CuAAC click chemistry accelerates the discovery of novel chemical scaffolds as promising protein tyrosine phosphatases inhibitors

Current Medicinal Chemistry

Volumn 19, Issue 15, 2012, Pages 2399-2405

  He, X P ^a,c   Xie, J ^c   Tang, Y ^a   Li, J ^b   Chen, G R ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^c Ecole Normale Superieure de Cachan   (France)

Author keywords

Amino acid; Bidentate; Carbohydrate; Click chemistry; Competitive inhibitor; CuAAC; Dephosphorylation; Drug discovery; In situ screening; Isoxazole acid; Ketocarboxylic acid; Protein tyrosine phosphatase; Salicylic acid; Tyrosine phosphorylation

Indexed keywords

AMYLOID BETA PROTEIN; AZIDE; COPPER; CYCLIN DEPENDENT KINASE; INSULIN RECEPTOR; INSULIN RECEPTOR SUBSTRATE; ISOXAZOLE; LEPTIN RECEPTOR; OSELTAMIVIR; PHOSPHOTYROSINE; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE INHIBITOR; PROTEIN TYROSINE PHOSPHATASE SHP 2; REACTIVE OXYGEN METABOLITE; SALICYLIC ACID; SCAFFOLD PROTEIN;

ARTICLE; AUTOIMMUNE DISEASE; CLICK CHEMISTRY; CLINICAL TRIAL (TOPIC); CROHN DISEASE; CYCLOADDITION; DEGENERATIVE DISEASE; DRUG INDUSTRY; HUMAN; IC 50; IN VIVO STUDY; INSULIN DEPENDENT DIABETES MELLITUS; NEOPLASM; NONHUMAN; OBESITY; ONCOGENE; RHEUMATOID ARTHRITIS; STEREOCHEMISTRY;

EID: 84860658359     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986712800269245     Document Type: Article

References (61)

