3D QSAR studies on protein tyrosine phosphatase 1B inhibitors: Comparison of the quality and predictivity among 3D QSAR models obtained from different conformer-based alignments

Journal of Chemical Information and Modeling

Volumn 46, Issue 6, 2006, Pages 2579-2590

  Pandey, Gyanendra ^a   Saxena, Anil K ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL GEOMETRY; COMPUTER SIMULATION; MATHEMATICAL MODELS; MOLECULAR STRUCTURE; PROTEINS;

COCRYSTALLIZED CONFORMER BASED ALIGNMENT (CCBA); COMPARATIVE MOLECULAR FIELD ANALYSIS (COMFA); PROTEIN TYROSINE PHOSPHATASE; QSAR MODELS;

ENZYME INHIBITION;

ENZYME INHIBITOR; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE, NON RECEPTOR TYPE 1; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION; DRUG ANTAGONISM; DRUG INDUSTRY; ELECTRICITY; HUMAN; HYDROGEN BOND; METHODOLOGY; PROTEIN BINDING; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REGRESSION ANALYSIS; THREE DIMENSIONAL IMAGING; X RAY; X RAY CRYSTALLOGRAPHY;

CHEMISTRY, PHARMACEUTICAL; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; DRUG INDUSTRY; ELECTROSTATICS; ENZYME INHIBITORS; HUMANS; HYDROGEN BONDING; IMAGING, THREE-DIMENSIONAL; LEAST-SQUARES ANALYSIS; MODELS, CHEMICAL; PROTEIN BINDING; PROTEIN-TYROSINE-PHOSPHATASE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; X-RAYS;

EID: 33845735189     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci600224n     Document Type: Article

References (47)

1. Sames, P. G.; Taylor, J. B. Comprehensive Medicinal Chemistry; Pergamon Press: Oxford, U. K., 1990; Vol. 4.
2. Hansch, C.; Fujita, T. p-σ-π Analysis: A Method for the Correlation of Biological Activity and Chemical Structure. J. Am. Chem. Soc. 1964, 86, 1616-1626.
3. Hansch, C.; Leo, A.; Hoekman, D. Exploring QSAR: Hydrophobic, Electronic and Steric Constants: American Chemical Society: Washington, DC, 1995.
4. Cramer, R. D., III.; Patterson, D. E.; Bunce, J. D. Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
5. Klebe, G.; Abraham, U.; Mietzner, T. Molecular Similarity Indices in a Comparative Analysis (CoMSIA) of Drug Molecules to Correlate and Predict Their Biological Activity. J. Med. Chem. 1994, 37, 4130-4146.
6. Geladi, P.; Kowalski, B. R. Partial Least-Squares Regression: A Tutorial. Anal Chim. Acta 1986, 185, 1-17.
7. (a) Green, S. M.; Marshall, G. R. 3D-QSAR: A Current Perspective. Trends Pharmacol. Sci. 1995, 16, 285-291.
8. (b) Amin, E. A.; Welsh, W. J. Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Models for a Novel Class of Piperazine-Based Stromelysin-1 (MMP-3) Inhibitors: Applying a "Divide and Conquer" Strategy. J. Med. Chem. 2001, 44, 3849-3855.
9. Sufrin, J. R.; Dunn, D. A.; Marshall, G. R. Steric Mapping of the L-Methionine Binding Site of ATP: L-Methionine 5-Adenosyltransferase. Mol. Pharmacol. 1981, 19, 307-313.
10. Hasegawa, K.; Arakawa, M.; Funatsu, K. 3D-QSAR Study of Insecticidal Neonicotinoid Compounds Based on 3-Way Partial Least Squares Model. Chemom. Intell. Lab. Syst. 1999, 47, 33-40.
11. Hasegawa, K.; Arakawa, M.; Funatsu, K. Rational Choice of Bioactive Conformations through Use of Conformation Analysis and 3-Way Partial Least Squares Modeling. Chemom. Intell. Lab. Syst. 2000, 50, 253-261.
