Hydroxyindole carboxylic acid-based inhibitors for receptor-type protein tyrosine protein phosphatase beta

Antioxidants and Redox Signaling

Volumn 20, Issue 14, 2014, Pages 2130-2140

  Zeng, Li Fan ^a   Zhang, Ruo Yu ^a   Bai, Yunpeng ^a   Wu, Li ^a   Gunawan, Andrea M ^a   Zhang, Zhong Yin ^a  

^a INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; GROWTH FACTOR; HYDROXYINDOLE CARBOXYLIC ACID DERIVATIVE; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE BETA; PROTEIN TYROSINE PHOSPHATASE INHIBITOR; SALICYLIC ACID; UNCLASSIFIED DRUG; CARBOXYLIC ACID; ENZYME INHIBITOR; INDOLE DERIVATIVE; PROTEIN TYROSINE PHOSPHATASE 1B;

ANGIOGENESIS; ARTICLE; BINDING AFFINITY; CLICK CHEMISTRY; DRUG SELECTIVITY; DRUG TARGETING; HUMAN; HUMAN CELL; IC 50; OXIDATION REDUCTION REACTION; PHARMACOPHORE; PRIORITY JOURNAL; SIGNAL TRANSDUCTION; UMBILICAL VEIN ENDOTHELIAL CELL; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; ENZYMOLOGY; HEK293 CELL LINE; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

CARBOXYLIC ACIDS; CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HEK293 CELLS; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; INDOLES; MOLECULAR STRUCTURE; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84898619537     PISSN: 15230864     EISSN: 15577716     Source Type: Journal    
DOI: 10.1089/ars.2013.5463     Document Type: Article

References (42)

