Butyltin(IV) Benzoates: Inhibition of Thioredoxin Reductase, Tumor Cell Growth Inhibition, and Interactions with Proteins

ChemMedChem

Volumn 8, Issue 2, 2013, Pages 256-264

  NavakoskideOliveira, Kely ^a   Andermark, Vincent ^a   vonGrafenstein, Susanne ^b   Onambele, Liliane A ^c   Dahl, Gregor ^c   Rubbiani, Riccardo ^a   Wolber, Gerhard ^d   Gabbiani, Chiara ^e   Messori, Luigi ^f   Prokop, Aram ^c   Ott, Ingo ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b UNIVERSITY OF INNSBRUCK   (Austria)

^c UNIVERSITY HOSPITAL OF COLOGNE   (Germany)

^d FREIE UNIVERSITÄT BERLIN   (Germany)

^e UNIVERSITY OF PISA   (Italy)

^f UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Antitumor agents; Bioorganometallics; Thioredoxin reductases; Tin; Virtual screening

Indexed keywords

ANTINEOPLASTIC AGENT; DI N BUTYLTIN (IV) BIS (3 ACETAMIDO 4 METHYLBENZOATE); DI N BUTYLTIN (IV) BIS (3 ACETAMIDOBENZOATE); DI N BUTYLTIN (IV) BIS (4 ACETAMIDO 3 METHYLBENZOATE); DI N BUTYLTIN (IV) BIS (4 ACETAMIDOBENZOATE); DI N BUTYLTIN (IV) BIS (4 AMINO 3 METHYLBENZOATE); DI N BUTYLTIN (IV) BIS 4 AMINOBENZOATE; DI N BUTYLTIN (IV) BIS 4 CHLOROBENZOATE; DI N BUTYLTIN (IV) BIS [4 (N,N DIMETHYLAMINO)BENZOATE]; THIOREDOXIN REDUCTASE; TRI N BUTYLTIN (IV) 4 METHYLBENZOATE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; ATOMIC ABSORPTION SPECTROMETRY; CANCER CELL CULTURE; CANCER INHIBITION; CELL PROLIFERATION; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; BENZOATES; CATTLE; CELL LINE, TUMOR; CELL PROLIFERATION; HT29 CELLS; HUMANS; NEOPLASMS; ORGANOTIN COMPOUNDS; SERUM ALBUMIN, BOVINE; THIOREDOXIN-DISULFIDE REDUCTASE; TRIALKYLTIN COMPOUNDS;

EID: 84873813842     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201200505     Document Type: Article

References (58)

