Use of protein tyrosine phosphatase inhibitors as promising targeted therapeutic drugs

Current Medicinal Chemistry

Volumn 16, Issue 6, 2009, Pages 706-733

  Heneberg, Petrhen ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Cancer; CD45; Diabetes mellitus; LAR; Protein tyrosine phosphatase inhibition; PTP1B; SHP 1; SHP 2

Indexed keywords

AMENTOFLAVONE; ANONAINE; ANTIDEPRESSANT AGENT; AURANOFIN; BENZIMIDAZOLE DERIVATIVE; BISPHOSPHONIC ACID DERIVATIVE; DEHYDRODIDEMNIN B; DIHYDROCAROLIC ACID; DYSIDIOLIDE; GALLIUM NITRATE; ISOXAZOLINE DERIVATIVE; KANJONE; KARANJIN; NATURAL PRODUCT; PENITRICIN D; PEPTIDE DERIVATIVE; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE INHIBITOR; PULCHELLALACTAM; QUINONE DERIVATIVE; SHORT HAIRPIN RNA; SMALL INTERFERING RNA; STEVASTELIN DERIVATIVE; STIBOGLUCONATE SODIUM; SURAMIN; TANSHINONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANADATE SODIUM; VANADIC ACID; VIOLACEIN;

AFRICAN TRYPANOSOMIASIS; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; B CELL LYMPHOMA; CANCER INHIBITION; CHEMICAL COMPOSITION; CLINICAL TRIAL; CONCENTRATION RESPONSE; DIABETES MELLITUS; DRUG CLASSIFICATION; DRUG EFFECT; DRUG EFFICACY; DRUG ISOLATION; DRUG MECHANISM; DRUG POTENCY; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME RELEASE; HUMAN; HYPERCALCEMIA; IC 50; LARGE CELL LYMPHOMA; LEISHMANIASIS; NON INSULIN DEPENDENT DIABETES MELLITUS; NONHUMAN; ONCHOCERCIASIS; OSTEOPOROSIS; PAGET BONE DISEASE; PROTEIN EXPRESSION; REVIEW;

ANIMALS; ENZYME INHIBITORS; HUMANS; PROTEIN TYROSINE PHOSPHATASES;

EID: 65649086812     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986709787458407     Document Type: Review

References (225)

1. Charbonneau, H.; Tonks, N. K.; Kumar, S.; Diltz, C. D.; Harrylock, M.; Cool, D. E.; Krebs, E. G.; Fischer, E. H.; Walsh, K. A. Human placenta protein-tyrosine-phosphatase: Amino acid sequence and relationship to a family of receptor-like proteins. Proc. Natl. Acad. Sci. U. S. A., 1989, 86, 5252-5256.
2. Elchebly, M.; Payette, P.; Michaliszyn, E.; Cromlish, W.; Collins, S.; Loy, A. L.; Normandin, D.; Cheng, A.; Himms-Hagen, J.; Chan, C. C.; Ramachandran, C.; Gresser, M. J.; Tremblay, M. L.; Kennedy, B. P. Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. Science, 1999, 283, 1544-1548.
3. Fu, Y.; Galan, J. E. A salmonella protein antagonizes Rac-1 and Cdc42 to mediate host-cell recovery after bacterial invasion. Nature, 1999, 401, 293-297.
4. Koul, A.; Choidas, A.; Treder, M.; Tyagi, A. K.; Drlica, K.; Singh, Y.; Ullrich, A. Cloning and characterization of secretory tyrosine phosphatases of Mycobacterium tuberculosis. J. Bacteriol., 2000, 182, 5425-5432.
5. Guan, K. L.; Dixon, J. E. Protein tyrosine phosphatase activity of an essential virulence determinant in Yersinia. Science, 1990, 249, 553-556.
6. Odenbreit, S.; Püls, J.; Sedlmaier, B.; Gerland, E.; Fischer, W.; Haas, R. Translocation of Helicobacter pylori CagA into gastric epithelial cells by type IV secretion. Science, 2000, 287, 1497-1500.
7. Topffer, S.; Muller-Schiffmann, A.; Matentzoglu, K.; Scheffner, M.; Steger, G. Protein tyrosine phosphatase H1 is a target of the E6 oncoprotein of high-risk genital human papillomaviruses. J. Gen. Virol., 2007, 88, 2956-2965.
8. Malentacchi, F.; Marzocchini, R.; Gelmini, S.; Orlando, C.; Serio, M.; Ramponi, G.; Raugei, G. Up-regulated expression of low molecular weight protein tyrosine phosphatases in different human cancers. Biochem. Biophys. Res. Commun., 2005, 334, 875-883.
9. c-src by overexpression of a protein tyrosine phosphatase. Nature, 1992, 359, 336-339.
10. LaForgia, S.; Morse, B.; Levy, J.; Barnea, G.; Cannizzaro, L. A.; Li, F.; Nowell, P. C.; Boghosian-Sell, L.; Glick, J.; Weston, A.; Harris, C. C.; Drabkin, H.; Patterson, D.; Croce, C. M.; Schlessinger, J.; Huebner, K. Receptor protein-tyrosine phosphatase-γ is a candidate tumor suppressor gene at human-chromosome region 3p21. Proc. Natl. Acad. Sci. U. S. A., 1991, 88, 5036-5040.
11. Gensler, M.; Buschbeck, M.; Ullrich, A. Negative regulation of HER2 signaling by the PEST-type protein-tyrosine phosphatase BDP1. J. Biol. Chem., 2004, 279, 12110-12116.
12. Zhu, J. H.; Chen, R.; Yi, W.; Cantin, G. T.; Fearns, C.; Yang, Y.; Yates, J. R., III; Lee, J. D. Protein tyrosine phosphatase PTPN13 negatively regulates Her2/ErbB2 malignant signaling. Oncogene, 2008, 27, 2525-2531.
13. Sato, T.; Irie, S.; Kitada, S.; Reed, J. C. Fap-1 - A protein-tyrosine-phosphatase that associates with Fas. Science, 1995, 268, 411-415.
14. Bjorge, J. D.; Pang, A.; Fujita, D. J. Identification of protein-tyrosine phosphatase 1B as the major tyrosine phosphatase activity capable of dephosphorylating and activating c-Src in several human breast cancer cell lines. J. Biol. Chem., 2000, 275, 41439-41446.
15. Wang, Z. H.; Shen, D.; Parsons, D. W.; Bardelli, A.; Sager, J.; Szabo, S.; Ptak, J.; Silliman, N.; Peters, B. A.; van der Heijden, M. S.; Parmigiani, G.; Yan, H.; Wang, T. L.; Riggins, G.; Powell, S. M.; Willson, J. K.; Markowitz, S.; Kinzler, K. W.; Vogelstein, B.; Velculescu, V. E. Mutational analysis of the tyrosine phosphatome in colorectal cancers. Science, 2004, 304, 1164-1166.
16. Imoto, M.; Kakeya, H.; Sawa, T.; Hayashi, C.; Hamada, M.; Takeuchi, T.; Umezawa, K. Dephostatin, a novel protein tyrosine phosphatase inhibitor produced by Streptomyces. I. Taxonomy, isolation, and characterization. J. Antibiot., 1993, 46, 1342-1346.
17. Ferreira, C. V.; Justo, G. Z.; Souza, A. C.; Queiroz, K. C.; Zambuzzi, W. F.; Aoyama, H.; Peppelenbosch, M. P. Natural compounds as a source of protein tyrosine phosphatase inhibitors: Application to the rational design of small-molecule derivatives. Biochimie, 2006, 88, 1859-1873.
18. Gunasekera, S. P.; McCarthy, P. J.; KellyBorges, M.; Lobkovsky, E.; Clardy, J. Dysidiolide: A novel protein phosphatase inhibitor from the Caribbean sponge Dysidea etheria de Laubenfels. J. Am. Chem. Soc., 1996, 118, 8759-8760.
19. Alvi, K. A.; Casey, A.; Nair, B. G. Pulchellalactam: A CD45 protein tyrosine phosphatase inhibitor from the marine fungus Corollospora pulchella. J. Antibiot., 1998, 51, 515-517.
20. Li, W. R.; Lin, S. T.; Hsu, N. M.; Chern, M. S. Efficient total synthesis of pulchellalactam, a CD45 protein tyrosine phosphatase inhibitor. J. Org. Chem., 2002, 67, 4702-4706.
21. Alvi, K. A.; Nair, B. G.; Rabenstein, J.; Davis, G.; Baker, D. D. CD45 tyrosine phosphatase inhibitory components from Aspergillus niger. J. Antibiot., 2000, 53, 110-113.
22. Morino, T.; Masuda, A.; Yamada, M.; Nishimoto, M.; Nishikiori, T.; Saito, S.; Shimada, N. Stevastelins, novel immunosuppressants produced by Penicillium. J. Antibiot., 1994, 47, 1341-1343.
23. Hamaguchi, T.; Masuda, A.; Morino, T.; Osada, H. Stevastelins, a novel group of immunosuppressants, inhibit dual-specificity protein phosphatases. Chem. Biol., 1997, 4, 279-286.
