3-arylcoumarin derivatives manifest anti-proliferative activity through Hsp90 inhibition

ACS Medicinal Chemistry Letters

Volumn 3, Issue 4, 2012, Pages 327-331

  Zhao, Huiping ^a   Yan, Bin ^a   Peterson, Laura B ^a   Blagg, Brian S J ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

3 arylcoumarin; breast cancer; heat shock protein 90; Hsp90 inhibitors; novobiocin; silybin

Indexed keywords

3 BENZO[B]THIOPHENECOUMARIN; ACTIN; COUMARIN DERIVATIVE; DIMETHYL SULFOXIDE; EPIDERMAL GROWTH FACTOR RECEPTOR 2; ESTROGEN RECEPTOR; GELDANAMYCIN; HEAT SHOCK PROTEIN 90; HEAT SHOCK PROTEIN 90 INHIBITOR; KU 398; PROTEIN KINASE B; RAF PROTEIN; SILIBININ; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BREAST CELL; CANCER CELL; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; IC 50; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN FOLDING; PROTEIN FUNCTION; PROTEIN STABILITY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; VILSMEIER HAACK REACTION; WESTERN BLOTTING;

EID: 84859771665     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml300018e     Document Type: Article

References (29)

1. Blagg, B. S. J.; Kerr, T. D. Hsp90 inhibitors: Small molecules that transform the Hsp90 protein folding machinery into a catalyst for protein degradation Med. Res. Rev. 2006, 26, 310-338
2. Picard, D. http://www.picard.ch/downloads/Hsp90interactors.pdf.
3. Taipale, M.; Jarosz, D. F.; Lindquist, S. HSP90 at the hub of protein homeostasis: emerging mechanistic insights Nat. Rev. Mol. Cell Biol. 2010, 11, 515-528
4. Workman, P. Altered states: Selectively drugging the Hsp90 cancer chaperone Trends Mol. Med. 2004, 10, 47-51 (Pubitemid 38210022)
5. Hanahan, D.; Weinberg, R. A. Hallmarks of cancer: the next generation Cell 2011, 144, 646-674
6. Workman, P.; Burrows, F.; Neckers, L.; Rosen, N. Drugging the cancer chaperone HSP90: combinatorial therapeutic expolitation on oncogene addiction and tumor stress Ann. N.Y. Acad. Sci. 2007, 1113, 202-216 (Pubitemid 350015011)
7. Zhang, H.; Burrows, F. Targeting multiple signal transduction pathways through inhibition of Hsp90 J. Mol. Med. 2004, 82, 488-499 (Pubitemid 39149859)
8. Kim, Y. S.; Alarcon, S. V.; Lee, S.; Lee, M. J.; Giaccone, G.; Neckers, L.; Trepel, J. B. Update on Hsp90 inhibitors in clinical trial Curr. Top. Med. Chem. 2009, 9, 1479-1492
9. Biamonte, M. A.; Van de Water, R.; Arndt, J. W.; Scannevin, R. H.; Perret, D.; Lee, W. C. Heat Shock Protein 90: Inhibitors in Clinical Trials J. Med. Chem. 2010, 53, 2332-2332
10. Peterson, L. B.; Blagg, B. S. J. To fold or not to fold: modulation and consequences of Hsp90 inhibition Future Med. Chem. 2009, 1, 267-283
11. Luo, W. J.; Sun, W. L.; Taldone, T.; Rodina, A.; Chiosis, G. Heat shock protein 90 in neurodegenerative diseases Mol. Neurodegener. 2010, 5
12. Gallo, K. A. Targeting HSP90 to halt neurodegeneration Chem. Biol. 2006, 13, 115-116 (Pubitemid 43255582)
13. Donnelly, A. C.; Mays, J. R.; Burlison, J. A.; Nelson, J. T.; Vielhauer, G.; Holzbeierlein, J.; Blagg, B. S. J. The design, synthesis, and evaluation of coumarin ring derivatives of the novobiocin scaffold that exhibit anti-proliferative activity J. Org. Chem. 2008, 73, 8901-8920