1. Blume-Jensen, P.; Hunter, T. Oncogenic kinase signalling. Nature, 2001, 411, 355-365. (Pubitemid 32467045)
2. Sawyers, C. Targeted cancer therapy. Nature, 2004, 432, 294-297. (Pubitemid 39551656)
3. Alonso, A.; Sasin, J.; Bottini, N.; Friedberg, I.; Osterman, A.; Godzik, A.; Hunter, T.; Dixon J.; Mustelin, T. Protein tyrosine phosphatases in the human genome. Cell, 2004, 117, 699-711. (Pubitemid 38748887)
4. Tonks, N.K. Protein tyrosine phosphatases: From genes, to function, to disease. Nat. Rev. Mol. Cell. Biol., 2006, 7, 833-846. (Pubitemid 44627477)
5. Pao, L.I.; Badour, K.; Siminovitch, K.A.; Neel, B.G. Nonreceptor proteintyrosine phosphatases in immune cell signaling. Annu. Rev. Immunol., 2007, 25, 473-523. (Pubitemid 46697915)
6. Tautz, L.; Pellecchia, M.; Mustelin, T. Targeting the PTPome in human diseases. Expert. Opin. Ther. Targets, 2006, 10, 157-177.
7. Bialy, L.; Waldmann, H. Inhibitors of protein tyrosine phosphatases: Nextgeneration of drugs? Angew. Chem. Int. Ed., 2005, 44, 3814-1839.
8. Elchelby, 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.
9. 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. (Pubitemid 30482885)
10. Tonks, N.K.; Muthuswamy, S.K. A brake becomes an accelerator: PTP1B-a new therapeutic target for breast cancer. Cancer Cell, 2007, 11, 214-216. (Pubitemid 46349848)
11. Zhang, S.; Chen, L.; Luo, Y.; Gunawan, A.; Lawrence, D.S.; Zhang, Z.-Y. Acquisition of a potent and selective TC-PTP inhibitor via a stepwise fluorophore-tagged combinatorial synthesis and screening strategy. J. Am. Chem. Soc., 2009, 131, 13072-13079.
12. You-Ten, K.E.; Muise, E.S.; Itie, A.; Michaliszyn, E.; Wager, 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. (Pubitemid 27381533)
13. Lavecchia, A.; Di Giovanni, C.D.; Novellino, E. Inhibitors of CDC25 phosphatases as anticancer agents: A patent review. Expert Opin. Ther. Patents, 2010, 20, 405-425.
14. Chan, G.; Kalaitzidis, D.; Neel, B.G. The tyrosine phosphatase Shp2 (PTPN11) in cancer. Cancer Metastasis Rev., 2008, 27, 179-192.
15. Muise, A.M.; Walters, T.; Wine, E.; Griffiths, A.M.; Turner, D.; Duerr, R.H.; Regueiro, M.D.; Ngan, B.Y.; Xu, W.; Sherman, P.M.; Silverberg, M.S.; Rotin, D. Protein-tyrosine phosphatase sigma is associated with ulcerative colitis. Curr. Biol., 2008, 17, 1212-1218.
16. Barr, A.J.; Knapp, S. MAPK-specific tyrosine phosphatases: New targets for drug discovery? Trends Pharmacol. Sci., 2006, 27, 525-530. (Pubitemid 44374759)
17. Braithwaite, S.P.; Paul, S.; Nairn, A.C.; Lombroso, P.J. Synaptic plasticity: One STEP at a time. Trends Neurosci., 2006, 29, 452-458. (Pubitemid 44118442)
18. Senis, Y.A.; Tomlinson, M.G.; Ellison, S.; Mazharian, A.; Lim, J.; Zhao, Y.; Kornerup, K.N.; Auger, J.M.; Thomas, S.G.; Dhanjal, T.; Kalia, N.; Zhu, J.W.; Weiss, A.; Watson, S.P. The tyrosine phosphatase CD148 is an essential positive regulator of platelet activation and thrombosis. Blood, 2009, 113, 4942-4954.
19. 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. (Pubitemid 44232020)
20. Vintonyak, V.V.; Antonchick, A.P.; Rauh D.; Waldmann, H. The therapeutic potential of phosphatase inhibitors. Curr. Opin. Chem. Biol., 2009, 13, 272-283.
21. Vintonyak, V.V.; Waldmann, H.; Rauh D. Using small molecules to target protein phosphatases. Bioorg. Med. Chem., 2011, 19, 2145-1255.
22. Kolb, H.C.; Finn, M.G.; Sharpless, K.B. Click chemistry: Diverse chemical function from a few good reactions. Angew. Chem. Int. Ed., 2001, 40, 2004-2021.
23. Rostovtsev, V.V.; Green, L.G.; Fokin, V.V.; Sharpless, K.B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem. Int. Ed., 2002, 41, 2596-2599. (Pubitemid 34803480)
24. Tornøe, C.W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3,-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem., 2002, 67, 3057-3064. (Pubitemid 34457265)