24. Ramana, M. M. V.; Potnis, P. V. Tandem acylation-cycloalkylation with cyclohexene 1-acetic acid: A new entry to aporphine alkaloids. Tetrahedron Lett., 1996, 37, 1671-1674.
25. Kuo, R. Y.; Chang, F. R.; Chen, C. Y.; Teng, C. M.; Yen, H. F.; Wu, Y. C. Antiplatelet activity of N-methoxycarbonyl aporphines from Rollinia mucosa. Phytochemistry, 2001, 57, 421-425.
26. Montenegro, H.; Gutiérrez, M.; Romero, L. I.; Ortega-Barr-acia, E.; Capson, T. L.; Rios, L. C. Aporphine alkaloids from Guatteria spp. with leishmanicidal activity. Planta Med., 2003, 69, 677-679.
27. Miski, M.; Shen, X.; Cooper, R.; Gillum, A. M.; Fisher, D. K.; Miller, R. W.; Higgins, T. J. Aporphine Alkaloids, Cd45 Protein-Tyrosine-Phosphatase Inhibitors, from Rollinia ulei. Bioorg. Med. Chem. Lett., 1995, 5, 1519-1522.
28. Na, M.; Kim, K. A.; Oh, H.; Kim, B. Y.; Oh, W. K.; Ahn, J. S. Protein tyrosine phosphatase 1B inhibitory activity of amentoflavone and its cellular effect on tyrosine phosphorylation of insulin receptors. Biol. Pharm. Bull., 2007, 30, 379-381.
29. Guruvayoorappan, C. S.; Kuttan, G. Amentoflavone inhibits experimental tumor metastasis through a regulatory mechanism involving MMP-2, MMP-9, prolyl hydroxylase, lysyl oxidase, VEGF, ERK-1, ERK-2, STAT-1, nm23 and cytokines in lung tissues of C57BL/6 Mice. Immunopharmacol. Immunotoxicol., 2008, 1-17.
30. Ahmad, G.; Mishra, P. K.; Gupta, P.; Yadav, P. P.; Tiwari, P.; Tamrakar, A. K.; Srivastava, A. K.; Maurya, R. Synthesis of novel benzofuran isoxazolines as protein tyrosine phosphatase 1B inhibitors. Bioorg. Med. Chem. Lett., 2006, 16, 2139-2143.
31. Han, Y. M.; Oh, H.; Na, M.; Kim, B. S.; Oh, W. K.; Kim, B. Y.; Jeong, D. G.; Ryu, S. E.; Sok, D.-E.; Ahn, J. S. PTP1B inhibitory effect of abietane diterpenes isolated from Salvia miltiorrhiza. Biol. Pharm. Bull., 2005, 28, 1795-1797.
32. Lee, S.; Wang, Q. Recent development of small molecular specific inhibitor of protein tyrosine phosphatase 1B. Med. Res. Rev., 2007, 27, 553-573.
33. Bromberg, N.; Justo, G. Z.; Haun, M.; Duran, N.; Ferreira, C. V. Violacein cytotoxicity on human blood lymphocytes and effect on phosphatases. J. Enzyme Inhib. Med. Chem., 2005, 20, 449-454.
34. Pallen, C. J.; Wang, H.; Lim, K. L.; Yeo, S. L.; Wang, Y.; Tan, Y. H. WO/ 2002/020525, 2002.
35. + channels in mice lacking protein tyrosine phosphatase ε. EMBO J., 2000, 19, 4036-4045.
36. Kagamizono, T.; Hamaguchi, T.; Ando, T.; Sugawara, K.; Adachi, T.; Osada, H. Phosphatoquinones A and B, novel tyrosine phosphatase inhibitors produced by Streptomyces sp. J. Antibiot., 1999, 52, 75-80.
37. Cebula, R. E.; Blanchard, J. L.; Boisclair, M. D.; Pal, K.; Bockovich, N. J. Synthesis and phosphatase inhibitory activity of analogs of sulfircin. Bioorg. Med. Chem. Lett., 1997, 7, 2015-2020.
38. Hamaguchi, T.; Takahashi, A.; Kagamizono, T.; Manaka, A.; Sato, M.; Osada, H. Synthesis and characterization of a potent and selective protein tyrosine phosphatase inhibitor, 2-[(4-methylthiopyridin-2-yl)methylsufinyl]benzimidazole. Bioorg. Med. Chem. Lett., 2000, 10, 2657-2660.
39. Hamaguchi, T.; Takahashi, A.; Manaka, A.; Sato, M.; Osada, H. TU-572, a potent and selective CD45 inhibitor, suppresses IgE-mediated anaphylaxis and murine contact hypersensitivity reactions. Int. Arch. Allergy Immunol., 2001, 126, 318-324.
40. Urbanek, R. A.; Suchard, S. J.; Steelman, G. B.; Knappenberger, K. S.; Sygowski, L. A.; Veale, C. A.; Chapdelaine, M. J. Potent reversible inhibitors of the protein tyrosine phosphatase CD45. J. Med. Chem., 2001, 44, 1777-1793.
41. Wrobel, J.; Sredy, J.; Moxham, C.; Dietrich, A.; Li, Z. N.; Sawicki, D. R.; Seestaller, L.; Wu, L.; Katz, A.; Sullivan, D.; Tio, C.; Zhang, Z. Y. PTP1B inhibition and antihyperglycemic activity in the ob/ob mouse model of novel 11-arylbenzo[b] naphtho[2,3-d]furans and 11-arylbenzo[b] naphtho [2,3-d] thiophenes. J. Med. Chem., 1999, 42, 3199-3202.
42. Sohn, J.; Kiburz, B.; Li, Z. T.; Deng, L.; Safi, A.; Pirrung, M. C.; Rudolph, J. Inhibition of Cdc25 phosphatases by indolyldihydroxyquinones. J. Med. Chem., 2003, 46, 2580-2588.
43. Chen, Y. T.; Xie, J.; Seto, C. T. Peptidic alpha-ketocarboxylic acids and sulfonamides as inhibitors of protein tyrosine phosphatases. J. Org. Chem., 2003, 68, 4123-4125.
44. Liu, G.; Xin, Z. L.; Pei, Z. G.; Hajduk, P. J.; Abad-Zapatero, C.; Hutchins, C. W.; Zhao, H. Y.; Lubben, T. H.; Ballaron, S. J.; Haasch, D. L.; Kaszubska, W.; Rondinone, C. M.; Trevillyan, J. M.; Jirousek, M. R. Fragment screening and assembly: A highly efficient approach to a selective and cell active protein tyrosine phosphatase 1B inhibitor. J. Med. Chem., 2003, 46, 4232-4235.
45. Liotta, A. S.; Kole, H. K.; Fales, H. M.; Roth, J.; Bernier, M. A synthetic tris-sulfotyrosyl dodecapeptide analogue of the insulin receptor 1146-kinase domain inhibits tyrosine dephosphorylation of the insulin receptor in situ. J. Biol. Chem., 1994, 269, 22996-23001.
46. Hiriyanna, K. T.; Buck, W. R.; Shen, S. S.; Ingebritsen, T. S. Thiophosphorylated RCM-lysozyme, an active site-directed protein tyrosine phosphatase inhibitor, inhibits G2/M transition during mitotic cell cycle and uncouples MPF activation from G2/M transition. Exp. Cell Res., 1995, 216, 21-29.
47. Jenkins, K. E.; Higson, A. P.; Seeberger, P. H.; Caruthers, M. H. Solid-phase synthesis and biochemical studies of O-boranophosphopeptides and O-dithiophosphopeptides. J. Am. Chem. Soc., 2002, 124, 6584-6593.
48. Marseigne, I.; Dor, A.; Begue, D.; Reibaud, M.; Zundel, J. L.; Blanchard, J. C.; Pelaprat, D.; Roques, B. P. Synthesis and biological activity of CCK26-33-related analogues modified in position 31. J. Med. Chem., 1988, 31, 966-970.
49. Kole, H. K.; Akamatsu, M.; Ye, B.; Yan, X.; Barford, D.; Roller, P. P.; Burke, T. R., Jr. Protein-tyrosine phosphatase inhibition by a peptide containing the phosphotyrosyl mimetic, L-O-malonyltyrosine. Biochem. Biophys. Res. Commun., 1995, 209, 817-822.
50. Burke, T. R., Jr.; Ye, B.; Akamatsu, M.; Ford, H., Jr.; Yan, X.; Kole, H. K.; Wolf, G.; Shoelson, S. E.; Roller, P. P. 4′-O-[2-(2-fluoromalonyl)]-L-tyrosine: A phosphotyrosyl mimic for the preparation of signal transduction inhibitory peptides. J. Med. Chem., 1996, 39, 1021-1027.
51. Burke, T. R., Jr.; Kole, H. K.; Roller, P. P. Potent inhibition of insulin receptor dephosphorylation by a hexamer peptide containing the phosphotyrosyl mimetic F2Pmp. Biochem. Biophys. Res. Commun., 1994, 204, 129-134.
52. Easty, D.; Gallagher, W.; Bennett, D. C. Protein tyrosine phosphatases, new targets for cancer therapy. Curr. Cancer Drug Targets, 2006, 6, 519-532.