1. I. Ott, R. Gust, Arch. Pharm. Chem. Life Sci. 2007, 340, 117-126.
2. G. Gasser, I. Ott, N. Metzler-Nolte, J. Med. Chem. 2011, 54, 3-25.
3. M. Patra, G. Gasser, ChemBioChem 2012, 13, 1232-1252.
4. B. Biersack, A. Ahmad, F. H. Sarkar, R. Schobert, Curr. Med. Chem. 2012, 19, 3949-3956.
5. S. Gromer, S. Urig, K. Becker, Med. Res. Rev. 2004, 24, 40-89.
6. G. Powis, D. L. Kirkpatrick, Curr. Opin. Pharmacol. 2007, 7, 392-397.
7. S. Urig, K. Becker, Semin. Cancer Biol. 2006, 16, 452-465.
8. A. Holmgren, J. Lu, Biochem. Biophys. Res. Commun. 2010, 396, 120-124.
9. J. D. Pennington, K. M. Jacobs, L. Sun, G. Bar-Sela, M. Mishra, D. Gius, Curr. Pharm. Des. 2007, 13, 3368-3377.
10. Q. Cheng, T. Sandalova, Y. Lindqvist, E. S. J. Arnér, J. Biol. Chem. 2009, 284, 3998-4008.
11. K. Fritz-Wolf, S. Kehr, M. Stumpf, S. Rahlfs, K. Becker, Nat. Commun. 2011, 2, 383.
12. Y.-C. Lo, T.-P. Ko, W.-C. Su, T.-L. Su, A. H.-J. Wang, J. Inorg. Biochem. 2009, 103, 1082-1092.
13. M. Gielen, A. ElKhloufi, M. Biesemans, B. Mahieu, R. Willem, Bull. Soc. Chim. Belg. 1992, 101, 243-248.
14. M. Gielen, M. Biesemans, R. Willem, Appl. Organomet. Chem. 2005, 19, 440-450.
15. A. Alama, B. Tasso, F. Novelli, F. Sparatore, Drug Discovery Today 2009, 14, 500-508.
16. M. Gielen, Coord. Chem. Rev. 1996, 151, 41-51.
17. S. K. Hadjikakou, N. Hadjiliadis, Coord. Chem. Rev. 2009, 253, 235-249.
18. G. N. Kaluderovic, H. Kommera, E. Hey-Hawkins, R. Paschke, S. Gómez-Ruiz, Metallomics 2010, 2, 419-428.
19. C. Pellerito, P. D′Agati, T. Fiore, C. Mansueto, V. Mansueto, G. Stocco, L. Nagy, L. Pellerito, J. Inorg. Biochem. 2005, 99, 1294-1305.
20. Y. Li, J. Liu, Q. Li, Mol. Carcinog. 2010, 49, 566-581.
21. M. Kemmer, M. Gielen, M. Biesemans, D. deVos, R. Willem, Met.-Based Drugs 1998, 5, 189-196.
22. S. Gómez-Ruiz, G. N. Kaluderovic, S. Prashar, E. Hey-Hawkins, A. Eric, Z. Zizak, Z. D. Juranic, J. Inorg. Biochem. 2008, 102, 2087-2096.
23. R. Rubbiani, S. Can, I. Kitanovic, H. Alborzinia, M. Stefanopoulou, M. Kokoschka, S. Mönchgesang, W. S. Sheldrick, S. Wölfl, I. Ott, J. Med. Chem. 2011, 54, 8646-8657.
24. L. Oehninger, H. Alborzinia, S. Ludewig, K. Baumann, S. Wölfl, I. Ott, ChemMedChem 2011, 6, 2142-2145.
25. S. Hadi, M. Rilyanti, N. Nurhasanah, Mod. Appl. Sci. 2009, 3, 12-17.
26. R. Zhang, J. Sun, C. Ma, J. Organomet. Chem. 2005, 690, 4366-4372.
27. M. M. Amini, A. Azadmehr, V. Alijani, H. R. Khavasi, T. Hajiashrafi, A. N. Kharat, Inorg. Chim. Acta 2009, 362, 355-360.
28. F. P. Pruchnik, M. BańbulŁa, Z. Ciunik, H. Chojnacki, M. Latocha, B. Skop, T. Wilczok, A. Opolski, J. Wietrzyk, A. Nasulewicz, Eur. J. Inorg. Chem. 2002, 3214-3221.
29. W. Rehman, M. K. Baloch, A. Badshah, S. Ali, J. Chin. Chem. Soc. 2005, 52, 231-236.
30. L. Tian, Y. Sun, H. Li, X. Zheng, Y. Cheng, X. Liu, B. Qian, J. Inorg. Biochem. 2005, 99, 1646-1652.
31. C. H. Williams, D. Arscott, S. Müller, B. W. Lennon, M. L. Ludwig, P.-F. Wang, D. M. Veine, K. Becker, H. Schirmer, Eur. J. Biochem. 2000, 267, 6110-6117.
