New 4-[(5-arylidene-2-arylimino-4-oxo-3-thiazolidinyl)methyl]benzoic acids active as protein tyrosine phosphatase inhibitors endowed with insulinomimetic effect on mouse C2C12 skeletal muscle cells

European Journal of Medicinal Chemistry

Volumn 50, Issue , 2012, Pages 332-343

  Ottanà, Rosaria ^a   MacCari, Rosanna ^a   Amuso, Simona ^a   Wolber, Gerhard ^b   Schuster, Daniela ^c   Herdlinger, Sonja ^c   Manao, Giampaolo ^d   Camici, Guido ^d   Paoli, Paolo ^d  

^a UNIVERSITY OF MESSINA   (Italy)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

^c UNIVERSITY OF INNSBRUCK   (Austria)

^d UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Diabetes mellitus; Enzyme inhibitor; Insulinomimetic agent; Molecular docking; Obesity; Protein tyrosine phosphatase

Indexed keywords

4 [[2 (4 METHOXYPHENYLIMINO) 4 OXO 5 (3 PHENOXYBENZYLIDENE) 3 THIAZOLIDINYL]METHYL]BENZOIC ACID; 4 [[2 (4 METHOXYPHENYLIMINO) 4 OXO 5 (4 PHENOXYBENZYLIDENE) 3 THIAZOLIDINYL]METHYL]BENZOIC ACID; 4 [[2 (4 TRIFLUOROMETHYLPHENYLIMINO) 4 OXO 5 (4 PHENOXYBENZYLIDENE) 3 THIAZOLIDINYL]METHYL]BENZOIC ACID; 4 [[2 (TRIFLUOROMETHYLPHENYLIMINO) 4 OXO 5 (3 PHENOXYBENZYLIDENE) 3 THIAZOLIDINYL]METHYL]BENZOIC ACID; 4 [[5 (3 BENZYLOXYBENZYLIDENE) 2 (4 METHOXYPHENYLIMINO) 4 OXO 3 THIAZOLIDINYL]METHYL]BENZOIC ACID; 4 [[5 (3 BENZYLOXYBENZYLIDENE) 2 (4 TRIFLUOROMETHYLPHENYLIMINO) 4 OXO 3 THIAZOLIDINYL]METHYL]BENZOIC ACID; 4 [[5 (4 BENZYLOXYBENZYLIDENE) 2 (4 METHOXYPHENYLIMINO) 4 OXO 3 THIAZOLIDINYL]METHYL]BENZOIC ACID; 4 [[5 (4 BENZYLOXYBENZYLIDENE) 2 (4 TRIFLUOROMETHYLPHENYLIMINO) 4 OXO 3 THIAZOLIDINYL]METHYL]BENZOIC ACID; BENZOIC ACID DERIVATIVE; ERTIPROTAFIB; INSULIN RECEPTOR; ISOPROTEIN; LOW MOLECULAR WEIGHT PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE INHIBITOR; TRODUSQUEMINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ACTIVITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; INSULINOMIMETIC EFFECT; MOLECULAR DOCKING; MOUSE; NONHUMAN; OBESITY; PROTEIN PHOSPHORYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SKELETAL MUSCLE;

ANIMALS; BENZOIC ACIDS; BIOMIMETICS; CELL PROLIFERATION; CELLS, CULTURED; ENZYME INHIBITORS; HUMANS; HYPOGLYCEMIC AGENTS; INSULIN; MICE; MODELS, CHEMICAL; MUSCLE, SKELETAL; PHOSPHORYLATION; PROTEIN CONFORMATION; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; RECEPTOR, INSULIN; THIAZOLIDINES; TYROSINE;

EID: 84858447117     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.02.012     Document Type: Article

References (73)

