Synthesis and biological evaluation of novobiocin analogues as potential heat shock protein 90 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 17, 2013, Pages 5118-5129

  Gunaherath, G M Kamal B ^a,c   Marron, Marilyn T ^a   Wijeratne, E M Kithsiri ^a   Whitesell, Luke ^b   Gunatilaka, A A Leslie ^a  

^a UNIVERSITY OF ARIZONA   (United States)

^b WHITEHEAD INSTITUTE FOR BIOMEDICAL RESEARCH   (United States)

^c OPEN UNIVERSITY OF SRI LANKA   (Sri Lanka)

Author keywords

Biological activity; Heat shock protein 90 (HSP90); Novobiocin analogues; Structure activity relationship; Synthesis

Indexed keywords

2 O ACETYLNOVOBIOCIN DERIVATIVE; 2' ACETYLNOVOBIOCIN DERIVATIVE; 3 AMIDO 7 NOVIOSYLCOUMARIN DERIVATIVE; 3 AMINONOVIOSYLCOUMARIN DERIVATIVE; 3 AMINONOVOSYLCOUMARIN DERIVATIVE; 5 METHYLPYRROLE 2 CARBOXYLIC ACID; 7 [[2 O ACETYL 3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 2,6 DIMETHYL 4H [1]BENZOPYRANO[3,4 D]OXAZOL 4 ONE-; 7 [[2 O ACETYL 3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 3 AMINO 4 HYDROXY 8 METHYL 2H 1 BENZOPYRAN 2 ONE; ADENOSINE TRIPHOSPHATE; ANTIINFECTIVE AGENT; COUMAMYCIN; DNA TOPOISOMERASE (ATP HYDROLYSING); EPIDERMAL GROWTH FACTOR RECEPTOR 2; HEAT SHOCK PROTEIN 90; HEAT SHOCK PROTEIN 90 INHIBITOR; N [7 [[3 O (AMINOCARBONYL) 5 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 4 HYDROXY 8 METHYL 2 OXO 2H 1 BENZOPYRAN 3 YL] 4 METHOXYBENZAMIDE; N [7 [[3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 4 HYDROXY 8 METHYL 2 OXO 2H 1 BENZOPYRAN 3 YL] 1H PYRROLE 2 CARBOXAMIDE; N [7 [[3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 4 HYDROXY 8 METHYL 2 OXO 2H 1 BENZOPYRAN 3 YL] 2 FURANCARBOXAMIDE; N [7 [[3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 4 HYDROXY 8 METHYL 2 OXO 2H 1 BENZOPYRAN 3 YL] 3 PHENYL 2 PROPENAMIDE; N [7 [[3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 4 HYDROXY 8 METHYL 2 OXO 2H 1 BENZOPYRAN 3 YL] 4 HYDROXYBENZAMIDE; N [7 [[3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 4 HYDROXY 8 METHYL 2 OXO 2H 1 BENZOPYRAN 3 YL] 4 NITROBENZAMIDE; N [7 [[3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 4 HYDROXY 8 METHYL 2 OXO 2H 1 BENZOPYRAN 3 YL] 5 METHYL 1H PYRROLE 2 CARBOXAMIDE; N [7 [[3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 4 HYDROXY 8 METHYL 2 OXO 2H 1 BENZOPYRAN 3 YL]BENZAMIDE; N [7 [[3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 4 HYDROXY 8 METHYL 2 OXO 2H 1 BENZOPYRAN 3 YL]CYCLOBUTANECARBOXAMIDE; N [7 [[3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 4 HYDROXY 8 METHYL 2 OXO 2H 1 BENZOPYRAN 3 YL]CYCLOHEXANECARBOXAMIDE; N [7 [[3 O (AMINOCARBONYL) 6 DEOXY 5 C METHYL 4 O METHYL ALPHA LYXOHEXOPYRANOSYL]OXY] 4 HYDROXY 8 METHYL 2 OXO 2H 1 BENZOPYRAN 3 YL]CYCLOPENTANECARBOXAMIDE; NOVIOSYLOXAZOLOCOUMARIN DERIVATIVE; NOVOBIOCIN; NOVOBIOCIN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING SITE; CARBOXY TERMINAL SEQUENCE; CELL CYCLE ARREST; CELL PROLIFERATION; CELL SURVIVAL; CONTROLLED STUDY; CYTOTOXICITY; DEACYLATION; DEOXYGENATION; DERIVATIZATION; DRUG BINDING; DRUG POTENCY; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVITY; ENZYME INHIBITION; HEAT SHOCK RESPONSE; HUMAN; HUMAN CELL; IN VITRO STUDY; METHYLATION; PROTEIN AGGREGATION; PROTEIN FUNCTION; PROTEIN REFOLDING; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

