Protein Tyrosine Phosphatase 1B (PTP1B) And Obesity

Vitamins and Hormones

Volumn 91, Issue , 2013, Pages 405-424

  Cho, Hyeongjin ^a  

^a Inha University   (South Korea)

Author keywords

Genetic deletion; Inhibitor; Insulin; Knockout mice; Leptin; Protein tyrosine phosphatase; PTP1B; Trodusquemine

Indexed keywords

EID: 84873863342     PISSN: 00836729     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-407766-9.00017-1     Document Type: Chapter

References (86)

1. Adams D.R., Abraham A., et al. 2-Aryl-3,3,3-trifluoro-2-hydroxypropionic acids: A new class of protein tyrosine phosphatase 1B inhibitors. Bioorganic & Medicinal Chemistry Letters 2007, 17(23):6579-6583.
2. Akamatsu M., Roller P.P., et al. Potent inhibition of protein-tyrosine phosphatase by phosphotyrosine-mimic containing cyclic peptides. Bioorganic & Medicinal Chemistry 1997, 5(1):157-163.
3. Alonso A., Sasin J., et al. Protein tyrosine phosphatases in the human genome. Cell 2004, 117(6):699-711.
4. Andersen H.S., Iversen L.F., et al. 2-(Oxalylamino) benzoic acid is a general, competitive inhibitor of protein tyrosine phosphatases. Journal of Biological Chemistry 2000, 275(10):7101-7108.
5. Andersen J.N., Mortensen O.H., et al. Structural and evolutionary relationships among protein tyrosine phosphatase domains. Molecular and Cellular Biology 2001, 21(21):7117-7136.
6. Arkan M.C., Hevener A.L., et al. IKK-β links inflammation to obesity-induced insulin resistance. Nature Medicine 2005, 11(2):191-198.
7. Asante-Appiah E., Kennedy B.P., et al. Protein tyrosine phosphatases: The quest for negative regulators of insulin action. American Journal of Physiology, Endocrinology and Metabolism 2003, 284(4):E663-E670.
8. Banks A.S., Davis S.M., et al. Activation of downstream signals by the long form of the leptin receptor. Journal of Biological Chemistry 2000, 275(19):14563-14572.
9. Banno R., Zimmer D., et al. PTP1B and SHP2 in POMC neurons reciprocally regulate energy balance in mice. The Journal of Clinical Investigation 2010, 120(3):720-734.
10. Barnes D., Bebernitz G.R., et al. 1,2,5-Thiadiazolidine derivatives useful for treating conditions mediated by protein tyrosine phosphatases (PTPase). PCT Int 2007, Novatis Institute for Biomedical Research Institute Inc, USA, WO2007067613, 38 pp (Novartis A.-G., Switzerland; Novartis Pharma G.m.b.H.).
11. Barr A.J. Protein tyrosine phosphatases as drug targets: Strategies and challenges of inhibitor development. Future Medicinal Chemistry 2010, 2(10):1563-1576.
12. Bence K.K., Delibegovic M., et al. Neuronal PTP1B regulates body weight, adiposity and leptin action. Nature Medicine 2006, 12(8):917-924.
13. Bhattarai B.R., Kafle B., et al. Thiazolidinedione derivatives as PTP1B inhibitors with antihyperglycemic and antiobesity effects. Bioorganic & Medicinal Chemistry Letters 2009, 19(21):6161-6165.
14. Bhattarai B.R., Kafle B., et al. Novel thiazolidinedione derivatives with anti-obesity effects: Dual action as PTP1B inhibitors and PPAR-γ activators. Bioorganic & Medicinal Chemistry Letters 2010, 20(22):6758-6763.
15. Black E., Breed J., et al. Structure-based design of protein tyrosine phosphatase-1B inhibitors. Bioorganic & Medicinal Chemistry Letters 2005, 15(10):2503-2507.
16. Bluüher M., Dodson Michael M., et al. Adipose tissue selective insulin receptor knockout protects against obesity and obesity-related glucose intolerance. Developmental Cell 2002, 3(1):25-38.
17. Boutselis I.G., Yu X., et al. Synthesis and cell-based activity of a potent and selective protein tyrosine phosphatase 1B inhibitor prodrug. Journal of Medicinal Chemistry 2007, 50(4):856-864.
18. Burke T.R., Kole H.K., et al. Potent inhibition of insulin receptor dephosphorylation by a hexamer peptide containing the phosphotyrosyl mimetic F2Pmp. Biochemical and Biophysical Research Communications 1994, 204(1):129-134.
19. Burke T.R., Yao Z.-J., et al. Enantioselective synthesis of nonphosphorous-containing phosphotyrosyl mimetics and their use in the preparation of tyrosine phophatase inhibitory peptides. Tetrahedron 1998, 54(34):9981-9994.