25. Wang, Q.; Hawker, C. Toward a few good reactions: Celebrating click chemistry's first decade. Chem. Asian J., 2011, 6, 2568-2569.
26. Meldal, M.; Tornøe, C.W. Cu-Catalyzed azide-alkyne cycloaddition. Chem. Rev., 2008, 108, 2952-3015.
27. Kappe, C.O.; Van der Eycken, E. Click chemistry under non-classical reaction conditions. Chem. Soc. Rev., 2010, 39, 1280-1290.
28. Moorhouse, A.D.; Moses, J.E. Click chemistry and medicinal chemistry: A case of "cyclo-addition". ChemMedChem, 2008, 3, 715-723.
29. Kalesh, K.A.; Shi, H.; Ge, J.; Yao, S.Q. The use of click chemistry in the emerging field of catalomics. Org. Biomol. Chem., 2010, 8, 1749-1762.
30. Aragão-Leoneti, V.; Campo, V.L.; Gomes, A.S.; Field, R.A.; Carvalho, I. Application of copper(I)-catalysed azide/alkyne cycloaddition (CuAAC) 'click chemistry' in carbohydrate drug and neoglycopolymer synthesis. Tetrahedron, 2010, 66, 9475-9492.
31. Mamidyala, S.K.; Finn, M.G. In situ click chemistry: Probing the binding landscapes of biological molecules. Chem. Soc. Rev., 2010, 39, 1252-1261.
32. Agalave, S.G.; Mauja, S.R.; Pore, V.S. Click chemistry: 1,2,3,-triazoles as pharmacophores. Chem. Asian J., 2011, 6, 2696-2718.
33. Combs, A.P. Recent advances in the discovery of competitive protein tyrosine phosphatase 1B inhibitors for the treatment of diabetes, obesity and cancer. J. Med. Chem., 2010, 53, 2333-2344.
34. Zhang, Z.-Y.; Protein tyrosine phosphatases: Structure and function, substrate specificity, and inhibitor development. Annu. Rev. Pharmacol. Toxicol., 2002, 42, 209-234. (Pubitemid 34160526)
35. Srinivasan, R.; Uttamchandani, M.; Yao, S.Q. Rapid assembly and in situ screening of bidentate inhibitors of protein tyrosine phosphatases. Org. Lett., 2006, 8, 713-716. (Pubitemid 43341997)
36. Liu, G.; Xin, Z.; Pei, Z.; Hajduk, P.J.; Abad-Zapatero, C.; Hutchins, C.W.; Zhao, H.; 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. (Pubitemid 37153003)
37. Srinivasan, R.; Uttamchandani, M.; Yao, S.Q. Rapid assembly and in situ screening of bidentate inhibitors of protein tyrosine phosphatases. Org. Lett., 2006, 8, 713-716. (Pubitemid 43341997)
38. Srinivasan, R.; Tan, L.P.; Wu, H.; Yang, P.-Y.; Kalesh, K.A.; Yao, S.Q. High-throughput synthesis of azide libraries suitable for direct "click" chemistry and in situ screening. Org. Biomol. Chem., 2009, 7, 1821-1828.
39. Tan, L. P.; Wu, H.; Yang, P.-Y.; Kalesh, K. A.; Zhang, X.; Hu, M.; Srinivasan, R.; Yao, S.Q. High-throughput discovery of mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) inhibitors using click chemistry. Org. Lett., 2009, 11, 5102-5105.
40. 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. (Pubitemid 30078146)
41. 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 lymphoidspecific tyrosine phosphatase implicated in autoimmnune diseases. Proc. Natl. Acad. Sci. USA, 2007, 104, 19767-19772.
42. Zhou, B.; He, Y.; Zhang, X.; Xu, J.; Luo, Y.; Wang, Y.; Franzblau, S.G.; Yang, Z.; Chan, R.J.; Liu, Y.; Zhang, J.; Zhang, Z.-Y. Targeting mycobacterium protein tyrosine phosphatase B for antituberculosis agents. Proc. Natl. Acad. Sci. USA, 2010, 107, 4573-4578.
43. Horton, D.A.; Bourne, G.T.; Smythe, M.L.; The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem. Rev., 2003, 103, 893-930.
44. Zhang, X.; He, Y.; Liu, S.; Yu, Z.; Jiang, Z.-X.; Yang, Z.; Dong, Y.; Nabinger, S.C.; Wu, L.; Gunawan, A.M.; Wang, L.; Chan, R.J.; Zhang, Z.-Y. Salicylic acid based small molecule inhibitor for the oncogenic Src Homology-2 domain containing protein tyrosine phosphatase-2 (SHP2). J. Med. Chem., 2010, 53, 2482-2493.
45. He, R.; Yu, Z.; He, Y.; Zeng, L.-F.; Xu, J.; Wu, L.; Gunawan, A.M.; Wang, L.; Jiang, Z.-X.; Zhang, Z.-Y. Double click reaction for the acquisition of a highly potent and selective mPTPB inhibitor. ChemMedChem, 2010, 5, 2051-2056.