4-PP; 4-PYRROLIDINOPYRIDINE; 4′,6-DIAMIDINO-2-PHENYLINDOLE; A BUFFER SOLUTION CONTAINING TRIS, NACL, EDTA, AND SDS; BIOLOGICAL ACTIVITY; DAPI; DCC; DICYCLOHEXYLCARBODIIMIDE; EDC; FITC; FLUORESCEIN ISOTHIOCYANATE; FORMALDEHYDE IN PHOSPHATE BUFFERED SALINE WITH BOVINE ALBUMIN; HEAT SHOCK PROTEIN 90 (HSP90); N-(3-DIMETHYLAMINOPROPYL)-N′-ETHYL-CARBODIIMIDE; NBT/BCIP; NITRO-BLUE TETRAZOLIUM CHLORIDE AND 5-BROMO-4-CHLORO-3′-INDOLYPHOSPHATE P-TOLUIDINE SALT; NOVOBIOCIN ANALOGUES; PBA; PFA; PHENYLMETHYLSULFONYL FLUORIDE; PHOSPHATE BUFFERED SALINE WITH BOVINE ALBUMIN; PMSF; STRUCTURE-ACTIVITY RELATIONSHIP; SYNTHESIS; TNES; TTBS; TWEEN 20 IN TRIS BUFFERED SALINE;

ANTINEOPLASTIC AGENTS; CELL CYCLE CHECKPOINTS; CELL LINE, TUMOR; CELL PROLIFERATION; HSP90 HEAT-SHOCK PROTEINS; HUMANS; MCF-7 CELLS; NOVOBIOCIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84881373610     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.06.042     Document Type: Article

References (41)