20. Considine R.V., Sinha M.K., et al. Serum immunoreactive-leptin concentrations in normal-weight and obese humans. The New England Journal of Medicine 1996, 334(5):292-295.
21. Cota D., Proulx K., et al. Hypothalamic mTOR signaling regulates food intake. Science 2006, 312(5775):927-930.
22. De Jonghe B.C., Hayes M.R., et al. Deficiency of PTP1B in POMC neurons leads to alterations in energy balance and homeostatic response to cold exposure. American Journal of Physiology, Endocrinology and Metabolism 2011, 300(6):E1002-E1011.
23. Delibegovic M., Bence K.K., et al. Improved glucose homeostasis in mice with muscle-specific deletion of protein-tyrosine phosphatase 1B. Molecular and Cellular Biology 2007, 27(21):7727-7734.
24. Delibegovic M., Zimmer D., et al. Liver-specific deletion of protein-tyrosine phosphatase 1B (PTP1B) improves metabolic syndrome and attenuates diet-induced endoplasmic reticulum stress. Diabetes 2009, 58(3):590-699.
25. Douty B., Wayland B., et al. Isothiazolidinone inhibitors of PTP1B containing imidazoles and imidazolines. Bioorganic & Medicinal Chemistry Letters 2008, 18(1):66-71.
26. Eizirik D.L., Cardozo A.K., et al. The role for endoplasmic reticulum stress in diabetes mellitus. Endocrine Reviews 2008, 29(1):42-61.
27. Elchebly M., Payette P., et al. Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. Science 1999, 283(5407):1544-1548.
28. Erbe D.V., Klaman L.D., et al. Prodrug delivery of novel PTP1B inhibitors to enhance insulin signaling. Diabetes, Obesity & Metabolism 2009, 11(6):579-588.
29. Erbe D.V., Wang S., et al. Ertiprotafib improves glycemic control and lowers lipids via multiple mechanisms. Molecular Pharmacology 2005, 67(1):69-77.
30. Fischer E.H., Charbonneau H., et al. Protein tyrosine phosphatases: A diverse family of intracellular and transmembrane enzymes. Science 1991, 253(5018):401-406.
31. Frangioni J.V., Beahm P.H., et al. The nontransmembrane tyrosine phosphatase PTP-1B localizes to the endoplasmic reticulum via its 35 amino acid C-terminal sequence. Cell 1992, 68(3):545-560.
32. Gao Q., Wolfgang M.J., et al. Disruption of neural signal transducer and activator of transcription 3 causes obesity, diabetes, infertility, and thermal dysregulation. Proceedings of the National Academy of Sciences 2004, 101(13):4661-4666.
33. Ghilardi N., Skoda R.C. The leptin receptor activates Janus Kinase 2 and signals for proliferation in a factor-dependent cell line. Molecular Endocrinology 1997, 11(4):393-399.
34. Han Y., Belley M., et al. Discovery of [(3-bromo-7-cyano-2-naphthyl) (difluoro)-methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor. Bioorganic & Medicinal Chemistry Letters 2008, 18(11):3200-3205.
35. Hiriyanna K.T., Baedke D., et al. Thiophosphorylated substrate analogs are potent active site-directed inhibitors of protein-tyrosine phosphatases. Analytical Biochemistry 1994, 223(1):51-58.
36. Houseknecht K.L., Portocarrero C.P., et al. Leptin and its receptors: Regulators of whole-body energy homeostasis. Domestic Animal Endocrinology 1998, 25(6):457-475.
37. Huang P., Ramphal J., et al. Structure-based design and discovery of novel inhibitors of protein tyrosine phosphatases. Bioorganic & Medicinal Chemistry 2003, 11(8):1835-1849.
38. Hussain M., Ahmed V., et al. A re-examination of the difluoromethylenesulfonic acid group as a phosphotyrosine mimic for PTP1B inhibition. Bioorganic & Medicinal Chemistry 2008, 16(14):6764-6777.
39. Iversen L.F., Andersen H.S., et al. Structure based design of a low molecular weight, non-phosphorous, non-peptide, and highly selective inhibitor of protein-tyrosine phosphatase 1B. Journal of Biological Chemistry 2000, 275(14):10300-10307.
40. Iversen L.F., Møller K.B., et al. Structure determination of T cell protein-tyrosine phosphatase. Journal of Biological Chemistry 2002, 277(22):19982-19990.
41. Kaszubska W., Falls H.D., et al. Protein tyrosine phosphatase 1B negatively regulates leptin signaling in a hypothalamic cell line. Molecular and Cellular Endocrinology 2002, 195(1-2):109-118.
