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Angewandte Chemie - International Edition

Volumn 51, Issue 4, 2012, Pages 905-911

Fragment deconstruction of small, potent factor xa inhibitors: Exploring the superadditivity energetics of fragment linking in protein-ligand complexes

(10) Nazaré, Marc a Matter, Hans a Will, David W a Wagner, Michael a Urmann, Matthias a Czech, Jörg a Schreuder, Herman a Bauer, Armin a Ritter, Kurt a Wehner, Volkmar a

a SANOFI AVENTIS DEUTSCHLAND GMBH (Germany)

Author keywords

additivity; drug discovery; fragment linking; molecular recognition; noncovalent interactions

Indexed keywords

ADDITIVITY; DRUG DISCOVERY; FACTOR XA INHIBITOR; FRAGMENT LINKING; G-VALUES; NON-COVALENT INTERACTION; ORDERS OF MAGNITUDE; PROTEIN-LIGAND COMPLEXES; SINGLE BOND; SUPERADDITIVITY;

MOLECULAR RECOGNITION;

COMPLEXATION;

AMIDE; BLOOD CLOTTING FACTOR 10A; LIGAND; SERINE PROTEINASE INHIBITOR;

ARTICLE; BINDING SITE; CHEMISTRY; DRUG ANTAGONISM; METABOLISM; PROTEIN TERTIARY STRUCTURE; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

AMIDES; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; FACTOR XA; LIGANDS; PROTEIN STRUCTURE, TERTIARY; SERINE PROTEINASE INHIBITORS; THERMODYNAMICS;

EID: 84856010975 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201107091 Document Type: Article

Times cited : (50)

References (44)

1
- 0029829066
- P. A. Rejto, G. M. Verkhivker, Proc. Natl. Acad. Sci. USA 1996, 93, 8945-8950.
- (1996) Proc. Natl. Acad. Sci. USA , vol.93 , pp. 8945-8950
- Rejto, P.A.¹ Verkhivker, G.M.²

2
- 1942453243
- A. L. Hopkins, C. R. Groom, A. Alex, Drug Discovery Today 2004, 9, 430-431
- (2004) Drug Discovery Today , vol.9 , pp. 430-431
- Hopkins, A.L.¹ Groom, C.R.² Alex, A.³

3
- 34447548576
- C. Abad-Zapatero, Expert Opin. Drug Discovery 2007, 2, 469-488
- (2007) Expert Opin. Drug Discovery , vol.2 , pp. 469-488
- Abad-Zapatero, C.¹

4
- 4344592378
- D. C. Rees, M. Congreve, C. W. Murray, R. Carr, Nat. Rev. Drug Discovery 2004, 3, 660-672
- (2004) Nat. Rev. Drug Discovery , vol.3 , pp. 660-672
- Rees, D.C.¹ Congreve, M.² Murray, C.W.³ Carr, R.⁴

5
- 77950560159
- E. Perola, J. Med. Chem. 2010, 53, 2986-2997.
- (2010) J. Med. Chem. , vol.53 , pp. 2986-2997
- Perola, E.¹

6
- 46849089254
- M. Congreve, G. Chessari, D. Tisi, A. J. Woodhead, J. Med. Chem. 2008, 51, 3661-3680
- (2008) J. Med. Chem. , vol.51 , pp. 3661-3680
- Congreve, M.¹ Chessari, G.² Tisi, D.³ Woodhead, A.J.⁴

7
- 33847381100
- P. J. Hajduk, J. Greer, Nat. Rev. Drug Discovery 2007, 6, 211-219.
- (2007) Nat. Rev. Drug Discovery , vol.6 , pp. 211-219
- Hajduk, P.J.¹ Greer, J.²

8
- 2542542373
- D. A. Erlanson, J. A. Wells, A. C. Braisted, Annu. Rev. Biophys. Biomol. Struct. 2004, 33, 199-223.
- (2004) Annu. Rev. Biophys. Biomol. Struct. , vol.33 , pp. 199-223
- Erlanson, D.A.¹ Wells, J.A.² Braisted, A.C.³

