Fragment screening and assembly: A highly efficient approach to a selective and cell active protein tyrosine phosphatase 1B inhibitor

Journal of Medicinal Chemistry

Volumn 46, Issue 20, 2003, Pages 4232-4235

  Liu, Gang ^a   Xin, Zhili ^a   Pei, Zhonghua ^a   Hajduk, Philip J ^a   Abad Zapatero, Cele ^a   Hutchins, Charles W ^a   Zhao, Hongyu ^a   Lubben, Thomas H ^a   Ballaron, Stephen J ^a   Haasch, Deanna L ^a   Kaszubska, Wiweka ^a   Rondinone, Cristina M ^a   Trevillyan, James M ^a   Jirousek, Michael R ^a,b  

^a ABBOTT LABORATORIES   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAMIC ACID; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE 1B; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; PROTEIN TYROSINE PHOSPHATASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING SITE; CATALYSIS; CHEMICAL STRUCTURE; DEPHOSPHORYLATION; ENZYME INHIBITION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN ASSEMBLY; T LYMPHOCYTE;

ANIMALS; BINDING SITES; CATALYTIC DOMAIN; COS CELLS; CRYSTALLOGRAPHY, X-RAY; DNA-BINDING PROTEINS; DRUG DESIGN; ENZYME INHIBITORS; MODELS, MOLECULAR; MOLECULAR MIMICRY; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXAMIC ACID; PHOSPHORYLATION; PROTEIN-TYROSINE-PHOSPHATASE; STAT3 TRANSCRIPTION FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP; TRANS-ACTIVATORS;

EID: 0141680857     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm034122o     Document Type: Article

References (30)