42. Kenner K.A., Anyanwu E., et al. Protein-tyrosine phosphatase 1B is a negative regulator of insulin- and insulin-like growth factor-I-stimulated signaling. Journal of Biological Chemistry 1996, 271(33):19810-19816.
43. Kim M.S., Pak Y.K., et al. Role of hypothalamic Foxo1 in the regulation of food intake and energy homeostasis. Nature Neuroscience 2006, 9(7):901-906.
44. Kitamura T., Feng Y., et al. Forkhead protein FoxO1 mediates Agrp-dependent effects of leptin on food intake. Nature Medicine 2006, 12(5):534-540.
45. Klaman L.D., Boss O., et al. Increased energy expenditure, decreased adiposity, and tissue-specific insulin sensitivity in protein-tyrosine phosphatase 1B-deficient mice. Molecular and Cellular Biology 2000, 20(15):5479-5489.
46. Klopfenstein S.R., Evdokimov A.G., et al. 1,2,3,4-Tetrahydroisoquinolinyl sulfamic acids as phosphatase PTP1B inhibitors. Bioorganic & Medicinal Chemistry Letters 2006, 16(6):1574-1578.
47. Kumar A., Maurya R.A., et al. Design and synthesis of 3,5-diarylisoxazole derivatives as novel class of anti-hyperglycemic and lipid lowering agents. Bioorganic & Medicinal Chemistry 2009, 17(14):5285-5292.
48. Kumar A., Sharma S., et al. Design and synthesis of 2,4-disubstituted polyhydroqunolines as prospective anti-hyperglycemic and lipid modulating agents. Bioorganic & Medicinal Chemistry 2010, 18(11):4138-4148.
49. Lantz K.A., Emeigh Hart S.G., et al. Inhibition of PTP1B by trodusquemine (MSI-1436) causes fat-specific weight loss in diet-induced obese mice. Obesity 2010, 18(8):1516-1523.
50. Lau C.K., Bayly C.I., et al. Structure based design of a series of potent and selective non peptidic PTP-1B inhibitors. Bioorganic & Medicinal Chemistry Letters 2004, 14(4):1043-1048.
51. Liljebris C., Larsen S.D., et al. 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. Journal of Medicinal Chemistry 2002, 45(9):1785-1798.
52. Liotta A.S., Kole H.K., et al. A synthetic tris-sulfotyrosyl dodecapeptide analogue of the insulin receptor 1146-kinase domain inhibits tyrosine dephosphorylation of the insulin receptor in situ. Journal of Biological Chemistry 1994, 269(37):22996-23001.
53. Liu F., Hill D.E., et al. Direct binding of the proline-rich region of protein tyrosine phosphatase 1B to the Src homology 3 domain of p130(Cas). Journal of Biological Chemistry 1996, 271(49):31290-31295.
54. Liu Z., Lee W., et al. Design, synthesis, and evaluation of bromo-retrochalcone derivatives as protein tyrosine phosphatase 1B inhibitors. Bioorganic & Medicinal Chemistry Letters 2011, 21(12):3755-3758.
55. Liu G., Xin Z., et al. Selective protein tyrosine phosphatase 1B inhibitors: Targeting the second phosphotyrosine binding site with non-carboxylic acid-containing ligands. Journal of Medicinal Chemistry 2003, 46(16):3437-3440.
56. Liu S., Zeng L.-F., et al. Targeting inactive enzyme conformation: Aryl diketoacid derivatives as a new class of PTP1B inhibitors. Journal of the American Chemical Society 2008, 130(50):17075-17084.
57. Matsuo K., Bettaieb A., et al. Regulation of brown fat adipogenesis by protein tyrosine phosphatase 1B. PLoS One 2011, 6(1):e16446.
58. Minokoshi Y., Alquier T., et al. AMP-kinase regulates food intake by responding to hormonal and nutrient signals in the hypothalamus. Nature 2004, 428(6982):569-574.
59. Morris D.L., Rui L. Recent advances in understanding leptin signaling and leptin resistance. American Journal of Physiology, Endocrinology and Metabolism 2009, 297(6):E1247-E1259.
60. Nedergaard J., Bengtsson T., et al. Unexpected evidence for active brown adipose tissue in adult humans. American Journal of Physiology, Endocrinology and Metabolism 2007, 293(2):E444-E452.
61. Niswender K.D., Morton G.J., et al. Intracellular signalling: Key enzyme in leptin-induced anorexia. Nature 2001, 413(6858):794-795.
62. Owen C., Czopek A., et al. Adipocyte-specific protein tyrosine phosphatase 1B deletion increases lipogenesis, adipocyte cell size and in a minor regulator of glucose homeostasis. PLoS One 2012, 7(2):e32700.