9
- 0015101706
- M. I. Page, W. P. Jencks, Proc. Natl. Acad. Sci. USA 1971, 68, 1678-1683.
- (1971) Proc. Natl. Acad. Sci. USA , vol.68 , pp. 1678-1683
- Page, M.I.¹ Jencks, W.P.²

10
- 0029836953
- S. B. Shuker, P. J. Hajduk, R. P. Meadows, S. W. Fesik, Science 1996, 274, 1531-1534.
- (1996) Science , vol.274 , pp. 1531-1534
- Shuker, S.B.¹ Hajduk, P.J.² Meadows, R.P.³ Fesik, S.W.⁴

11
- 0036821028
- C. W. Murray, M. L. Verdonk, J. Comput.-Aided Mol. Des. 2002, 16, 741-753.
- (2002) J. Comput.-Aided Mol. Des. , vol.16 , pp. 741-753
- Murray, C.W.¹ Verdonk, M.L.²

12
- 0031022887
- K. A. Dill, J. Biol. Chem. 1997, 272, 701-704
- (1997) J. Biol. Chem. , vol.272 , pp. 701-704
- Dill, K.A.¹

13
- 0028334097
- A. E. Mark, W. F. van Gunsteren, J. Mol. Biol. 1994, 240, 167-176
- (1994) J. Mol. Biol. , vol.240 , pp. 167-176
- Mark, A.E.¹ Van Gunsteren, W.F.²

14
- 77950022453
- B. Baum, L. Muley, M. Smolinski, A. Heine, D. Hangauer, G. Klebe, J. Mol. Biol. 2010, 397, 1042-1054.
- (2010) J. Mol. Biol. , vol.397 , pp. 1042-1054
- Baum, B.¹ Muley, L.² Smolinski, M.³ Heine, A.⁴ Hangauer, D.⁵ Klebe, G.⁶

15
- 77952713014
- V. Borsi, V. Calderone, M. Fragai, C. Luchinat, N. Sarti, J. Med. Chem. 2010, 53, 4285-4289.
- (2010) J. Med. Chem. , vol.53 , pp. 4285-4289
- Borsi, V.¹ Calderone, V.² Fragai, M.³ Luchinat, C.⁴ Sarti, N.⁵

16
- 0030829408
- E. T. Olejniczak, P. J. Hajduk, P. A. Marcotte, D. G. Nettesheim, R. P. Meadows, E. Edalji, T. F. Holzman, S. W. Fesik, J. Am. Chem. Soc. 1997, 119, 5828-5832.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 5828-5832
- Olejniczak, E.T.¹ Hajduk, P.J.² Marcotte, P.A.³ Nettesheim, D.G.⁴ Meadows, R.P.⁵ Edalji, E.⁶ Holzman, T.F.⁷ Fesik, S.W.⁸

17
- 33751076241
- K. Babaoglu, B. K. Shoichet, Nat. Chem. Biol. 2006, 2, 720-723.
- (2006) Nat. Chem. Biol. , vol.2 , pp. 720-723
- Babaoglu, K.¹ Shoichet, B.K.²

18
- 22244460783
- M. Nazaré, D. W. Will, H. Matter, H. Schreuder, K. Ritter, M. Urmann, M. Essrich, A. Bauer, M. Wagner, J. Czech, M. Lorenz, V. Laux, V. Wehner, J. Med. Chem. 2005, 48, 4511-4525.
- (2005) J. Med. Chem. , vol.48 , pp. 4511-4525
- Nazaré, M.¹ Will, D.W.² Matter, H.³ Schreuder, H.⁴ Ritter, K.⁵ Urmann, M.⁶ Essrich, M.⁷ Bauer, A.⁸ Wagner, M.⁹ Czech, J.¹⁰ Lorenz, M.¹¹ Laux, V.¹² Wehner, V.¹³

19
- 84873064115
- WO 2006122661.
- M. Wagner, M. Urmann, V. Wehner, M. Lorenz, A. Bauer, M. Nazaré, H. Matter, WO 2006122661, 2006.
- (2006)
- Wagner, M.¹ Urmann, M.² Wehner, V.³ Lorenz, M.⁴ Bauer, A.⁵ Nazaré, M.⁶ Matter, H.⁷