1. Amarasinghe KKD, Evidokimov AG, Xu K, Clark CM, Maier MB, Srivastava A, Colson AO, Gerwe GS, Stake GE, Howard BW, Pokross ME, Graya JL, and Peters KG. Design and synthesis of potent, non-peptidic inhibitors of HPTPb. Bioorg Med Chem Lett 16: 4252-4256, 2006.
2. Barrett WC, DeGnore JP, Keng YF, Zhang ZY, Yim MB, and Chock PB. Roles of superoxide radical anion in signal transduction mediated by reversible regulation of proteintyrosine phosphatase 1B. J Biol Chem 274: 34543-34546, 1999.
3. Baumer S, Keller L, Holtmann A, Funke R, August B, Gamp A, Wolburg H, Wolburg-Buchholz K, Deutsch U, and Vestweber D. Vascular endothelial cell-specific phosphotyrosine phosphatase (VE-PTP) activity is required for blood vessel development. Blood 107: 4754-4762, 2006.
4. Bova MP, Mattson MN, Vasile S, Tam D, Holsinger L, Bremer M, Hui T, McMahon G, Rice A, and Fukuto JM. The oxidative mechanism of action of ortho-quinone inhibitors of protein-tyrosine phosphatase alpha is mediated by hydrogen peroxide. Arch Biochem Biophys 429: 30-41, 2004.
5. Carr AN, Davis MG, Eby-Wilkens E, Howard BW, Towne BA, Dufresne TE, and Peters KG. Tyrosine phosphatase inhibition augments collateral blood flow in a rat model of peripheral vascular disease. Am J Physiol Heart Circ Physiol 287: 268-276, 2004.
6. Chae JK, Kim I, Lim ST, Chung MJ, Kim WH, Kim HG, Ko JK, and Koh GY. Coadministration of angiopoietin-1 and vascular endothelial growth factor enhances collateral vascularization. Arterioscler Thromb Vasc Biol 20: 2573-2578, 2000.
7. Cohen P and Alessi DR. Kinase drug discovery-what's next in the field? ACS Chem Biol 8: 96-104, 2013.
8. De Munter S, Kohn M, and Bollen M. Challenges and opportunities in the development of protein phosphatase-directed therapeutics. ACS Chem Biol 8: 36-45, 2013.
9. Denu JM and Tanner KG. Specific and reversible inactivation of protein tyrosine phosphatases by hydrogen peroxide, evidence for a sulfenic acid intermediate and implications for redox regulation. Biochemistry 37: 5633-5642, 1998.
10. Dominguez MG, Hughes VC, Pan L, Simmons M, Daly C, Anderson K, Noguera-Troise I, Murphy AJ, Valenzuela DM, Davis S, Thurston G, Yancopoulos GD, and Gale NW. Vascular endothelial tyrosine phosphatase (VE-PTP)-null mice undergo vasculogenesis but die embryonically because of defects in angiogenesis. Proc Natl Acad Sci USA 104: 3243-3248 2007.
11. Fachinger G, Deutsch U, and Risau W. Functional interaction of vascular endothelial-protein-tyrosine phosphatase with the Angiopoietin receptor Tie-2. Oncogene 18: 5948-5953, 1999.
12. Gale NW and Yancopoulos GD. Growth factors acting via endothelial cell-specific receptor tyrosine kinases: VEGFs, angiopoietins, and ephrins in vascular development. Genes Dev 13: 1055-1066, 1999.
13. Hayashi M, Majumdar A, Li X, Adler J, Sun Z, Vertuani S, Hellberg C, Mellberg S, Koch S, Dimberg A, Koh GY, Dejana E, Belting HG, Affolter M, Thurston G, Holmgren L, Vestweber D, and Claesson-Welsh L. VE-PTP regulates VEGFR2 activity in stalk cells to establish endothelial cell polarity and lumen formation. Nat Commun 4: 1672, 2013.
14. Heneberg P, Dráberová L, Bambousková M, Pompach P, and Dráber P. Down-regulation of protein-tyrosine phosphatases activates an immune receptor in the absence of its translocation into lipid rafts. J Biol Chem 285: 12787-12802, 2010.
15. Huang P, Ramphal J, Wei J, Liang C, Jallal B, McMahon G, and Tang C. Structure-based design and discovery of novel inhibitors of protein tyrosine phosphatases. Bioorg Med Chem 11: 1835-1849, 2003.
16. Hunter T. Tyrosine phosphorylation: thirty years and counting. Curr Opin Cell Biol 21: 140-146, 2009.
17. Julien SG, Dubé N, Hardy S, and Tremblay ML. Inside the human cancer tyrosine phosphatome. Nat Rev Cancer 11: 35-49, 2011.
18. Kaplan R, Morse B, Huebner K, Croce C, Howk R, Ravera M, Ricca G, Jaye M, and Schlessinger J. Cloning of three human tyrosine phosphatases reveals a multigene family of receptor-linked protein-tyrosine-phosphatases expressed in brain. Proc Natl Acad Sci USA 87: 7000-7004, 1990.
19. Karisch R, Fernandez M, Taylor P, Virtanen C, St-Germain JR, Jin LL, Harris IS, Mori J, Mak TW, Senis YA, Ö stman A, Moran MF, and Neel BG. Global proteomic assessment of the classical protein-tyrosine phosphatome and "Redoxome". Cell 146: 826-840, 2011.
20. Lee SR, Kwon KS, Kim SR, and Rhee SG. Reversible inactivation of protein-tyrosine phosphatase 1B in A431 cells stimulated with epidermal growth factor. J Biol Chem 273: 15366-15372, 1998.
