SCOPUS 정보 검색 플랫폼

Volumn 16, Issue 34, 2010, Pages 10366-10372

Inhibition of Hsp90 with resorcylic acid macrolactones: Synthesis and binding studies

(10) Day, James E H a Sharp, Swee Y b Rowlands, Martin G b Aherne, Wynne b Lewis, William a Mark Roe, S c Prodromou, Chrisostomos c Pearl, Laurence H c Workman, Paul b Moody, Christopher J a

a UNIVERSITY OF NOTTINGHAM (United Kingdom)

b IMPERIAL CANCER RESEARCH FUND (United Kingdom)

c INSTITUTE OF CANCER RESEARCH (United Kingdom)

Author keywords

Anticancer agents; Enzyme inhibitors; Macrocycles; Macrocyclic compounds; Metathesis; Proteins

Indexed keywords

ANTI-CANCER AGENTS; ENZYME INHIBITORS; MACROCYCLES; MACROCYCLIC COMPOUNDS; METATHESIS;

ACIDS; CONFORMATIONS; ENZYMES; ESTERS; MACROMOLECULES; METHANOL; PHENOLS; SYNTHESIS (CHEMICAL);

COMPLEXATION;

ANTINEOPLASTIC AGENT; HEAT SHOCK PROTEIN 90; MACROCYCLIC COMPOUND; MACROLIDE;

ARTICLE; BINDING SITE; CHEMISTRY; CONFORMATION; DRUG ANTAGONISM; HUMAN; METABOLISM; NEOPLASM; PROTEIN BINDING; SYNTHESIS; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; BINDING SITES; CELL LINE, TUMOR; CRYSTALLOGRAPHY, X-RAY; HSP90 HEAT-SHOCK PROTEINS; HUMANS; MACROCYCLIC COMPOUNDS; MACROLIDES; MOLECULAR CONFORMATION; NEOPLASMS; PROTEIN BINDING;

EID: 77956429649 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201001119 Document Type: Article

Times cited : (21)

References (56)

1
- 35348890981
- P. Workman, F. Burrows, L. Neckers, N. Rosen, Ann. N. Y. Acad. Sci. 2007, 1113, 202.
- (2007) Ann. N. Y. Acad. Sci. , vol.1113 , pp. 202
- Workman, P.¹ Burrows, F.² Neckers, L.³ Rosen, N.⁴

2
- 37649024109
- D. B. Solit, G. Chiosis, Drug Discovery Today 2008, 13, 38.
- (2008) Drug Discovery Today , vol.13 , pp. 38
- Solit, D.B.¹ Chiosis, G.²

3
- 51449093764
- T. Taldone, A. Gozman, R. Maharaj, G. Chiosis, Curr. Opin. Pharmacol. 2008, 8, 370.
- (2008) Curr. Opin. Pharmacol. , vol.8 , pp. 370
- Taldone, T.¹ Gozman, A.² Maharaj, R.³ Chiosis, G.⁴

4
- 47249153969
- M. J. Drysdale, P. A. Brough, Curr. Top. Med. Chem. 2008, 8, 859.
- (2008) Curr. Top. Med. Chem. , vol.8 , pp. 859
- Drysdale, M.J.¹ Brough, P.A.²

5
- 41149111451
- L. H. Pearl, C. Prodromou, P. Workman, Biochem. J. 2008, 410, 439.
- (2008) Biochem. J. , vol.410 , pp. 439
- Pearl, L.H.¹ Prodromou, C.² Workman, P.³

6
- 66149125584
- D. Mahalingam, R. Swords, J. S. Carew, S. T. Nawrocki, K. Bhalla, F. J. Giles, Br. J. Cancer 2009, 100, 1523.
- (2009) Br. J. Cancer , vol.100 , pp. 1523
- Mahalingam, D.¹ Swords, R.² Carew, J.S.³ Nawrocki, S.T.⁴ Bhalla, K.⁵ Giles, F.J.⁶

7
- 62149135294
- T. Taldone, W. Sun, G. Chiosis, Bioorg. Med. Chem. 2009, 17, 2225.
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 2225
- Taldone, T.¹ Sun, W.² Chiosis, G.³

8
- 75649151374
- J. S. Hahn, BMB Rep. 2009, 42, 623.
- (2009) BMB Rep. , vol.42 , pp. 623
- Hahn, J.S.¹

9
- 77952544010
- Y. L. Janin, Drug Discovery Today 2010, 15, 342.
- (2010) Drug Discovery Today , vol.15 , pp. 342
- Janin, Y.L.¹