20
- 0035382791
- S. Maignan, V. Mikol, Curr. Top. Med. Chem. 2001, 1, 161-174.
- (2001) Curr. Top. Med. Chem. , vol.1 , pp. 161-174
- Maignan, S.¹ Mikol, V.²

21
- 77954058952
- H. Matter, M. Nazaré, S. Güssregen, D. W. Will, H. Schreuder, A. Bauer, M. Urmann, K. Ritter, M. Wagner, V. Wehner, Angew. Chem. 2009, 121, 2955-2960
- (2009) Angew. Chem. , vol.121 , pp. 2955-2960
- Matter, H.¹ Nazaré, M.² Güssregen, S.³ Will, D.W.⁴ Schreuder, H.⁵ Bauer, A.⁶ Urmann, M.⁷ Ritter, K.⁸ Wagner, M.⁹ Wehner, V.¹⁰

22
- 70349786321
- Angew. Chem. Int. Ed. 2009, 48, 2911-2916.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2911-2916

23
- 18344364519
- H. Matter, D. W. Will, M. Nazaré, H. Schreuder, V. Laux, V. Wehner, J. Med. Chem. 2005, 48, 3290-3312.
- (2005) J. Med. Chem. , vol.48 , pp. 3290-3312
- Matter, H.¹ Will, D.W.² Nazaré, M.³ Schreuder, H.⁴ Laux, V.⁵ Wehner, V.⁶

24
- 15444357642
- T. J. Tucker, S. F. Brady, W. C. Lumma, S. D. Lewis, S. J. Gardell, A. M. Naylor-Olsen, Y. Yan, J. T. Sisko, K. J. Stauffer, B. J. Lucas, J. J. Lynch, J. J. Cook, M. T. Stranieri, M. A. Holahan, E. A. Lyle, E. P. Baskin, I. W. Chen, K. B. Dancheck, J. A. Krueger, C. M. Cooper, J. P. Vacca, J. Med. Chem. 1998, 41, 3210-3219
- (1998) J. Med. Chem. , vol.41 , pp. 3210-3219
- Tucker, T.J.¹ Brady, S.F.² Lumma, W.C.³ Lewis, S.D.⁴ Gardell, S.J.⁵ Naylor-Olsen, A.M.⁶ Yan, Y.⁷ Sisko, J.T.⁸ Stauffer, K.J.⁹ Lucas, B.J.¹⁰ Lynch, J.J.¹¹ Cook, J.J.¹² Stranieri, M.T.¹³ Holahan, M.A.¹⁴ Lyle, E.A.¹⁵ Baskin, E.P.¹⁶ Chen, I.W.¹⁷ Dancheck, K.B.¹⁸ Krueger, J.A.¹⁹ Cooper, C.M.²⁰ Vacca, J.P.²¹ more..

25
- 0037207123
- M. Adler, M. J. Kochanny, B. Ye, G. Rumennik, D. R. Light, S. Biancalana, M. Whitlow, Biochemistry 2002, 41, 15514-15523
- (2002) Biochemistry , vol.41 , pp. 15514-15523
- Adler, M.¹ Kochanny, M.J.² Ye, B.³ Rumennik, G.⁴ Light, D.R.⁵ Biancalana, S.⁶ Whitlow, M.⁷

26
- 0036523422
- M. T. Stubbs, S. Reyda, F. Dullweber, M. Moller, G. Klebe, D. Dorsch, W. W. K. R. Mederski, H. Wurziger, ChemBioChem 2002, 3, 246-249
- (2002) ChemBioChem , vol.3 , pp. 246-249
- Stubbs, M.T.¹ Reyda, S.² Dullweber, F.³ Moller, M.⁴ Klebe, G.⁵ Dorsch, D.⁶ Mederski, W.W.K.R.⁷ Wurziger, H.⁸