32. A. Varshney, P. Sen, E. Ahmad, M. Rehan, N. Subbarao, R. H. Khan, Chirality 2010, 22, 77-87.
33. A. Bindoli, M. P. Rigobello, G. Scutari, C. Gabbiani, A. Casini, L. Messori, Coord. Chem. Rev. 2009, 253, 1692-1707.
34. S. Nobili, E. Mini, I. Landini, C. Gabbiani, A. Casini, L. Messori, Med. Res. Rev. 2010, 30, 550-580.
35. I. Ott, Coord. Chem. Rev. 2009, 253, 1670-1681.
36. S. Gromer, L. D. Arscott, C. H. Williams, R. H. Schirmer, K. Becker, J. Biol. Chem. 1998, 273, 20096-20101.
37. S. Urig, K. Fritz-Wolf, R. Reau, C. Herold-Mende, K. Toth, E. Davioud-Charvet, K. Becker, Angew. Chem. 2006, 118, 1915-1920; Angew. Chem. Int. Ed. 2006, 45, 1881-1886.
38. R. Rubbiani, I. Kitanovic, H. Alborzinia, S. Can, A. Kitanovic, L. A. Onambele, M. Stefanopoulou, Y. Geldmacher, W. S. Sheldrick, G. Wolber, A. Prokop, S. Wölfl, I. Ott, J. Med. Chem. 2010, 53, 8608-8618.
39. A.-B. Witte, K. Anestal, E. Jerremalm, H. Ehrsson, E. S. J. Arnér, Free Radical Biol. Med. 2005, 39, 696-703.
40. F. Sorrentino, A. Karioti, P. Gratteri, M. P. Rigobello, G. Scutari, L. Messori, A. Bindoli, M. Chioccioli, C. Gabbiani, M. C. Bergonzi, A. R. Bilia, Bioorg. Med. Chem. 2011, 19, 631-641.
41. Y. Hu, S. Urig, S. Koncarevic, X. Wu, M. Fischer, S. Rahlfs, V. Mersch-Sundermann, K. Becker, Biol. Chem. 2007, 388, 1069-1081.
42. J. Lu, L. V. Papp, J. Fang, S. Rodriguez-Nieto, B. Zhivotovsky, A. Holmgren, Cancer Res. 2006, 66, 4410-4418.
43. P. Mura, M. Camalli, A. Bindoli, F. Sorrentino, A. Casini, C. Gabbiani, M. Corsini, P. Zanello, M. P. Rigobello, L. Messori, J. Med. Chem. 2007, 50, 5871-5874.
44. W. Cai, L. Zhang, Y. Song, B. Wang, B. Zhang, X. Cui, G. Hu, Y. Liu, J. Wu, J. Fang, Free Radical Biol. Med. 2012, 52, 257-265.
45. P. J. Goodford, J. Med. Chem. 1985, 28, 849-857.
46. S. Gromer, L. A. Wessjohann, J. Eubel, W. Brandt, ChemBioChem 2006, 7, 1649-1652.
47. H. M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T. N. Bhat, H. Weissig, I. N. Shindyalov, P. E. Bourne, Nucl. Acid. Res. 2000, 28, 235-242.
48. G. Wolber, T. Langer, J. Chem. Inf. Model. 2005, 45, 160-169.
49. G. Wolber, T. Seidel, F. Bendix, T. Langer, Drug Discovery Today 2008, 13, 23-29.
50. G. Wolber, A. A. Dornhofer, T. Langer, J. Comput. Aided Mol. Des. 2006, 20, 773-788.
51. M. S. Klebanov, I. M. Shologon, Zh. Obshch. Khim. 1979, 49, 812-816.
52. D. W. Allen, J. S. Brooks, R. Formstone, A. J. Crowe, P. J. Smith, J. Organomet. Chem. 1978, 156, 359-368.
53. D. L. Alleston, A. G. Davies, J. Chem. Soc. 1962, 2050-2054.
54. A. K. Sawyer, H. G. Kuivila, J. Org. Chem. 1962, 27, 610-614.
55. H. R. Kricheldorf, A. Stricker, D. Langanke, Macromol. Chem. Phys. 2001, 202, 2963-2970.
56. A. Casini, G. Mastrobuoni, C. Temperini, C. Gabbiani, S. Francese, G. Moneti, C. T. Supuran, A. Scozzafava, L. Messori, Chem. Commun. 2007, 156-158.
57. I. Ott, R. Gust, Biometals 2005, 18, 171-177.
58. H. Scheffler, Y. You, I. Ott, Polyhedron 2010, 29, 66-69.