1. A. Alonso, J. Sasin, N. Bottini, I. Friedberg, A. Osterman, A. Godzik, T. Hunter, J. Dixon, and T. Mustelin Cell 117 2004 699 711
2. T. Hunter Cell 100 2000 113 127
3. B.G. Neel, and N.K. Tonks Curr. Opin. Cell Biol. 9 1997 193 204
4. N.K. Tonks Nat. Rev. Mol. Cell Biol. 7 2006 833 846
5. S. Koren, and I.G. Fantus Best Pract. Res. Cl. En. 21 2007 621 640
6. N. Dub, and M.L. Tremblay Biochim. Biophys. Acta 1754 2005 108 117
7. A. Ostman, C. Hellberg, and F.D. Böhmer Nat. Rev. Cancer 6 2006 307 320
8. V.V. Vintonyak, A.P. Antonchick, D. Rauh, and H. Waldmann Curr. Opin. Chem. Biol. 13 2009 272 283
9. J. Zang, P.L. Yang, and N.S. Gray Nat. Rev. Cancer 9 2009 28 39
10. V.R.H. Huijsduijnen, A. Bombrum, and D. Swinnen Drug Discov. Today 7 2002 1013 1019
11. M.A.T. Blaskovich Cur. Med. Chem. 16 2009 2095 2176
12. P. Heneberg Curr. Med. Chem. 16 2009 706 733
13. V.V. Vintonyak, H. Waldmann, and D. Rauh Bioorg. Med. Chem. 19 2011 2145 2155
14. M. Elchebly, P. Payette, E. Michaliszyn, W. Cromlish, S. Collins, A.L. Loy, D. Normandin, A. Cheng, J. Himms-Hagen, C. Chan, C. Ramachandran, M.J. Gresser, M.L. Tremblay, and B.P. Kennedy Science 283 1999 1544 1548
15. L.D. Klaman, O. Boss, O.D. Peroni, J.K. Kim, J.L. Martino, J.M. Zabolotny, N. Moghal, M. Lubkin, Y.B. Kim, A.H. Sharpe, A. Stricker-Krongrad, G.I. Shulman, B.G. Neel, and B.B. Kahn Mol. Cell. Biol. 20 2000 5479 5489
16. N.K. Tonks FEBS Lett. 546 2003 140 148
17. G. Liu Curr. Opin. Mol. Ther. 6 2004 331 336
18. A. Cheng, N. Uetani, P.D. Simoncic, V.P. Chaubey, A. Lee-Loy, J. McGlade, B.P. Kennedy, and M.L. Tremblay Dev. Cell 2 2002 497 503
19. J.M. Zabolotny, K.K. Bence-Hanulec, A. Stricker-Krongrad, F. Haj, Y. Wang, Y. Minokoshi, Y.B. Kim, J.K. Elmquist, L.A. Tartaglia, B.B. Kahn, and B.G. Neel Dev. Cell 2 2002 489 495
20. T. Tiganis, and A.M. Bennett Biochem. J. 402 2007 1 15
21. K.A. Kenner, E. Anyanwu, J.M. Olefsky, and J. Kusari J. Biol. Chem. 33 1996 19810 19816
22. B.A. Zinker, C.M. Rondinone, J.M. Trevillyan, R.J. Gum, J.E. Clampit, J.F. Waring, N. Xie, D. Wilcox, P. Jacobson, L. Frost, P.E. Kroeger, R.M. Reilly, S. Koterski, T.J. Opgenorth, R.G. Ulrich, S. Crosby, M. Butler, S.F. Murray, R.A. McKay, S. Bhanot, B.P. Monia, and M.R. Jirousek Proc. Natl. Acad. Sci. USA 17 2002 11357 11362
23. M.M. Swarbrick, P.J. Havel, A.A. Levin, A.A. Bremer, K.L. Stanhope, M. Butler, S.L. Booten, J.L. Graham, R.A. Mckay, S.F. Murray, L.M. Watts, B.P. Monia, and S. Bhanot Endocrinology 150 2009 1670 1679
24. T.O. Johnson, J. Ermolieff, and M.R. Jirousek Nat. Rev. Drug Discov. 1 2002 696 709
25. B.P. Montalibet, and B.P. Kennedy Drug Discov. Today Ther. Strateg. 2 2005 129 135
26. A.M. Hennige, N. Stefan, K. Kapp, R. Lehmann, C. Weigert, A. Beck, K. Moeschel, J. Mushack, E. Schleicher, and H.-U. Haring FASEB J. 20 2006 E381 E389
27. G. Sesti Best Pract. Res. Cl. En. 20 2006 665 679
