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MedChemComm

Volumn 5, Issue 12, 2014, Pages 1834-1842

Evaluation of functional groups as acetyl-lysine mimetics for BET bromodomain inhibition

(4) Sharp, Phillip P a,b Garnier, Jean Marc a,b Huang, David C S a,b Burns, Christopher J a,b,c

a WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH (Australia)

b UNIVERSITY OF MELBOURNE (Australia)

c UNIVERSITY OF MELBOURNE (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ARYLSULFONAMIDE; BRD2 PROTEIN; BRD3 PROTEIN; BRD4 PROTEIN; BROMO AND EXTRA TERMINAL DOMAIN PROTEIN; BROMODOMAIN INHIBITOR; CARRIER PROTEINS AND BINDING PROTEINS; LYSINE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; BIOASSAY; MICROSOME; MOLECULAR RECOGNITION; PROTEIN ANALYSIS; PROTEIN BINDING; PROTEIN DEGRADATION; PROTEIN DOMAIN; PROTEIN FUNCTION; PROTEIN PROTEIN INTERACTION; PROTEIN STABILITY; STRUCTURE ACTIVITY RELATION;

EID: 84911904021 PISSN: 20402503 EISSN: 20402511 Source Type: Journal
DOI: 10.1039/c4md00182f Document Type: Article

Times cited : (23)

References (29)

1
- 70149105669
- R. Sanchez M. M. Zhou Curr. Opin. Drug Discovery Dev. 2009 5 659
- (2009) Curr. Opin. Drug Discovery Dev. , vol.5 , pp. 659
- Sanchez, R.¹ Zhou, M.M.²

2
- 85048786485
- S. Muller P. Filippakopoulos S. Knapp Expert Rev. Mol. Med. 2011 13 1
- (2011) Expert Rev. Mol. Med. , vol.13 , pp. 1
- Muller, S.¹ Filippakopoulos, P.² Knapp, S.³

3
- 0034654011
- T. Kouzarides EMBO J. 2000 19 1176
- (2000) EMBO J. , vol.19 , pp. 1176
- Kouzarides, T.¹

4
- 84876855540
- S.-Y. Wu A.-Y. Lee H.-T. Lai H. Zhang C.-M. Chiang Mol. Cell 2013 49 843
- (2013) Mol. Cell , vol.49 , pp. 843
- Wu, S.-Y.¹ Lee, A.-Y.² Lai, H.-T.³ Zhang, H.⁴ Chiang, C.-M.⁵

5
- 7044250740
- X.-J. Yang BioEssays 2004 26 1076
- (2004) BioEssays , vol.26 , pp. 1076
- Yang, X.-J.¹

6
- 72449150767
- F. Wang H. Liu W. P. Blanton A. Belkina N. K. Lebrasseur G. V. Denis Biochem. J. 2010 425 71
- (2010) Biochem. J. , vol.425 , pp. 71
- Wang, F.¹ Liu, H.² Blanton, W.P.³ Belkina, A.⁴ Lebrasseur, N.K.⁵ Denis, G.V.⁶

7
- 84911896201
- J. M. Lamonica W. Deng S. Kadauke A. E. Cambell R. Gamsjaeger H. Wand Y. Cheng A. N. Billin R. C. Hardison J. P. Mackay G. A. Blobel Proc. Natl. Acad. Sci. U. S. A. 2011 22 8927
- (2011) Proc. Natl. Acad. Sci. U. S. A. , vol.22 , pp. 8927
- Lamonica, J.M.¹ Deng, W.² Kadauke, S.³ Cambell, A.E.⁴ Gamsjaeger, R.⁵ Wand, H.⁶ Cheng, Y.⁷ Billin, A.N.⁸ Hardison, R.C.⁹ MacKay, J.P.¹⁰ Blobel, G.A.¹¹

8
- 80055000824
- J. Zuber J. Shi E. Wang A. R. Rappaport H. Herrmann E. A. Sison D. Magoon J. Qi K. Blatt M. Wunderlich M. J. Taylor C. Johns A. Chicas J. C. Mulloy S. C. Kogan P. Brown P. Valent J. E. Bradner S. W. Lowe C. R. Vakoc Nature 2011 478 524
- (2011) Nature , vol.478 , pp. 524
- Zuber, J.¹ Shi, J.² Wang, E.³ Rappaport, A.R.⁴ Herrmann, H.⁵ Sison, E.A.⁶ Magoon, D.⁷ Qi, J.⁸ Blatt, K.⁹ Wunderlich, M.¹⁰ Taylor, M.J.¹¹ Johns, C.¹² Chicas, A.¹³ Mulloy, J.C.¹⁴ Kogan, S.C.¹⁵ Brown, P.¹⁶ Valent, P.¹⁷ Bradner, J.E.¹⁸ Lowe, S.W.¹⁹ Vakoc, C.R.²⁰ more..