53. Chen, L.; Wu, L.; Otaka, A.; Smyth, M. S.; Roller, P. P.; Burke, T. R.; Denhertog, J.; Zhang, Z. Y. Why is phosphonodifluoromethyl phenylalanine a more potent inhibitory moiety than phosphonomethyl phenylalanine toward protein-tyrosine phosphatases. Biochem. Biophys. Res. Commun., 1995, 216, 976-984.
54. Shen, K.; Keng, Y. F.; Wu, L.; Guo, X. L.; Lawrence, D. S.; Zhang, Z. Y. Acquisition of a specific and potent PTP1B inhibitor from a novel combinatorial library and screening procedure. J. Biol. Chem., 2001, 276, 47311-47319.
55. Park, J.; Pei, D. trans-Beta-nitrostyrene derivatives as slow-binding inhibitors of protein tyrosine phosphatases. Biochemistry, 2004, 43, 15014-15021.
56. Moran, E. J.; Sarshar, S.; Cargill, J. F.; Shahbaz, M. M.; Lio, A.; Mjalli, A. M. M.; Armstrong, R. W. Radio-frequency Tag encoded combinatorial library method for the discovery of tripeptide-substituted cinnamic acid inhibitors of the protein-tyrosine-phosphatase PTP1B. J. Am. Chem. Soc., 1995, 117, 10787-10788.
57. Fu, H.; Park, J.; Pei, D. Peptidyl aldehydes as reversible covalent inhibitors of protein tyrosine phosphatases. Biochemistry, 2002, 41, 10700-10709.
58. Bleasdale, J. E.; Ogg, D.; Palazuk, B. J.; Jacob, C. S.; Swanson, M. L.; Wang, X. Y.; Thompson, D. P.; Conradi, R. A.; Mathews, W. R.; Laborde, A. L.; Stuchly, C. W.; Heijbel, A.; Bergdahl, K.; Bannow, C. A.; Smith, C. W.; Svensson, C.; Liljebris, C.; Schostarez, H. J.; May, P. D.; Stevens, F. C.; Larsen, S. D. Small molecule peptidomimetics containing a novel phosphotyrosine bioisostere inhibit protein tyrosine phosphatase 1B and augment insulin action. Biochemistry, 2001, 40, 5642-5654.
59. Taing, M.; Keng, Y. F.; Shen, K.; Wu, L.; Lawrence, D. S.; Zhang, Z. Y. Potent and highly selective inhibitors of the protein tyrosine phosphatase 1B. Biochemistry, 1999, 38, 3793-3803.
60. Kole, H. K.; Smyth, M. S.; Russ, P. L.; Burke, T. R., Jr. Phosphonate inhibitors of protein-tyrosine and serine/threonine phosphatases. Biochem. J., 1995, 311, 1025-1031.
61. Sarmiento, M.; Wu, L.; Keng, Y. F.; Song, L.; Luo, Z.; Huang, Z.; Wu, G. Z.; Yuan, A. K.; Zhang, Z. Y. Structure-based discovery of small molecule inhibitors targeted to protein tyrosine phosphatase 1B. J. Med. Chem., 2000, 43, 146-155.
62. Murthy, V. S.; Kulkarni, V. M. Molecular modeling of protein tyrosine phosphatase 1B (PTP 1B) inhibitors. Bioorg. Med. Chem., 2002, 10, 897-906.
63. Ghosh, J.; Miller, R. A. Suramin, an experimental chemotherapeutic drug, irreversibly blocks T cell CD45-protein tyrosine phosphatase in vitro. Biochem. Biophys. Res. Commun., 1993, 194, 36-44.
64. Abdo, M.; Liu, S.; Zhou, B.; Walls, C. D.; Wu, L.; Knapp, S.; Zhang, Z. Y. Seleninate in place of phosphate: Irreversible inhibition of protein tyrosine phosphatases. J. Am. Chem. Soc., 2008, 130, 13196-13197.
65. Lazo, J. S.; Aslan, D. C.; Southwick, E. C.; Cooley, K. A.; Ducruet, A. P.; Joo, B.; Vogt, A.; Wipf, P. Discovery and biological evaluation of a new family of potent inhibitors of the dual specificity protein phosphatase Cdc25. J. Med. Chem., 2001, 44, 4042-4049.
66. Malamas, M. S.; Sredy, J.; Gunawan, I.; Mihan, B.; Sawicki, D. R.; Seestaller, L.; Sullivan, D.; Flam, B. R. New azolidinediones as inhibitors of protein tyrosine phosphatase 1B with antihyperglycemic properties. J. Med. Chem., 2000, 43, 995-1010.
67. Arabaci, G.; Yi, T.; Fu, H.; Porter, M. E.; Beebe, K. D.; Pei, D. ??- bromoacetophenone derivatives as neutral protein tyrosine phosphatase inhibitors: Structure-Activity relationship. Bioorg. Med. Chem. Lett., 2002, 12, 3047-3050.
68. Peng, H.; Xie, W.; Otterness, D. M.; Cogswell, J. P.; McConnell, R. T.; Carter, H. L.; Powis, G.; Abraham, R. T.; Zalkow, L. H. Syntheses and biological activities of a novel group of steroidal derived inhibitors for human Cdc25A protein phosphatase. J. Med. Chem., 2001, 44, 834-848.
69. Sodeoka, M.; Sampe, R.; Kojima, S.; Baba, Y.; Usui, T.; Ueda, K.; Osada, H. Synthesis of a tetronic acid library focused on inhibitors of tyrosine and dual-specificity protein phosphatases and its evaluation regarding VHR and cdc25B inhibition. J. Med. Chem., 2001, 44, 3216-3222.
70. Malamas, M. S.; Sredy, J.; Moxham, C.; Katz, A.; Xu, W.; McDevitt, R.; Adebayo, F. O.; Sawicki, D. R.; Seestaller, L.; Sullivan, D.; Taylor, J. R. Novel benzofuran and benzothiophene biphenyls as inhibitors of protein tyrosine phosphatase 1B with antihyperglycemic properties. J. Med. Chem., 2000, 43, 1293-1310.
71. Seiner, D. R.; LaButti, J. N.; Gates, K. S. Kinetics and mechanism of protein tyrosine phosphatase 1B inactivation by acrolein. Chem. Res. Toxicol., 2007, 20, 1315-1320.
72. Shim, Y. S.; Kim, K. C.; Chi, D. Y.; Lee, K. H.; Cho, H. Formylchromone derivatives as a novel class of protein tyrosine phosphatase 1B inhibitors. Bioorg. Med. Chem. Lett., 2003, 13, 2561-2563.
73. Denu, J. M.; Lohse, D. L.; Vijayalakshmi, J.; Saper, M. A.; Dixon, J. E. Visualization of intermediate and transition-state structures in protein-tyrosine phosphatase catalysis. Proc. Natl. Acad. Sci. U. S. A., 1996, 93, 2493-2498.
74. Zhang, M.; Zhou, M.; VanEtten, R. L.; Stauffacher, C. V. Crystal structure of bovine low molecular weight phosphotyrosyl phosphatase complexed with the transition state analog vanadate. Biochemistry, 1997, 36, 15-23.
75. Tracey, A. S. Hydroxamido vanadates: Aqueous chemistry and function in protein tyrosine phosphatases and cell cultures. J. Inorg. Biochem., 2000, 80, 11-16.
76. Heneberg, P.; Draber, P. Regulation of Cys-based protein tyrosine phosphatases via reactive oxygen and nitrogen species in mast cells and basophils. Curr. Med. Chem., 2005, 12, 1859-1871.
77. Olivier, M.; Romero-Gallo, B.-J.; Matte, C.; Blanchette, J.; Posner, B. I.; Tremblay, M. J.; Faure, R. Modulation of interferon-γ-induced macrophage activation by phosphotyrosine phosphatases inhibition. Effect on murine Leishmaniasis progression. J. Biol. Chem., 1998, 273, 13944-13949.
78. Huyer, G.; Liu, S.; Kelly, J.; Moffat, J.; Payette, P.; Kennedy, B.; Tsaprailis, G.; Gresser, M. J.; Ramachandran, C. Mechanism of inhibition of protein-tyrosine phosphatases by vanadate and pervanadate. J. Biol. Chem., 1997, 272, 843-851.
79. Fletcher, M. C.; Samelson, L. E.; June, C. H. Complex Effects of Phenylarsine Oxide in T-Cells - Induction of Tyrosine Phosphorylation and Calcium Mobilization Independent of CD45 Expression. J. Biol. Chem., 1993, 268, 23697-23703.
80. Berggren, M. M.; Burns, L. A.; Abraham, R. T.; Powis, G. Inhibition of Protein Tyrosine Phosphatase by the Antitumor Agent Gallium Nitrate. Cancer Res., 1993, 53, 1862-1866.
81. Wang, Q. P.; Janzen, N.; Ramachandran, C.; Jirik, F. Mechanism of inhibition of protein-tyrosine phosphatases by disodium aurothiomalate. Biochem. Pharmacol., 1997, 54, 703-711.
82. Tonks, N. K. Redox redux: Revisiting PTPs and the control of cell signaling. Cell, 2005, 121, 667-670.
83. 3POOH). J. Am. Chem. Soc., 2007, 129, 5320-5321.
