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Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 15, 2011, Pages 4457-4461

Structure-activity study on a series of α-glutamic acid scaffold based compounds as new ADAMTS inhibitors

(8) Peng, Lijie a,b Duan, Lei a Liu, Xiaofeng c Shen, Mengjie a,b Li, Yingjun a,b Yan, Jiajie a,b Li, Honglin c Ding, Ke a

a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH (China)

b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES (China)

c EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY (China)

Author keywords

ADAMTS; Aggrecanase; Glutamic acid scaffold; Osteoarthritis

Indexed keywords

4 (BENZAMIDO) 4 (1,3,4 OXADIAZOL 2 YL)BUTANOIC ACID; AGGRECANASE 1; AGGRECANASE 2; GLUTAMIC ACID; METALLOPROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; MOLECULAR DOCKING; OSTEOARTHRITIS; STRUCTURE ACTIVITY RELATION;

ADAM PROTEINS; BINDING SITES; COMPUTER SIMULATION; GAMMA-AMINOBUTYRIC ACID; GLUTAMIC ACID; HUMANS; OXADIAZOLES; PROCOLLAGEN N-ENDOPEPTIDASE; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79960371941 PISSN: 0960894X EISSN: 14643405 Source Type: Journal
DOI: 10.1016/j.bmcl.2011.06.009 Document Type: Article

Times cited : (9)

References (25)

1
- 0038639763
- H. Nagase, and M. Kashiwagi Arthritis Res. Ther. 5 2003 94
- (2003) Arthritis Res. Ther. , vol.5 , pp. 94
- Nagase, H.¹ Kashiwagi, M.²

2
- 0345211445
- M.D. Tortorella, T.C. Burn, M.A. Pratta, I. Abbaszade, J.M. Hollis, R. Liu, S.A. Rosenfeld, R.A. Copeland, C.P. Decicco, R. Wynn, A. Rockwell, F. Yang, J.L. Duke, K. Solomon, H. George, R. Bruckner, H. Nagase, Y. Itoh, D.M. Ellis, H. Ross, B.H. Wisswall, K. Murphy, M.C. Hillman, G.F. Hollis, R.C. Newton, R.L. Magolda, J.M. Trzaskos, and E.C. Arner Science 284 1999 1664
- (1999) Science , vol.284 , pp. 1664
- Tortorella, M.D.¹ Burn, T.C.² Pratta, M.A.³ Abbaszade, I.⁴ Hollis, J.M.⁵ Liu, R.⁶ Rosenfeld, S.A.⁷ Copeland, R.A.⁸ Decicco, C.P.⁹ Wynn, R.¹⁰ Rockwell, A.¹¹ Yang, F.¹² Duke, J.L.¹³ Solomon, K.¹⁴ George, H.¹⁵ Bruckner, R.¹⁶ Nagase, H.¹⁷ Itoh, Y.¹⁸ Ellis, D.M.¹⁹ Ross, H.²⁰ more..

3
- 0033551844
- I. Abbaszade, R.Q. Liu, F. Yang, S.A. Rosenfeld, O.H. Ross, J.R. Link, D.M. Ellis, M.D. Tortorella, M.A. Pratta, J.M. Hollis, R. Wynn, J.L. Duke, H.J. George, M.C. Hillman Jr., K. Murphy, B.H. Wiswall, R.A. Copeland, C.P. Decicco, R. Bruckner, H. Nagase, Y. Itoh, R.C. Newton, R.L. Magolda, J.M. Trzaskos, and T.C. Burn J. Biol. Chem. 274 1999 23443
- (1999) J. Biol. Chem. , vol.274 , pp. 23443
- Abbaszade, I.¹ Liu, R.Q.² Yang, F.³ Rosenfeld, S.A.⁴ Ross, O.H.⁵ Link, J.R.⁶ Ellis, D.M.⁷ Tortorella, M.D.⁸ Pratta, M.A.⁹ Hollis, J.M.¹⁰ Wynn, R.¹¹ Duke, J.L.¹² George, H.J.¹³ Hillman, Jr.M.C.¹⁴ Murphy, K.¹⁵ Wiswall, B.H.¹⁶ Copeland, R.A.¹⁷ Decicco, C.P.¹⁸ Bruckner, R.¹⁹ Nagase, H.²⁰ more..

