Bicyclic cyclohexenones as inhibitors of NF-κB signaling

ACS Medicinal Chemistry Letters

Volumn 3, Issue 6, 2012, Pages 459-464

  Hexum, Joseph K ^a   Tello Aburto, Rodolfo ^b   Struntz, Nicholas B ^a   Harned, Andrew M ^b   Harki, Daniel A ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b University of Minnesota   (United States)

Author keywords

anticancer agents; Natural product analogues; NF B inhibitors; Pd catalyzed acetoxylation

Indexed keywords

2 CYCLOHEXENONE; ANTINEOPLASTIC AGENT; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INTERLEUKIN 8; PROTEIN P50; SYNAPTOTAGMIN I;

ARTICLE; CANCER CELL CULTURE; CELL PROLIFERATION; CYTOTOXICITY; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL; PROTEIN EXPRESSION; WESTERN BLOTTING;

EID: 84862277852     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml300034a     Document Type: Article

References (37)

1. Hayden, M. S.; Ghosh, S. Shared principles in NF-κB signaling Cell 2008, 132, 344-362
2. Ruland, J. Return to homeostasis: downregulation of NF-κB responses Nat. Immunol. 2011, 12, 709-714
3. Sen, R.; Baltimore, D. Multiple nuclear factors interact with the immunoglobulin enhancer sequences Cell 1986, 46, 705-716 (Pubitemid 16020062)
4. Chaturvedi, M. M.; Sung, B.; Yadav, V. R.; Kannappan, R.; Aggarwal, B. B. NF-κB addiction and its role in cancer: 'one size does not fit all' Oncogene 2011, 30, 1615-1630
5. Karin, M. Nuclear factor-κB in cancer development and progression Nature 2006, 441, 431-436 (Pubitemid 44050137)
6. Karin, M.; Greten, F. R. NF-κB: linking inflammation and immunity to cancer development and progression Nat. Rev. Immunol. 2005, 5, 749-759 (Pubitemid 41400849)
7. Naugler, W. E.; Karin, M. NF-κB and cancer-identifying targets and mechanisms Curr. Opin. Genet. Dev. 2008, 18, 19-26
8. Aggarwal, B. B. Nuclear factor-κB: the enemy within Cancer Cell 2004, 6, 203-208
9. Karin, M.; Yamamoto, Y.; Wang, Q. M. The IKK NF-κB system: a treasure trove for drug development Nat. Rev. Drug Discovery 2004, 3, 17-26 (Pubitemid 38088695)
10. Bremner, P.; Heinrich, M. Natural products as targeted modulators of the nuclear factor-κB pathway J. Pharm. Pharmacol. 2002, 54, 453-472 (Pubitemid 34308488)
11. Folmer, F.; Harrison, W. T. A.; Tabudravu, J. N.; Jaspars, M.; Aalbersberg, W.; Feussner, K.; Wright, A. D.; Dicato, M.; Diederich, M. NF-κB-inhibiting naphthopyrones from the Fijian echinoderm Comanthus parvicirrus J. Nat. Prod. 2008, 71, 106-111 (Pubitemid 351236406)
12. Müller, S.; Murillo, R.; Castro, V.; Brecht, V.; Merfort, I. Sesquiterpene lactones from Montanoa hibiscifolia that inhibit the transcription factor NF-κB J. Nat. Prod. 2004, 67, 622-630 (Pubitemid 38533934)
13. Rüngeler, P.; Castro, V.; Mora, G.; Gören, N.; Vichnewski, W.; Pahl, H. L.; Merfort, I.; Schmidt, T. J. Inhibition of transcription factor NF-κB by sesquiterpene lactones: a proposed molecular mechanism of action Bioorg. Med. Chem. 1999, 7, 2343-2352 (Pubitemid 30122736)
14. Nam, N.-H. Naturally occurring NF-κB inhibitors Mini Rev. Med. Chem. 2006, 6, 945-951
15. Merfort, I. Perspectives on sesquiterpene lactones in inflammation and cancer Curr. Drug Targets 2011, 12, 1560-1573
16. Singh, J.; Petter, R. C.; Baillie, T. A.; Whitty, A. The resurgence of covalent drugs Nat. Rev. Drug Discovery 2011, 10, 307-317
17. Dumontet, V.; Gaspard, C.; Van Hung, N.; Fahy, J.; Tchertanov, L.; Sévenet, T.; Guéritte, F. New cytotoxic flavonoids from Cryptocarya infectoria Tetrahedron 2001, 57, 6189-6196 (Pubitemid 32709689)
18. Govindachari, T. R.; Parthasarathy, P. C. Cryptocaryone, a novel 5′,6′-dihydrochalcone, from Cryptocarya bourdilloni gamb Tetrahedron Lett. 1972, 13, 3419-3420
19. Maddry, J. A.; Joshi, B. S.; Gary Newton, M.; William Pelletier, S.; Parthasarathy, P. C. Cryptocaryone: A revised structure Tetrahedron Lett. 1985, 26, 5491-5492 (Pubitemid 16197127)