84. Gross, S.; Knebel, A.; Tenev, T.; Neininger, A.; Gaestel, M.; Herrlich, P.; Bohmer, F. D. Inactivation of protein-tyrosine phosphatases as mechanism of UV-induced signal transduction. J. Biol. Chem., 1999, 274, 26378-26386.
85. MacKeigan, J. P.; Murphy, L. O.; Blenis, J. Sensitized RNAi screen of human kinases and phosphatases identifies new regulators of apoptosis and chemoresistance. Nat. Cell Biol., 2005, 7, 591-U19.
86. Bompard, G.; Puech, C.; Prebois, C.; Vignon, F.; Freiss, G. Protein- tyrosine phosphatase PTPL1/FAP-1 triggers apoptosis in human breast cancer cells. J. Biol. Chem., 2002, 277, 47861-47869.
87. Skarnes, W. C.; Moss, J. E.; Hurtley, S. M.; Beddington, R. S. P. Capturing Genes Encoding Membrane and Secreted Proteins Important for Mouse Development. Proc. Natl. Acad. Sci. U. S. A., 1995, 92, 6592-6596.
88. Cohen, N.; Halberstam, M.; Shlimovich, P.; Chang, C. J.; Shamoon, H.; Rossetti, L. Oral vanadyl sulfate improves hepatic and peripheral insulin sensitivity in patients with non-insulin-dependent diabetes mellitus. J. Clin. Invest., 1995, 95, 2501-2509.
89. Goldfine, A. B.; Simonson, D. C.; Folli, F.; Patti, M. E.; Kahn, C. R. In vivo and in vitro studies of vanadate in human and rodent diabetes mellitus. Mol. Cell Biochem., 1995, 153, 217-231.
90. Lyonnet, B.; Martz, X.; Martin, E. L'emploi thérapeutique des. dérivés du vanadium. La Presse Médicale 1899, 32, 191-192.
91. Meyerovitch, J.; Farfel, Z.; Sack, J.; Shechter, Y. Oral administration of vanadate normalizes blood glucose levels in streptozotocintreated rats. Characterization and mode of action. J. Biol. Chem., 1987, 262, 6658-6662.
92. Sakurai, H.; Tsuchiya, K.; Nakatsuka, M.; Kawada, J.; Ishikawa, S.; Yoshida, H.; Komatsu, M. Insulin-mimetic action of vanadyl complexes. J. Clin. Biochem. Nutr., 1990, 8, 193-200.
93. Zhang, Y. L.; Keng, Y. F.; Zhao, Y.; Wu, L.; Zhang, Z. Y. Suramin is an active site-directed, reversible, and tight-binding inhibitor of protein-tyrosine phosphatases. J. Biol. Chem., 1998, 273, 12281-12287.
94. Taddei, M. L.; Chiarugi, P.; Cuevas, C.; Ramponi, G.; Raugei, G. Oxidation and inactivation of low molecular weight protein tyrosine phosphatase by the anticancer drug Aplidin. Int. J. Cancer, 2006, 118, 2082-2088.
95. Pathak, M. K.; Yi, T. L. Sodium stibogluconate is a potent inhibitor of protein tyrosine phosphatases and augments cytokine responses in hemopoietic cell lines. J. Immunol., 2001, 167, 3391-3397.
96. Garcia-Morales, P.; Minami, Y.; Luong, E.; Klausner, R. D.; Samelson, L. E. Tyrosine phosphorylation in T cells is regulated by phosphatase activity: Studies with phenylarsine oxide. Proc. Natl. Acad. Sci. U. S. A., 1990, 87, 9255-9259.
97. Schmidt, A.; Rutledge, S. J.; Endo, N.; Opas, E. E.; Tanaka, H.; Wesolowski, G.; Leu, C. T.; Huang, Z.; Ramachandaran, C.; Rodan, S. B.; Rodan, G. A. Protein-tyrosine phosphatase activity regulates osteoclast formation and function: Inhibition by alendronate. Proc. Natl. Acad. Sci. U. S. A., 1996, 93, 3068-3073.
98. Dewang, P. M.; Hsu, N. M.; Peng, S. Z.; Li, W. R. Protein tyrosine phosphatases and their inhibitors. Curr. Med. Chem., 2005, 12, 1-22.
99. Soriano, P.; Montgomery, C.; Geske, R.; Bradley, A. Targeted disruption of the c-Src protooncogene leads to osteopetrosis in mice. Cell, 1991, 64, 693-702.
100. Boyce, B. F.; Yoneda, T.; Lowe, C.; Soriano, P.; Mundy, G. R. Requirement of Pp60C-Src expression for osteoclasts to form ruffled borders and resorb bone in mice. J. Clin. Invest., 1992, 90, 1622-1627.
101. De Guzman, B. B.; Hisatsune, J.; Nakayama, M.; Yahiro, K.; Wada, A.; Yamasaki, E.; Nishi, Y.; Yamazaki, S.; Azuma, T.; Ito, Y.; Ohtani, M.; van der Wijk, T.; den Hertog, J.; Moss, J.; Hirayama, T. Cytotoxicity and recognition of receptor-like protein tyrosine phosphatases, RPTP α and RPTP β, by Helicobacter pylori m2VacA. Cell Microbiol., 2005, 7, 1285-1293.
102. Hao, Q.; Rutherford, S. A.; Low, B.; Tang, H. Suppression of the phosphorylation of receptor tyrosine phosphatase-α on the Src-independent site tyrosine 789 by reactive oxygen species. Mol. Pharmacol., 2006, 69, 1938-1944.
103. van der Wijk, T.; Blanchetot, C.; Overvoorde, J.; den Hertog, J. Redox-regulated rotational coupling of receptor protein-tyrosine phosphatase alpha dimers. J. Biol. Chem., 2003, 278, 13968-13974.
104. Mccain, D. F.; Wu, L.; Nickel, P.; Kassack, M. U.; Kreimeyer, A.; Gagliardi, A.; Collins, D. C.; Zhang, Z. Y. Suramin derivatives as inhibitors and activators of protein-tyrosine phosphatases. J. Biol. Chem., 2004, 279, 14713-14725.
105. Huang, P.; Ramphal, J.; Wei, J.; Liang, C.; Jallal, B.; McMahon, G.; Tang, C. Structure-based design and discovery of novel inhibitors of protein tyrosine phosphatases. Bioorg. Med. Chem., 2003, 11, 1835-1849.
106. Cho, H.; Krishnaraj, R.; Itoh, M.; Kitas, E.; Bannwarth, W.; Saito, H.; Walsh, C. T. Substrate specificities of catalytic fragments of protein tyrosine phosphatases (HPTP ??, LAR, and CD45) toward phosphotyrosylpeptide substrates and thiophosphotyrosylated peptides as inhibitors. Protein Sci., 1993, 2, 977-984.
107. McNeill, L.; Salmond, R. J.; Cooper, J. C.; Carret, C. K.; Cassady- Cain, R. L.; Roche-Molina, M.; Tandon, P.; Holmes, N.; Alexander, D. R. The differential regulation of lck kinase phosphorylation sites by CD45 is critical for T cell receptor signaling responses. Immunity, 2007, 27, 425-437.
108. Lazarovits, A. I.; Poppema, S.; Zhang, Z.; Khandaker, M.; LeFeuvre, C. E.; Singhal, S. K.; Garcia, B. M.; Ogasa, N.; Jevnikar, A. M.; White, M. J.; Singh, G.; Stiller, C. R.; Zhong, R. Z. Prevention and reversal of renal allograft rejection by antibody against CD45RB. Nature, 1996, 380, 717-720.
109. Hubbard, C. E.; Barrios, A. M. A highly efficient route to enantiomerically pure l-N-Bz-Pmp(t-Bu)2-OH and incorporation into a peptide-based protein tyrosine phosphatase inhibitor. Bioorg. Med. Chem. Lett., 2008, in press.
110. Beers, S. A.; Malloy, E. A.; Wu, W.; Wachter, M. P.; Gunnia, U.; Cavender, D.; Harris, C.; Davis, J.; Brosius, R.; Pellegrino-Gensey, J. L.; Siekierka, J. Nitroarylhydroxymethylphosphonic acids as inhibitors of CD45. Bioorg. Med. Chem., 1997, 5, 2203-2211.
111. Skorey, K.; Ly, H. D.; Kelly, J.; Hammond, M.; Ramachandran, C.; Huang, Z.; Gresser, M. J.; Wang, Q. P. How does alendronate inhibit protein-tyrosine phosphatases? J. Biol. Chem., 1997, 272, 22472-22480.
112. Ledbetter, J. A.; Schieven, G. L.; Uckun, F. M.; Imboden, J. B. CD45 cross-linking regulates phospholipase-C activation and tyrosine phosphorylation of specific substrates in CD3 Ti-stimulated T-cells. J. Immunol., 1991, 146, 1577-1583.