63. Patel D., Jain M., et al. Discovery of potent, selective and orally bioavailable triaryl-sulfonamide based PTP1B inhibitors. Bioorganic & Medicinal Chemistry Letters 2012, 22(2):1111-1117.
64. Plum L., Belgardt B.F., et al. Central insulin action in energy and glucose homeostasis. The Journal of Clinical Investigation 2006, 116(7):1761-1766.
65. Puius Y.A., Zhao Y., et al. Identification of a second aryl phosphate-binding site in protein-tyrosine phosphatase 1B: A paradigm for inhibitor design. Proceedings of the National Academy of Sciences 1997, 94(25):13420-13425.
66. Rao M.N., Shinnar A.E., et al. Aminosterols from the Dogfish Shark Squalus acanthias. Journal of Natural Products 2000, 63(5):631-635.
67. Sahu A. Intracellular leptin-signaling pathways in hypothalamic neurons: The emerging role of phosphatidylinositol-3 kinase-phosphodiesterase-3B-cAMP pathway. Neuroendocrinology 2011, 93(4):201-210.
68. Shen K., Keng Y.-F., et al. Acquisition of a specific and potent PTP1B inhibitor from a novel combinatorial library and screening procedure. Journal of Biological Chemistry 2001, 276(50):47311-47319.
69. Shi D., Li J., et al. Bromophenols as inhibitors of protein tyrosine phosphatase 1B with antidiabetic properties. Bioorganic & Medicinal Chemistry Letters 2012, 22(8):2827-2832.
70. Shrestha S., Bhattarai B.R., et al. PTP1B inhibitor Ertiprotafib is also a potent inhibitor of IκB kinase β (IKK-β). Bioorganic & Medicinal Chemistry Letters 2007, 17(10):2728-2730.
71. Shrestha S., Bhattarai B.R., et al. Mono- and disalicylic acid derivatives: PTP1B inhibitors as potential anti-obesity drugs. Bioorganic & Medicinal Chemistry 2007, 15(20):6535-6548.
72. Sparks R.B., Polam P., et al. Benzothiazole benzimidazole (S)-isothiazolidinone derivatives as protein tyrosine phosphatase-1B inhibitors. Bioorganic & Medicinal Chemistry Letters 2007, 17(3):736-740.
73. Stuible M., Zhao L., et al. Cellular inhibition of protein tyrosine phosphatase 1B by uncharged thioxothiazolidinone derivatives. ChemBioChem 2007, 8(2):179-186.
74. Tartaglia L.A., Dembski M., et al. Identification and expression cloning of a leptin receptor, OB-R. Cell 1995, 83(7):1263-1271.
75. Tonks N.K. PTP1B: From the sidelines to the front lines. FEBS Letters 2003, 546(1):140-148.
76. Tonks N.K., Diltz C.D., et al. Purification of the major protein-tyrosine-phosphatases of human placenta. Journal of Biological Chemistry 1988, 263(14):6722-6730.
77. Wan Z.-K., Follows B., et al. Probing acid replacements of thiophene PTP1B inhibitors. Bioorganic & Medicinal Chemistry Letters 2007, 17(10):2913-2920.
78. Wellen K.E., Hotamisligil G.S. Inflammation, stress, and diabetes. The Journal of Clinical Investigation 2005, 115(5):1111-1119.
79. Wiesmann C., Barr K.J., et al. Allosteric inhibition of protein tyrosine phosphatase 1B. Nature Structural and Molecular Biology 2004, 11(8):730-737.
80. Wilson D.P., Wan Z.-K., et al. Structure-based optimization of protein tyrosine phosphatase 1B inhibitors: From the active site to the second phosphotyrosine binding site. Journal of Medicinal Chemistry 2007, 50(19):4681-4698.
81. Ye D., Zhang Y., et al. Novel thiophene derivatives as PTP1B inhibitors with selectivity and cellular activity. Bioorganic & Medicinal Chemistry 2010, 18(5):1773-1782.
82. Yuan M., Konstantopoulos N., et al. Reversal of obesity- and diet-induced insulin resistance with salicylates or targeted disruption of Ikkβ. Molecular Sciences 2001, 293(5535):1673-1677.
83. Zabolotny J.M., Bence-Hanulec K.K., et al. PTP1B regulates leptin signal transduction in vivo. Developmental Cell 2002, 2(4):489-495.
84. Zhang Y., Proenca R., et al. Positional cloning of the mouse obese gene and its human homologue. Nature 1994, 372(6505):425-432.
85. Zhao A.Z., Huan J.-N., et al. A phosphatidylinositol 3-kinase phosphodiesterase 3B-cyclic AMP pathway in hypothalamic action of leptin on feeding. Nature Neuroscience 2002, 5(8):727-728.
86. Zhao H., Liu G., et al. Isoxazole carboxylic acids as protein tyrosine phosphatase 1B (PTP1B) inhibitors. Bioorganic & Medicinal Chemistry Letters 2004, 14(22):5543-5546.