20. Meragelman, T. L.; Scudiero, D. A.; Davis, R. E.; Staudt, L. M.; McCloud, T. G.; Cardellina, J. H., 2nd; Shoemaker, R. H. Inhibitors of the NF-κB activation pathway from Cryptocarya rugulosa J. Nat. Prod. 2009, 72, 336-339
21. Fujioka, H.; Nakahara, K.; Oki, T.; Hirano, K.; Hayashi, T.; Kita, Y. The first asymmetric total syntheses of both enantiomers of cryptocaryone Tetrahedron Lett. 2010, 51, 1945-1946
22. Franck, G.; Brödner, K.; Helmchen, G. Enantioselective modular synthesis of cyclohexenones: total syntheses of (+)-crypto- and (+)-infectocaryone Org. Lett. 2010, 12, 3886-3889
23. Tello-Aburto, R.; Harned, A. M. Palladium-catalyzed reactions of cyclohexadienones: regioselective cyclizations triggered by alkyne acetoxylation Org. Lett. 2009, 11, 3998-4000
24. Palayoor, S. T.; Youmell, M. Y.; Calderwood, S. K.; Coleman, C. N.; Price, B. D. Constitutive activation of IκB kinase α and NF-κB in prostate cancer cells is inhibited by ibuprofen Oncogene 1999, 18, 7389-7394 (Pubitemid 30032121)
25. Suh, J.; Payvandi, F.; Edelstein, L. C.; Amenta, P. S.; Zong, W.-X.; Gélinas, C.; Rabson, A. B. Mechanisms of constitutive NF-κB activation in human prostate cancer cells Prostate 2002, 52, 183-200 (Pubitemid 34791221)
26. Chen, Y.-C.; Kung, F.-L.; Tsai, I.-L.; Chou, T.-H.; Chen, I.-S.; Guh, J.-H. Cryptocaryone, a natural dihydrochalcone, induces apoptosis in human androgen independent prostate cancer cells by death receptor clustering in lipid raft and nonraft compartments J. Urol. 2010, 183, 2409-2418
27. Raj, L.; Ide, T.; Gurkar, A. U.; Foley, M.; Schenone, M.; Li, X.; Tolliday, N. J.; Golub, T. R.; Carr, S. A.; Shamji, A. F.; Stern, A. M.; Mandinova, A.; Schreiber, S. L.; Lee, S. W. Selective killing of cancer cells by a small molecule targeting the stress response to ROS Nature 2011, 475, 231-234
28. Moraski, G. C.; Markley, L. D.; Hipskind, P. A.; Boshoff, H.; Cho, S.; Franzblau, S. G.; Miller, M. J. Advent of Imidazo[1,2-α]pyridine-3- carboxamides with potent multi- and extended drug resistant antituberculosis activity ACS Med. Chem. Lett. 2011, 2, 466-470
29. Li, X. C.; Babu, K. S.; Jacob, M. R.; Khan, S. I.; Agarwal, A. K.; Clark, A. M. Natural product-based 6-hydroxy-2, 3, 4, 6-tetrahydropyrrolo[1, 2-α]pyrimidinium scaffold as a new antifungal template ACS Med. Chem. Lett. 2011, 2, 391-395
30. Webber, M. M.; Bello, D.; Quader, S. Immortalized and tumorigenic adult human prostatic epithelial cell lines: characteristics and applications. Part I. Cell markers and immortalized nontumorigenic cell lines Prostate 1996, 29, 386-394 (Pubitemid 27014354)
31. Bello, D.; Webber, M. M.; Kleinman, H. K.; Wartinger, D. D.; Rhim, J. S. Androgen responsive adult human prostatic epithelial cell lines immortalized by human papillomavirus 18 Carcinogenesis 1997, 18, 1215-1223 (Pubitemid 28132513)
32. Zhou, J.; Geng, G.; Batist, G.; Wu, J. H. Syntheses and potential anti-prostate cancer activities of ionone-based chalcones Bioorg. Med. Chem. Lett. 2009, 19, 1183-1186
33. Avonto, C.; Taglialatela-Scafati, O.; Pollastro, F.; Minassi, A.; Di Marzo, V.; De Petrocellis, L.; Appendino, G. An NMR spectroscopic method to identify and classify thiol-trapping agents: revival of Michael acceptors for drug discovery? Angew. Chem. Int. Ed. 2011, 50, 467-471
34. Kunsch, C.; Rosen, C. A. NF-κB subunit-specific regulation of the interleukin-8 promoter Mol. Cell. Biol. 1993, 13, 6137-6146 (Pubitemid 23292608)
35. Xie, K. Interleukin-8 and human cancer biology Cytokine Growth Factor Rev. 2001, 12, 375-391 (Pubitemid 32851749)
36. Lindenmeyer, M. T.; Hrenn, A.; Kern, C.; Castro, V.; Murillo, R.; Müller, S.; Laufer, S.; Schulte-Mönting, J.; Siedle, B.; Merfort, I. Sesquiterpene lactones as inhibitors of IL-8 expression in HeLa cells Bioorg. Med. Chem. 2006, 14, 2487-2497 (Pubitemid 43343635)
37. Lötscher, D.; Rupprecht, S.; Stoeckli-Evans, H.; von Zelewsky, A. Enantioselective catalytic cyclopropanation of styrenes by copper complexes with chiral pinene-[5,6]-bipyridine ligands Tetrahedron: Asymmetry 2000, 11, 4341-4357