SCOPUS 정보 검색 플랫폼

Volumn 9, Issue 4, 2014, Pages 833-846

Methyl, ethyl, propyl, butyl: Futile but not for water, as the correlation of structure and thermodynamic signature shows in a congeneric series of thermolysin inhibitors

(4) Krimmer, Stefan G a Betz, Michael a Heine, Andreas a Klebe, Gerhard a

a PHILIPPS UNIVERSITY MARBURG (Germany)

Author keywords

crystal structure analysis; isothermal titration calorimetry; protein ligand interactions; structure activity relationships; water network formation

Indexed keywords

BUTANE; ETHANE; METALLOPROTEINASE INHIBITOR; METHYL GROUP; PHOSPHONIC ACID DERIVATIVE; PROPANE; THERMOLYSIN; THERMOLYSIN INHIBITOR; UNCLASSIFIED DRUG; WATER; ENZYME INHIBITOR;

ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG STRUCTURE; ENTHALPY; ENTROPY; HYDROPHOBICITY; ISOTHERMAL TITRATION CALORIMETRY; LIGAND BINDING; MOLECULAR SIZE; PRIORITY JOURNAL; SOLVATION; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; METABOLISM; SYNTHESIS;

DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOPHOSPHONATES; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS; THERMOLYSIN; WATER;

EID: 84898006931 PISSN: 18607179 EISSN: 18607187 Source Type: Journal
DOI: 10.1002/cmdc.201400013 Document Type: Article

Times cited : (67)

References (64)

1
- 85013786675
- Elsevier, Amsterdam, p. .
- C. G. Wermuth, The Practice of Medicinal Chemistry, 3rd ed., Elsevier, Amsterdam, 2008, p. 283.
- (2008) The Practice of Medicinal Chemistry, 3rd Ed. , pp. 283
- Wermuth, C.G.¹

2
- 0344443175
- E. D. Sloan, Nature 2003, 426, 353-363.
- (2003) Nature , vol.426 , pp. 353-363
- Sloan, E.D.¹

3
- 0001554681
- M. M. Teeter, Proc. Natl. Acad. Sci. USA 1984, 81, 6014-6018.
- (1984) Proc. Natl. Acad. Sci. USA , vol.81 , pp. 6014-6018
- Teeter, M.M.¹

4
- 23744466879
- N. S. Oxtoby, A. J. Blake, N. R. Champness, C. Wilson, Chemistry 2005, 11, 4643-4654.
- (2005) Chemistry , vol.11 , pp. 4643-4654
- Oxtoby, N.S.¹ Blake, A.J.² Champness, N.R.³ Wilson, C.⁴

5
- 34447108978
- S. W. Homans, Drug Discovery Today 2007, 12, 534-539.
- (2007) Drug Discovery Today , vol.12 , pp. 534-539
- Homans, S.W.¹

6
- 77953631827
- C. Bissantz, B. Kuhn, M. Stahl, J. Med. Chem. 2010, 53, 5061-5084.
- (2010) J. Med. Chem. , vol.53 , pp. 5061-5084
- Bissantz, C.¹ Kuhn, B.² Stahl, M.³

7
- 14144252682
- C. K. Engel, B. Pirard, S. Schimanski, R. Kirsch, J. Habermann, O. Klingler, V. Schlotte, K. U. Weithmann, K. U. Wendt, Chem. Biol. 2005, 12, 181-189.
- (2005) Chem. Biol. , vol.12 , pp. 181-189
- Engel, C.K.¹ Pirard, B.² Schimanski, S.³ Kirsch, R.⁴ Habermann, J.⁵ Klingler, O.⁶ Schlotte, V.⁷ Weithmann, K.U.⁸ Wendt, K.U.⁹