14. Burlison, J. A.; Neckers, L.; Smith, A. B.; Maxwell, A.; Blagg, B. S. J. Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of Hsp90 J. Am. Chem. Soc. 2006, 128, 15529-15536 (Pubitemid 44876029)
15. Yu, X. M.; Shen, G.; Neckers, L.; Blake, H.; Holzbeierlein, J.; Cronk, B.; Blagg, B. S. J. Hsp90 inhibitors identified from a library of novobiocin analogues J. Am. Chem. Soc. 2005, 127, 12778-12779 (Pubitemid 41339147)
16. Donnelly, A. C.; Zhao, H. P.; Kusuma, B. R.; Blagg, B. S. J. Cytotoxic sugar analogues of an optimized novobiocin scaffold Med. Chem. Commun. 2010, 1, 165-170
17. Zhao, H. P.; Kusuma, B. R.; Blagg, B. S. J. Synthesis and evaluation of noviose replacements on novobiocin that manifest anti-proliferative activity ACS Med. Chem. Lett. 2010, 1, 311-315
18. Zhao, H. P.; Donnelly, A. C.; Kusuma, B. R.; Brandt, G. E. L.; Brown, D.; Rajewski, R. A.; Vielhauer, G.; Holzbeierlein, J.; Cohen, M. S.; Blagg, B. S. J. Engineering an antibiotic to fight cancer: optimization of the novobiocin scaffold to produce anti-proliferative agents J. Med. Chem. 2011, 54, 3839-3853
19. Burlison, J. A.; Avila, C.; Vielhauer, G.; Lubbers, D. J.; Holzbeierlein, J.; Blagg, B. S. J. Development of novobiocin analogues that manifest anti-proliferative activity against several cancer cell lines J. Org. Chem. 2008, 73, 2130-2137 (Pubitemid 351497740)
20. Zhao, H. P.; Brandt, G. E.; Galam, L.; Matts, R. L.; Blagg, B. S. J. Identification and initial SAR of silybin: an Hsp90 inhibitor Bioorg. Med. Chem. Lett. 2011, 21, 2659-2664
21. Demizu, S.; Kajiyama, K.; Takahashi, K.; Hiraga, Y.; Yamamoto, S.; Tamura, Y.; Okada, K.; Kinoshita, T. Antioxidant and antimicrobial constituents of licorice-isolation and structure ellucidation of a new benzofuran derivative Chem. Pharm. Bull. 1988, 36, 3474-3479
22. El-Seedi, H. R. Antimicrobial arylcoumarins from Asphodelus microcarpus J. Nat. Prod. 2007, 70, 118-120
23. Fukai, T.; Marumo, A.; Kaitou, K.; Kanda, T.; Terada, S.; Nomura, T. Anti-helicobacter pylori flavonoids from licorice extract Life Sci. 2002, 71, 1449-1463 (Pubitemid 34786288)
24. You, L. S.; An, R.; Wang, X. H.; Li, Y. M. Discovery of novel osthole derivatives as potential anti-breast cancer treatment Bioorg. Med. Chem. Lett. 2010, 20, 7426-7428
25. Peterson, L. B.; Blagg, B. S. J. Click chemistry to probe Hsp90: synthesis and evaluation of a series of triazole-containing novobiocin analogs Bioorg. Med. Chem. Lett. 2010, 20, 3957-3960
26. Das, B.; Venkateswarlu, K.; Majhi, A.; Siddaiah, V.; Reddy, K. R. A facile nuclear bromination of phenols and anilines using NBS in the presence of ammonium acetate as a catalyst J. Mol. Catal. A: Chem. 2007, 267, 30-33 (Pubitemid 46441923)
27. Ganguly, N. C.; De, P.; Dutta, S. Mild regioselective monobromination of activated aromatics and hetero-aromatics with N-bromosuccinimide in tetrabutylammonium bromide Synthesis-Stuttgart 2005, 1103-1108 (Pubitemid 40676003)
28. Venkateswarlu, K.; Suneel, K.; Das, B.; Reddy, K. N.; Reddy, T. S. Simple catalyst-free regio- and chemoselective monobromination of aromatics using NBS in polyethylene glycol Synth. Commun. 2009, 39, 215-219
29. Tran, P.; Kim, S. A.; Choi, H. S.; Yoon, J. H.; Ahn, S. G. Epigallocatechin-3-gallate suppresses the expression of HSP70 and HSP90 and exhibits anti-tumor activity in vitro and in vivo BMC Cancer 2010, 10, 276