27
- 0037468471
- S. Maignan, J.-P. Guilloteau, Y. M. Choi-Sledeski, M. R. Becker, W. R. Ewing, H. W. Pauls, A. P. Spada, V. Mikol, J. Med. Chem. 2003, 46, 685-690
- (2003) J. Med. Chem. , vol.46 , pp. 685-690
- Maignan, S.¹ Guilloteau, J.-P.² Choi-Sledeski, Y.M.³ Becker, M.R.⁴ Ewing, W.R.⁵ Pauls, H.W.⁶ Spada, A.P.⁷ Mikol, V.⁸

28
- 24944536065
- S. Roehrig, A. Straub, J. Pohlmann, T. Lampe, J. Pernerstorfer, K.-H. Schlemmer, P. Reinemer, E. Perzborn, J. Med. Chem. 2005, 48, 5900-5908
- (2005) J. Med. Chem. , vol.48 , pp. 5900-5908
- Roehrig, S.¹ Straub, A.² Pohlmann, J.³ Lampe, T.⁴ Pernerstorfer, J.⁵ Schlemmer, K.-H.⁶ Reinemer, P.⁷ Perzborn, E.⁸

29
- 12344318177
- M. J. Hartshorn, C. W. Murray, A. Cleasby, M. Frederickson, I. J. Tickle, H. Jhoti, J. Med. Chem. 2005, 48, 403-413
- (2005) J. Med. Chem. , vol.48 , pp. 403-413
- Hartshorn, M.J.¹ Murray, C.W.² Cleasby, A.³ Frederickson, M.⁴ Tickle, I.J.⁵ Jhoti, H.⁶

30
- 57349194524
- Y. Shi, D. Sitkoff, J. Zhang, H. E. Klei, K. Kish, E. C.-K. Liu, K. S. Hartl, S. M. Seiler, M. Chang, C. Huang, S. Youssef, T. E. Steinbacher, W. A. Schumacher, Y. Grazier, A. Pudzianowski, A. Apedo, L. Doscenza, J. Yanchunas, P. D. Stein, K. S. Atwal, J. Med. Chem. 2008, 51, 7541-7551
- (2008) J. Med. Chem. , vol.51 , pp. 7541-7551
- Shi, Y.¹ Sitkoff, D.² Zhang, J.³ Klei, H.E.⁴ Kish, K.⁵ Liu, E.C.-K.⁶ Hartl, K.S.⁷ Seiler, S.M.⁸ Chang, M.⁹ Huang, C.¹⁰ Youssef, S.¹¹ Steinbacher, T.E.¹² Schumacher, W.A.¹³ Grazier, Y.¹⁴ Pudzianowski, A.¹⁵ Apedo, A.¹⁶ Doscenza, L.¹⁷ Yanchunas, J.¹⁸ Stein, P.D.¹⁹ Atwal, K.S.²⁰ more..

31
- 77949483011
- A. Straub, S. Roehrig, A. Hillisch, Curr. Top. Med. Chem. 2010, 10, 257-269.
- (2010) Curr. Top. Med. Chem. , vol.10 , pp. 257-269
- Straub, A.¹ Roehrig, S.² Hillisch, A.³

32
- 3142727707
- M. Nazaré, M. Essrich, D. W. Will, H. Matter, K. Ritter, M. Urmann, A. Bauer, H. Schreuder, J. Czech, M. Lorenz, V. Laux, V. Wehner, Bioorg. Med. Chem. Lett. 2004, 14, 4197-4201.
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 4197-4201
- Nazaré, M.¹ Essrich, M.² Will, D.W.³ Matter, H.⁴ Ritter, K.⁵ Urmann, M.⁶ Bauer, A.⁷ Schreuder, H.⁸ Czech, J.⁹ Lorenz, M.¹⁰ Laux, V.¹¹ Wehner, V.¹²

33
- 0033578302
- P. Gallivan, D. A. Dougherty, Proc. Natl. Acad. Sci. USA 1999, 96, 9459-9464.
- (1999) Proc. Natl. Acad. Sci. USA , vol.96 , pp. 9459-9464
- Gallivan, P.¹ Dougherty, D.A.²