8
- 0030471364
- J. R. Tame, S. H. Sleigh, A. J. Wilkinson, J. E. Ladbury, Nat. Struct. Biol. 1996, 3, 998-1001.
- (1996) Nat. Struct. Biol. , vol.3 , pp. 998-1001
- Tame, J.R.¹ Sleigh, S.H.² Wilkinson, A.J.³ Ladbury, J.E.⁴

9
- 0037168045
- T. Wang, R. C. Wade, J. Med. Chem. 2002, 45, 4828-4837.
- (2002) J. Med. Chem. , vol.45 , pp. 4828-4837
- Wang, T.¹ Wade, R.C.²

10
- 49149124735
- B. W. Matthews, P. M. Colman, J. N. Jansonius, K. Titani, K. A. Walsh, H. Neurath, Nat. New Biol. 1972, 238, 41-43.
- (1972) Nat. New Biol. , vol.238 , pp. 41-43
- Matthews, B.W.¹ Colman, P.M.² Jansonius, J.N.³ Titani, K.⁴ Walsh, K.A.⁵ Neurath, H.⁶

11
- 0016320853
- B. W. Matthews, L. H. Weaver, W. R. Kester, J. Biol. Chem. 1974, 249, 8030-8044.
- (1974) J. Biol. Chem. , vol.249 , pp. 8030-8044
- Matthews, B.W.¹ Weaver, L.H.² Kester, W.R.³

12
- 0020462668
- M. A. Holmes, B. W. Matthews, J. Mol. Biol. 1982, 160, 623-639.
- (1982) J. Mol. Biol. , vol.160 , pp. 623-639
- Holmes, M.A.¹ Matthews, B.W.²

13
- 0035044857
- A. C. English, C. R. Groom, R. E. Hubbard, Protein Eng. 2001, 14, 47-59.
- (2001) Protein Eng. , vol.14 , pp. 47-59
- English, A.C.¹ Groom, C.R.² Hubbard, R.E.³

14
- 77953092035
- L. Englert, K. Silber, H. Steuber, S. Brass, B. Over, H.-D. Gerber, A. Heine, W. E. Diederich, G. Klebe, ChemMedChem 2010, 5, 930-940.
- (2010) ChemMedChem , vol.5 , pp. 930-940
- Englert, L.¹ Silber, K.² Steuber, H.³ Brass, S.⁴ Over, B.⁵ Gerber, H.-D.⁶ Heine, A.⁷ Diederich, W.E.⁸ Klebe, G.⁹

15
- 84856383770
- J. Behnen, H. Köster, G. Neudert, T. Craan, A. Heine, G. Klebe, ChemMedChem 2012, 7, 248-261.
- (2012) ChemMedChem , vol.7 , pp. 248-261
- Behnen, J.¹ Köster, H.² Neudert, G.³ Craan, T.⁴ Heine, A.⁵ Klebe, G.⁶

16
- 77956268336
- L. Englert, A. Biela, M. Zayed, A. Heine, D. Hangauer, G. Klebe, Biochim. Biophys. Acta Gen. Subj. 2010, 1800, 1192-1202.
- (2010) Biochim. Biophys. Acta Gen. Subj. , vol.1800 , pp. 1192-1202
- Englert, L.¹ Biela, A.² Zayed, M.³ Heine, A.⁴ Hangauer, D.⁵ Klebe, G.⁶

17
- 84864400966
- A. Biela, M. Betz, A. Heine, G. Klebe, ChemMedChem 2012, 7, 1423-1434.
- (2012) ChemMedChem , vol.7 , pp. 1423-1434
- Biela, A.¹ Betz, M.² Heine, A.³ Klebe, G.⁴

18
- 84873351927
- A. Biela, N. N. Nasief, M. Betz, A. Heine, D. Hangauer, G. Klebe, Angew. Chem. Int. Ed. 2013, 52, 1822-1828
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 1822-1828
- Biela, A.¹ Nasief, N.N.² Betz, M.³ Heine, A.⁴ Hangauer, D.⁵ Klebe, G.⁶