28. J.E. Shaw, R.A. Sicree, and P.Z. Zimmet Diabetes Res. Clin. Pract. 87 2010 4 14
29. A.P. Combs J. Med. Chem. 53 2010 2333 2344
30. S. Lee, and Q. Wang Med. Res. Rev. 27 2007 553 573
31. S. Zhang, and Z.Y. Zhang Drug Discov. Today 12 2007 373 381
32. D.V. Erbe, S. Wang, Y.L. Zhang, K. Harding, L. Kung, M. Tam, L. Stolz, Y. Xing, S. Furey, A. Qadri, L.D. Klaman, and J.F. Tobin Mol. Pharmacol. 67 2005 69 77
33. N. Takahashi, Y. Qi, H.R. Patel, and R.S. Ahima J. Hepatol. 41 2004 391 398
34. K.A. Lantz, S.G. Hart, S.L. Planey, M.F. Roitman, I.A. Ruiz-White, H.R. Wolfe, and M.P. McLane Obesity 18 2010 1516 1523
35. S.K. Pandey, X.X. Yu, L.M. Watts, M.D. Michael, K.W. Sloop, A.R. Rivard, T.A. Leedom, V.P. Manchem, L. Samadzadeh, R.A. McKay, B.P. Monia, and S. Bhanot J. Biol. Chem. 282 2007 14291 14298
36. P. Chiarugi, P. Cirri, F. Marra, G. Raugei, G. Camici, G. Manao, and G. Ramponi Biochem. Biophys. Res. Commun. 238 1997 676 682
37. M.L. Taddei, P. Chiarugi, P. Cirri, D. Talini, G. Camici, G. Manao, G. Raugei, and G. Ramponi Biochem. Biophys. Res. Commun. 270 2000 564 569
38. R. Maccari, and R. Ottanà J. Med. Chem. 55 2012 2 22
39. L.F. Iversen, K.B. Møller, A.K. Pedersen, G.H. Peters, A.S. Petersen, H.S. Andersen, S. Branner, S.B. Mortensen, and N.P.H. Møller J. Biol. Chem. 277 2002 19982 19990
40. A. Bourdeau, N. Dubé, and M.L. Tremblay Curr. Opin. Cell Biol. 17 2005 203 209
41. K.M. Heinon, K.M. Heinonen, F.P. Nestel, E.W. Newell, G. Charette, T.A. Seemayer, M.L. Tremblay, and W.S. Lapp Blood 103 2004 3457 3464
42. S. Galic, C. Hauser, B.B. Kahn, F.G. Haj, B.G. Neel, M.K. Tonks, and T. Tiganis Mol. Cell. Biol. 25 2005 819 829
43. S. Galic, M. Klingler-Hoffmann, M.T. Fodero-Tavoletti, M.A. Puryer, T.-C. Meng, M.K. Tonks, and T. Tiganis Mol. Cell. Biol. 23 2003 2096 2108
44. A. Fukushima, K. Loh, S. Galic, B. Fam, B. Shields, F. Wiede, M.L. Tremblay, M.J. Watt, S. Andrikopoulos, and T. Tiganis Diabetes 59 2010 1906 1914
45. K. Loh, A. Fukushima, X. Zhang, S. Galic, D. Briggs, P.J. Enriori, S. Simonds, F. Wiede, A. Reichenbach, C. Hauser, N.A. Sims, K.K. Bence, S. Zhang, Z.-Y. Zhang, B. Kahn, B.G. Neel, Z.B. Andrews, M.A. Cowley, and T. Tiganis Cell Metab. 14 2011 684 698
46. A.J. Nichols, R.D. Mashal, and B. Balkan Drug Develop. Res. 67 2006 559 566
47. C. Li, X.-P. He, Y.-J. Zhang, Z. Li, L.-X. Gao, X.-X. Shi, J. Xie, J. Li, G.-R. Chen, and Y. Tang Eur. J. Med. Chem. 46 2011 4212 4218
48. L. Tabernero, A.R. Aricescu, E.Y. Jones, and S.E. Szedlacsek FEBS J. 275 2008 867 882
49. G. Scapin, S.B. Patel, J.W. Becker, Q. Wang, C. Desponts, D. Waddleton, K. Skorey, W. Cromlish, C. Bayly, M. Therien, J.Y. Gauthier, C.S. Li, C.K. Lau, C. Ramachandran, B.P. Kennedy, and E. Asante-Appiah Biochemistry 42 2003 11451 11459
50. Y.A. Puius, Y. Zhao, M. Sullivan, D.S. Lawrence, S.C. Almo, and Z.Y. Zhang Proc. Natl. Acad. Sci. USA 94 1997 13420 13425
