Application of encoded library technology (ELT) to a protein-protein interaction target: Discovery of a potent class of integrin lymphocyte function-associated antigen 1 (LFA-1) antagonists

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 7, 2014, Pages 2353-2365

  Kollmann, Christopher S ^a   Bai, Xiaopeng ^a   Tsai, Ching Hsuan ^a   Yang, Hongfang ^a   Lind, Kenneth E ^a   Skinner, Steven R ^a   Zhu, Zhengrong ^a   Israel, David I ^a   Cuozzo, John W ^a   Morgan, Barry A ^a   Yuki, Koichi ^b,c   Xie, Can ^b   Springer, Timothy A ^b   Shimaoka, Motomu ^b,d   Evindar, Ghotas ^a  

^a GLAXOSMITHKLINE   (United States)

^b BOSTON CHILDREN S HOSPITAL   (United States)

^c Peking University   (China)

^d MIE UNIVERSITY   (Japan)

Author keywords

Affinity based selections; DNA encoded libraries; Encoded Library Technology; Intercellular Adhesion Molecule 1; Lymphocyte Function associated Antigen 1; Protein Protein Interactions

Indexed keywords

2 [[4 (BENZYLAMINO) 6 [5 [3 (TRIFLUOROMETHYL)BENZOYL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL] 1,3,5 TRIAZIN 2 YL]AMINO] N ETHYL 2,3 DIHYDRO 1H INDENE 2 CARBOXAMIDE; 2 [[4 [(3,4 DICHLOROPHENETHYL)AMINO] 6 [5 [3 (TRIFLUOROMETHYL)BENZOYL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL] 1,3,5 TRIAZIN 2 YL]AMINO] 2,3 DIHYDRO 1H INDENE 2 CARBOXYLIC ACID; 2 [[4 [(3,4 DICHLOROPHENETHYL)AMINO] 6 [5 [[2 (TRIFLUOROMETHOXY)PHENYL]SULFONYL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL] 1,3,5 TRIAZIN 2 YL]AMINO] 2,3 DIHYDRO 1H INDENE 2 CARBOXYLIC ACID; 2 [[4 [(3,4 DICHLOROPHENETHYL)AMINO] 6 [5 [[2 (TRIFLUOROMETHOXY)PHENYL]SULFONYL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL] 1,3,5 TRIAZIN 2 YL]AMINO] N ETHYL 2,3 DIHYDRO 1H INDENE 2 CARBOXAMIDE; 2 [[4 [[1 (4 BROMOPHENYL)ETHYL]AMINO] 6 [5 [3 (TRIFLUOROMETHYL)BENZOYL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL] 1,3,5 TRIAZIN 2 YL]AMINO] N ETHYL 2,3 DIHYDRO 1H INDENE 2 CARBOXAMIDE; 2 [[4 [[1 (4 BROMOPHENYL)ETHYL]AMINO] 6 [5 [[2 (TRIFLUOROMETHOXY)PHENYL]SULFONYL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL] 1,3,5 TRIAZIN 2 YL]AMINO] N ETHYL 2,3 DIHYDRO 1H INDENE 2 CARBOXAMIDE; 2 [[4 [[3,4 DICHLOROETHYL]AMINO] 6 [5 [3 (TRIFLUOROMETHYL)BENZOYL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL] 1,3,5 TRIAZIN 2 YL]AMINO] N ETHYL 2,3 DIHYDRO 1H INDENE 2 CARBOXAMIDE; 2 [[4 [[3,4 DICHLOROPHENETHYL]AMINO] 6 (PYRROLIDIN 1 YL) 1,3,5 TRIAZIN 2 YL]AMINO] N ETHYL 2,3 DIHYDRO 1H INDENE 2 CARBOXAMIDE; DNA; INTERCELLULAR ADHESION MOLECULE 1; LYMPHOCYTE FUNCTION ASSOCIATED ANTIGEN 1 ANTAGONIST; N ETHYL 2 [4 (1 PHENYLETHYLAMINO) 6 [5 [3 (TRIFLUOROMETHYL)BENZOYL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL] 1,3,5 TRIAZIN 2 YLAMINO] 2,3 DIHYDRO 1H INDENE 2 CARBOXAMIDE; N ETHYL 2 [4 (PHENETHYLAMINO) 6 [5 [3 (TRIFLUOROMETHYL)BENZOYL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL] 1,3,5 TRIAZIN 2 YLAMINO] 2,3 DIHYDRO 1H INDENE 2 CARBOXAMIDE; N ETHYL 2 [[4 (ETHYLAMINO) 6 [5 [3 (TRIFLUOROMETHYL)BENZOYL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL] 1,3,5 TRIAZIN 2 YL]AMINO] 2,3 DIHYDRO 1H INDENE 2 CARBOXAMIDE; PROTEIN INHIBITOR; UNCLASSIFIED DRUG; [5 [4 (CYCLOPENTYLAMINO) 6 [(3,4 DICHLOROPHENETHYL)AMINO] 1,3,5 TRIAZIN 2 YL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL][3 (TRIFLUOROMETHYL)PHENYL]METHANONE; [5 [4 [(3,4 DICHLOROPHENETHYL)AMINO] 6 [(2,3 DIHYDRO 1H INDEN 2 YL)AMINO] 1,3,5 TRIAZIN 2 YL] 2,5 DIAZABICYCLO[2.2.1]HEPTAN 2 YL][3 (TRIFLUOROMETHYL)PHENYL]METHANONE; LIGAND; LYMPHOCYTE FUNCTION ASSOCIATED ANTIGEN 1; MOLECULAR LIBRARY; PROTEIN BINDING;