19
- 84882269188
- Angew. Chem. 2013, 125, 1868-1876.
- (2013) Angew. Chem. , vol.125 , pp. 1868-1876

20
- 0033081137
- O. Carugoa, D. Bordo, Acta Crystallogr. Sect. D 1999, 55, 479-483.
- (1999) Acta Crystallogr. Sect. D , vol.55 , pp. 479-483
- Carugoa, O.¹ Bordo, D.²

21
- 84867342383
- N. N. Nasief, H. Tan, J. Kong, D. Hangauer, J. Med. Chem. 2012, 55, 8283-8302.
- (2012) J. Med. Chem. , vol.55 , pp. 8283-8302
- Nasief, N.N.¹ Tan, H.² Kong, J.³ Hangauer, D.⁴

22
- 0003914038
- Oxford University Press, Oxford.
- G. A. Jeffrey, An Introduction to Hydrogen Bonding, Oxford University Press, Oxford, 1997.
- (1997) An Introduction to Hydrogen Bonding
- Jeffrey, G.A.¹

23
- 0037008160
- H. Gohlke, G. Klebe, Angew. Chem. Int. Ed. 2002, 41, 2644-2676
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2644-2676
- Gohlke, H.¹ Klebe, G.²

24
- 0038459881
- Angew. Chem. 2002, 114, 2764-2798.
- (2002) Angew. Chem. , vol.114 , pp. 2764-2798

25
- 0024356301
- T. Wiseman, S. Williston, J. F. Brandts, L. Lin, Anal. Biochem. 1989, 179, 131-137.
- (1989) Anal. Biochem. , vol.179 , pp. 131-137
- Wiseman, T.¹ Williston, S.² Brandts, J.F.³ Lin, L.⁴

26
- 35448962899
- M. W. Freyer, E. A. Lewis, Methods Cell Biol. 2008, 84, 79-113.
- (2008) Methods Cell Biol. , vol.84 , pp. 79-113
- Freyer, M.W.¹ Lewis, E.A.²

27
- 0029395478
- J. D. Dunitz, Chem. Biol. 1995, 2, 709-712.
- (1995) Chem. Biol. , vol.2 , pp. 709-712
- Dunitz, J.D.¹

28
- 0035107447
- K. Sharp, Protein Sci. 2001, 10, 661-667.
- (2001) Protein Sci. , vol.10 , pp. 661-667
- Sharp, K.¹

29
- 33748563642
- G. M. Whitesides, V. M. Krishnamurthy, Q. Rev. Biophys. 2005, 38, 385-395.
- (2005) Q. Rev. Biophys. , vol.38 , pp. 385-395
- Whitesides, G.M.¹ Krishnamurthy, V.M.²

30
- 84860390480
- T. S. G. Olsson, J. E. Ladbury, W. R. Pitt, M. A. Williams, Protein Sci. 2011, 20, 1607-1618.
- (2011) Protein Sci. , vol.20 , pp. 1607-1618
- Olsson, T.S.G.¹ Ladbury, J.E.² Pitt, W.R.³ Williams, M.A.⁴

31
- 67349109896
- B. Baum, M. Mohamed, M. Zayed, C. Gerlach, A. Heine, D. Hangauer, G. Klebe, J. Mol. Biol. 2009, 390, 56-69.
- (2009) J. Mol. Biol. , vol.390 , pp. 56-69
- Baum, B.¹ Mohamed, M.² Zayed, M.³ Gerlach, C.⁴ Heine, A.⁵ Hangauer, D.⁶ Klebe, G.⁷

32
- 81055130316
- P. W. Snyder, J. Mecinovic̈, D. T. Moustakas, S. W. Thomas III, M. Harder, E. T. Mack, M. R. Lockett, A. Héroux, W. Sherman, G. M. Whitesides, Proc. Natl. Acad. Sci. USA 2011, 108, 17889-17894.
- (2011) Proc. Natl. Acad. Sci. USA , vol.108 , pp. 17889-17894
- Snyder, P.W.¹ Mecinovic̈, J.² Moustakas, D.T.³ Thomas III, S.W.⁴ Harder, M.⁵ Mack, E.T.⁶ Lockett, M.R.⁷ Héroux, A.⁸ Sherman, W.⁹ Whitesides, G.M.¹⁰

