Synthesis, activity and molecular modeling of a new series of chromones as low molecular weight protein tyrosine phosphatase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 7, 2009, Pages 2658-2672

  Forghieri, Marco ^a   Laggner, Christian ^b   Paoli, Paolo ^c   Langer, Thierry ^d   Manao, Giampaolo ^c   Camici, Guido ^e   Bondioli, Lucia ^a   Prati, Fabio ^a   Costantino, Luca ^a  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^b UNIVERSITY OF INNSBRUCK   (Austria)

^c UNIVERSITY OF FLORENCE   (Italy)

^d Prestwick Chemical Inc   (France)

^e Center of Excellence for Scientific Research DENOTHE   (Italy)

Author keywords

Antitumoral drugs; Chromones; Diabetes; Low molecular weight protein tyrosine phosphatases; Protein tyrosine phosphatase 1B

Indexed keywords

2 (4' HYDROXYPHENYL) 3 [(3'',4'' DIHYDROXY 1,1' BIPHENYL 4 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 2 (4' HYDROXYPHENYL) 3 [(4'' CARBOXY 3'' HYDROXY 1,1' BIPHENYL 4 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 2',4' DIHYDROXY 1,1' BIPHENYL; 3'',4' DIHYDROXY 1,1' BIPHENYL; 4' CARBOXY 3' HYDROXY 1,1' BIPHENYL; 6,7 DIHYDROXY 2 (4' HYDROXYPHENYL) 3 [(1,1' BIPHENYL 4 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 7 HYDROXY 2 (4' HYDROXYBENZYL) 3 [(1,1' BIPHENYL 4 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 7 HYDROXY 2 (4' HYDROXYPHENYL) 3 [(1,1' BIPHENYL 4 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 7 HYDROXY 2 (4' HYDROXYPHENYL) 3 [(3'' CARBOXY 1,1' BIPHENYL 4 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 7 HYDROXY 2 (4' HYDROXYPHENYL) 3 [(3'',4'' DIHYDROXY 1,1' BIPHENYL 3 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 7 HYDROXY 2 (4' HYDROXYPHENYL) 3 [(3'',4'' DIHYDROXY 1,1' BIPHENYL 4 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 7 HYDROXY 2 (4' HYDROXYPHENYL) 3 [(4'' CARBOXY 3'' HYDROXY 1,1' BIPHENYL 3 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 7 HYDROXY 2 (4' HYDROXYPHENYL) 3 [(4'' CARBOXY 3'' HYDROXY 1,1' BIPHENYL 4 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 7 HYDROXY 2 (4' HYDROXYPHENYL) 3 [(4'' HYDROXY 1,1' BIPHENYL 4 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 7 HYDROXY 2 (4' HYDROXYPHENYLETYL) 3 [(1,1' BIPHENYL 4 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; 7 HYDROXY 2 (4' HYDROXYPHENYLPROPYL) 3 [(1,1' BIPHENYL 4 YL)METHYL] 4H 1 BENZOPYRAN 4 ONE; CHROMONE DERIVATIVE; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; PROTEIN TYROSINE PHOSPHATASE INHIBITOR; QUERCETIN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; MOLECULAR DOCKING; MOLECULAR MODEL; MOLECULAR WEIGHT; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE; CHROMONES; COMPUTER SIMULATION; DIABETES MELLITUS, TYPE 2; ENZYME INHIBITORS; HUMANS; ISOENZYMES; MODELS, MOLECULAR; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; PROTEIN TYROSINE PHOSPHATASES; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP;

EUKARYOTA;

EID: 62949246802     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.02.060     Document Type: Article

References (46)