4
- 0032978988
- B.L. Tang, and W. Hong FEBS Lett. 445 1999 223
- (1999) FEBS Lett. , vol.445 , pp. 223
- Tang, B.L.¹ Hong, W.²

5
- 15844384854
- H. Stanton, F.M. Rogerson, C.J. East, S.B. Golub, K.E. Lawlor, C.T. Meeker, C.B. Little, K. Last, P.J. Farmer, I.K. Campbell, A.M. Fourie, and A.J. Fosang Nature 434 2005 648
- (2005) Nature , vol.434 , pp. 648
- Stanton, H.¹ Rogerson, F.M.² East, C.J.³ Golub, S.B.⁴ Lawlor, K.E.⁵ Meeker, C.T.⁶ Little, C.B.⁷ Last, K.⁸ Farmer, P.J.⁹ Campbell, I.K.¹⁰ Fourie, A.M.¹¹ Fosang, A.J.¹²

6
- 33847010576
- R.H. Song, M.D. Tortorella, A.M. Malfait, J.T. Alston, Z. Yang, E.C. Arner, and D.W. Griggs Arthritis Rheum. 56 2007 575
- (2007) Arthritis Rheum. , vol.56 , pp. 575
- Song, R.H.¹ Tortorella, M.D.² Malfait, A.M.³ Alston, J.T.⁴ Yang, Z.⁵ Arner, E.C.⁶ Griggs, D.W.⁷

7
- 48749106644
- A.J. Fosang, and C.B. Little Nat. Clin. Pract. Rheumatol. 4 2008 420
- (2008) Nat. Clin. Pract. Rheumatol. , vol.4 , pp. 420
- Fosang, A.J.¹ Little, C.B.²

8
- 77951035922
- C.R. Flannery Curr. Drug Targets 11 2010 614
- (2010) Curr. Drug Targets , vol.11 , pp. 614
- Flannery, C.R.¹

9
- 0035846124
- W. Yao, Z.R. Wasserman, M. Chao, G. Reddy, E. Shi, R.-Q. Liu, M.B. Covington, E.C. Arner, M.A. Pratta, M. Tortorella, R.L. Magolda, R. Newton, M. Qian, M.D. Ribadeneira, D. Christ, R.R. Wexler, and C.P. Decicco J. Med. Chem. 44 2001 3347
- (2001) J. Med. Chem. , vol.44 , pp. 3347
- Yao, W.¹ Wasserman, Z.R.² Chao, M.³ Reddy, G.⁴ Shi, E.⁵ Liu, R.-Q.⁶ Covington, M.B.⁷ Arner, E.C.⁸ Pratta, M.A.⁹ Tortorella, M.¹⁰ Magolda, R.L.¹¹ Newton, R.¹² Qian, M.¹³ Ribadeneira, M.D.¹⁴ Christ, D.¹⁵ Wexler, R.R.¹⁶ Decicco, C.P.¹⁷

10
- 20844448902
- R.Q. Liu, and J.M. Trzaskos Curr. Med. Chem. Anti-inflamm. Anti-Allergy Agents 4 2005 251
- (2005) Curr. Med. Chem. Anti-inflamm. Anti-Allergy Agents , vol.4 , pp. 251
- Liu, R.Q.¹ Trzaskos, J.M.²

11
- 70349378351
- F. De Rienzo, P. Saxena, F. Filomia, G. Caselli, F. Colace, L. Stasi, A. Giordani, and M.C. Menziani Curr. Med. Chem. 16 2009 2395
- (2009) Curr. Med. Chem. , vol.16 , pp. 2395
- De Rienzo, F.¹ Saxena, P.² Filomia, F.³ Caselli, G.⁴ Colace, F.⁵ Stasi, L.⁶ Giordani, A.⁷ Menziani, M.C.⁸

12
- 51349093700
- J. Charton, B.P. Déprez, and R.F. Déprez-Poulain Bioorg. Med. Chem. Lett. 18 2008 4968
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 4968
- Charton, J.¹ Déprez, B.P.² Déprez-Poulain, R.F.³

13
- 56249124956
- A.M. Gilbert, M.G. Bursavich, S. Lombardi, K.E. Georgiadis, E. Reifenberg, C.R. Flannery, and E.A. Morris Bioorg. Med. Chem. Lett. 18 2008 6454
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 6454
- Gilbert, A.M.¹ Bursavich, M.G.² Lombardi, S.³ Georgiadis, K.E.⁴ Reifenberg, E.⁵ Flannery, C.R.⁶ Morris, E.A.⁷

14
- 61349194588
- M. Shiozaki, K. Maeda, T. Miura, Y. Ogoshi, J. Haas, A.M. Fryer, E.R. Laird, N.M. Littmann, S.W. Andrews, J.A. Josey, T. Mimura, Y. Shinozaki, H. Yoshiuchi, and T. Inaba Bioorg. Med. Chem. Lett. 19 2009 1575
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 1575
- Shiozaki, M.¹ Maeda, K.² Miura, T.³ Ogoshi, Y.⁴ Haas, J.⁵ Fryer, A.M.⁶ Laird, E.R.⁷ Littmann, N.M.⁸ Andrews, S.W.⁹ Josey, J.A.¹⁰ Mimura, T.¹¹ Shinozaki, Y.¹² Yoshiuchi, H.¹³ Inaba, T.¹⁴