33
- 84863812540
- A. Biela, F. Sielaff, F. Terwesten, A. Heine, T. Steinmetzer, G. Klebe, J. Med. Chem. 2012, 55, 6094-6110.
- (2012) J. Med. Chem. , vol.55 , pp. 6094-6110
- Biela, A.¹ Sielaff, F.² Terwesten, F.³ Heine, A.⁴ Steinmetzer, T.⁵ Klebe, G.⁶

34
- 84878914295
- S. F. Martin, J. H. Clements, Annu. Rev. Biochem. 2013, 82, 267-293.
- (2013) Annu. Rev. Biochem. , vol.82 , pp. 267-293
- Martin, S.F.¹ Clements, J.H.²

35
- 84886933840
- B. Breiten, M. R. Lockett, W. Sherman, S. Fujita, M. Al-Sayah, H. Lange, C. M. Bowers, A. Heroux, G. Krilov, G. M. Whitesides, J. Am. Chem. Soc. 2013, 135, 15579-15584.
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 15579-15584
- Breiten, B.¹ Lockett, M.R.² Sherman, W.³ Fujita, S.⁴ Al-Sayah, M.⁵ Lange, H.⁶ Bowers, C.M.⁷ Heroux, A.⁸ Krilov, G.⁹ Whitesides, G.M.¹⁰

36
- 33749238188
- N. Shimokhina, A. Bronowska, S. W. Homans, Angew. Chem. Int. Ed. 2006, 45, 6374-6376
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 6374-6376
- Shimokhina, N.¹ Bronowska, A.² Homans, S.W.³

37
- 34548781846
- Angew. Chem. 2006, 118, 6522-6524.
- (2006) Angew. Chem. , vol.118 , pp. 6522-6524

38
- 0002638463
- J. M. Sturtevant, Proc. Natl. Acad. Sci. USA 1977, 74, 2236-2240.
- (1977) Proc. Natl. Acad. Sci. USA , vol.74 , pp. 2236-2240
- Sturtevant, J.M.¹

39
- 0017884417
- C. Tanford, Science 1978, 200, 1012-1018.
- (1978) Science , vol.200 , pp. 1012-1018
- Tanford, C.¹

40
- 28044466911
- D. M. Ford, J. Am. Chem. Soc. 2005, 127, 16167-16170.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 16167-16170
- Ford, D.M.¹

41
- 0015222647
- B. Lee, F. M. Richards, J. Mol. Biol. 1971, 55, 379-490.
- (1971) J. Mol. Biol. , vol.55 , pp. 379-490
- Lee, B.¹ Richards, F.M.²

42
- 0014620371
- D. D. F. Shiao, J. M. Sturtevant, Biochemistry 1969, 8, 4910-4917.
- (1969) Biochemistry , vol.8 , pp. 4910-4917
- Shiao, D.D.F.¹ Sturtevant, J.M.²

43
- 0242417008
- E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. Int. Ed. 2003, 42, 1210-1250
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1210-1250
- Meyer, E.A.¹ Castellano, R.K.² Diederich, F.³

44
- 0037955629
- Angew. Chem. 2003, 115, 1244-1287.
- (2003) Angew. Chem. , vol.115 , pp. 1244-1287

45
- 0002624470
- B. W. Matthews, J. N. Jansonius, P. M. Colman, B. P. Schoenborn, D. Dupourque, Nat. New Biol. 1972, 238, 37-41.
- (1972) Nat. New Biol. , vol.238 , pp. 37-41
- Matthews, B.W.¹ Jansonius, J.N.² Colman, P.M.³ Schoenborn, B.P.⁴ Dupourque, D.⁵