51. P. Cirri, T. Fiaschi, P. Chiarugi, G. Camici, G. Manao, G. Raugei, and G. Ramponi J. Biol. Chem. 271 1996 2604 2607
52. A.P.R. Zabell, A.D. Schroff, B.E. Bain, R.L. Van Etten, O. Wiest, and C.V. Stauffacher J. Biol. Chem. 281 2006 2604 2607
53. R. Maccari, P. Paoli, R. Ottanà, M. Jacomelli, R. Ciurleo, G. Manao, T. Steindl, T. Langer, M.G. Vigorita, and G. Camici Bioorg. Med. Chem. 15 2007 5137 5149
54. R. Maccari, R. Ottanà, R. Ciurleo, P. Paoli, G. Manao, G. Camici, C. Laggner, and T. Langer ChemMedChem 4 2009 957 962
55. R. Ottanà, R. Maccari, R. Ciurleo, P. Paoli, M. Jacomelli, G. Manao, G. Camici, C. Laggner, and T. Langer Bioorg. Med. Chem. 17 2009 1928 1937
56. R. Ottanà, R. Maccari, M.L. Barreca, G. Bruno, A. Rotondo, A. Rossi, G. Chiricosta, R. Di Paola, L. Saubetin, S. Cuzzocrea, and M.G. Vigorita Bioorg. Med. Chem. 13 2005 4243 4252
57. G. Bruno, L. Costantino, C. Curinga, R. Maccari, F. Monforte, F. Nicol, R. Ottanà, and M.G. Vigorita Bioorg. Med. Chem. 10 2002 1077 1084
58. Y. Momose, K. Meguro, H. Ikeda, C. Hatanaka, S. Oi, and T. Sohada Chem. Pharm. Bull. 39 1991 1440 1445
59. T. Ispida, Y. In, M. Inoue, C. Tanaka, and N. Hamanaka J. Chem. Soc. Perkin Trans. 2 1990 1085 1091
60. U. Iannaccone, A. Bergamaschi, A. Magrini, G. Marino, N. Bottini, P. Lucarelli, E. Bottini, and F. Gloria-Bottini Metab. Clin. Exp. 54 2005 891 894
61. H.L. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne Nucl. Acids Res. 28 2000 235 242
62. D.P. Wilson, Z.-K. Wan, W.-X. Xu, S.J. Kirincich, B.C. Follows, D. Joseph-McCarthy, K. Foreman, A. Moretto, J. Wu, M. Zhu, E. Binnun, Y.-L. Zhang, M. Tam, D.V. Erbe, J. Tobin, X. Xu, L. Leung, A. Shilling, S.Y. Tam, T.S. Mansour, and J. Lee J. Med. Chem. 20 2007 4681 4698
63. M. Zhang, C.V. Stauffacher, D. Lin, and R.L. Van Etten J. Biol. Chem. 273 1998 21714 21720
64. A.P.R. Zabell, A.D. Schroff Jr., B.E. Bain, R.L. Van Etten, O. Wiest, and C.V. Stauffacher J. Biol. Chem. 281 2006 6520 6527
65. G. Jones, P. Willett, and R.C. Glen J. Mol. Biol. 245 1995 43 53
66. G. Wolber, and T. Langer J. Chem. Inf. Model. 45 2005 160 169
67. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Taylor J. Mol. Biol. 267 1997 727 748
68. Molecular operating environment (MOE), version 2010.20, Chemical Computing group, 1010 Sherbrooke St. W, Suite 910, Montreal, Quebec, Canada.
69. T. Seidel, G. Ibis, F. Bendix, and G. Wolber Drug Discov. Today Tecnologies 7 2010 e221 e228
70. G. Wolber, A.A. Dornhofer, and T. Langer J. Comput. Aid. Mol. Des 20 2006 773 788
71. R. Marzocchini, M. Bucciantini, M. Stefani, N. Taddei, M.G.M.M. Thunnissen, P. Nordlund, and G. Ramponi FEBS Lett. 426 1998 52 56
72. U.K. Laemmli Nature 227 1970 680 685
73. FigSys® 2003, A Graphing, Charting and Data Analysis Software Package, is produced by BIOSOFT®, 2D Dolphin Way, Stapleford Cambridge, CB2 5DW, UK.