10
- 33746364784
- L. H. Pearl, C. Prodromou, Annu. Rev. Biochem. 2006, 75, 271.
- (2006) Annu. Rev. Biochem. , vol.75 , pp. 271
- Pearl, L.H.¹ Prodromou, C.²

11
- 74249085361
- Y. S. Kim, S. V. Alarcon, S. Lee, M. J. Lee, G. Giaccone, L. Neckers, J. B. Trepel, Curr. Top. Med. Chem. 2009, 9, 1479.
- (2009) Curr. Top. Med. Chem. , vol.9 , pp. 1479
- Kim, Y.S.¹ Alarcon, S.V.² Lee, S.³ Lee, M.J.⁴ Giaccone, G.⁵ Neckers, L.⁶ Trepel, J.B.⁷

12
- 74849111762
- M. A. Biamonte, R. Van de Water, J. W. Arndt, R. H. Scannevin, D. Perret, W. C. Lee, J. Med. Chem. 2010, 53, 3.
- (2010) J. Med. Chem. , vol.53 , pp. 3
- Biamonte, M.A.¹ Van De Water, R.² Arndt, J.W.³ Scannevin, R.H.⁴ Perret, D.⁵ Lee, W.C.⁶

13
- 0031444238
- C. Prodromou, S. M. Roe, R. O'Brien, J. E. Ladbury, P. W. Piper, L. H. Pearl, Cell 1997, 90, 65.
- (1997) Cell , vol.90 , pp. 65
- Prodromou, C.¹ Roe, S.M.² O'Brien, R.³ Ladbury, J.E.⁴ Piper, P.W.⁵ Pearl, L.H.⁶

14
- 0032959590
- S. M. Roe, C. Prodromou, R. O'Brien, J. E. Ladbury, P. W. Piper, L. H. Pearl, J. Med. Chem. 1999, 42, 260.
- (1999) J. Med. Chem. , vol.42 , pp. 260
- Roe, S.M.¹ Prodromou, C.² O'Brien, R.³ Ladbury, J.E.⁴ Piper, P.W.⁵ Pearl, L.H.⁶

15
- 33646176246
- M. M. U. Ali, S. M. Roe, C. K. Vaughan, P. Meyer, B. Panaretou, P. W. Piper, C. Prodromou, L. H. Pearl, Nature 2006, 440, 1013.
- (2006) Nature , vol.440 , pp. 1013
- Ali, M.M.U.¹ Roe, S.M.² Vaughan, C.K.³ Meyer, P.⁴ Panaretou, B.⁵ Piper, P.W.⁶ Prodromou, C.⁷ Pearl, L.H.⁸

16
- 33845481603
- N. Winssinger, S. Barluenga, J. Chem. Soc. Chem. Commun. 2007, 22.
- (2007) J. Chem. Soc. Chem. Commun. , pp. 22
- Winssinger, N.¹ Barluenga, S.²

17
- 57049163500
- S. Barluenga, P. Y. Dakas, M. Boulifa, E. Moulin, N. Winssinger, C. R. Chim. 2008, 11, 1306.
- (2008) C. R. Chim. , vol.11 , pp. 1306
- Barluenga, S.¹ Dakas, P.Y.² Boulifa, M.³ Moulin, E.⁴ Winssinger, N.⁵

18
- 57149127991
- T. Hofmann, K. H. Altmann, C. R. Chim. 2008, 11, 1318.
- (2008) C. R. Chim. , vol.11 , pp. 1318
- Hofmann, T.¹ Altmann, K.H.²

19
- 74249106421
- N. Winssinger, J. G. Fontaine, S. Barluenga, Curr. Top. Med. Chem. 2009, 9, 1419.
- (2009) Curr. Top. Med. Chem. , vol.9 , pp. 1419
- Winssinger, N.¹ Fontaine, J.G.² Barluenga, S.³

20
- 0032554763
- S. V. Sharma, T. Agatsuma, H. Nakano, Oncogene 1998, 16, 2639.
- (1998) Oncogene , vol.16 , pp. 2639
- Sharma, S.V.¹ Agatsuma, T.² Nakano, H.³

21
- 0033564430
- S. Soga, L. M. Neckers, T. W. Schulte, Y. Shiotsu, K. Akasaka, H. Narumi, T. Agatsuma, Y. Ikuina, C. Murakata, T. Tamaoki, S. Akinaga, Cancer Res. 1999, 59, 2931.
- (1999) Cancer Res. , vol.59 , pp. 2931
- Soga, S.¹ Neckers, L.M.² Schulte, T.W.³ Shiotsu, Y.⁴ Akasaka, K.⁵ Narumi, H.⁶ Agatsuma, T.⁷ Ikuina, Y.⁸ Murakata, C.⁹ Tamaoki, T.¹⁰ Akinaga, S.¹¹