113. Purdie, K. J.; Lambert, S. R.; Teh, M. T.; Chaplin, T.; Molloy, G.; Raghavan, M.; Kelsell, D. R.; Leigh, I. M.; Harwood, C. A.; Proby, C. M.; Young, B. D. Allelic imbalances and microdeletions affecting the PTPRD gene in cutaneous squamous cell carcinomas detected using single nucleotide polymorphism microarray analysis. Genes Chromosomes Cancer, 2007, 46, 661-669.
114. Sato, M.; Takahashi, K.; Nagayama, K.; Arai, Y.; Ito, N.; Okada, M.; Minna, J. D.; Yokota, J.; Kohno, T. Identification of chromosome arm 9p as the most frequent target of homozygous deletions in lung cancer. Genes Chromosomes Cancer, 2005, 44, 405-414.
115. Marlo, J. E.; Desai, C. J. Loss of phosphatase activity in Ptp69D alleles supporting axon guidance defects. J. Cell Biochem., 2006, 98, 1296-1307.
116. Sines, T.; Granot-Attas, S.; Weisman-Welcher, S.; Elson, A. Association of tyrosine phosphatase ?? with microtubules inhibits phosphatase activity and is regulated by the epidermal growth factor receptor. Mol. Cell Biol., 2007, 27, 7102-7112.
117. Toledano-Katchalski, H.; Kraut, J.; Sines, T.; Granot-Attas, S.; Shohat, G.; Gil-Henn, H.; Yung, Y.; Elson, A. Protein tyrosine phosphatase ε inhibits signaling by mitogen-activated protein kinases. Mol. Cancer Res., 2003, 1, 541-550.
118. Toledano-Katchalski, H.; Tiran, Z.; Sines, T.; Shani, G.; Granot-Attas, S.; den Hertog, J.; Elson, A. Dimerization in vivo and inhibition of the nonreceptor form of protein tyrosine phosphatase ε. Mol. Cell Biol., 2003, 23, 5460-5471.
119. Koh, C. H. V.; Qi, R. Z.; Qu, D.; Melendez, A.; Manikandan, J.; Bay, B. H.; Duan, W.; Cheung, N. S. U18666A-mediated apoptosis in cultured murine cortical neurons: Role of caspases, calpains and kinases. Cell. Signal., 2006, 18, 1572-1583.
120. Zabolotny, J. M.; Kim, Y. B.; Peroni, O. D.; Kim, J. K.; Pani, M. A.; Boss, O.; Klaman, L. D.; Kamatkar, S.; Shulman, G. I.; Kahn, B. B.; Neel, B. G. Overexpression of the LAR (leukocyte antigenrelated) protein-tyrosine phosphatase in muscle causes insulin resistance. Proc. Natl. Acad. Sci. U. S. A., 2001, 98, 5187-5192.
121. Tisi, M. A.; Xie, Y. M.; Yeo, T. T.; Longo, F. M. Downregulation of LAR tyrosine phosphatase prevents apoptosis and augments NGF-induced neurite outgrowth. J. Neurobiol., 2000, 42, 477-486.
122. Levea, C. M.; Mcgary, C. T.; Symons, J. R.; Mooney, R. A. PTP LAR expression compared to prognostic indices in metastatic and non-metastatic breast cancer. Breast Cancer Res. Treat., 2000, 64, 221-228.
123. Kulas, D. T.; Zhang, W. R.; Goldstein, B. J.; Furlanetto, R. W.; Mooney, R. A. Insulin-receptor signaling is augmented by antisense inhibition of the protein-tyrosine-phosphatase LAR. J. Biol. Chem., 1995, 270, 2435-2438.
124. Xie, Y. M.; Massa, S. M.; Ensslen-Craig, S. E.; Major, D. L.; Yang, T.; Tisi, M. A.; Derevyanny, V. D.; Runge, W. O.; Mehta, B. P.; Moore, L. A.; Brady-Kalnay, S. M.; Longo, F. M. Proteintyrosine phosphatase (PTP) wedge domain peptides - A novel approach for inhibition of PTP function and augmentation of proteintyrosine kinase function. J. Biol. Chem., 2006, 281, 16482-16492.
125. Yang, X. N.; Li, J. Y.; Zhou, Y. Y.; Shen, Q.; Chen, J. W.; Li, J. Discovery of novel inhibitor of human leukocyte common antigenrelated phosphatase. Biochim. Biophys. Acta, 2005, 1726, 34-41.
126. Aicher, B.; Lerch, M. M.; Muller, T.; Schilling, J.; Ullrich, A. Cellular redistribution of protein tyrosine phosphatases LAR and PTPø by inducible proteolytic processing. J. Cell Biol., 1997, 138, 681-696.
127. Chang, H. L.; Sugimoto, Y.; Liu, S.; Ye, W.; Wang, L. S.; Huang, Y. W.; Lin, Y. C. Keratinocyte growth factor (KGF) induces tamoxifen (Tam) resistance in human breast cancer MCF-7 cells. Anticancer Res., 2006, 26, 1773-1784.
128. Liu, S.; Sugimoto, Y.; Kulp, S. K.; Jiang, J.; Chang, H. L.; Park, K. Y.; Kashida, Y.; Lin, Y. C. Estrogenic down-regulation of protein tyrosine phosphatase γ (PTP γ) in human breast is associated with estrogen receptor α. Anticancer Res., 2002, 22, 3917-3923.
129. Walchli, S.; Espanel, X.; van Huijsduijnen, R. H. Sap-1/PTPRH activity is regulated by reversible dimerization. Biochem. Biophys. Res. Commun., 2005, 331, 497-502.
130. Iuliano, R.; Le, P., I; Cristofaro, C.; Baudi, F.; Arturi, F.; Pallante, P.; Martelli, M. L.; Trapasso, F.; Chiariotti, L.; Fusco, A. The tyrosine phosphatase PTPRJ/DEP-1 genotype affects thyroid carcinogenesis. Oncogene, 2004, 23, 8432-8438.
131. Takahashi, T.; Takahashi, K.; Mernaugh, R. L.; Tsuboi, N.; Liu, H.; Daniel, T. O. A monoclonal antibody against CD148, a receptor-like tyrosine phosphatase, inhibits endothelial-cell growth and angiogenesis. Blood, 2006, 108, 1234-1242.
132. Asano, A.; Tsubomatsu, K.; Jung, C.-G.; Sasaki, N.; Agui, T. A deletion mutation of the protein tyrosine phosphatase kappa (Ptprk) gene is responsible for T-helper immunodeficiency (thid) in the LEC rat. Mamm. Genome, 2007, 18, 779-786.
133. Flavell, J. R.; Baumforth, K. R.; Wood, V. H.; Davies, G. L.; Wei, W.; Reynolds, G. M.; Morgan, S.; Boyce, A.; Kelly, G. L.; Young, L. S.; Murray, P. G. Down-regulation of the TGF-β target gene, PTPRK, by the Epstein-Barr virus encoded EBNA1 contributes to the growth and survival of Hodgkin lymphoma cells. Blood, 2008, 111, 292-301.
134. Xu, Y.; Shao, Y.; Voorhees, J. J.; Fisher, G. J. Oxidative inhibition of receptor-type protein-tyrosine phosphatase κ by ultraviolet irradiation activates epidermal growth factor receptor in human keratinocytes. J. Biol. Chem., 2006, 281, 27389-27397.
135. Anders, L.; Mertins, P.; Lammich, S.; Murgia, M.; Hartmann, D.; Saftig, P.; Haass, C.; Ullrich, A. Furin-, ADAM 10-, and γ-secretase-mediated cleavage of a receptor tyrosine phosphatase and regulation of β-catenin's transcriptional activity. Mol. Cell Biol., 2006, 26, 3917-3934.
136. Aricescu, A. R.; Siebold, C.; Choudhuri, K.; Chang, V. T.; Lu, W.; Davis, S. J.; van der Merwe, P. A.; Jones, E. Y. Structure of a tyrosine phosphatase adhesive interaction reveals a spacer-clamp mechanism. Science, 2007, 317, 1217-1220.
137. Choudhuri, K.; Wiseman, D.; Brown, M. H.; Gould, K.; van der Merwe, P. A. T-cell receptor triggering is critically dependent on the dimensions of its peptide-MHC ligand. Nature, 2005, 436, 578-582.
138. Davis, S. J.; van der Merwe, P. A. The kinetic-segregation model: TCR triggering and beyond. Nat. Immunol., 2006, 7, 803-809.
139. Solis, M.; Wilkinson, P.; Romieu, R.; Hernandez, E.; Wainberg, M. A.; Hiscott, J. Gene expression profiling of the host response to HIV-1 B, C, or A/E infection in monocyte-derived dendritic cells. Virology, 2006, 352, 86-99.
140. Drake, P. G.; Peters, G. H.; Andersen, H. S.; Hendriks, W.; Moller, N. P. A novel strategy for the development of selective active-site inhibitors of the protein tyrosine phosphatase-like proteins islet-cell antigen 512 (IA-2) and phogrin (IA-2beta). Biochem. J., 2003, 373, 393-401.
141. Steinbrenner, H.; Nguyen, T. B.; Wohlrab, U.; Scherbaum, W. A.; Seissler, J. Effect of proinflammatory cytokines on gene expression of the diabetes-associated autoantigen IA-2 in INS-1 cells. Endocrinology, 2002, 143, 3839-3845.
