7911
84. A.-C. Tenchiu, I.D. Kostas, D. Kovala-Demertzi, and A. Terzis Carbohydr. Res. 344 2009 1352
85. S.I. Pascu, P.A. Waghorn, W.C. Kennedy, R.L. Arrowsmith, S.R. Bayly, J.R. Dilworth, M. Christlieb, R.M. Tyrell, J. Zhong, R.M. Kowalczyk, D. Collison, P.K. Aley, G.C. Churchill, and F.I. Aigbirhio Chem. - An Asian J. 5 2010 506 519
86. S.I. Pascu, P.A. Waghorn, T.D. Conry, B. Lin, H.M. Betts, J.R. Dilworth, R.B. Sim, G.C. Churchill, F.I. Aigbirhio, and J.E. Warren Dalton Trans. 2008 2107
87. R.L. Arrowsmith, J. Zhong, G. Kociok-Kohn, P.A. Waghorn, P. Burgos, J.R. Dilworth, S.W. Botchway, F.I. Aigbirhio, R.M. Tyrrell, S.I. Pascu, Abstracts of Papers, 240th ACS National Meeting, Boston, MA, United States, 2010.
88. A. Yokoyama, Y. Terauchi, K. Horiuchi, H. Tanaka, and T. Odori J. Nucl. Med. 17 1976 816
89. T. Hosotani, A. Yokoyama, Y. Arano, K. Horiuchi, H. Wasaki, H. Saji, and K. Torizuka Int. J. Nucl. Med. Biol. 12 1986 431
90. Y. Arano, Y. Magata, and A. Yokoyama J. Label. Compds Radiopharm. 21 1984 1023
91. R.L. Arrowsmith, P.A. Waghorn, M.A. Jones, A. Bauman, S. Brayshaw, Z. Hu, G. Kociok-Kohn, T. Mindt, R. Tyrrell, S.W. Botchway, J.R. Dilworth, and S.I. Pascu Dalton Trans. 40 2011 6238
92. A.R. Cowley, J.R. Dilworth, P.S. Donnelly, E. Labisbal, and A. Sousa J. Am. Chem. Soc. 124 2002 5270
93. J.L.J. Dearling, and P.J. Blower Chem. Commun. 1998 2531
94. J.P. Holland, P.J. Barnard, D. Collison, J.R. Dilworth, R. Edge, J.C. Green, and E.J.L. McInnes Chem. Eur. J. 14 2008 5890
95. J.P. Holland, P.J. Barnard, D. Collison, J.R. Dilworth, R. Edge, J.C. Green, J.M. Heslop, E.J.L. McInnes, C.G. Salzmann, and A.L. Thompson Eur. J. Inorg. Chem. 2008 3549
96. J.P. Holland, P.J. Barnard, S.R. Bayly, J.R. Dilworth, and J.C. Green Inorg. Chim. Acta 362 2009 402
97. M. Christlieb, J.P. Holland, and J.R. Dilworth Inorg. Chim. Acta 363 2010 1133
98. H.M. Betts, P.J. Barnard, S.R. Bayly, J.R. Dilworth, A.D. Gee, and J.P. Holland Angew. Chem., Int. Ed. 47 2008 8416
99. I. Hall, C. Lackey, T. Kistler, J. Ives, H. Beraldo, L. Ackerman, and D. West Arch. Pharm. 333 2000 217
100. L. Bica, J. Meyerowitz, S. Parker, A. Caragounis, T. Du, B. Paterson, K. Barnham, P. Crouch, A. White, and P. Donnelly Biometals 24 2011 117
101. A. Sartorelli, A. Welch, and B. Booth Fed. Proc. 24 1965 454
102. B. Booth, and A. Sartorelli Nature 210 1966 104
103. A. Sartorelli, and B. Booth Cancer Res. 27 1967 1614
104. P.J. Crouch, L.W. Hung, P.A. Adlard, M. Cortes, V. Lal, G. Filiz, K.A. Perez, M. Nurjono, A. Cragounis, T. Du, K. Laughton, I. Volitakis, A. Bush, Q.-X. Li, C.L. Masters, R. Cappai, R.A. Cherny, P.S. Donnelly, A.R. White, and K.J. Barnham Proc. Natl. Acad. Sci. U S A, Early Ed. 2009 1
105. J.L.J. Dearling, J.S. Lewis, G.E.D. Mullen, M.J. Welch, and P.J. Blower J. Biol. Inorg. Chem. 7 2002 249
106. K.A. Price, P.J. Crouch, I. Volitakis, B.M. Paterson, S. Lim, P.S. Donnelly, and A.R. White Inorg. Chem. 50 2011 9594
107. M. Green, C. Mathias, M. Welch, A. Mcguire, D. Perry, F. Fernandezrubio, J. Perlmutter, M. Raichle, and S. Bergmann J. Nucl. Med. 31 1990 1989
108. M. Green, D. Klippenstein, and J. Tennison J. Nucl. Med. 29 1988 1549
109. M. Shelton, M. Green, C. Mathias, M. Welch, and S. Bergmann Circulation 82 1990 990
110. E.K. John, and M.A. Green J. Med. Chem. 33 1990 1764