ARTICLE; CELL ADHESION ASSAY; CELL STRAIN K 562; CHEMICAL MODIFICATION; CONTROLLED STUDY; DNA ENCODED LIBRARY TECHNOLOGY; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; HUMAN; HUMAN CELL; IC 50; LEUKEMIA CELL LINE; LIGAND BINDING; MOLECULAR DOCKING; MOLECULAR LIBRARY; PROTEIN ANALYSIS; PROTEIN EXPRESSION; PROTEIN FAMILY; PROTEIN PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION; CELL ADHESION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG DEVELOPMENT; DRUG EFFECTS; JURKAT CELL LINE; METABOLISM; PHARMACOLOGY; SYNTHESIS;

CELL ADHESION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; HUMANS; JURKAT CELLS; LIGANDS; LYMPHOCYTE FUNCTION-ASSOCIATED ANTIGEN-1; MOLECULAR STRUCTURE; PROTEIN BINDING; SMALL MOLECULE LIBRARIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84897459461     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.01.050     Document Type: Article

References (33)

1. A.L. Hopkins, and C.R. Groom Nat. Rev. Drug Disc. 1 2002 727
2. J.A. Wells, and C.L. McClendon Nature 450 2007 1001
3. S. Jones, and J.M. Thornton Proc. Natl. Acad. Sci. U.S.A. 93 1996 13
4. R. Evans, I. Patzak, L. Svensson, K. De Filippo, K. Jones, A. McDowall, and N. Hogg J. Cell Sci. 122 2009 215
5. M. Shimaoka, and T.A. Springer Nat. Rev. Drug Disc. 2 2003 703
6. M.E. Anderson, and T.J. Siahaan Peptides 24 2003 487
7. T. Zimmerman, and F.J. Blanco Curr. Pharm. Des. 14 2008 2128
8. D. Cox, M. Brennan, and N. Moran Nat. Rev. Drug Disc. 9 2010 804
9. M. Lebwohl, S.K. Tyring, T.K. Hamilton, D. Toth, S. Glazer, N.H. Tawfik, P. Walicke, W. Dummer, X. Wang, M.R. Garovoy, and D. Pariser New Eng. J. Med. 349 2003 2004
10. L.J. Faia, H.N. Sen, Z. Li, S. Yeh, K.J. Wroblewski, and R.B. Nussenblatt Invest. Ophthalmol. Vis. Sci. 52 2011 6919
11. D.M. Paskowitz, Q.D. Nguyen, P. Gehlbach, J.T. Handa, S. Solomon, W. Stark, O. Shaikh, C. Semba, T.R. Gadek, and D.V. Do Eye 26 2012 944
12. M. Shimaoka, J. Takagi, and T.A. Springer Annu. Rev. Biophys. Biomol. 31 2002 485
13. J. Kallen, K. Welzenbach, P. Ramage, D. Geyl, R. Kriwacki, G. Legge, S. Cottens, G. Weitz-Schmidt, and U. Hommel J. Mol. Biol. 292 1999 1
14. K. Last-Barney, W. Davidson, M. Cardozo, L.L. Frye, C.A. Grygon, J.L. Hopkins, D.D. Jeanfavre, S. Pav, C. Qian, J.M. Stevenson, L. Tong, R. Zindell, and T.A. Kelly J. Am. Chem. Soc. 123 2001 5643
15. G. Liu, J.T. Link, Z. Pei, E.B. Reilly, S. Leitza, B. Nguyen, K.C. Marsh, G.F. Okasinski, T.W. von Geldern, M. Ormes, K. Fowler, and M. Gallatin J. Med. Chem. 43 2000 4025
16. M.P. Crump, T.A. Ceska, L. Spyracopoulos, A. Henry, S.C. Archibald, R. Alexander, R.J. Taylor, S.C. Findlow, J. O'Connell, M.K. Robinson, and A. Shock Biochemistry 43 2004 2394