46. Xie, J.; Seto, C.T. A two stage click-based library of protein tyrosine phosphatase inhibitors. Bioorg. Med. Chem., 2007, 15, 458-473. (Pubitemid 44738556)
47. Duval, R.; Kolb, S.; Braud, E.; Genest, D.; Garbay, C. Rapid discovery of triazolobenzylidene-thiazolopyrimidines (TBTP) as CDC25 phosphatase inhibitors by parallel click chemistry and in situ screening. J. Comb. Chem., 2009, 11, 947-950.
48. Ernst, B.; Magnani, J.L. From carbohydrate leads to glycomimetic drugs. Nature Rev. Drug Discov., 2009, 8, 661-677
49. Meutermans, W.; Le, G.T.; Becker, B. Carbohydrates as scaffolds in drug discovery. ChemMedChem, 2006, 1, 1164-1194. (Pubitemid 44786923)
50. Magano, J. Synthetic approaches to the neuraminidase inhibitors zanamivir (relenza) and oseltamivir phosphate (tamiflu) for the treatment of influenza. Chem. Rev., 2009, 109, 4398-4438.
51. Seo, C.; Sohn, J.H.; Oh, H.; Kim, B.Y.; Ahn, J.S. Isolation of the protein tyrosine phosphatase 1B inhibitory metabolite from the marine-derived fungus Cosmospora sp. SF-5060. Bioorg. Med. Chem. Lett., 2009, 19, 6095-6097.
52. Yang, J.-W.; Li, C.; He, X.-P.; Zhao, H.; Gao, L.-X.; Zhang, W.; Shi, X.-X.; Tang, Y.; Li, J.; Chen, G.-R. Microwave-accelerated click chemistry: Expeditious synthesis of novel triazole-linked salicylic β-D-O-glycosides with PTP1B inhibitory activity. Bull. Korean Chem. Soc., 2010, 31, 3359-3365.
53. Li, C.; He, X.-P.; Zhang, Y.-J.; Li, Z.; Gao, L.-X.; Shi, X.-X.; Xie, J.; Li, J.; Chen, G.-R.; Tang, Y. Click to a focused library of benzyl 6-triazolo(hydroxy)benzoic glucosides: Novel construction of PTP1B inhibitors on a sugar scaffold. Eur. J. Med. Chem., 2011, 46, 4212-4218.
54. Song, Z.; He, X.-P.; Li, C.; Gao, L.-X.; Wang, Z.-X.; Tang, Y.; Xie, J.; Li, J.; Chen, G.-R. Preparation of triazole-linked glycosylated a-ketocarboxylic acid derivatives as new PTP1B inhibitors. Carbohydr. Res., 2011, 346, 140-145.
55. Song, Z.; He, X.-P.; Jin, X.-P.; Gao, L.-X.; Sheng, L.; Zhou, Y.-B.; Li, J.; Chen, G.-R. 'Click' to bidentate bis-triazolyl sugar derivatives with promising biological and optical features. Tetrahedron Lett., 2011, 52, 894-898.
56. 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. USA, 1997, 94, 13420-13425.
57. Yang, J.-W.; He, X.-P.; Li, C.; Gao, L.-X.; Sheng, L.; Xie, J.; Shi, X.-X.; Tang, Y.; Li, J.; Chen, G.-R. A unique and rapid approach toward the efficient development of novel protein tyrosine phosphatase (PTP) inhibitors based on 'clicked' pseudo-glycopeptides. Bioorg. Med. Chem. Lett., 2011, 21, 1092-1096.
58. He, X.-P.; Deng, Q.; Gao, L.-X.; Li, C.; Zhang, W.; Zhou, Y.-B.; Tang, Y.; Shi, X.-X.; Xie, J.; Li, J.; Chen, G.-R.; Chen, K. Facile fabrication of promising protein tyrosine phosphatase (PTP) inhibitors entities based on 'clicked' serine/threonine-monosaccharide hybrids. Bioorg. Med. Chem., 2011, 19, 3892-3900.
59. He, X.-P.; Li, C.; Jin, X.-P.; Song, Z.; Zhang, H.-L.; Zhu, C.-J.; Shen, Q.; Zhang, W.; Sheng, L.; Shi, X.-X.; Tang, Y.; Li, J.; Chen, G.-R.; Xie, J. Microwave-assisted construction of triazole-linked amino acid-glucoside conjugates as novel PTP1B inhibitors. New J. Chem., 2011, 35, 622-631.
60. He, X.-P.; Wang, X.-W.; Jin, X.-P.; Zhou, H.; Shi, X.-X.; Chen, G.-R.; Long, Y.-T. Epimeric monosaccharide-quinone hybrids on gold electrodes toward the electrochemical probing of specific carbohydrate-protein recognitions. J. Am. Chem. Soc., 2011, 133, 3649-3657.
61. He, X.-P.; Li, C.; Wang, Z.-Z.; Gao, L.-X.; Shi, X.-X.; Tang, Y.; Xie, J.; Li, J.; Chen, G.-R.; Chen, K. Discovering the distinct inhibitory effects between C4-epimeric glycosyl amino acids: New insight into the development of protein tyrosine phosphatase inhibitors. Glycoconj. J., 2011, 28, 493-497.