15
- 71749093118
- M. Shiozaki, H. Imai, K. Maeda, T. Miura, K. Yasue, A. Suma, M. Yokota, Y. Ogoshi, J. Haas, A.M. Fryer, E.R. Laird, N.M. Littmann, S.W. Andrews, J.A. Josey, T. Mimura, Y. Shinozaki, H. Yoshiuchi, and T. Inaba Bioorg. Med. Chem. Lett. 19 2009 6213
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 6213
- Shiozaki, M.¹ Imai, H.² Maeda, K.³ Miura, T.⁴ Yasue, K.⁵ Suma, A.⁶ Yokota, M.⁷ Ogoshi, Y.⁸ Haas, J.⁹ Fryer, A.M.¹⁰ Laird, E.R.¹¹ Littmann, N.M.¹² Andrews, S.W.¹³ Josey, J.A.¹⁴ Mimura, T.¹⁵ Shinozaki, Y.¹⁶ Yoshiuchi, H.¹⁷ Inaba, T.¹⁸

16
- 64249127623
- D.W. Hopper, M.D. Vera, D. How, J. Sabatini, J.S. Xiang, M. Ipek, J. Thomason, Y. Hu, E. Feyfant, Q. Wang, K.E. Georgiadis, E. Reifenberg, R.T. Sheldon, C.C. Keohan, M.K. Majumdar, E.A. Morris, J. Skotnicki, and P.-E. Sum Bioorg. Med. Chem. Lett. 19 2009 2487
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 2487
- Hopper, D.W.¹ Vera, M.D.² How, D.³ Sabatini, J.⁴ Xiang, J.S.⁵ Ipek, M.⁶ Thomason, J.⁷ Hu, Y.⁸ Feyfant, E.⁹ Wang, Q.¹⁰ Georgiadis, K.E.¹¹ Reifenberg, E.¹² Sheldon, R.T.¹³ Keohan, C.C.¹⁴ Majumdar, M.K.¹⁵ Morris, E.A.¹⁶ Skotnicki, J.¹⁷ Sum, P.-E.¹⁸

17
- 77957877525
- L. Maingot, F. Leroux, V. Landry, J. Dumont, H. Nagase, B. Villoutreix, O. Sperandio, R. Deprez-Poulain, and B. Deprez Bioorg. Med. Chem. Lett. 20 2010 6213
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 6213
- Maingot, L.¹ Leroux, F.² Landry, V.³ Dumont, J.⁴ Nagase, H.⁵ Villoutreix, B.⁶ Sperandio, O.⁷ Deprez-Poulain, R.⁸ Deprez, B.⁹

18
- 79951692827
- C. De Savi, A. Pape, J.G. Cumming, A. Ting, P.D. Smith, J.N. Burrows, M. Mills, C. Davies, S. Lamont, D. Milne, C. Cook, P. Moore, Y. Sawyer, and S. Gerhardt Bioorg. Med. Chem. Lett. 21 2011 1376
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 1376
- De Savi, C.¹ Pape, A.² Cumming, J.G.³ Ting, A.⁴ Smith, P.D.⁵ Burrows, J.N.⁶ Mills, M.⁷ Davies, C.⁸ Lamont, S.⁹ Milne, D.¹⁰ Cook, C.¹¹ Moore, P.¹² Sawyer, Y.¹³ Gerhardt, S.¹⁴

19
- 0037033136
- W. Yao, M. Chao, Z.R. Wasserman, R.-Q. Liu, M.B. Covington, R. Newton, D. Christ, R.R. Wexler, and C.P. Decicco Bioorg. Med. Chem. Lett. 12 2002 101
- (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 101
- Yao, W.¹ Chao, M.² Wasserman, Z.R.³ Liu, R.-Q.⁴ Covington, M.B.⁵ Newton, R.⁶ Christ, D.⁷ Wexler, R.R.⁸ Decicco, C.P.⁹

20
- 37549037806
- L. Mosyak, K. Georgiadis, T. Shane, K. Svenson, T. Hebert, T. Mcdonagh, S. Mackie, S. Olland, L. Lin, X. Zhong, R. Kriz, E.L. Reifenberg, L.A. Collins-Racie, C. Corcoran, B. Freeman, R. Zollner, T. Marvell, M. Vera, P.-E. Sum, E.R. Lavallie, M. Stahl, and W. Somers Protein Sci. 17 2008 16
- (2008) Protein Sci. , vol.17 , pp. 16
- Mosyak, L.¹ Georgiadis, K.² Shane, T.³ Svenson, K.⁴ Hebert, T.⁵ McDonagh, T.⁶ MacKie, S.⁷ Olland, S.⁸ Lin, L.⁹ Zhong, X.¹⁰ Kriz, R.¹¹ Reifenberg, E.L.¹² Collins-Racie, L.A.¹³ Corcoran, C.¹⁴ Freeman, B.¹⁵ Zollner, R.¹⁶ Marvell, T.¹⁷ Vera, M.¹⁸ Sum, P.-E.¹⁹ Lavallie, E.R.²⁰ Stahl, M.²¹ Somers, W.²² more..