22
- 0141485333
- S. Soga, Y. Shiotsu, S. Akinaga, S. V. Sharma, Curr. Cancer Drug Targets 2003, 3, 359.
- (2003) Curr. Cancer Drug Targets , vol.3 , pp. 359
- Soga, S.¹ Shiotsu, Y.² Akinaga, S.³ Sharma, S.V.⁴

23
- 0036836678
- T. Agatsuma, H. Ogawa, K. Akasaka, A. Asai, Y. Yamashita, T. Mizukami, S. Akinaga, Y. Saitoh, Bioorg. Med. Chem. 2002, 10, 3445.
- (2002) Bioorg. Med. Chem. , vol.10 , pp. 3445
- Agatsuma, T.¹ Ogawa, H.² Akasaka, K.³ Asai, A.⁴ Yamashita, Y.⁵ Mizukami, T.⁶ Akinaga, S.⁷ Saitoh, Y.⁸

24
- 3142717486
- X. D. Geng, Z. Q. Yang, S. J. Danishefsky, Synlett 2004, 1325.
- (2004) Synlett , pp. 1325
- Geng, X.D.¹ Yang, Z.Q.² Danishefsky, S.J.³

25
- 53849085500
- X. G. Lei, S. J. Danishefsky, Adv. Synth. Catal. 2008, 350, 1677.
- (2008) Adv. Synth. Catal. , vol.350 , pp. 1677
- Lei, X.G.¹ Danishefsky, S.J.²

26
- 18744411808
- E. Moulin, V. Zoete, S. Barluenga, M. Karplus, N. Winssinger, J. Am. Chem. Soc. 2005, 127, 6999.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 6999
- Moulin, E.¹ Zoete, V.² Barluenga, S.³ Karplus, M.⁴ Winssinger, N.⁵

27
- 69749128624
- S. Barluenga, C. H. Wang, J. G. Fontaine, K. Aouadi, K. Beebe, S. Tsutsumi, L. Neckers, N. Winssinger, Angew. Chem. 2008, 120, 4504;
- (2008) Angew. Chem. , vol.120 , pp. 4504
- Barluenga, S.¹ Wang, C.H.² Fontaine, J.G.³ Aouadi, K.⁴ Beebe, K.⁵ Tsutsumi, S.⁶ Neckers, L.⁷ Winssinger, N.⁸

28
- 46749131522
- Angew. Chem. Int. Ed. 2008, 47, 4432.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4432

29
- 73149098975
- S. Barluenga, J. G. Fontaine, C. H. Wang, K. Aouadi, R. H. Chen, K. Beebe, L. Neckers, N. Winssinger, ChemBioChem 2009, 10, 2753.
- (2009) ChemBioChem , vol.10 , pp. 2753
- Barluenga, S.¹ Fontaine, J.G.² Wang, C.H.³ Aouadi, K.⁴ Chen, R.H.⁵ Beebe, K.⁶ Neckers, L.⁷ Winssinger, N.⁸

30
- 33750986790
- N. Proisy, S. Y. Sharp, K. Boxall, S. Connelly, S. M. Roe, C. Prodromou, A. M. Z. Slawin, L. H. Pearl, P. Workman, C. J. Moody, Chem. Biol. 2006, 13, 1203.
- (2006) Chem. Biol. , vol.13 , pp. 1203
- Proisy, N.¹ Sharp, S.Y.² Boxall, K.³ Connelly, S.⁴ Roe, S.M.⁵ Prodromou, C.⁶ Slawin, A.M.Z.⁷ Pearl, L.H.⁸ Workman, P.⁹ Moody, C.J.¹⁰

31
- 77149140097
- J. E. H. Day, S. Y. Sharp, M. G. Rowlands, W. Aherne, P. Workman, C. J. Moody, Chem. Eur. J. 2010, 16, 2758.
- (2010) Chem. Eur. J. , vol.16 , pp. 2758
- Day, J.E.H.¹ Sharp, S.Y.² Rowlands, M.G.³ Aherne, W.⁴ Workman, P.⁵ Moody, C.J.⁶

32
- 0026592609
- M. Lampilas, R. Lett, Tetrahedron Lett. 1992, 33, 773.
- (1992) Tetrahedron Lett. , vol.33 , pp. 773
- Lampilas, M.¹ Lett, R.²

33
- 0026513918
- M. Lampilas, R. Lett, Tetrahedron Lett. 1992, 33, 777.
- (1992) Tetrahedron Lett. , vol.33 , pp. 777
- Lampilas, M.¹ Lett, R.²