142. Kubosaki, A.; Nakamura, S.; Clark, A.; Morris, J. F.; Notkins, A. L. Disruption of the transmembrane dense core vesicle proteins IA-2 and IA-2beta causes female infertility. Endocrinology, 2006, 147, 811-815.
143. Lobner, K.; Steinbrenner, H.; Roberts, G. A.; Ling, Z.; Huang, G. C.; Piquer, S.; Pipeleers, D. G.; Seissler, J.; Christie, M. R. Different regulated expression of the tyrosine phosphatase-like proteins IA-2 and phogrin by glucose and insulin in pancreatic islets: Relationship to development of insulin secretory responses in early life. Diabetes, 2002, 51, 2982-2988.
144. Xu, X.; Hong, Y.; Kong, C.; Xu, L.; Tan, J.; Liang, Q.; Huang, B.; Lu, J. Protein tyrosine phosphatase receptor-type O (PTPRO) is coregulated by E2F1 and miR-17-92. FEBS Lett., 2008, 582, 2850-2856.
145. Chirivi, R. G.; Noordman, Y. E.; Van der Zee, C. E.; Hendriks, W. J. Altered MAP kinase phosphorylation and impaired motor coordination in PTPRR deficient mice. J. Neurochem., 2007, 101, 829-840.
146. Noordman, Y. E.; Augustus, E. D.; Schepens, J. T.; Chirivi, R. G.; Rios, P.; Pulido, R.; Hendriks, W. J. Multimerisation of receptortype protein tyrosine phosphatases PTPBR7 and PTP-SL attenuates enzymatic activity. Biochim. Biophys. Acta, 2007.
147. McLean, J.; Batt, J.; Doering, L. C.; Rotin, D.; Bain, J. R. Enhanced rate of nerve regeneration and directional errors after sciatic nerve injury in receptor protein tyrosine phosphatase σ knock-out mice. J. Neurosci., 2002, 22, 5481-5491.
148. Wallace, M. J.; Fladd, C.; Batt, J.; Rotin, D. The second catalytic domain of protein tyrosine phosphatase δ (PTP δ) binds to and inhibits the first catalytic domain of PTP σ. Mol. Cell Biol., 1998, 18, 2608-2616.
149. Harroch, S.; Furtado, G. C.; Brueck, W.; Rosenbluth, J.; Lafaille, J.; Chao, M.; Buxbaum, J. D.; Schlessinger, J. A critical role for the protein tyrosine phosphatase receptor type Z in functional recovery from demyelinating lesions. Nat. Genet., 2002, 32, 411-414.
150. Fujikawa, A.; Shirasaka, D.; Yamamoto, S.; Ota, H.; Yahiro, K.; Fukada, M.; Shintani, T.; Wada, A.; Aoyama, N.; Hirayama, T.; Fukamachi, H.; Noda, M. Mice deficient in protein tyrosine phosphatase receptor type Z are resistant to gastric ulcer induction by VacA of Helicobacter pylori. Nat. Genet., 2003, 33, 375-381.
151. Bence, K. K.; Delibegovic, M.; Xue, B.; Gorgun, C. Z.; Hotamisligil, G. S.; Neel, B. G.; Kahn, B. B. Neuronal PTP1B regulates body weight, adiposity and leptin action. Nat. Med., 2006, 12, 917-924.
152. Heinonen, K. M.; Dube, N.; Bourdeau, A.; Lapp, W. S.; Tremblay, M. L. Protein tyrosine phosphatase 1B negatively regulates macrophage development through CSF-1 signaling. Proc. Natl. Acad. Sci. U. S. A., 2006, 103, 2776-2781.
153. Julien, S. G.; Dube, N.; Read, M.; Penney, J.; Paquet, M.; Han, Y. X.; Kennedy, B. P.; Muller, W. J.; Tremblay, M. L. Protein tyrosine phosphatase 1B deficiency or inhibition delays ErbB2-induced mammary tumorigenesis and protects from lung metastasis. Nat. Genet., 2007, 39, 338-346.
154. Zhang, S.; Zhang, Z. Y. PTP1B as a drug target: Recent developments in PTP1B inhibitor discovery. Drug Discov. Today, 2007, 12, 373-381.
155. Liu, G. Technology evaluation: ISIS-113715, lsis. Curr. Opin. Mol. Ther., 2004, 6, 331-336.
156. Shen, K.; Keng, Y. F.; Wu, L.; Guo, X. L.; Lawrence, D. S.; Zhang, Z. Y. Acquisition of a specific and potent PTP1B inhibitor from a novel combinatorial library and screening procedure. J. Biol. Chem., 2001, 276, 47311-47319.
157. Leung, C.; Grzyb, J.; Lee, J.; Meyer, N.; Hum, G.; Jia, C. G.; Liu, S. F.; Taylor, S. D. The difluoromethylenesulfonic acid group as a monoanionic phosphate surrogate for obtaining PTP1B inhibitors. Bioorg. Med. Chem., 2002, 10, 2309-2323.
158. Umezawa, K.; Kawakami, M.; Watanabe, T. Molecular design and biological activities of protein-tyrosine phosphatase inhibitors. Pharmacology & Therapeutics, 2003, 99, 15-24.
159. Liljebris, C.; Larsen, S. D.; Ogg, D.; Palazuk, B. J.; Bleasdale, J. E. Investigation of potential bioisosteric replacements for the carboxyl groups of peptidomimetic inhibitors of protein tyrosine phosphatase 1B: Identification of a tetrazole-containing inhibitor with cellular activity. J. Med. Chem., 2002, 45, 1785-1798.
160. Zhang, W.; Hong, D.; Zhou, Y.; Zhang, Y.; Shen, Q.; Li, J. Y.; Hu, L. H.; Li, J. Ursolic acid and its derivative inhibit protein tyrosine phosphatase 1B, enhancing insulin receptor phosphorylation and stimulating glucose uptake. Biochim. Biophys. Acta, 2006, 1760, 1505-1512.
161. Cheon, H. G.; Kim, S. M.; Yang, S. D.; Du Ha, J.; Choi, J. K. Discovery of a novel protein tyrosine phosphatase-1B inhibitor, KR61639: Potential development as an antihyperglycemic agent. Eur. J. Pharmacol., 2004, 485, 333-339.
162. Yue, E. W.; Wayland, B.; Douty, B.; Crawley, M. L.; McLaughlin, E.; Takvorian, A.; Wasserman, Z.; Bower, M. J.; Wei, M.; Li, Y. L.; Ala, P. J.; Gonneville, L.; Wynn, R.; Burn, T. C.; Liu, P. C. C.; Combs, A. P. Isothiazolidinone heterocycles as inhibitors of protein tyrosine phosphatases: Synthesis and structure-activity relationships of a peptide scaffold. Bioorg. Med. Chem., 2006, 14, 5833-5849.
163. Montalibet, J.; Skorey, K.; McKay, D.; Scapin, G.; Asante-Appiah, G.; Kennedy, B. P. Residues distant from the active site influence protein-tyrosine phosphatase 1B inhibitor binding. J. Biol. Chem., 2006, 281, 5258-5266.
164. Bourdeau, A.; Dube, N.; Heinonen, K. M.; Theberge, J. F.; Doody, K. M.; Tremblay, M. L. TC-PTP-deficient bone marrow stromal cells fail to support normal B lymphopoiesis due to abnormal secretion of interferon-γ. Blood, 2007, 109, 4220-4228.
165. Xu, J. F.; Li, L.; Hong, J.; Huang, W. Effects of small interference RNA against PTP1B and TCPTP on insulin signaling pathway in mouse liver: Evidence for non-synergetic cooperation. Cell Biology Int., 2007, 31, 88-91.
166. Xie, J.; Seto, C. T. A two stage click-based library of protein tyrosine phosphatase inhibitors. Bioorg. Med. Chem., 2007, 15, 458-473.
167. Blair, E. R.; Hoffman, H. E.; Bishop, A. C. Engineering nonnatural inhibitor sensitivity in protein tyrosine phosphatase H1. Bioorg. Med. Chem., 2006, 14, 464-471.
168. Patrignani, C.; Magnone, M. C.; Tavano, P.; Ardizzone, M.; Muzio, V.; Greco, B.; Zaratin, P. F. Knockout mice reveal a role for protein tyrosine phosphatase H1 in cognition. Behav. Brain Funct., 2008, 4, 36.
169. Bauler, T. J.; Hughes, E. D.; Arimura, Y.; Mustelin, T.; Saunders, T. L.; King, P. D. Normal TCR signal transduction in mice that lack catalytically active PTPN3 protein tyrosine phosphatase. J. Immunol., 2007, 178, 3680-3687.
170. Jing, M.; Bohl, J.; Brimer, N.; Kinter, M.; Vande Pol, S. B. Degradation of tyrosine phosphatase PTPN3 (PTPH1) by association with oncogenic human papillomavirus E6 proteins. J. Virol., 2007, 81, 2231-2239.