21
- 34548855068
- K.P. Moore, H. Zhu, H.A. Rajapakse, G.B. McGaughey, D. Colussi, E.A. Price, S. Sankaranarayanan, A.J. Simon, N.T. Pudvah, J.H. Hochman, T. Allison, S.K. Munshi, S.L. Graham, J.P. Vacca, and P.G. Nantermet Bioorg. Med. Chem. Lett. 17 2007 5831
- (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 5831
- Moore, K.P.¹ Zhu, H.² Rajapakse, H.A.³ McGaughey, G.B.⁴ Colussi, D.⁵ Price, E.A.⁶ Sankaranarayanan, S.⁷ Simon, A.J.⁸ Pudvah, N.T.⁹ Hochman, J.H.¹⁰ Allison, T.¹¹ Munshi, S.K.¹² Graham, S.L.¹³ Vacca, J.P.¹⁴ Nantermet, P.G.¹⁵

22
- 76649097630
- H. Zhu, M.B. Young, P.G. Nantermet, S.L. Graham, D. Colussi, M.-T. Lai, B. Pietrak, E.A. Price, S. Sankaranarayanan, X. Shi, K. Tugusheva, M.A. Holahan, M.S. Michener, J.J. Cook, A. Simon, D.J. Hazuda, J.P. Vacca, and H.A. Rajapakse Bioorg. Med. Chem. Lett. 20 2010 1779
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 1779
- Zhu, H.¹ Young, M.B.² Nantermet, P.G.³ Graham, S.L.⁴ Colussi, D.⁵ Lai, M.-T.⁶ Pietrak, B.⁷ Price, E.A.⁸ Sankaranarayanan, S.⁹ Shi, X.¹⁰ Tugusheva, K.¹¹ Holahan, M.A.¹² Michener, M.S.¹³ Cook, J.J.¹⁴ Simon, A.¹⁵ Hazuda, D.J.¹⁶ Vacca, J.P.¹⁷ Rajapakse, H.A.¹⁸

23
- 84856313525
- The biological evaluation was performed following the manufactory instruction from the ANASPEC (www.anaspect.com).
- The Biological Evaluation Was Performed Following the Manufactory Instruction from the ANASPEC

24
- 84856312064
- Crystal structures of ADAMTS-4 (2RJP) and ADAMTS-5(2RJQ) were selected for docking (Glide, Schrödinger Inc., www.schrodinger.com). Amino acid residues located within 14 from the complexed inhibitors were defined as part of the binding site and prepared with the Protein Preparation Wizard of Schrödinger to add hydrogen atoms and appropriate protonation states without further energy minimization. The Glide XP mode was applied for docking with default settings and the top ranked configurations were observed as the predicted binding poses. Results are presented in Supplementary data.
- Docking protocol: Prior to docking, compound 1h was prepared to create meaningful protonation states and cover potential tautomers (LigPrep, Schrödinger Inc., www.schrodinger.com). Crystal structures of ADAMTS-4 (2RJP) and ADAMTS-5(2RJQ) were selected for docking (Glide, Schrödinger Inc., www.schrodinger.com). Amino acid residues located within 14 from the complexed inhibitors were defined as part of the binding site and prepared with the Protein Preparation Wizard of Schrödinger to add hydrogen atoms and appropriate protonation states without further energy minimization. The Glide XP mode was applied for docking with default settings and the top ranked configurations were observed as the predicted binding poses. Results are presented in Supplementary data.
- Docking Protocol: Prior to Docking, Compound 1h Was Prepared to Create Meaningful Protonation States and Cover Potential Tautomers (LigPrep, Schrödinger Inc.)

25
- 79953188347
- H.-S. Shieh, A.G. Tomasselli, K.J. Mathis, M.E. Schnute, S.S. Woodard, N. Caspers, J.M. Williams, J.R. Kiefer, G. Munie, A. Wittwer, A.-M. Malfait, and M.D. Tortorella Protein Sci. 20 2011 735
- (2011) Protein Sci. , vol.20 , pp. 735
- Shieh, H.-S.¹ Tomasselli, A.G.² Mathis, K.J.³ Schnute, M.E.⁴ Woodard, S.S.⁵ Caspers, N.⁶ Williams, J.M.⁷ Kiefer, J.R.⁸ Munie, G.⁹ Wittwer, A.¹⁰ Malfait, A.-M.¹¹ Tortorella, M.D.¹²

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