34
- 3042685847
- Z. Q. Yang, X. D. Geng, D. Solit, C. A. Pratilas, N. Rosen, S. J. Danishefsky, J. Am. Chem. Soc. 2004, 126, 7881.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 7881
- Yang, Z.Q.¹ Geng, X.D.² Solit, D.³ Pratilas, C.A.⁴ Rosen, N.⁵ Danishefsky, S.J.⁶

35
- 0035823817
- R. M. Garbaccio, S. J. Stachel, D. K. Baeschlin, S. J. Danishefsky, J. Am. Chem. Soc. 2001, 123, 10903.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 10903
- Garbaccio, R.M.¹ Stachel, S.J.² Baeschlin, D.K.³ Danishefsky, S.J.⁴

36
- 22844438996
- S. Barluenga, P. Lopez, E. Moulin, N. Winssinger, Angew. Chem. 2004, 116, 3549;
- (2004) Angew. Chem. , vol.116 , pp. 3549
- Barluenga, S.¹ Lopez, P.² Moulin, E.³ Winssinger, N.⁴

37
- 4544334262
- Angew. Chem. Int. Ed. 2004, 43, 3467.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3467

38
- 24344442417
- S. Barluenga, E. Moulin, P. Lopez, N. Winssinger, Chem. Eur. J. 2005, 11, 4935.
- (2005) Chem. Eur. J. , vol.11 , pp. 4935
- Barluenga, S.¹ Moulin, E.² Lopez, P.³ Winssinger, N.⁴

39
- 33845213862
- E. Moulin, S. Barluenga, F. Totzke, N. Winssinger, Chem. Eur. J. 2006, 12, 8819.
- (2006) Chem. Eur. J. , vol.12 , pp. 8819
- Moulin, E.¹ Barluenga, S.² Totzke, F.³ Winssinger, N.⁴

40
- 0036351598
- S. L. Boulet, L. A. Paquette, Synthesis 2002, 895.
- (2002) Synthesis , pp. 895
- Boulet, S.L.¹ Paquette, L.A.²

41
- 33845460963
- Z. Geng, B. Chen, P. Chiu, Angew. Chem. 2006, 118, 6343;
- (2006) Angew. Chem. , vol.118 , pp. 6343
- Geng, Z.¹ Chen, B.² Chiu, P.³

42
- 33749006267
- Angew. Chem. Int. Ed. 2006, 45, 6197.
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 6197

43
- 3242892786
- C. M. Thompson, J. A. Frick, J. Org. Chem. 1989, 54, 890.
- (1989) J. Org. Chem. , vol.54 , pp. 890
- Thompson, C.M.¹ Frick, J.A.²

44
- 0029084414
- J. M. Williams, R. B. Jobson, N. Yasuda, G. Marchesini, U.-H. Dolling, E. J. J. Grabowski, Tetrahedron Lett. 1995, 36, 5461.
- (1995) Tetrahedron Lett. , vol.36 , pp. 5461
- Williams, J.M.¹ Jobson, R.B.² Yasuda, N.³ Marchesini, G.⁴ Dolling, U.-H.⁵ Grabowski, E.J.J.⁶

45
- 37049109199
- T. A. Carpenter, G. E. Evans, F. J. Leeper, J. Staunton, M. R. Wilkinson, J. Chem. Soc. Perkin Trans. 1 1984, 1043.
- (1984) J. Chem. Soc. Perkin Trans. 1 , pp. 1043
- Carpenter, T.A.¹ Evans, G.E.² Leeper, F.J.³ Staunton, J.⁴ Wilkinson, M.R.⁵

46
- 0008940573
- F. M. Hauser, R. P. Rhee, J. Org. Chem. 1977, 42, 4155.
- (1977) J. Org. Chem. , vol.42 , pp. 4155
- Hauser, F.M.¹ Rhee, R.P.²

47
- 0037593065
- F. M. Hauser, R. Rhee, J. Am. Chem. Soc. 1977, 99, 4533.
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 4533
- Hauser, F.M.¹ Rhee, R.²

48
- 45749125689
- H. R. Tsou, M. Otteng, T. Tran, M. B. Floyd, M. Reich, G. Birnberg, K. Kutterer, S. Ayral-Kaloustian, M. Ravi, R. Nilakantan, M. Grillo, J. P. McGinnis, S. K. Rabindran, J. Med. Chem. 2008, 51, 3507.
- (2008) J. Med. Chem. , vol.51 , pp. 3507
- Tsou, H.R.¹ Otteng, M.² Tran, T.³ Floyd, M.B.⁴ Reich, M.⁵ Birnberg, G.⁶ Kutterer, K.⁷ Ayral-Kaloustian, S.⁸ Ravi, M.⁹ Nilakantan, R.¹⁰ Grillo, M.¹¹ McGinnis, J.P.¹² Rabindran, S.K.¹³