1. (a) Cheng, A.; Dubé, N.; Gu, F.; Tremblay, M. L. Coordinated Action of Protein Tyrosine Phosphatases in Insulin Signal Transduction. Eur. J. Biochem. 2002, 269, 1050-1059.
2. (b) Zhang, Z.-Y.; Lee, S. Y. PTP1B Inhibitors as Potential Therapeutics in the Treatment of Type 2 Diabetes and Obesity. Expert Opin. Invest. Drugs 2003, 12, 223-233.
3. 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.
4. Klaman, L. D.; Boss, O.; Peroni, O. D.; Kim, J. K.; Martino, J. L.; Zabolotny, J. M.; Moghal, N.; Lubkin, M.; Kim, Y. B.; Sharpe, A. H.; Stricker-Krongrad, A.; Shulman, G. I.; Neel, B. G.; Kahn, B. B. Increased Energy Expenditure, Decreased Adiposity, and Tissue-Specific Insulin Sensitivity in Protein-Tyrosine Phosphatase 1B-Deficient Mice. Mol. Cell. Biol. 2000, 20, 5479-5489.
5. Barford, D. Colworth Medal Lecture. Structural Studies of Reversible Protein Phosphorylation and Protein Phosphatases. Biochem. Soc. Trans. 1999, 27, 751-766.
6. Barford, D.; Flint, A. J.; Tonks, N. K. Crystal Structure of Human Protein Tyrosine Phosphatase 1B. Science 1994, 263, 1397-1404.
7. Sarmiento, M.; Puius, Y. A.; Vetter, S. W.; Keng, Y. F.; Wu, L.; Zhao, Y.; Lawrence, D. S.; Almo, S. C.; Zhang, Z.-Y. Structural Basis of Plasticity in Protein Tyrosine Phosphatase 1B Substrate Recognition. Biochemistry 2000, 39, 8171-8179.
8. Johnson, T. O.; Ermolieff, J.; Jirousek, M. R. Protein Tyrosine Phosphatase 1B Inhibitors for Diabetes. Nat. Rev. Drug Discovery 2002, 1, 696-709.
9. Blaskovich, M. A.; Kim, H. O. Recent Discovery and Development of Protein Tyrosine Phosphatase Inhibitors. Expert Opin. Ther. Pat. 2002, 12, 871-905.
10. Liu, G.; Trevillyan, J. M. Protein Tyrosine Phosphatase 1B as a Target for the Treatment of Impaired Glucose Tolerance and Type 2 Diabetes. Curr. Opin. Invest. Drugs 2002, 3, 1608-1616.
11. Puius, Y. A.; Zhao, Y.; Sullivan, M.; Lawrence, D. S.; Almo, S. C.; Zhang, Z.-Y. Identification of a Second Aryl Phosphate-Binding Site in Protein-Tyrosine Phosphatase 1B: A Paradigm for Inhibitor Design. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 13420-13425.
12. Szczepankiewicz, B. G.; Liu, G.; Pei, Z.; Xin, Z.; Lubben, T. H.; Trevillyan, J. M.; Stashko, M. A.; Ballaron, S. J.; Hajduk, P. J.; Liang, H.; Huang, F.; Hutchins, C. W.; Abad-Zapatero, C.; Jirousek, M. R.; Fesik, S. W. Discovery of a Potent, Selective Protein Tyrosine Phosphatase 1B Inhibitor Using a Linked-Fragment Based Strategy. J. Am. Chem. Soc. 2003, 125, 4087-4096.
13. Xin, Z.; Oost, T.; Abad-Zapatero, C.; Hajduk, P. J.; Pei, Z.; Szczepankiewicz, B. G.; Hutchins, C. W.; Ballaron, S. J.; Stashko, M. A.; Lubben, T.; Trevillyan, J. M.; Jirousek, M. R.; Liu, G. Potent, Selective Inhibitors of Protein Tyrosine Phosphatase 1B. Bioorg. Med. Chem. Lett. 2003, 13, 1887-1890.
14. Shuker, S. B.; Hajduk, P. J.; Meadows, R. P.; Fesik, S. W. Discovering High-Affinity Ligands for Proteins: SAR by NMR. Science 1996, 274, 1531-1534.
15. Liu, G.; Xin, Z.; Liang, H.; Abad-Zapatero, C.; Hajduk, P. J.; Janowick, D. A.; Szczepankiewicz, B. G.; Pei, Z.; Hutchins, C. W.; Ballaron, S. J.; Stashko, M. A.; Lubben, T. H.; Berg, C. E.; Rondinone, C. M.; Trevillyan, J. M. ; Jirousek, M. R. Selective Protein Tyrosine Phosphatase 1B Inhibitors: Targeting the Second Phosphotyrosine Binding Site with Non-Carboxylic Acid-Containing Ligands. J. Med. Chem. 2003, 46, 3437-3440.
16. Møller, N. P. H.; Iversen, L. F.; Andersen, H. S.; McCormack, J. G. Protein Tyrosine Phosphatases (PTPs) as Drug Targets: Inhibitors of PTP1B for the Treatment of Diabetes. Curr. Opin. Drug Discovery Dev. 2000, 3, 527-540.
17. 13C-Labeled Methyl Groups. J. Am. Chem. Soc. 2000, 122, 7898-7904.
18. Ibarra-Sanchez, M. D. J.; Simoncic, P. D.; Nestel, F. R.; Duplay, P.; Lapp, W. S.; Trembley, M. L. The T-Cell Protein Tyrosine Phosphatase. Semin. Immunol. 2000, 12, 379-386.
19. Iversen, L. F.; Møller, K. B.; Pedersen, A. K.; Peters, G. H.; Petersen, A. S.; Andersen, H. S.; Branner, S.; Mortensen, S. B.; Moller, N. P. H. Structure Determination of T Cell Protein-Tyrosine Phosphatase. J. Biol. Chem. 2002, 277, 19982-19990.
20. See ref 14 for the discussion of possible origin of TCPTP selectivity derived from interaction with site 2 of PTP1B.
21. i = 2.4 nM) with 10-fold TCPTP selectivity, see: Sun, J.-P.; Fedorov, A. A.; Lee, S.-Y.; Guo, X.-L.; Shen, K.; Lawrence, D. S.; Almo, S. C.; Zhang, Z.-Y. Crystal Structure of PTP1B Complexed with a Potent and Selective Bidentate Inhibitor. J. Biol. Chem. 2003, 278, 12406-12414 and references therein.
22. Mitchell, T. N. Palladium-Catalysed Reactions of Organotin Compounds. Synthesis 1992, 803-815.
23. Refined crystallographic coordinates for the structure of PTP1B complexed with 9 have been deposited with the Protein Data Bank (www.rcsb.org) with entry code 1Q1M.
24. Kaszubska, W.; Falls, H, D.; Schaefer, V. G.; Haasch, D.; Frost. L.; Hessler, P.; Kroeger, P. E.; White, D. W.; Jirousek, M. R.; Trevillyan, J. M. Protein Tyrosine Phosphatase 1B Negatively Regulates Leptin Signaling in a Hypothalamic Cell Line. Mol. Cell. Endocrinol. 2002, 195, 109-118.
25. Zabolotny, J. M.; Bence-Hanulec, K. K.; Stricker-Krongrad, A.; Haj, F.; Wang, Y.; Minokoshi, Y.; Kim, Y. B.; Elmquist, J. K.; Tartaglia, L. A.; Kahn, B. B.; Neel, B. G. PTP1B Regulates Leptin Signal Transduction in Vivo. Dev. Cell 2002, 2, 489-495.
26. Posner, B. I.; Faure, R.; Burgess, J. W.; Bevan, A. P.; Lachance, D.; Zhang-Sun, G.; Fantus, I. G.; Ng, J. B.; Hall, D. A.; Lum, B. S. Peroxovanadium Compounds. A New Class of Potent Phosphotyrosine Phosphatase Inhibitors Which Are Insulin Mimetics. J. Biol. Chem, 1994, 269, 4596-4604.
27. Yee, S. In Vitro Permeability across Caco-2 Cells (Colonic) Can Predict in Vivo (Small Intestinal) Absorption in Man-Fact or Myth. Pharm. Res. 1997, 14, 763-766.
28. Chambers, R. D. In Interscience Monographs in Organic Chemistry: Fluorine in Organic Chemistry; John Wiley and Sons: New York, 1973.
29. 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.
30. Larsen, S. D.; Stevens, F. C.; Lindberg, T. J.; Bodnar, P. M.; O'Sullivan, T. J.; Schostarez, H. J.; Palazuk, B. J.; Bleasdale, J. E. Modification of the N-Terminus of Peptidomimetic Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitors: Identification of Analogues with Cellular Activity. Bioorg. Med. Chem. Lett. 2003, 13, 971-975.