9
- 84865229469
- M. M. Matzuk M. R. McKeown P. Filippakopoulos G. Li L. Ma J. E. Agno M. E. Lemieux S. Picaud R. N. Yu J. Qi S. Knapp J. E. Bradner Cell 2012 150 673
- (2012) Cell , vol.150 , pp. 673
- Matzuk, M.M.¹ McKeown, M.R.² Filippakopoulos, P.³ Li, G.⁴ Ma, L.⁵ Agno, J.E.⁶ Lemieux, M.E.⁷ Picaud, S.⁸ Yu, R.N.⁹ Qi, J.¹⁰ Knapp, S.¹¹ Bradner, J.E.¹²

10
- 84871420585
- C.-W. Chung D. F. Tough Drug Discovery Today: Ther. Strategies 2012 9 e111
- (2012) Drug Discovery Today: Ther. Strategies , vol.9 , pp. e111
- Chung, C.-W.¹ Tough, D.F.²

11
- 84862817809
- R. K. Prinjha J. Witherington K. Lee Trends Pharmacol. Sci. 2012 3 146
- (2012) Trends Pharmacol. Sci. , vol.3 , pp. 146
- Prinjha, R.K.¹ Witherington, J.² Lee, K.³

12
- 84857331171
- S. D. Furdas L. Carlino W. Sippl M. Jung MedChemComm 2012 3 123
- (2012) MedChemComm , vol.3 , pp. 123
- Furdas, S.D.¹ Carlino, L.² Sippl, W.³ Jung, M.⁴

13
- 84889663966
- S. Picaud C. Wells I. Felletar D. Brotherton S. Martin P. Savitsky B. Diez- Dacal M. Philpott C. Bountra H. Lingard O. Fedorov S. Müller P. E. Brennan S. Knapp P. Filippakopoulos Proc. Natl. Acad. Sci. U. S. A. 2013 110 19754
- (2013) Proc. Natl. Acad. Sci. U. S. A. , vol.110 , pp. 19754
- Picaud, S.¹ Wells, C.² Felletar, I.³ Brotherton, D.⁴ Martin, S.⁵ Savitsky, P.⁶ Diez- Dacal, B.⁷ Philpott, M.⁸ Bountra, C.⁹ Lingard, H.¹⁰ Fedorov, O.¹¹ Müller, S.¹² Brennan, P.E.¹³ Knapp, S.¹⁴ Filippakopoulos, P.¹⁵

14
- 84866353161
- S. J. Conway ACS Med. Chem. Lett. 2012 9 691
- (2012) ACS Med. Chem. Lett. , vol.9 , pp. 691
- Conway, S.J.¹

15
- 84895114818
- S. Müller S. Knapp MedChemComm 2014 5 288
- (2014) MedChemComm , vol.5 , pp. 288
- Müller, S.¹ Knapp, S.²

16
- 84892703622
- J.-M. Garnier P. P. Sharp C. J. Burns Expert Opin. Ther. Pat. 2014 185
- (2014) Expert Opin. Ther. Pat. , pp. 185
- Garnier, J.-M.¹ Sharp, P.P.² Burns, C.J.³

17
- 80054984945
- M. A. Dawson R. K. Prinjha A. Dittmann G. Giotopoulos M. Bantscheff W.-I. Chan S. C. Robson C.-W. Chung C. Hopf M. M. Savitski C. Huthmacher E. Gudgin D. Lugo S. Beinke T. D. Chapman E. J. Roberts P. E. Soden K. R. Auger O. Mirguet K. Doehner R. Delwel A. K. Burnett P. Jeffrey G. Drewes K. Lee B. J. P. Huntly T. Kouzarides Nature 2011 478 529
- (2011) Nature , vol.478 , pp. 529
- Dawson, M.A.¹ Prinjha, R.K.² Dittmann, A.³ Giotopoulos, G.⁴ Bantscheff, M.⁵ Chan, W.-I.⁶ Robson, S.C.⁷ Chung, C.-W.⁸ Hopf, C.⁹ Savitski, M.M.¹⁰ Huthmacher, C.¹¹ Gudgin, E.¹² Lugo, D.¹³ Beinke, S.¹⁴ Chapman, T.D.¹⁵ Roberts, E.J.¹⁶ Soden, P.E.¹⁷ Auger, K.R.¹⁸ Mirguet, O.¹⁹ Doehner, K.²⁰ more..