21. Lund IK, Andersen HS, Iversen LF, Olsen OH, Møller KB, Pedersen AK, Ge Y, Holsworth DD, Newman MJ, Axe FU, and Møller NPH. Structure-based design of selective and potent inhibitors of protein-tyrosine phosphatase b. J Biol Chem 279: 24226-24235, 2004.
22. Mali RS, Ma P, Zeng LF, Martin H, Ramdas B, He Y, Sims E, Gosh J, Nabinger S, Li S, Munugalavadla V, Craig AW, Bunting KD, Feng GS, Chan RJ, Zhang ZY, and Kapur R. Role of SHP2 phosphatase in KIT-induced transformation: identification of SHP2 as a druggable target in diseases involving oncogenic KIT. Blood 120: 2669-2678, 2012.
23. Mellberg S, Dimberg A, Bahram F, Hayashi M, Rennel E, Ameur A, Westholm JO, Larsson E, Lindahl P, Cross MJ, and Claesson-Welsh L. Transcriptional profiling reveals a critical role for tyrosine phosphatase VE-PTP in regulation of VEGFR2 activity and endothelial cell morphogenesis. FASEB J 23: 1490-1502, 2009.
24. Meng FG and Zhang ZY. Redox regulation of protein tyrosine phosphatase activity by hydroxyl radical. Biochim Biophys Acta 1834: 464-469, 2013.
25. Meng TC, Fukada T, and Tonks NK. Reversible oxidation and inactivation of protein tyrosine phosphatases in vivo. Mol Cell 9: 387-399, 2002.
26. Noren-Muller A, Reis-Correa I, Prinz H, Rosenbaum C, Saxena K, Schwalbe HJ, Vestweber D, Cagna G, Schunk S, Schwarz O, Schiewe H, and Waldmann H. Discovery of protein phosphatase inhibitor classes by biologyoriented synthesis. Proc Natl Acad Sci USA 103, 10606-10611, 2006.
27. Ö stman A, Hellberg C, and Böhmer FD. Protein-tyrosine phosphatases and cancer. Nat Rev Cancer 6: 307-320, 2006.
28. Puius YA, Zhao Y, Sullivan M, Lawrence DS, Almo SC, and Zhang ZY. Identification of a second aryl phosphatebinding site in protein-tyrosine phosphatase 1B: a paradigm for inhibitor design. Proc Natl Acad Sci USA 94: 13420-13425, 1997.
29. Tonks NK. Protein tyrosine phosphatases: from genes, to function, to disease. Nat Rev Mol Cell Biol 7: 833-846, 2006.
30. Wang Q, Dubé D, Friesen RW, LeRiche TG, Bateman KP, Trimble L, Sanghara J, Pollex R, Ramachandran C, Gresser MJ, and Huang Z. Catalytic inactivation of protein tyrosine phosphatase CD45 and protein tyrosine phosphatase 1B by polyaromatic quinones. Biochemistry 43: 4294-4303, 2004.
31. Winderlich M, Keller L, Cagna G, Broermann A, Kamenyeva O, Kiefer F, Deutsch U, Nottebaum AF, and Vestweber D. VE-PTP controls blood vessel development by balancing Tie-2 activity. J Cell Biol 185: 657-671, 2009.
32. Wright MB, Seifert RA, and Bowen-Pope DF. Protein-tyrosine phosphatases in the vessel wall differential expression after acute arterial injury. Arterioscler Thromb Vasc Biol 20: 1189-1198, 2000.
33. Xu D, Rovira II, and Finkel T. Oxidants painting the cysteine chapel: redox regulation of PTPs. Dev Cell 2: 251-252, 2002.
34. Xu Y, Xia W, Baker D, Zhou J, Cha HC, Voorhees JJ, and Fisher GJ. Receptor-type protein tyrosine phosphatase b (RPTP-b) directly dephosphorylates and regulates hepatocyte growth factor receptor (HGFR/Met) function. J Biol Chem 286: 15980-15988, 2011.
35. Yu X, Sun JP, He Y, Guo XL, Liu S, Zhou B, Hudmon A, and Zhang ZY. Structure, inhibitor, and regulatory mechanism of Lyp, a lymphoid-specific tyrosine phosphatase implicated in autoimmune diseases. Proc Natl Acad Sci USA 104: 19767-19772, 2007.
36. Yue D and Larock RC. Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines. Org Lett 6: 1037-1040, 2004.
37. Zeng LF, Xu J, He Y, He R, Wu L, Gunawan AM, and Zhang ZY. A facile hydroxyindole carboxylic acid-based focused library approach for potent and selective inhibitors of mycobacterium protein tyrosine phosphatase B. ChemMedChem 8: 904-908, 2013.
38. Zhang X, He Y, Liu S, Yu Z, Jiang ZX, Yang Z, Dong Y, Nabinger SC, Wu L, Gunawan AM, Wang L, Chan RJ, and Zhang ZY. Salicylic acid-based small molecule inhibitor for the oncogenic Src homology-2 domain containing protein tyrosine phosphatase-2 (SHP2). J Med Chem 53: 2482-2493, 2010.
39. Zhang ZY. Protein tyrosine phosphatases: prospects for therapeutics. Curr Opin Chem Biol 5: 416-423, 2001.
40. Zhang ZY. Protein tyrosine phosphatases: structure and function, substrate specificity, and inhibitor development. Annu Rev Pharmacol Toxicol 42: 209-234, 2002.
41. Zhang ZY and Dixon JE. Active site labeling of the Yersinia protein tyrosine phosphatase: The determination of the pKa of the active site cysteine and the function of the conserved histidine 402. Biochemistry 32: 9340-9345, 1993.
42. Zhou B, He Y, Zhang X, Xu J, Luo Y, Wang Y, Franzblau SG, Yang Z, Chan RJ, Liu Y, Zheng J, and Zhang ZY. Targeting mycobacterium protein tyrosine phosphatase B for anti-tuberculosis agents. Proc Natl Acad Sci USA 107: 4573-4578, 2010.