17. T. Zimmerman, J. Oyarzabal, E.S. Sebastián, S. Majumdar, B.A. Tejo, T.J. Siahaan, and F.J. Blanco Chem. Biol. Drug Des. 70 2007 347
18. M.A. Clark Curr. Opin. Chem. Biol. 14 2010 396
19. M.A. Clark, R.A. Acharya, C.C. Arico-Muendel, S.L. Belyanskaya, D.R. Benjamin, N.R. Carlson, P.A. Centrella, C.H. Chiu, S.P. Creaser, J.W. Cuozzo, C.P. Davie, Y. Ding, G.J. Franklin, K.D. Franzen, M.L. Gefter, S.P. Hale, N.J.V. Hansen, D.I. Israel, J. Jiang, M.J. Kavarana, M.S. Kelley, C.S. Kollmann, F. Li, K. Lind, S. Mataruse, P.F. Medeiros, J.A. Messer, P. Myers, H. O'Keefe, M.C. Oliff, C.E. Rise, A.L. Satz, S.R. Skinner, J.L. Svendsen, L. Tang, K. van Vloten, R.W. Wagner, G. Yao, B. Zhao, and B.A. Morgan Nat. Chem. Biol. 5 2009 647
20. H. Deng, H. O'Keefe, C.P. Davie, K.E. Lind, R.A. Acharya, G.J. Franklin, J. Larkin, R. Matico, M. Neeb, M.M. Thompson, T. Lohr, J.W. Gross, P.A. Centrella, G.K. O'Donovan, K.L. Bedard, K. van Vloten, S. Mataruse, S.R. Skinner, S.L. Belyanskaya, T.Y. Carpenter, T.W. Shearer, M.A. Clark, J.W. Cuozzo, C.C. Arico-Muendel, and B.A. Morgan J. Med. Chem. 55 2012 7061
21. J.S. Disch, G. Evindar, C.H. Chui, C.A. Blum, H. Dai, L. Jin, E. Schuman, K.E. Lind, S.L. Belyanskaya, J. Deng, F.T. Coppo, L. Aquilani, T.L. Graybill, J.W. Cuozzo, S. Lavu, C. Mao, G.P. Vlasuk, and R.B. Perni J. Med. Chem. 56 2013 3666
22. F. Buller, Y. Zhang, J. Scheuermann, J. Schafer, P. Buhlmann, and D. Neri Chem. Biol. 16 2009 1075
23. S. Melkko, L. Mannocci, C.E. Dumelin, A. Villa, R. Sommavilla, Y. Zhang, M.G. Grutter, N. Keller, L. Jermutus, R.H. Jackson, J. Scheuermann, and D. Neri ChemMedChem 5 2010 584
24. M. Leimbacher, Y. Zhang, L. Mannocci, M. Stravs, T. Geppert, J. Scheuermann, G. Schneider, and D. Neri Chem. Eur. J. 18 2012 7729
25. F. Sanchez-Madrid, J.A. Nagy, E. Robbins, P. Simon, and T.A. Springer J. Exp. Med. 158 1983 1785
26. C. Lu, M. Shimaoka, M. Ferzly, C. Oxvig, J. Takagi, and T.A. Springer Proc. Natl. Acad. Sci. U.S.A. 98 2001 2387
27. M. Shimaoka, A. Salas, W. Yang, G. Weitz-Schmidt, and T.A. Springer Immunity 19 2003 391
28. G. Weitz-Schmidt, K. Welzenbach, V. Brinkmann, T. Kamata, J. Kallen, C. Bruns, S. Cottens, Y. Takada, and U. Hommel Nat. Med. 7 2001 687
29. C.F. Lu, and T.A. Springer J. Immunol. 159 1997 268
30. M. Shimaoka, T. Xiao, J.H. Liu, Y. Yang, Y. Dong, C.D. Jun, A. McCormack, R. Zhang, A. Joachimiak, J. Takagi, J.H. Wang, and T.A. Springer Cell 112 2003 99
31. N. Nishida, C. Xie, M. Shimaoka, Y. Cheng, T. Walz, and T.A. Springer Immunity 25 2006 583
32. G. Weitz-Schmidt, and S.p. Chreng Cell Adhesion Assays M. Shimaoka, Integrin and Cell Adhesion Molecules 757th ed. 2012 Humana Press 15 30
33. K. Yuki Cell-Free Ligand-Binding Assays for Integrin LFA-1 M. Shimaoka, Integrin and Cell Adhesion Molecules 757th ed. 2012 Humana Press 73 78