18
- 84870046749
- P. V. Fish P. Filippakopoulos G. Bish P. E. Brennan M. E. Bunnage A. S. Cook O. Federov B. S. Gerstenberger H. Jones S. Knapp B. Marsden K. Nocka D. R. Owen M. Philpott S. Picaud M. J. Primiano M. J. Ralph N. Sciammetta J. D. Trzupek J. Med. Chem. 2012 55 9831
- (2012) J. Med. Chem. , vol.55 , pp. 9831
- Fish, P.V.¹ Filippakopoulos, P.² Bish, G.³ Brennan, P.E.⁴ Bunnage, M.E.⁵ Cook, A.S.⁶ Federov, O.⁷ Gerstenberger, B.S.⁸ Jones, H.⁹ Knapp, S.¹⁰ Marsden, B.¹¹ Nocka, K.¹² Owen, D.R.¹³ Philpott, M.¹⁴ Picaud, S.¹⁵ Primiano, M.J.¹⁶ Ralph, M.J.¹⁷ Sciammetta, N.¹⁸ Trzupek, J.D.¹⁹

19
- 79958078949
- C.-W. Chung H. Coste J. H. White O. Mirguet J. Wilde R. L. Gosmini C. Delves S. M. Magny R. Woodward S. A. Hughes E. V. Boursier H. Flynn A. M. Bouillot P. Bamborough J.-M. G. Brusq F. J. Gellibert E. J. Jones A. M. Riou P. Homes S. L. Martin I. J. Uings J. Toum C. A. Clement A.-B. Boullay R. L. Grimley F. M. Blandel R. K. Prinjha K. Lee J. Kirilovsky E. Nicodeme J. Med. Chem. 2011 54 3827
- (2011) J. Med. Chem. , vol.54 , pp. 3827
- Chung, C.-W.¹ Coste, H.² White, J.H.³ Mirguet, O.⁴ Wilde, J.⁵ Gosmini, R.L.⁶ Delves, C.⁷ Magny, S.M.⁸ Woodward, R.⁹ Hughes, S.A.¹⁰ Boursier, E.V.¹¹ Flynn, H.¹² Bouillot, A.M.¹³ Bamborough, P.¹⁴ Brusq, J.-M.G.¹⁵ Gellibert, F.J.¹⁶ Jones, E.J.¹⁷ Riou, A.M.¹⁸ Homes, P.¹⁹ Martin, S.L.²⁰ more..

20
- 84856399470
- P. Bamborough H. Diallo J. D. Goodacre L. Gordon A. Lewis J. T. Seal D. M. Wilson M. D. Woodrow C.-W. Chung J. Med. Chem. 2012 55 587
- (2012) J. Med. Chem. , vol.55 , pp. 587
- Bamborough, P.¹ Diallo, H.² Goodacre, J.D.³ Gordon, L.⁴ Lewis, A.⁵ Seal, J.T.⁶ Wilson, D.M.⁷ Woodrow, M.D.⁸ Chung, C.-W.⁹

21
- 84878029292
- PDB codes PFI-1 (4E96), JQ1 (3MXF), IBET-151 (4ALG), IBET-762 (2YEK), compound 5 (4HXL cyclohexyl derivative), compound 6 (no PDB code, see ref. 21 for crystal structures of related derivatives)
- L. Zhao D. Cao T. Chen Y. Wang Z. Miao Y. Xu W. Chen X. Wang Y. Li Z. Du B. Xiong J. Li C. Xu N. Zhang J. He J. Shen J. Med. Chem. 2013 56 3833
- (2013) J. Med. Chem. , vol.56 , pp. 3833
- Zhao, L.¹ Cao, D.² Chen, T.³ Wang, Y.⁴ Miao, Z.⁵ Xu, Y.⁶ Chen, W.⁷ Wang, X.⁸ Li, Y.⁹ Du, Z.¹⁰ Xiong, B.¹¹ Li, J.¹² Xu, C.¹³ Zhang, N.¹⁴ He, J.¹⁵ Shen, J.¹⁶

22
- 84866338076
- L. R. Vidler N. Brown S. Knapp S. Hoelder J. Med. Chem. 2012 55 7346
- (2012) J. Med. Chem. , vol.55 , pp. 7346
- Vidler, L.R.¹ Brown, N.² Knapp, S.³ Hoelder, S.⁴

23
- 84864578590
- P. Filippakopoulos S. Knapp FEBS Lett. 2012 586 2692
- (2012) FEBS Lett. , vol.586 , pp. 2692
- Filippakopoulos, P.¹ Knapp, S.²

24
- 84856397832
- C.-W. Chung A. W. Dean J. M. Woolven P. Bamborough J. Med. Chem. 2012 55 576
- (2012) J. Med. Chem. , vol.55 , pp. 576
- Chung, C.-W.¹ Dean, A.W.² Woolven, J.M.³ Bamborough, P.⁴