46
- 84860129612
- U. Mueller, N. Darowski, M. R. Fuchs, R. Förster, M. Hellmig, K. S. Paithankar, S. Pühringer, M. Steffien, G. Zocher, M. S. Weiss, J. Synchrotron Radiat. 2012, 19, 442-449.
- (2012) J. Synchrotron Radiat. , vol.19 , pp. 442-449
- Mueller, U.¹ Darowski, N.² Fuchs, M.R.³ Förster, R.⁴ Hellmig, M.⁵ Paithankar, K.S.⁶ Pühringer, S.⁷ Steffien, M.⁸ Zocher, G.⁹ Weiss, M.S.¹⁰

47
- 0031059866
- Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326.
- (1997) Methods Enzymol. , vol.276 , pp. 307-326
- Otwinowski, Z.¹ Minor, W.²

48
- 0026489329
- D. R. Holland, D. E. Tronrud, H. W. Pley, K. M. Flaherty, W. Stark, J. N. Jansonius, D. B. McKay, B. W. Matthews, Biochemistry 1992, 31, 11310-11316.
- (1992) Biochemistry , vol.31 , pp. 11310-11316
- Holland, D.R.¹ Tronrud, D.E.² Pley, H.W.³ Flaherty, K.M.⁴ Stark, W.⁵ Jansonius, J.N.⁶ McKay, D.B.⁷ Matthews, B.W.⁸

49
- 34447508216
- A. J. McCoy, R. W. Grosse-Kunstleve, P. D. Adams, M. D. Winn, L. C. Storoni, R. J. Read, J. Appl. Crystallogr. 2007, 40, 658-674.
- (2007) J. Appl. Crystallogr. , vol.40 , pp. 658-674
- McCoy, A.J.¹ Grosse-Kunstleve, R.W.² Adams, P.D.³ Winn, M.D.⁴ Storoni, L.C.⁵ Read, R.J.⁶

50
- 0028103275
- Collaborative Computational Project, Number 4, Acta Crystallogr. D 1994, 50, 760-763.
- (1994) Collaborative Computational Project, Number 4, Acta Crystallogr. D , vol.50 , pp. 760-763

51
- 13244281317
- P. Emsley, K. Cowtan, Acta Crystallogr. Sect. D 2004, 60, 2126-2132.
- (2004) Acta Crystallogr. Sect. D , vol.60 , pp. 2126-2132
- Emsley, P.¹ Cowtan, K.²

52
- 76449098262
- P. D. Adams, P. V. Afonine, G. Bunkoczi, V. B. Chen, I. W. Davis, N. Echols, J. J. Headd, L. W. Hung, G. J. Kapral, R. W. Grosse-Kunstleve, A. J. McCoy, N. W. Moriarty, R. Oener, R. J. Read, D. C. Richardson, J. S. Richardson, T. C. Terwilliger, P. H. Zwart, Acta Crystallogr. Sect. D 2010, 66, 213-221.
- (2010) Acta Crystallogr. Sect. D , vol.66 , pp. 213-221
- Adams, P.D.¹ Afonine, P.V.² Bunkoczi, G.³ Chen, V.B.⁴ Davis, I.W.⁵ Echols, N.⁶ Headd, J.J.⁷ Hung, L.W.⁸ Kapral, G.J.⁹ Grosse-Kunstleve, R.W.¹⁰ McCoy, A.J.¹¹ Moriarty, N.W.¹² Oener, R.¹³ Read, R.J.¹⁴ Richardson, D.C.¹⁵ Richardson, J.S.¹⁶ Terwilliger, T.C.¹⁷ Zwart, P.H.¹⁸

53
- 84897993229
- Chemical Computing Group, Montreal, QC (Canada)
- MOE, version 2012, Chemical Computing Group, Montreal, QC (Canada).
- MOE, Version 2012