171. Andersen, H. S.; Iversen, L. F.; Jeppesen, C. B.; Branner, S.; Norris, K.; Rasmussen, H. B.; Møller, K. B.; Møller, N. P. H. 2-(oxalylamino)-benzoic acid is a general, competitive inhibitor of protein-tyrosine phosphatases. J. Biol. Chem., 2000, 275, 7101-7108.
172. Gu, M.; Meng, K.; Majerus, P. W. The effect of overexpression of the protein tyrosine phosphatase PTPMEG on cell growth and on colony formation in soft agar in COS-7 cells. Proc. Natl. Acad. Sci. U. S. A., 1996, 93, 12980-12985.
173. Kina, S.; Tezuka, T.; Kusakawa, S.; Kishimoto, Y.; Kakizawa, S.; Hashimoto, K.; Ohsugi, M.; Kiyama, Y.; Horai, R.; Sudo, K.; Kakuta, S.; Iwakura, Y.; Iino, M.; Kano, M.; Manabe, T.; Yamamoto, T. Involvement of protein-tyrosine phosphatase PTPMEG in motor learning and cerebellar long-term depression. Eur. J. Neurosci., 2007, 26, 2269-2278.
174. Opas, E. E.; Rutledge, S. J.; Golub, E.; Stern, A.; Zimolo, Z.; Rodan, G. A.; Schmidt, A. Alendronate inhibition of proteintyrosine-phosphatase-meg1. Biochem. Pharmacol., 1997, 54, 721-727.
175. Choi, Y. S.; Lin, S. L.; Lee, B.; Kurup, P.; Cho, H. Y.; Naegele, J. R.; Lombroso, P. J.; Obrietan, K. Status epilepticus-induced somatostatinergic hilar interneuron degeneration is regulated by striatal enriched protein tyrosine phosphatase. J. Neurosci., 2007, 27, 2999-3009.
176. Hu, Y.; Zhang, Y.; Venkitaramani, D. V.; Lombroso, P. J. Translation of striatal-enriched protein tyrosine phosphatase (STEP) after β1-adrenergic receptor stimulation. J. Neurochem., 2007, 103, 531-541.
177. Boulanger, L. M.; Lombroso, P. J.; Raghunathan, A.; During, M. J.; Wahle, P.; Naegele, J. R. Cellular and molecular characterization of a brain-enriched protein tyrosine phosphatase. J. Neurosci., 1995, 15, 1532-1544.
178. Kamata, T.; Yamashita, M.; Kimura, M.; Murata, K.; Inami, M.; Shimizu, C.; Sugaya, K.; Wang, C. R.; Taniguchi, M.; Nakayama, T. Src homology 2 domain-containing tyrosine phosphatase SHP-1 controls the development of allergic airway inflammation. J. Clin. Invest., 2003, 111, 109-119.
179. Dubois, M. J.; Bergeron, S.; Kim, H. J.; Dombrowski, L.; Perreault, M.; Fournes, B.; Faure, R.; Olivier, M.; Beauchemin, N.; Shulman, G. I.; Siminovitch, K. A.; Kim, J. K.; Marette, A. The SHP-1 protein tyrosine phosphatase negatively modulates glucose homeostasis. Nat. Med., 2006, 12, 549-556.
180. Zhang, J. Y.; Somani, A. K.; Siminovitch, K. A. Roles of the SHP-1 tyrosine phosphatase in the negative regulation of cell signalling. Semin. Immunol., 2000, 12, 361-378.
181. Chen, L.; Sung, S. S.; Yip, M. L.; Lawrence, H. R.; Ren, Y.; Guida, W. C.; Sebti, S. M.; Lawrence, N. J.; Wu, J. Discovery of a novel shp2 protein tyrosine phosphatase inhibitor. Mol. Pharmacol., 2006, 70, 562-570.
182. Yi, T.; Pathak, M. K.; Lindner, D. J.; Ketterer, M. E.; Farver, C.; Borden, E. C. Anticancer activity of sodium stibogluconate in synergy with IFNs. J. Immunol., 2002, 169, 5978-5985.
183. Pettiford, S. M.; Herbst, R. The protein tyrosine phosphatase HePTP regulates nuclear translocation of ERK2 and can modulate megakaryocytic differentiation of K562 cells. Leukemia, 2003, 17, 366-378.
184. 2 regulates the activation of distinct MAPK pathways. Free Radic. Biol. Med., 2002, 33, 1121-1132.
185. Xiaodong, C.; Moran, E. J.; Siev, D.; Lio, A.; Ohashi, C.; Mjalli, A. M. M. Synthesis of NH-acyl-a-aminoamides on rink resin: Inhibitors of the hematopoietic protein tyrosine phosphatase (HePTP). Bioorg. Med. Chem. Lett., 1995, 5, 2953-2958.
186. Cho, C. Y.; Koo, S. H.; Wang, Y.; Callaway, S.; Hedrick, S.; Mak, P. A.; Orth, A. P.; Peters, E. C.; Saez, E.; Montminy, M.; Schultz, P. G.; Chanda, S. K. Identification of the tyrosine phosphatase PTP-MEG2 as an antagonist of hepatic insulin signaling. Cell Metab., 2006, 3, 367-378.
187. Perkins, L. A.; Larsen, I.; Perrimon, N. corkscrew encodes a putative protein tyrosine phosphatase that functions to transduce the terminal signal from the receptor tyrosine kinase torso. Cell, 1992, 70, 225-236.
188. Tartaglia, M.; Mehler, E. L.; Goldberg, R.; Zampino, G.; Brunner, H. G.; Kremer, H.; van, d. B., I; Crosby, A. H.; Ion, A.; Jeffery, S.; Kalidas, K.; Patton, M. A.; Kucherlapati, R. S.; Gelb, B. D. Mutations in PTPN11, encoding the protein tyrosine phosphatase SHP-2, cause Noonan syndrome. Nat. Genet., 2001, 29, 465-468.
189. Tartaglia, M.; Niemeyer, C. M.; Fragale, A.; Song, X.; Buechner, J.; Jung, A.; Hahlen, K.; Hasle, H.; Licht, J. D.; Gelb, B. D. Somatic mutations in PTPN11 in juvenile myelomonocytic leukemia, myelodysplastic syndromes and acute myeloid leukemia. Nat. Genet., 2003, 34, 148-150.
190. Bentires-Alj, M.; Paez, J. G.; David, F. S.; Keilhack, H.; Halmos, B.; Naoki, K.; Maris, J. M.; Richardson, A.; Bardelli, A.; Sugarbaker, D. J.; Richards, W. G.; Du, J.; Girard, L.; Minna, J. D.; Loh, M. L.; Fisher, D. E.; Velculescu, V. E.; Vogelstein, B.; Meyerson, M.; Sellers, W. R.; Neel, B. G. Activating mutations of the noonan syndrome-associated SHP2/PTPN11 gene in human solid tumors and adult acute myelogenous leukemia. Cancer Res., 2004, 64, 8816-8820.
191. Heneberg, P.; Dráber, P. Nonreceptor protein tyrosine and lipid phosphatases in type I Fc?? receptor-mediated activation of mast cells and basophils. Int. Arch. Allergy Immunol., 2002, 128, 253-263.
192. Salmond, R. J.; Alexander, D. R. SHP2 forecast for the immune system: fog gradually clearing. Trends Immunol., 2006, 27, 154-160.
193. Tolarová, H.; Dráberová, L.; Heneberg, P.; Dráber, P. Involvement of filamentous actin in setting the threshold for degranulation in mast cells. Eur. J. Immunol., 2004, 34, 1627-1636.
194. Volná, P.; Lebduška, P.; Dráberová, L.; Šímová, S.; Heneberg, P.; Boubelík, M.; Bugajev, V.; Malissen, B.; Wilson, B. S.; Horejší, V.; Malissen, M.; Dráber, P. Negative regulation of mast cell signaling and function by the adaptor LAB/NTAL. J. Exp. Med., 2004, 200, 1001-1013.
195. Pazdrak, K.; Adachi, T.; Alam, R. Src homology 2 protein tyrosine phosphatase (SHPTP2)/Src homology 2 phosphatase 2 (SHP2) tyrosine phosphatase is a positive regulator of the interleukin 5 receptor signal transduction pathways leading to the prolongation of eosinophil survival. J. Exp. Med., 1997, 186, 561-568.
196. Streit, S.; Ruhe, J. E.; Knyazev, P.; Knyazeva, T.; Iacobelli, S.; Peter, S.; Hoefler, H.; Ullrich, A. PTP-PEST phosphatase variations in human cancer. Cancer Genet. Cytogenet., 2006, 170, 48-53.
197. Halle, M.; Liu, Y. C.; Hardy, S.; Theberge, J. F.; Blanchetot, C.; Bourdeau, A.; Meng, T. C.; Tremblay, M. L. Caspase-3 regulates catalytic activity and scaffolding functions of the protein tyrosine phosphatase PEST, a novel modulator of the apoptotic response. Mol. Cell Biol., 2007, 27, 1172-1190.
198. Davidson, D.; Veillette, A. PTP-PEST, a scaffold protein tyrosine phosphatase, negatively regulates lymphocyte activation by targeting a unique set of substrates. EMBO J., 2001, 20, 3414-3426.