25
- 84876833549
- D. S. Hewings O. Fedorov P. Filippakopoulos S. Martin S. Picaud A. Tumber A. Wells M. M. Olcina K. Freeman A. Gill A. J. Ritchie D. W. Sheppard A. J. Russell E. M. Hammond S. Knapp P. E. Brennan S. J. Conway J. Med. Chem. 2013 56 3217
- (2013) J. Med. Chem. , vol.56 , pp. 3217
- Hewings, D.S.¹ Fedorov, O.² Filippakopoulos, P.³ Martin, S.⁴ Picaud, S.⁵ Tumber, A.⁶ Wells, A.⁷ Olcina, M.M.⁸ Freeman, K.⁹ Gill, A.¹⁰ Ritchie, A.J.¹¹ Sheppard, D.W.¹² Russell, A.J.¹³ Hammond, E.M.¹⁴ Knapp, S.¹⁵ Brennan, P.E.¹⁶ Conway, S.J.¹⁷

26
- 84886504602
- For example [PDB code 4HXL for a cyclohexyl derivative] also see ref. 20 For example, Bamborough et al. (ref. 18) showed that both 5 and the corresponding congener where the 2-methyl group was substituted for a methoxy group, both had moderate binding affinity (0.6 and 2.2 μM in TR-FRET assay respectively against BRD4)
- L. R. Vidler P. Filippakopoulos O. Fedorov S. Picaud S. Martin M. Tomsett H. Woodward N. Brown S. Knapp S. Hoelder J. Med. Chem. 2013 56 8073
- (2013) J. Med. Chem. , vol.56 , pp. 8073
- Vidler, L.R.¹ Filippakopoulos, P.² Fedorov, O.³ Picaud, S.⁴ Martin, S.⁵ Tomsett, M.⁶ Woodward, H.⁷ Brown, N.⁸ Knapp, S.⁹ Hoelder, S.¹⁰

27
- 48549089345
- In cases where a tert-butoxycarbonyl group was present on the boronic acid or ester coupling partners, it was cleaved under the conditions of the Suzuki-Miyaura cross-coupling reaction The tetra-acetylated peptide used in the ALPHAscreen assays in this work has similar binding affinity for BRD4 (D1) and BRD2 (D1) of 2.8 μM and 3.7 μM respectively (comparative data for BRD3 (D1) obtained in the same assay is not available but is expected to be similar based on sequence homology). See ref. 24
- M. G. Organ M. Abdel-Hadi S. Avola I. Dubovyk N. Hadei E. A. B. Kantchev C. J. O'Brien M. Sayah C. Valente Chem.-Eur. J. 2008 14 2443
- (2008) Chem.-Eur. J. , vol.14 , pp. 2443
- Organ, M.G.¹ Abdel-Hadi, M.² Avola, S.³ Dubovyk, I.⁴ Hadei, N.⁵ Kantchev, E.A.B.⁶ O'Brien, C.J.⁷ Sayah, M.⁸ Valente, C.⁹

28
- 67650763061
- C. Laurence K. A. Brameld J. Graton J.-Y. Le Questel E. Renault J. Med. Chem. 2009 52 4073
- (2009) J. Med. Chem. , vol.52 , pp. 4073
- Laurence, C.¹ Brameld, K.A.² Graton, J.³ Le Questel, J.-Y.⁴ Renault, E.⁵

29
- 78650806593
- E.g. 3,5-dimethyl-4-phenylisoxazole logP = 2.32 vs. 3,5-dimethyl-4-phenyl-4H-1,2,4-triazole logP = 0.51, MarvinSketch Calculator Plugins were used for structure property prediction, Marvin 6.0.6, 2013, ChemAxon
- E. Nicodeme K. L. Jeffrey U. Schaefer S. Beinke S. Dewell C.-W. Chung R. Chandwani I. Marazzi P. Wilson H. Coste J. White J. Kirilovsky C. M. Rice J. M. Lora R. K. Prinjha K. Lee A. Tarakhovsky Nature 2010 468 1119
- (2010) Nature , vol.468 , pp. 1119
- Nicodeme, E.¹ Jeffrey, K.L.² Schaefer, U.³ Beinke, S.⁴ Dewell, S.⁵ Chung, C.-W.⁶ Chandwani, R.⁷ Marazzi, I.⁸ Wilson, P.⁹ Coste, H.¹⁰ White, J.¹¹ Kirilovsky, J.¹² Rice, C.M.¹³ Lora, J.M.¹⁴ Prinjha, R.K.¹⁵ Lee, K.¹⁶ Tarakhovsky, A.¹⁷

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