12. Sippl, W. Receptor-Based 3D QSAR Analysis of Estrogen Receptor Ligands - Merging the Accuracy of Receptor-Based Alignments with the Computational Efficiency of Ligand-Based Methods. J. Comput.-Aided Mol. Des. 2000, 14, 559-572.
13. Liu, H.; Huang, X.; Shen, J.; Luo, X.; Li, M.; Xiong, B.; Chen, G.; Yang, Y.; Jiang, H.; Chen, K. Inhibitory Mode of 1,5-Diarylpyrazole Derivatives against Cyclooxygenase-2 and Cyclooxygenase-1: Molecular Docking and 3D QSAR Analyses. J. Med. Chem. 2002, 45, 4816-4827.
14. Buolamwini, J. K.; Assefa, H. CoMFA and CoMSIA 3D QSAR and Docking Studies on Conformationally Restrained Cinnamoyl HIV-1 Integrase Inhibitors: Exploration of a Binding Mode at the Active Site. J. Med. Chem. 2002, 45, 841-852.
15. Cui, M.; Huang, X.; Luo, X.; Briggs, J. M.; Ji, R.; Chen, K.; Shen, J.; Jiang, H. Molecular Docking and 3D-QSAR Studies on Gag Peptide Analogue Inhibitors Interacting with Human Cyclophilin A. J. Med. Chem. 2002, 45, 5249-5259.
16. Huang, X.; Xu, L.; Luo, X.; Fan, K.; Ji, R.; Pei, G.; Chen, K.; Jiang, H. Elucidating the Inhibiting Mode of AHPBA Derivatives against HIV-1 Protease and Building Predictive 3D-QSAR Models. J. Med. Chem. 2002, 45, 333-343.
17. Neel, B. G.; Tonks, N. K. Protein Tyrosine Phosphatases in Signal Transduction. Curr. Opin. Cell Biol. 1997, 9, 193-204.
18. Denu, J. M.; Stuckey, J. A.; Saper, M. A.; Dixon, J. E. Form and Function in Protein Dephosphorylation. Cell 1996, 87, 361-364.
19. Jia, Z. Protein Phosphatases: Structures and Implications. Biochem. Cell Biol. 1997, 75, 17-26.
20. Zhang, Z. Y. Protein-Tyrosine Phosphatases: Biological Function, Structural Characteristics, and Mechanism of Catalysis. Crit. Rev. Biochem. Mol. Biol. 1998, 33, 1-5.
21. Lander, E. S.; Linton, L. M.; Birren, B.; Nusbaum, C.; Zody, M. C.; Baldwin, J.; Devon, K.; Dewar, K.; Doyle, M.; Fitzhugh, W.; Funke, R.; Gage, D.; Harris, K.; Heaford, A.; Howland, J.; Kann, L.; Lehoczky, J.; LeVine, R.; McEwan, P.; McKernan, K.; Meldrim, J.; Mesirov, J. P.; Miranda, C.; Morris, W.; Naylor, J.; Raymond, C.; Rosetti, M.; Santos, R.; Sheridan, A.; Sougnez, C.; Stange-Thomann, N.; Stojanovic, N.; Subramanian, A.; Wyman, D.; Rogers, J.; Sulston, J.; Ainscough, R.; Beck, S.; Bentley, D.; Burton, J.; Clee, C.; Carter, N.; Coulson, A.; Deadman, R.; Deloukas, P.; Dunham, A.; Dunham, I.; Durbin, R.; French, L.; Grafham, D.; Gregory, S.; Hubbard, T.; Humphrey, S.; Hunt, A.; Jones, M.; Lloyd, C.; McMurray, A.; Matthews, L.; Mercer, S.; Milne, S.; Mullikin, J. C.; Mungall, A.; Plumb, R.; Ross, M.; Shownkeen, R.; Sims, S.; Waterson, R. H.; Wilson, R. K.; Hillier, L. W.; McPherson, J. D.; Marra, M. A.; Mardis, E. R.; Fulton, L. A.; Chinwalla, A. T.; Pepin, K. H.; Gish, W. R.; Chissoe, S. L.; Wendl, M. C.; Delehaunty, K. D.; Miner, T. L.; Delehaunty, A.; Kramer, J. B.; Cook, L. L.; Fulton, R. S.; Johnson, D. L.; Minx, P. J.; Clifton, S. W.; Hawkins, T.; Branscomb, E.; Predki, P.; Richardson, P.; Wenning, S.; Slezak, T.; Doggett, N.; Cheng, J. F.; Olsen, A.; Lucas, S.; Elkin, C.; Uberbacher, E.; Frazier, M.; Gibbs, R. A.; Muzny, D. M.; Scherer, S. E.; Bouck, J. B.; Sodergren, E. J.; Worley, K. C.; Rives, C. M.; Gorrell, J. H.; Metzker, M. L.; Naylor, S. L.; Kucherlapati, R. S.; Nelson, D. L.; Weinstock, G. M.; Sakaki, Y.; Fujiyama, A.; Hattori, M.; Yada, T.; Toyoda, A.; Itoh, T.; Kawagoe, C.; Watanabe, H.; Totoki, Y.; Taylor, T.; Weissenbach, J.; Heilig, R.; Saurin, W.; Artiguenave, F.; Brottier, P.; Bruis, T.; Pelletier, E.; Robert, C.; Wincker, P.; Smith, D. R.; Doucette-Stamm, L.; Rubenfield, M.; Weinstock, K.; Lee, H. M.; Dubois, J.; Rosenthal, A.; Platzer, M.; Nyakatura, G.; Taudien, S.; Rump, A.; Yang, H.; Yu, J.; Wang, J.; Huang, G.; Gu, J.; Hood, L.; Rowen, L.; Madan, A.; Qin, S.; Davis, R. W.; Federspiel, N. A.; Abola, A. P.; Proctor, M. J.; Myers, R. M.; Schmutz, J.; Dickson, M.; Grimwood, J.; Cox, D. R.; Olson, M. V.; Kaul, R.; Raymond, C.; Shimizu, N.; Kawasaki, K.; Minoshima, S.; Evans, G. A.; Athanasiou, M.; Schultz, R.; Roe, B. A.; Chen, F.; Pan, H.; Ramser, J.; Lehrach, H.; Reinhardt, R.; McCombie, W. R.; De la Bastide, M.; Dedhia, N.; Blocker, H.; Hornischer, K.; Nordsiek, G.; Agarwala, R.; Aravind, L.; Bailey, J. A.; Bateman, A.; Batzoglou, S.; Birney, E.; Bork, P.; Brown, D. G.; Burge, C. B.; Cerutti, L.; Chen, H. C.; Church, D.; Clamp, M.; Copley, R. R.; Doerks, T.; Eddy, S. R.; Eichler, E. E.; Furey, T. S.; Galagan, J.; Gilbert, J. G.; Harmon, C.; Hayashizaki, Y.; Haussler, D.; Hermjakob, H.; Hokamp, K.; Jang, W.; Johnson, L. S.; Jones, T. A.; Kasif, S.; Kaspryzk, A.; Kennedy, S.; Kent, W. J.; Kitts, P.; Koonin, E. V.; Korf, I.; Kulp, D.; Lancet, D.; Lowe, T. M.; McLysaght, A.; Mikkelsen, T.; Moran, J. V.; Mulder, N.; Pollara, V. J.; Ponting, C. P.; Schuler, G.; Schultz, J.; Slater, G.; Smit, A. F.; Stupka, E.; Szustakowski, J.; Thierry-Mieg, D.; Thierry-Mieg, J.; Wagner, L.; Wallis, J.; Wheeler, R.; Williams, A.; Wolf, Y. I.; Wolfe, K. H.; Yang, S. P.; Yeh, R. F.; Collins, F.; Guyer, M. S.; Peterson, J.; Felsenfeld, A.; Wetterstrand, K. A.; Patrinos, A.; Morgan, M. J.; De Jong, P.; Catanese, J. J.; Osoegawa, K.; Shizuya, H.; Choi, S.; Chen, Y. J. Initial Sequencing and Analysis of the Human Genome. Nature 2001, 409, 860-921.