199. Chellaiah, M. A.; Kuppuswamy, D.; Lasky, L.; Linder, S. Phosphorylation of a Wiscott-Aldrich syndrome protein-associated signal complex is critical in osteoclast bone resorption. J. Biol. Chem., 2007, 282, 10104-10116.
200. Krishnamurthy, D.; Karver, M. R.; Fiorillo, E.; Orru, V.; Stanford, S. M.; Bottini, N.; Barrios, A. M. Gold(I)-mediated inhibition of protein tyrosine phosphatases: A detailed in vitro and cellular study. J. Med. Chem., 2008, 51, 4790-4795.
201. Abaan, O. D.; Toretsky, J. A. PTPL1: A large phosphatase with a split personality. Cancer Metastasis Rev., 2008, 27, 205-214.
202. Mishima, K.; Nariai, Y.; Yoshimura, Y. Etodolac, a selective cyclo-oxygenase-2 inhibitor, enhances carboplatin-induced apoptosis of human tongue carcinoma cells by down-regulation of FAP-1 expression. Oral Oncol., 2005, 41, 77-81.
203. Ungefroren, H.; Kruse, M. L.; Trauzold, A.; Roeschmann, S.; Roeder, C.; Arlt, A.; Henne-Bruns, D.; Kalthoff, H. FAP-1 in pancreatic cancer cells: Functional and mechanistic studies on its inhibitory role in CD95-mediated apoptosis. J. Cell Sci., 2001, 114, 2735-2746.
204. Otani, T.; Sugimoto, Y.; Aoyagi, Y.; Igarashi, Y.; Furumai, T.; Saito, N.; Yamada, Y.; Asao, T.; Oki, T. New Cdc25B tyrosine phosphatase inhibitors, nocardiones A and B, produced by Nocardia sp. TP-A0248: taxonomy, fermentation, isolation, structural elucidation and biological properties. J. Antibiot., 2000, 53, 337-344.
205. Song, E.; Chen, J.; Antus, B.; Wang, M.; Xie, Y.; Yao, H.; Exton, M. S. Interleukin-2 enhances susceptibility of colon cancer cells to FasR mediated apoptosis by up-regulating Fas receptor level and down-regulating FAP-1 expression. Int. J. Immunopathol. Pharmacol., 2000, 13, 113-122.
206. Wieckowski, E.; Atarashi, Y.; Stanson, J.; Sato, T. A.; Whiteside, T. L. FAP-1-mediated activation of NF-κB induces resistance of head and neck cancer to Fas-induced apoptosis. J. Cell Biochem., 2007, 100, 16-28.
207. Fodero-Tavoletti, M. T.; Hardy, M. P.; Cornell, B.; Katsis, F.; Sadek, C. M.; Mitchell, C. A.; Kemp, B. E.; Tiganis, T. Protein tyrosine phosphatase hPTPN20a is targeted to sites of actin polymerization. Biochem. J., 2005, 389, 343-354.
208. Cardone, L.; Carlucci, A.; Affaitati, A.; Livigni, A.; deCristofaro, T.; Garbi, C.; Varrone, S.; Ullrich, A.; Gottesman, M. E.; Avvedimento, E. V.; Feliciello, A. Mitochondrial AKAP121 binds and targets protein tyrosine phosphatase D1, a novel positive regulator of src signaling. Mol. Cell Biol., 2004, 24, 4613-4626.
209. Carlucci, A.; Gedressi, C.; Lignitto, L.; Nezi, L.; Villa-Moruzzi, E.; Avvedimento, E. V.; Gottesman, M. E.; Garbi, C.; Feliciello, A. Protein tyrosine phosphatase PTPD1 regulates Fak autophosphorylation and cell migration. J. Biol. Chem., 2008.
210. Zheng, W.; She, J. X. Genetic association between a lymphoid tyrosine phosphatase (PTPN22) and type 1 diabetes. Diabetes, 2005, 54, 906-908.
211. Bottini, N.; Musumeci, L.; Alonso, A.; Rahmouni, S.; Nika, K.; Rostamkhani, M.; MacMurray, J.; Meloni, G. F.; Lucarelli, P.; Pellecchia, M.; Eisenbarth, G. S.; Comings, D.; Mustelin, T. A functional variant of lymphoid tyrosine phosphatase is associated with type I diabetes. Nat. Genet., 2004, 36, 337-338.
212. Laberge, G. S.; Bennett, D. C.; Fain, P. R.; Spritz, R. A. PTPN22 Is Genetically Associated with Risk of Generalized Vitiligo, but CTLA4 Is Not. J. Invest. Dermatol., 2008.
213. Wu, J.; Katrekar, A.; Honigberg, L. A.; Smith, A. M.; Conn, M. T.; Tang, J.; Jeffery, D.; Mortara, K.; Sampang, J.; Williams, S. R.; Buggy, J.; Clark, J. M. Identification of substrates of human protein-tyrosine phosphatase PTPN22. J. Biol. Chem., 2006, 281, 11002-11010.
214. Yu, X.; Sun, J. P.; He, Y.; Guo, X.; Liu, S.; Zhou, B.; Hudmon, A.; Zhang, Z. Y. Structure, inhibitor, and regulatory mechanism of Lyp, a lymphoid-specific tyrosine phosphatase implicated in autoimmune diseases. Proc. Natl. Acad. Sci. U. S. A., 2007, 104, 19767-19772.
215. Xie, Y.; Liu, Y.; Gong, G.; Rinderspacher, A.; Deng, S. X.; Smith, D. H.; Toebben, U.; Tzilianos, E.; Branden, L.; Vidovic, D.; Chung, C.; Schurer, S.; Tautz, L.; Landry, D. W. Discovery of a novel submicromolar inhibitor of the lymphoid specific tyrosine phosphatase. Bioorg. Med. Chem. Lett., 2008, 18, 2840-2844.
216. Castiglioni, S.; Maier, J. A.; Mariotti, M. The tyrosine phosphatase HD-PTP: A novel player in endothelial migration. Biochem. Biophys. Res. Commun., 2007, 364, 534-539.
217. Tautz, L.; Pellecchia, M.; Mustelin, T. Targeting the PTPome in human disease. Expert. Opin. Ther. Targets., 2006, 10, 157-177.
218. Bhattacharya, S.; LaButti, J. N.; Seiner, D. R.; Gates, K. S. Oxidative inactivation of protein tyrosine phosphatase 1B by organic hydroperoxides. Bioorg. Med. Chem. Lett., 2008, 18, 5856-5859.
219. Gracanin, M.; Davies, M. J. Inhibition of protein tyrosine phosphatases by amino acid, peptide, and protein hydroperoxides: Potential modulation of cell signaling by protein oxidation products. Free Radical Biology and Medicine, 2007, 42, 1543-1551.
220. Chan, T. A.; Glockner, S.; Yi, J. M.; Chen, W.; Van Neste, L.; Cope, L.; Herman, J. G.; Velculescu, V.; Schuebel, K. E.; Ahuja, N.; Baylin, S. B. Convergence of mutation and epigenetic alterations identifies common genes in cancer that predict for poor prognosis. PLoS. Med., 2008, 5, e114.
221. You-Ten, K. E.; Muise, E. S.; Itie, A.; Michaliszyn, E.; Wagner, J.; Jothy, S.; Lapp, W. S.; Tremblay, M. L. Impaired bone marrow microenvironment and immune function in T cell protein tyrosine phosphatase-deficient mice. J. Exp. Med., 1997, 186, 683-693.
222. Blanchard, J. L.; Epstein, D. M.; Boisclair, M. D.; Rudolph, J.; Pal, K. Dysidiolide and related γ-hydroxy butenolide compounds as inhibitors of the protein tyrosine phosphatase, CDC25. Bioorg. Med. Chem. Lett., 1999, 9, 2537-2538.
223. Takahashi, M.; Dodo, K.; Sugimoto, Y.; Aoyagi, Y.; Yamada, Y.; Hashimoto, Y.; Shirai, R. Synthesis of the novel analogues of dysidiolide and their structure-activity relationship. Bioorg. Med. Chem. Lett., 2000, 10, 2571-2574.
224. Andersen, H. S.; Olsen, O. H.; Iversen, L. F.; Sorensen, A. L. P.; Mortensen, S. B.; Christensen, M. S.; Branner, S.; Hansen, T. K.; Lau, J. F.; Jeppesen, L.; Moran, E. J.; Su, J.; Bakir, F.; Judge, L.; Shahbaz, M.; Collins, T.; Vo, T.; Newman, M. J.; Ripka, W. C.; Moller, N. P. H. Discovery and SAR of a novel selective and orally bioavailable nonpeptide classical competitive inhibitor class of protein-tyrosine phosphatase 1B. J. Med. Chem., 2002, 45, 4443-4459.
225. Iversen, L. F.; Andersen, H. S.; Branner, S.; Mortensen, S. B.; Peters, G. H.; Norris, K.; Olsen, O. H.; Jeppesen, C. B.; Lundt, B. F.; Ripka, W.; Moller, K. B.; Møller, N. P. H. Structure-based design of a low molecular weight, nonphosphorus, nonpeptide, and highly selective inhibitor of protein-tyrosine phosphatase 1B. J. Biol. Chem., 2000, 275, 10300-10307.