49
- 65449126280
- H. R. Tsou, X. Liu, G. Birnberg, J. Kaplan, M. Otteng, T. Tran, K. Kutterer, Z. L. Tang, R. Suayan, A. Zask, M. Ravi, A. Bretz, M. Grillo, J. P. McGinnis, S. K. Rabindran, S. Ayral-Kaloustian, T. S. Mansour, J. Med. Chem. 2009, 52, 2289.
- (2009) J. Med. Chem. , vol.52 , pp. 2289
- Tsou, H.R.¹ Liu, X.² Birnberg, G.³ Kaplan, J.⁴ Otteng, M.⁵ Tran, T.⁶ Kutterer, K.⁷ Tang, Z.L.⁸ Suayan, R.⁹ Zask, A.¹⁰ Ravi, M.¹¹ Bretz, A.¹² Grillo, M.¹³ McGinnis, J.P.¹⁴ Rabindran, S.K.¹⁵ Ayral-Kaloustian, S.¹⁶ Mansour, T.S.¹⁷

50
- 77956431255
- WO2008021213A1
- N. Winssinger, S. Barluenga, M. Karplus, WO2008021213A1, 2008.
- (2008)
- Winssinger, N.¹ Barluenga, S.² Karplus, M.³

51
- 51049094897
- M. Meldal, C. W. Tornoe, Chem. Rev. 2008, 108, 2952.
- (2008) Chem. Rev. , vol.108 , pp. 2952
- Meldal, M.¹ Tornoe, C.W.²

52
- 21244505104
- B. W. Dymock, X. Barril, P. A. Brough, J. E. Cansfield, A. Massey, E. McDonald, R. E. Hubbard, A. Surgenor, S. D. Roughley, P. Webb, P. Workman, L. Wright, M. J. Drysdale, J. Med. Chem. 2005, 48, 4212.
- (2005) J. Med. Chem. , vol.48 , pp. 4212
- Dymock, B.W.¹ Barril, X.² Brough, P.A.³ Cansfield, J.E.⁴ Massey, A.⁵ McDonald, E.⁶ Hubbard, R.E.⁷ Surgenor, A.⁸ Roughley, S.D.⁹ Webb, P.¹⁰ Workman, P.¹¹ Wright, L.¹² Drysdale, M.J.¹³

53
- 33644665083
- R. Howes, X. Barril, B. W. Dymock, K. Grant, C. J. Northfield, A. G. S. Robertson, A. Surgenor, J. Wayne, L. Wright, K. James, T. Matthews, K. M. Cheung, E. McDonald, P. Workman, M. J. Drysdale, Anal. Biochem. 2006, 350, 202.
- (2006) Anal. Biochem. , vol.350 , pp. 202
- Howes, R.¹ Barril, X.² Dymock, B.W.³ Grant, K.⁴ Northfield, C.J.⁵ Robertson, A.G.S.⁶ Surgenor, A.⁷ Wayne, J.⁸ Wright, L.⁹ James, K.¹⁰ Matthews, T.¹¹ Cheung, K.M.¹² McDonald, E.¹³ Workman, P.¹⁴ Drysdale, M.J.¹⁵

54
- 3242722132
- V. Zhou, S. L. Han, A. Brinker, H. Klock, J. Caldwell, X. J. Gu, Anal. Biochem. 2004, 331, 349.
- (2004) Anal. Biochem. , vol.331 , pp. 349
- Zhou, V.¹ Han, S.L.² Brinker, A.³ Klock, H.⁴ Caldwell, J.⁵ Gu, X.J.⁶

55
- 0029797764
- C. Prodromou, P. W. Piper, L. H. Pearl, Proteins 1996, 25, 517.
- (1996) Proteins , vol.25 , pp. 517
- Prodromou, C.¹ Piper, P.W.² Pearl, L.H.³

56
- 0033785989
- S. Y. Sharp, L. R. Kelland, M. R. Valenti, L. A. Brunton, S. Hobbs, P. Workman, Mol. Pharmacol. 2000, 58, 1146.
- (2000) Mol. Pharmacol. , vol.58 , pp. 1146
- Sharp, S.Y.¹ Kelland, L.R.² Valenti, M.R.³ Brunton, L.A.⁴ Hobbs, S.⁵ Workman, P.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.