111. Y. Fujibayashi, H. Taniuchi, Y. Yonekura, H. Ohtani, J. Konishi, and A. Yokoyama J. Nucl. Med. 38 1997 1155
112. J.L.J. Dearling, J.S. Lewis, G.E.D. Mullen, M.T. Rae, J. Zweit, and P.J. Blower Eur. J. Nucl. Med. 25 1998 788
113. J.S. Lewis, D.W. McCarthy, T.J. McCarthy, Y. Fujibayashi, and M.J. Welch J. Nucl. Med. 40 1999 177
114. R.I. Maurer, P.J. Blower, J.R. Dilworth, C.A. Reynolds, Y. Zheng, and G.E.D. Mullen J. Med. Chem. 45 2002 1420
115. A. Obata, E. Yoshimi, A. Waki, J.S. Lewis, N. Oyama, M.J. Welch, H. Saji, Y. Yonekura, and Y. Fujibayashi Ann. Nucl. Med. 15 2001 499
116. P. Burgman, J. O'Donoghue, J. Lewis, M. Welch, J. Humm, and C. Ling Nucl. Med. Biol. 32 2005 623
117. J.S. Lewis, R. Laforest, T.L. Buettner, S.-K. Song, Y. Fujibayashi, J.M. Connett, and M.J. Welch Proc. Natl. Acad. Sci. U S A 98 2001 1206
118. R. Aft, J. Lewis, F. Zhang, J. Kim, and M. Welch Canc. Res. 63 2003 5496
119. A.L. Vavere, and J.S. Lewis Nucl. Med. Biol. 35 2008 273
120. R. Hueting, V. Kersemans, B. Cornelissen, M. Tredwell, K. Hussein, M. Christlieb, A. Gee, J. Passchier, S. Smart, J. Dilworth, V. Gouverneur, R. Muschel, unpublished results, 2011.
121. P.J. Blower, A.J. Weeks, R.L. Paul, P.K. Marsden, and D.R. Lloyd Eur. J. Nucl. Med. Mol. Imaging 37 2010 330
122. J.S. Lewis, T.L. Sharp, R. Laforest, Y. Fujibayashi, and M.J. Welch J. Nucl. Med. 42 2001 655
123. H. Yuan, T. Schroeder, J.E. Bowsher, L.W. Hedlund, T. Wong, and M.W. Dewhirst J. Nucl. Med. 47 2006 989
124. K.-I. Matsumoto, L. Szajek, M.C. Krishna, J.A. Cook, J. Seidel, K. Grimes, J. Carson, A.L. Sowers, S. English, M.V. Green, S.L. Bacharach, W.C. Eckelman, and J.B. Mitchell Int. J. Oncol. 30 2007 873
125. C.S. Dence, D.E. Ponde, M.J. Welch, and J.S. Lewis Nucl. Med. Biol. 35 2008 713
126. M. Oh, T. Tanaka, M. Kobayashi, T. Furukawa, T. Mori, T. Kudo, S. Fujieda, and Y. Fujibayashi Nucl. Med. Biol. 36 2009 419
127. S. Lewis Jason, P. Herrero, L. Sharp Terry, A. Engelbach John, Y. Fujibayashi, R. Laforest, A. Kovacs, J. Gropler Robert, and J. Welch Michael Nucl. Med. Biol. 43 2002 1557
128. J.L.J. Dearling, and A.B. Packard Nucl. Med. Biol. 37 2010 237
129. R. Hueting, M. Christlieb, J.R. Dilworth, E.G. Garayoa, V. Gouverneur, M.W. Jones, V. Maes, R. Schibli, X. Sun, and D.A. Tourwe Dalton Trans. 39 2010 3620
130. S.R. Bowen, A.J. van der Kogel, M. Nordsmark, S.M. Betzen, and R. Jeraj Nucl. Med. Biol. 38 2011 771
131. F. Dehdashti, P. Grigsby, M. Mintun, J. Lewis, B. Siegel, and M. Welch Int. J. Rad. Oncol. Biol. Phys. 55 2003 1233
132. F. Dehdashti, P. Grigsby, J. Lewis, R. Laforest, B. Siegel, and M. Welch J. Nucl. Med. 49 2008 201
133. J. Lewis, R. Laforest, F. Dehdashti, P. Grigsby, M. Welch, and B. Siegel J. Nucl. Med. 49 2008 1177
134. F. Dehdashti, M. Mintun, J. Lewis, J. Bradley, R. Govindan, R. Laforest, M. Welch, and B. Siegel Eur. J. Nucl. Med. 30 2003 844
135. T. Wong, J. Lacy, N. Petry, T. Hawk, T. Sporn, M. Dewhirst, and G. Vlahovic Am. J. Roentgenol. 190 2008 427
136. K. Chao, W. Bosch, S. Mutic, J. Lewis, F. Dehdashti, M. Mintun, J. Dempsey, C. Perez, J. Purdy, and M. Welch Int. J. Rad. Oncol. Biol. Phys 49 2001 1171
137. D. Dietz, F. Dehdashti, P. Grigsby, R. Malyapa, R. Myerson, J. Picus, J. Ritter, J. Lewis, M. Welch, and B. Siegel Dis. Colon Rectum 51 2008 1641