54
- 84897984231
- Tripos International, St. Louis, MO (USA)
- SYBYL-X, version 2.0, Tripos International, St. Louis, MO (USA).
- SYBYL-X, Version 2.0

55
- 74549178560
- V. B. Chen, W. B. Arendall, J. J. Headd, D. A. Keedy, R. M. Immormino, G. J. Kapral, L. W. Murray, J. S. Richardson, D. C. Richardson, Acta Crystallogr. Sect. D 2010, 66, 12-21.
- (2010) Acta Crystallogr. Sect. D , vol.66 , pp. 12-21
- Chen, V.B.¹ Arendall, W.B.² Headd, J.J.³ Keedy, D.A.⁴ Immormino, R.M.⁵ Kapral, G.J.⁶ Murray, L.W.⁷ Richardson, J.S.⁸ Richardson, D.C.⁹

56
- 0031979332
- K. Inouye, K. Kuzuya, B. Tonomura, J. Biochem. 1998, 123, 847-852.
- (1998) J. Biochem. , vol.123 , pp. 847-852
- Inouye, K.¹ Kuzuya, K.² Tonomura, B.³

57
- 79955878936
- C. L. D. Gibb, B. C. Gibb, J. Am. Chem. Soc. 2011, 133, 7344-7347.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 7344-7347
- Gibb, C.L.D.¹ Gibb, B.C.²

58
- 0000538815
- M. L. Connolly, J. Appl. Crystallogr. 1983, 16, 548-558.
- (1983) J. Appl. Crystallogr. , vol.16 , pp. 548-558
- Connolly, M.L.¹

59
- 0018780591
- B. R. Gelin, M. Karplus, Biochemistry 1979, 18, 1256-1268.
- (1979) Biochemistry , vol.18 , pp. 1256-1268
- Gelin, B.R.¹ Karplus, M.²

60
- 79954580509
- Schrödinger LLC, New York, NY (USA)
- The PyMOL Molecular Graphics System, version 1.2r3pre, Schrödinger LLC, New York, NY (USA).
- The PyMOL Molecular Graphics System, Version 1.2r3pre

61
- 0017411710
- F. C. Bernstein, T. F. Koetzle, G. J. Williams, E. E. Meyer, M. D. Brice, J. R. Rodgers, O. Kennard, T. Shimanouchi, M. Tasumi, J. Mol. Biol. 1977, 112, 535-542.
- (1977) J. Mol. Biol. , vol.112 , pp. 535-542
- Bernstein, F.C.¹ Koetzle, T.F.² Williams, G.J.³ Meyer, E.E.⁴ Brice, M.D.⁵ Rodgers, J.R.⁶ Kennard, O.⁷ Shimanouchi, T.⁸ Tasumi, M.⁹

62
- 0000243829
- R. A. Laskowski, M. W. MacArthur, D. S. Moss, J. M. Thornton, J. Appl. Crystallogr. 1993, 26, 283-291.
- (1993) J. Appl. Crystallogr. , vol.26 , pp. 283-291
- Laskowski, R.A.¹ Macarthur, M.W.² Moss, D.S.³ Thornton, J.M.⁴

63
- 0000252066
- B. W. Matthews, Macromolecules 1972, 5, 818-819.
- (1972) Macromolecules , vol.5 , pp. 818-819
- Matthews, B.W.¹

64
- 0002906346
- in (Eds.: M. G. Rossmann, E. Arnold), Springer Netherlands, Dordrecht, .
- G. J. Kleywegt, J.-Y. Zou, M. Kjeldgaard, T. A. Jones, in International Tables for Crystallography, Vol. F (Eds.:, M. G. Rossmann, E. Arnold,), Springer Netherlands, Dordrecht, 2001, pp. 353-356.
- (2001) International Tables for Crystallography, Vol. F , pp. 353-356
- Kleywegt, G.J.¹ Zou, J.-Y.² Kjeldgaard, M.³ Jones, T.A.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.