22. Venter, J. C.; Adams, M. D.; Myers, E. W.; Li, P. W.; Mural, R. J.; Sutton, G. G.; Smith, H. O.; Yandell, M.; Evans, C. A.; Holt, R. A.; Gocayne, J. D.; Amanatides, P.; Ballew, R. M.; Huson, D. H.; Wortman, J. R.; Zhang, Q.; Kodira, C. D.; Zheng, X. H.; Chen, L.; Skupski, M.; Subramanian, G.; Thomas, P. D.; Zhang, J.; Gabor Miklos, G. L.; Nelson, C.; Broder, S.; Clark, A. G.; Nadeau, J.; McKusick, V. A.; Zinder, N.; Levine, A. J.; Roberts, R. J.; Simon, M.; Slayman, C.; Hunkapiller, M.; Bolanos, R.; Delcher, A.; Dew, I.; Fasulo, D.; Flanigan, M.; Florea, L.; Halpern, A.; Hannenhalli, S.; Kravitz, S.; Levy, S.; Mobarry, C.; Reinert, K.; Remington, K.; AbuThreideh, J.; Beasley, E.; Biddick, K.; Bonazzi, V.; Brandon, R.; Cargill, M.; Chandramouliswaran, I.; Charlab, R.; Chaturvedi, K.; Deng, Z.; Di Francesco, V.; Dunn, P.; Eilbeck, K.; Evangelista, C.; Gabrielian, A. E.; Gan, W.; Ge, W.; Gong, F.; Gu, Z.; Guan, P.; Heiman, T. J.; Higgins, M. E.; Ji, R. R.; Ke, Z.; Ketchum, K. A.; Lai, Z.; Lei, Y.; Li, Z.; Li, J.; Liang, Y.; Lin, X.; Lu, F.; Merkulov, G. V.; Milshina, N.; Moore, H. M.; Naik, A. K.; Narayan, V. A.; Neelam, B.; Nusskern, D.; Rusch, D. B.; Salzberg, S.; Shao, W.; Shue, B.; Sun, J.; Wang, Z.; Wang, A.; Wang, X.; Wang, J.; Wei, M.; Wides, R.; Xiao, C.; Yan, C.; Yao, A.; Ye, J.; Zhan, M.; Zhang, W.; Zhang, H.; Zhao, Q.; Zheng, L.; Zhong, F.; Zhong, W.; Zhu, S.; Zhao, S.; Gilbert, D.; Baumhueter, S.; Spier, G.; Carter, C.; Cravchik, A.; Woodage, T.; Ali, F.; An, H.; Awe, A.; Baldwin, D.; Baden, H.; Barnstead, M.; Barrow, I.; Beeson, K.; Busam, D.; Carver, A.; Center, A.; Cheng, M. L.; Curry, L.; Danaher, S.; Davenport, L.; Desilets, R.; Dietz, S.; Dodson, K.; Doup, L.; Ferriera, S.; Garg, N.; Gluecksmann, A.; Hart, B.; Haynes, J.; Haynes, C.; Heiner, C.; Hladun, S.; Hostin, D.; Houck, J.; Howland, T.; Ibegwam, C.; Johnson, J.; Kalush, F.; Kline, L.; Koduru, S.; Love, A.; Mann, F.; May, D.; McCawley, S.; McIntosh, T.; McMullen, I.; Moy, M.; Moy, L.; Murphy, B.; Nelson, K.; Pfannkoch, C.; Pratts, E.; Puri, V.; Qureshi, H.; Reardon, M.; Rodriguez, R.; Rogers, Y. H.; Romblad, D.; Ruhfel, B.; Scott, R.; Sitter, C.; Smallwood, M.; Stewart, E.; Strong, R.; Suh, E.; Thomas, R.; Tint, N. N.; Tse, S.; Vech, C.; Wang, G.; Wetter, J.; Williams, S.; Williams, M.; Windsor, S.; Winn-Deen, E.; Wolfe, K.; Zaveri, J.; Zaveri, K.; Abril, J. F.; Guigo, R.; Campbell, M. J.; Sjolander, K. V.; Karlak, B.; Kejariwal, A.; Mi, H.; Lazareva, B.; Hatton, T.; Narechania, A.; Diemer, K.; Muruganujan, A.; Guo, N.; Sato, S.; Bafna, V.; Istrail, S.; Lippert, R.; Schwartz, R.; Walenz, B.; Yooseph, S.; Allen, D.; Basu, A.; Baxendale, J.; Blick, L.; Caminha, M.; Carnes-Stine, J.; Caulk, P.; Chiang, Y. H.; Coyne, M.; Dahlke, C.; Mays, A.; Dombroski, M.; Donnelly, M.; Ely, D.; Esparham, S.; Fosler, C.; Gire, H.; Glanowski, S.; Glasser, K.; Glodek, A.; Gorokhov, M.; Graham, K.; Gropman, B.; Harris, M.; Heil, J.; Henderson, S.; Hoover, J.; Jennings, D.; Jordan, C.; Jordan, J.; Kasha, J.; Kagan, L.; Kraft, C.; Levitsky, A.; Lewis, M.; Liu, X.; Lopez, J.; Ma, D.; Majoras, W.; McDaniel, J.; Murphy, S.; Newman, M.; Nguyen, T.; Nguyen, N.; Nodell, M.; Pan, S.; Peck, J.; Peterson, M.; Rowe, W.; Sanders, R.; Scott, J.; Simpson, M.; Smith, T.; Sprague, A.; Stockwell, T.; Turner, R.; Venter, E.; Wang, M.; Wen, M.; Wu, D.; Wu, M.; Xia, A.; Zandieh, A.; Zhu, X. The Sequence of the Human Genome, Science 2001, 291, 1304-1351.
23. Evans, J. L.; Jallal, B. Protein Tyrosine Phosphatases: Their Role in Insulin Action and Potential as Drug Targets. Expert Opin. Invest. Drugs 1999, 5, 139-160.
24. Burke, T. R.; Zhang, Z. Y., Jr. Protein-Tyrosine Phosphatases: Structure, Mechanism, and Inhibitor Discovery. Biopolymers 1998, 47, 225-241.
25. Ahn, N. Introduction: Protein Phosphorylation and Signaling. Chem. Rev. 2001, 101, 2207-2208.
26. Bandyopadhyay, D.; Kusari, A.; Kenner, K. A.; Liu, F.; Chernoff, J.; Gustafson, T. A.; Kusari, J. Protein-Tyrosine Phosphatase 1B Complexes with the Insulin Receptor in Vivo and is Tyrosine-Phosphorylated in the Presence of Insulin. J. Biol. Chem. 1997, 272, 1639-1645.
27. Wang, X. Y.; Bergdahl, K.; Heijbel, A.; Liljebris, C.; Bleasdale, J. E. Analysis of in Vitro Interactions of Protein Tyrosine Phosphatase 1B with Insulin Receptors. Mol. Cell. Endocrinol. 2001, 173, 109-119.
28. Jacob, K. K.; Sap, J.; Stanley, F. M. Receptor-Like Protein-Tyrosine Phosphatase α Specifically Inhibits Insulin-Increased Prolactin Gene Expression. J. Biol. Chem. 1998, 273, 4800-4809.
29. Goldstein, B. I. Protein-Tyrosine Phosphatases and the Regulation of Insulin Action. J. Cell. Biochem. 1992, 48, 33-42.
30. 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.
31. Klaman, L. D.; Boss, O.; Peroni, O. D.; Kim, J. K.; Martino, J. L.; Zabolotny, J. M.; Moghai, 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.
32. Murthy, V. S.; Kulkarni, V. M. 3D-QSAR CoMFA and CoMSIA on Protein Tyrosine Phosphatase 1B Inhibitors. Bio. Med. Chem. 2002, 10 (7), 2267-2282.
33. Hu, X.; Stebbins, C. E. Molecular Docking and 3D-QSAR Studies of Yersinia Protein Tyrosine Phosphatase YopH Inhibitors. Bio. Med. Chem. 2005, 13 (4), 1101-1109.
34. Zhou, M.; Ji, M. Molecular Docking and 3D-QSAR on 2-(Oxalylamino) Benzoic Acid and Its Analogues as Protein Tyrosine Phosphatase 1B Inhibitors. Bio. Med. Chem. Lett. 2005, 15 (24), 5521-5525.