1. M. Taipale, D.F. Jarosz, and S. Lindquist Nat. Rev. Mol. Cell Biol. 11 2010 515 528
2. W. Xu, M. Mollapour, C. Prodromou, S. Wang, B.T. Scroggins, Z. Palchick, K. Beebe, M. Siderius, M.-J. Lee, A. Couvillon, A.B. Trepel, Y. Miyata, R. Matts, and L. Neckers Mol. Cell. 47 2012 434 443
3. L. Whitesell, and S.L. Lindquist Nat. Rev. Cancer 5 2005 76 772
4. M.L. Mendillo, S. Santagata, M. Koeva, G.W. Bell, R. Hu, R.M. Tamimi, E. Fraenkel, T.A. Ince, L. Whitesell, and S. Lindquist Cell 150 2012 549 562
5. A.S. Duerfeldt, and B.S.J. Blagg Bioorg. Med. Chem. Lett. 20 2010 4983 4987
6. M.G. Marcu, A. Chadli, L. Bouhouche, M. Catelli, and L.M. Neckers J. Biol. Chem. 275 2000 37181 37186
7. R.L. Matts, A. Dixit, L.B. Peterson, L. Sun, S. Voruganti, P. Kalyanaraman, S.D. Hartson, G.M. Verkhivker, and B.S.J. Blagg ACS Chem. Biol. 6 2011 800 807
8. M.G. Marcu, T.W. Schulte, and L. Neckers J. Natl. Cancer Inst. 92 2000 242 248
9. T.J. Turbyville, E.M.K. Wijeratne, M.X. Liu, A.M. Burns, C.J. Seliga, L.A. Luevano, C.D. David, S.H. Faeth, L. Whitesell, and A.A.L. Gunatilaka J. Nat. Prod. 69 2006 178 184
10. S. Santagata, Y. Xu, E.M.K. Wijeratne, R. Kontnik, C. Rooney, C.C. Perley, H. Kwon, J. Clardy, S. Kesari, L. Whitesell, S. Lindquist, and A.A.L. Gunatilaka ACS Chem. Biol. 7 2012 340 349
11. X.M. Yu, G. Shen, L. Neckers, H. Blake, J. Holzbeierlein, B. Cronk, and B.S.J.J. Blagg Am. Chem. Soc. 127 2005 12778 12779
12. J.A. Burlison, L. Neckers, A.B. Smith, A. Maxwell, and B.S.J.J. Blagg Am. Chem. Soc. 128 2006 15529 15536
13. J.A. Burlison, C. Avila, G. Vielhauer, D.J. Lubbers, J. Holzbeierlein, and B.S.J.J. Blagg Org. Chem. 73 2008 2130 2137
14. M.W. Powers, P.A. Clarke, and P. Workman Cancer Cell 14 2008 250 262
15. G. Le Bras, C. Radanyi, J.-F. Peyrat, J.D. Brion, M. Alami, V. Marsaud, B. Stella, and J.-M. Renior J. Med. Chem. 50 2007 6189 6200
16. C. Radanyi, G. Le Bras, S. Messaoudi, C. Bouclier, J.-F. Peyrat, J.-D. Brion, V. Marsaud, J.-M. Renoir, and M. Alami Bioorg. Med. Chem. Lett. 18 2008 2495 2498
17. H. Zhao, B.R. Kusuma, and B.S.J. Blagg ACS Med Chem. Lett. 1 2010 311 315
18. A.C. Donnelly, H. Zhao, B.R. Kusuma, and B.S. Blagg J. 1 2010 165 170
19. H. Zhao, A.C. Donnelly, B.R. Kusuma, G.E.L. Brandt, D. Brown, R.A. Rajewski, G. Vielhauer, J. Holzbeierlein, M.S. Cohen, and B.S.J. Blagg J. Med. Chem. 54 2011 3839 3853
20. B.R. Kusuma, A.S. Duerfeldt, and B.S.J. Blagg Bioorg. Med. Chem. Lett. 21 2011 7170 7174
21. B.R. Kusuma, L.B. Peterson, H. Zhao, G. Vielhauer, J. Holzbeierlein, and B.S.J. Blagg J. Med. Chem. 54 2011 6234 6253
22. H. Zhao, B. Yan, L.B. Peterson, and B.S.J. Blagg ACS Med Chem. Lett. 3 2012 327 331
23. H. Zhao, E. Moroni, B. Yan, G. Colombo, and B.S.J. Blagg ACS Med Chem. Lett. 4 2013 57 62
24. H. Zhao, and B.S.J. Blagg Bioorg. Med. Chem. Lett. 23 2013 552 557
25. X.Y. Huang, Z.J. Shan, H.L. Zhai, L.N. Li, and X.Y. Zhang J. Chem. Inf. Model. 51 2011 1999 2006
26. Y. Berkov-Zrihen, R. Rutenberg, and M. Fridman Tetrahedron 68 2012 2306 2312
27. J.W. Hinmann, E.L. Caron, and H. Hoeksema J. Am. Chem. Soc. 79 1957 3789 3800
28. Y. Ueda, J.M. Chuang, L.B. Crast, and R.A. Partyka J. Org. Chem. 53 1988 5107 5113
29. A.G. Godfrey, and B. Ganem Tetrahedron Lett. 33 1992 7461 7464
30. H. He, D. Zatorska, J. Kim, J. Aguirre, L. Llauger, Y. She, N. Wu, R.M. Immormino, D.T. Gewirth, and G. Chiosis J. Med. Chem. 49 2006 381 390
31. C. Chavany, E. Mimnaugh, P. Miller, R. Bitton, P. Nguyen, J. Trepel, L. Whitesell, R. Schnur, J.D. Moyer, and L. Neckers J. Biol. Chem. 271 1996 4974 4977
32. J. Zou, Y. Guo, T. Guettouche, D.F. Smith, and R. Voellmy Cell 94 1998 471 480
33. R. Bagatell, G.D. Paine-Murietta, C.W. Taylor, E.J. Pulcini, S. Akinaga, I.J. Benjamin, and L. Whitesell Clin. Cancer Res. 6 2000 3312 3318
34. T.P. Curran, and M.T. Keaney J. Org. Chem. 61 1996 9068 9069
35. S.H. Olsan, and L.H. Slossberg Synthesis of coumermycin A1 Tetrahedron Lett. 44 2003 61 63
36. Dolak, L. A. US Patent 3 890 297, 1975.
37. Keil, J. G.; Hooper, I. R. US Patent 3 454 548, 1969.
38. Keil, J. G.; Hooper, I. R. US Patent 3 428 623, 1969.
39. F.W. Crow, W.K. Duholke, K.A. Farley, C.E. Hadden, D.A. Hahn, B.D. Kaluzny, C.S. Mallory, G.E. Martin, R.F. Smith, and T.J. Thamann J. Heterocycl. Chem. 36 1999 365 370
40. R.J. Schumacher, R. Hurst, W.P. Sullivan, N.J. McMahon, D.O. Toft, and R.L. Matts J. Biol. Chem. 269 1994 9493 9499
41. R. Ling, M. Yoshida, and P.S. Mariano J. Org. Chem. 61 1996 4439 4449