34
- 79955667621
- L. M. Salonen, C. Bucher, D. W. Banner, W. Haap, J.-L. Mary, J. Benz, O. Kuster, P. Seiler, W. B. Schweizer, F. Diederich, Angew. Chem. 2009, 121, 825-828
- (2009) Angew. Chem. , vol.121 , pp. 825-828
- Salonen, L.M.¹ Bucher, C.² Banner, D.W.³ Haap, W.⁴ Mary, J.-L.⁵ Benz, J.⁶ Kuster, O.⁷ Seiler, P.⁸ Schweizer, W.B.⁹ Diederich, F.¹⁰

35
- 58249100150
- Angew. Chem. Int. Ed. 2009, 48, 811-814.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 811-814

36
- 33846447291
- K. Schärer, M. Morgenthaler, R. Paulini, U. Obst-Sander, D. W. Banner, D. Schlatter, J. Benz, M. Stihle, F. Diederich, Angew. Chem. 2005, 117, 4474-4479
- (2005) Angew. Chem. , vol.117 , pp. 4474-4479
- Schärer, K.¹ Morgenthaler, M.² Paulini, R.³ Obst-Sander, U.⁴ Banner, D.W.⁵ Schlatter, D.⁶ Benz, J.⁷ Stihle, M.⁸ Diederich, F.⁹

37
- 22744448212
- Angew. Chem. Int. Ed. 2005, 44, 4400-4404.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4400-4404

38
- 77956318578
- D. J. P. Pinto, J. M. Smallheer, D. L. Cheney, R. M. Knabb, R. R. Wexler, J. Med. Chem. 2010, 53, 6243-6274.
- (2010) J. Med. Chem. , vol.53 , pp. 6243-6274
- Pinto, D.J.P.¹ Smallheer, J.M.² Cheney, D.L.³ Knabb, R.M.⁴ Wexler, R.R.⁵

39
- 37249023309
- F. Milletti, L. Storchi, G. Sforna, G. Cruciani, J. Chem. Inf. Model. 2007, 47, 2172-2181
- (2007) J. Chem. Inf. Model. , vol.47 , pp. 2172-2181
- Milletti, F.¹ Storchi, L.² Sforna, G.³ Cruciani, G.⁴

40
- 77955552577
- F. Milletti, L. Storchi, L. Goracci, S. Bendels, B. Wagner, M. Kansy, G. Cruciani, Eur. J. Med. Chem. 2010, 45, 4270-4279.
- (2010) Eur. J. Med. Chem. , vol.45 , pp. 4270-4279
- Milletti, F.¹ Storchi, L.² Goracci, L.³ Bendels, S.⁴ Wagner, B.⁵ Kansy, M.⁶ Cruciani, G.⁷

41
- 33746885488
- A. Ciulli, G. Williams, A. G. Smith, T. L. Blundell, C. Abell, J. Med. Chem. 2006, 49, 4992-5000.
- (2006) J. Med. Chem. , vol.49 , pp. 4992-5000
- Ciulli, A.¹ Williams, G.² Smith, A.G.³ Blundell, T.L.⁴ Abell, C.⁵

42
- 77949837779
- S. Barelier, J. Pons, O. Marcillat, J.-M. Lancelin, I. Krimm, J. Med. Chem. 2010, 53, 2577-2588.
- (2010) J. Med. Chem. , vol.53 , pp. 2577-2588
- Barelier, S.¹ Pons, J.² Marcillat, O.³ Lancelin, J.-M.⁴ Krimm, I.⁵

43
- 0031181346
- C. McMartin, R. S. Bohacek, J. Comput.-Aided Mol. Des. 1997, 11, 333-344.
- (1997) J. Comput.-Aided Mol. Des. , vol.11 , pp. 333-344
- McMartin, C.¹ Bohacek, R.S.²

44
- 84913537730
- W. Heiden, T. Goetze, J. Brickmann, J. Comput. Chem. 1993, 14, 246-250
- (1993) J. Comput. Chem. , vol.14 , pp. 246-250
- Heiden, W.¹ Goetze, T.² Brickmann, J.³

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