35. Larsen, S. D.; Barf, T.; Liljebris, C.; May, P. D.; Ogg, D.; O'Sullivan, T. J.; Palazuk, B. J.; Schostarez, H. J.; Stevens, F. C. Synthesis and Biological Activity of a Novel Class of Small Molecular Weight Peptidomimetic Competitive Inhibitors of PTP1B. J. Med. Chem. 2002, 45, 598-622.
36. Desai, B.; Sureja, D.; Naliapara, Y.; Shah, A.; Saxena, A. K. Synthesis and QSAR Studies of 4-Substituted Phenyl-2,6-dimethyl-3,5-bis-N-(substituted phenyl) Carbamoyl-1,4-dihydropyridines as Potential Antitubercular Agents. Bio. Med. Chem. 2001, 9 (8), 1993-1998.
37. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated Docking Using a Lamarckian Genetic Algorithm and Empirical Binding Free Energy Function. J. Comput. Chem. 1998, 19, 1639-1662.
38. Bohacek, R. S.; McMartin, C. Definition and Display of Steric, Hydrophobic, and Hydrogen Bonding Properties of Ligand Binding Sites in Proteins using Lee and Richards Accessible Surface: Valida-tion of a High-Resolution Graphical Tool for Drug Design. J. Med. Chem. 1992, 35, 1671-1684.
39. Kroemer, R. T.; Hecht, P. Replacement of Steric 6-12 Potential-Derived Interaction Energies by Atom-Based Indicator Variables in CoMFA Leads to Models of Higher Consistency. J. Comput.-Aided Mol. Des. 1995, 9, 205-212.
40. Bush, B. L.; Nachbar, R. B., Jr. Sample-Distance Partial Least Squares: PLS Optimized for Many Variables, with Application to CoMFA. J. Comput.-Aided Mol. Des. 1993, 7, 587-619.
41. Böhm, M.; Stürzebecher, J.; Klebe, G. Three-Dimensional Quantitative Structure-Activity Relationship Analyses Using Comparative Molecular Field Analysis and Comparative Molecular Similarity Indices Analysis to Elucidate Selectivity Differences of Inhibitors Binding to Trypsin, Thrombin, and Factor Xa. J. Med. Chem. 1999, 42, 458-477.
42. Dixit, A.; Kashaw, S. K.; Gaur, S.; Saxena, A. K. Development of CoMFA, Advance CoMFA and CoMSIA Models in Pyrroloquinazolines as Thrombin Receptor Antagonist. Bioorg. Med. Chem. 2004, 12, 63-69.
43. Peters, G. H.; Frimurer, T. N.; Andersen, J. N.; Olsen, O. H. Molecular Dynamic Simulations of Protein Tyrosine Phosphatase 1B.II Substrate Enzyme Interactions and Dynamics. Biophys. J. 2000, 78, 2191-2200.
44. Sarmiento, M.; Puius, Y. A.; Vetter, S. W.; Keng, Y. F.; Wu, L.; Zhao, Y.; Lawrence, D. S.; Almp, S. C.; Zhang, Z. Y. Structural Basis of Plasticity in Protein Tyrosine Phosphatase 1B Substrate Recognition Biochemistry. Biochemistry 2000, 39, 8171-8179.
45. Jia, Z.; Barford, D.; Flint, A. J.; Tonks, N. K. Structural Basis of Phosphotyrosine Peptide Recognition by PTP1B. Science 1995, 208, 1754-1758.
46. Sekar, N.; Li, J.; Shechter, Y. Vanadium Salts as Insulin Substitutes: Mechanisms of Action, a Scientific and Therapeutic Tool in Diabetes Mellitus Research. Crit. Rev. Biochem. Mol. Biol. 1996, 31, 339-359.
47. Goldstein, B. J.; Bittner-Kowalczyk, A.; White, M. F.; Harbeck, M. Tyrosine Dephosphorylation and Deactivation of Insulin Receptor Substrate-1 by Protein-Tyrosine Phosphatase 1B. Possible Facilitation by the Formation of a Ternary Complex with the GRB2 Adaptor Protein. J. Biol. Chem. 2000, 275, 4283-4289.