1. Fischer E.H. Adv. Enzyme Regul. 39 (1999) 359
2. Hubbard S.R., and Till J.H. Annu. Rev. Biochem. 69 (2000) 373
3. Hunter T. Cell 100 (2000) 113
4. Neel B.G., and Tonks N.K. Curr. Opin. Cell Biol. 9 (1997) 193
5. Andersen J.N., Mortensen O.H., Peters G.H., Drake P.G., Iversen L.F., Olsen O.H., Jansen P.G., Andersen H.S., Tonks N.K., and Moller N.P. Mol. Cell Biol. 21 (2001) 7117
6. Caselli A., Marzocchini R., Camici G., Manao G., Moneti G., Pieraccini G., and Ramponi G. J. Biol. Chem. 273 (1998) 32554
7. Wo Y.Y.P., McCormack A.L., Shabanowitz J., Hunt D.F., Davis J.P., Mitchell G.L., and Van Etten R.L. J. Biol. Chem. 267 (1992) 10856
8. Chiarugi P., Taddei M.L., Schiavone N., Papucci L., Giannoni E., Fiaschi T., Capaccioli S., Raugei G., and Ramponi G. Oncogene 23 (2004) 3905
9. Kikawa K.D., Vidale D.R., van Etten R.L., and Kinch M.S. J. Biol. Chem. 277 (2002) 39274
10. Malentacchi F., Marzocchini R., Gelmini S., Orlando C., Serio M., Ramponi G., and Raugei G. Biochem. Biophys. Res. Commun. 334 (2005) 875
11. Chiarugi P., Cirri P., Marra F., Raugei G., Camici G., Manao G., and Ramponi G. Biochem. Biophys. Res. Commun. 238 (1997) 676
12. Taddei M.L., Chiarugi P., Cirri P., Talini D., Camici G., Manao G., Raugei G., and Ramponi G. Biochem. Biophys. Res. Commun. 270 (2000) 564
13. Sarabu R., and Tilley J. Ann. Rep. Med. Chem. 40 (2005) 167
14. Zhang M., Stauffacher C.V., Lin D., and Van Etten R.L. J. Biol. Chem. 273 (1998) 21714
15. Bleasdale J.E., Ogg D., Palazuk B.J., Jacob C.S., Swanson M.L., Wang X.Y., Thompson D.P., Conradi R.A., Mathews W.R., Laborde A.L., Stuchly C.W., Heijbel A., Bergdahl K., Bannow C.A., Smith C.W., Svensson C., Liljebris C., Schostarez H.J., May P.D., Stevens F.C., and Larsen S.D. Biochemistry 40 (2001) 5642
16. Maccari R., Paoli P., Ottanà R., Jacomelli M., Ciurlo R., Manao G., Steindl T., Langer T., Vigorita M.G., and Camici G. Bioorg. Med. Chem. 15 (2007) 5137
17. Vidal D., Blobel J., Perez Y., Thormann M., and Pons M. Eur. J. Med. Chem. 42 (2007) 1102
18. Miranda M.A., Okamoto A.K., Ferreira C.V., Silva T.L., Granjeiro J.M., and Aoyama H. J. Enzyme Inhib. Med. Chem. 21 (2006) 419
19. Wang S., Tabernero L., Zhang M., Harms E., Van Etten R.L., and Stauffacher C.V. Biochemistry 39 (2000) 1903
20. Zabell A.P.R., Corden S., Helquist P., Stauffacher C.V., and Wiest O. Bioorg. Med. Chem. 12 (2004) 1867
21. Ferrell J.E., Chang Sing P.D., Loew G., King R., Mansour J.M., and Mansour T.E. Mol. Pharmacol. 16 (1979) 556
22. Wang S., Stauffacher C.V., and Van Etten R.L. Biochemistry 39 (2000) 1234
23. Chen R.M., Hu L.H., An T.Y., Li J., and Shen Q. Bioorg. Med. Chem. Lett. 12 (2002) 3387
24. Costantino L., Rastelli G., Gamberini M.C., Vinson J.A., Bose P., Iannone A., Staffieri M., Antolini L., Del Corso A., Mura U., and Albasini A. J. Med. Chem. 42 (1999) 1881
25. Schrödinger Suite 2007; Schrödinger, LLC; New York, NY, USA, 2007.
26. Malamas M.S., Sredy J., Moxham C., Katz A., Xu W., McDevitt R., Adebayo F.O., Sawicki D.R., Seestaller L., Sullivan D., and Taylor J.R. J. Med. Chem. 43 (2000) 1293
27. Wolfbeis O.S., Leiner M., Hochmuth P., and Geiger H. Ber. Bunsenges. Phys. Chem. 88 (1984) 759
28. Maccari R., Ottanà R., Ciurleo R., Rakowitz D., Matuszczak B., Laggner C., and Langer T. Bioorg. Med. Chem. 16 (2008) 5840
29. Steuber H., Zentgraf M., Podjarny A., Heine A., and Klebe G. J. Mol. Biol. 356 (2006) 45
30. Said H., Karickhoff S.W., and Carreira L.A. Quant. Struct.-Act. Relat. 14 (1995) 348
31. SPARC on line calculator v4.1, http://ibmlc2.chem.uga.edu/sparc/, accessed Jan. 2008.
32. Herrero-Martínez J.M., Sanmartin M., Rosés M., Bosch E., and Ràfols C. Electrophoresis 26 (2005) 1886
33. Zabell A.P., Schroff A.D., Bain B.E., Van Etten R.L., Wiest O., and Stauffacher C.V. J. Biol. Chem. 281 (2006) 6520
34. Sherman W., Day T., Jacobson M.P., Friesner R.A., and Farid R. J. Med. Chem. 49 (2006) 534
35. Zhang M., Zhou M., Van Etten R.L., and Stauffacher C.V. Biochemistry 36 (1997) 15
36. Zhao P.L., Liu C.L., Huang W., Wang Y.Z., and Yang G.F. J. Agric. Food Chem. 55 (2007) 5697
37. Bargellini G., and Monti L. Gazz. Chim. Ital. 44 (1914) 25
38. Lin P.H., Sangaiah R., Ranasinghe A., Ball L.M., Swenberg J.A., and Gold A. Org. Biomol. Chem. 2 (2004) 2624
39. Walker J. J. Chem. Soc. (1939) 120
40. Suter C.M., and Perrin G.S. J. Am. Chem. Soc. 61 (1939) 166
41. pymol Molecular Graphics System v0.99, DeLano Scientific, Palo Alto, CA, USA, 2006.
42. Wolber G., Dornhofer A., and Langer T. J. Comput. Aided Mol. Des. 20 (2006) 773
43. Wolber G., and Langer T. J. Chem. Inf. Comput. Sci. 45 (2005) 160-169
44. ligandscout 2.0; Inte:Ligand GmbH, Vienna, Austria, 2008.
45. Marzocchini R., Bucciantini M., Stefani M., Taddei N., Thunnissen M.G.M.M., Nordlund P., and Ramponi G. FEBS Lett. 426 (1998) 52
46. Laemmli U.K. Nature 227 (1970) 680