The tunable functionality of α,β-unsaturated carbonyl compounds enables their differential application in biological systems

ChemMedChem

Volumn 5, Issue 3, 2010, Pages 351-356

  Amslinger, Sabine ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

, unsaturated carbonyl compounds; Drug design; Keap1 Nrf2 pathway; Michael addition; NF B

Indexed keywords

3',4',5',3,4,5 HEXAMETHOXYCHALCONE; 4 [3 CHLORO 4 (2 PYRIDINYLMETHOXY)ANILINO] 3 CYANO 6 (4 DIMETHYLAMINOCROTONAMIDO) 7 ETHOXYQUINOLINE; ALPHA MODENONE DERIVATIVE; ANTINEOPLASTIC AGENT; CARBONYL DERIVATIVE; CHALCONE DERIVATIVE; ELECTROPHILE; EPIDERMAL GROWTH FACTOR RECEPTOR; ERLOTINIB; ETACRYNIC ACID; FUMARIC ACID DIMETHYL ESTER; GEFITINIB; HELENALIN; HEME OXYGENASE 1; HERBIMYCIN A; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; KELCH LIKE ECH ASSOCIATED PROTEIN 1; NADPH QUINONE OXIDOREDUCTASE; NATURAL PRODUCT; PELITINIB; PF 299804; PROSTAGLANDIN; PROSTAGLANDIN 15D PGJ 2; RADICAL; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RUPINTRIVIR; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG; XANTHOHUMOL;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; BINDING AFFINITY; BIOLOGICAL ACTIVITY; CANCER THERAPY; CARBON NUCLEAR MAGNETIC RESONANCE; CARCINOGENICITY; CELL DAMAGE; CELL PROTECTION; CHEMICAL BOND; CHEMICAL MODIFICATION; CLINICAL TRIAL; COFFEE; COVALENT BOND; CYTOTOXICITY; DRUG DESIGN; DRUG EFFICACY; DRUG STRUCTURE; ENZYME ACTIVATION; FLUORESCENCE; GENE EXPRESSION REGULATION; HUMAN; ISOMERIZATION; LUNG NON SMALL CELL CANCER; MICHAEL ADDITION; MICROTUBULE ASSEMBLY; MITOSIS INHIBITION; MUTAGENESIS; OXIDATION; PRIORITY JOURNAL; REVIEW; RHINOVIRUS INFECTION; SIGNAL TRANSDUCTION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

ALDEHYDES; BIOLOGICAL PRODUCTS; DRUG DESIGN; FLAVONOIDS; KETONES; MOLECULAR STRUCTURE; NF-E2-RELATED FACTOR 2; NF-KAPPA B; ORGANIC CHEMICALS; PHENOLS;

EID: 77249145461     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200900499     Document Type: Review

References (46)

1. P. Talalay, M. J. De Long, H. J. Prochaska, Proc. Natl. Acad. Sci. USA 1988, 85, 8261-8265.
2. C. Cavin, M. Marin-Kuan, S. Langouët, C. Bezençon, G. Guignard, C. Verguet, D. Piguet, D. Holzhäuser, R. Cornaz, B. Schilter, Food Chem. Toxicol. 2008, 46, 1239-1248.
3. A. T. Dinkova-Kostova, P. Talalay, Mol. Nutr. Food Res. 2008, 52 Suppl. 1, S128-S138.
4. J. Nishida, J. Kawabata, Biosci. Biotechnol. Biochem. 2006, 70, 193-202.
5. R. Stocker, Antioxid. Redox Signaling 2004, 6, 841-849.
6. J.-S. Yang, G.-J. Huang, Y.-H. Liu, S.-M. Peng, Chem. Commun. 2008, 1344-1346.
7. K. P. Cusack, L. D. Arnold, C. E. Barberis, H. Chen, A. M. Ericsson, G. S. Gaza-Bulseco, T. D. Gordon, C. M. Grinnell, A. Harsch, M. Pellegrini, E. Tarcsa, Bioorg. Med. Chem. Lett. 2004, 14, 5503-5507.
8. V. Zoete, M. Rougée, A. T. Dinkova-Kostova, P. Talalay, R. V. Bensasson, Free Radical Biol. Med. 2004, 36, 1418-1423.
9. R. Gacche, M. Khsirsagar, S. Kamble, B. Bandgar, N. Dhole, K. Shisode, A. Chaudhari, Chem. Pharm. Bull. 2008, 56, 897-901.
10. M. Suzuki, M. Mori, T. Niwa, R. Hirata, K. Furuta, T. Ishikawa, R. Noyori, J. Am. Chem. Soc. 1997, 119, 2376-2385.
11. Y. K. Koleva, J. C. Madden, M. T. D. Cronin, Chem. Res. Toxicol. 2008, 21, 2300-2312.
12. a) K. Chan, R. Poon, P. J. O'Brien, J. Appl. Toxicol. 2008, 28, 1027-1039;
13. b) K. Chan, P. J. O'Brien, J. Appl. Toxicol. 2008, 28, 1004-1015.
14. a) C. Kontogiorgis, M. Mantzanidou, D. Hadjipavlou-Litina, Mini-Rev. Med. Chem. 2008, 8, 1224-1242;
15. b) J. Loa, P. Chow, K. Zhang, Cancer Chemother. Pharmacol. 2009, 63, 1007-1016.
16. a) S. H. Lee, D. H. Sohn, X. Y. Jin, S. W. Kim, S. C. Choi, G. S. Seo, Biochem. Pharmacol. 2007, 74, 870-880;
17. b) P.-H. Park, H. S. Kim, X. Y. Jin, F. Jin, J. Hur, G. Ko, D. H. Sohn, Eur. J. Pharmacol. 2009, 606, 215-224.
18. S. M. Verbitski, J. E. Mullally, F. A. Fitzpatrick, C. M. Ireland, J. Med. Chem. 2004, 47, 2062-2070.
19. T. Satoh, S. A. Lipton, Trends Neurosci. 2007, 30, 37-45.
20. M. J. Alcaraz, A. M. Vicente, A. Araico, J. N. Dominguez, M. C. Terencio, M. L. Ferrandiz, Br. J. Pharmacol. 2004, 142, 1191-1199.
21. K. B. Harikumar, A. B. Kunnumakkara, K. S. Ahn, P. Anand, S. Krishnan, S. Guha, B. B. Aggarwal, Blood 2009, 113, 2003-2013.
22. B. B. Aggarwal, P. Gehlot, Curr. Opin. Pharmacol. 2009, 9, 351-369.
23. S. Ogino, K. Tsuruma, T. Uehara, Y. Nomura, Mol. Pharmacol. 2004, 65, 1344-1351.
24. T. J. Schmidt, Bioorg. Med. Chem. 1997, 5, 645-653.
25. G. Zhao, T. Yu, R. Wang, X. Wang, Y. Jing, Bioorg. Med. Chem. 2005, 13, 4056-4062.
26. S. L. Binford, F. Maldonado, M. A. Brothers, P. T. Weady, L. S. Zalman, J. W. Meador III, D. A. Matthews, A. K. Patick, Antimicrob. Agents Chemother. 2005, 49, 619-626.
27. Ö. D. Ekici, Z. Z. Li, A. J. Campbell, K. E. James, J. L. Asgian, J. Mikolajczyk, G. S. Salvesen, R. Ganesan, S. Jelakovic, M. G. Grutter, J. C. Powers, J. Med. Chem. 2006, 49, 5728-5749.
28. H.-Y. P. Choo, K.-H. Peak, J. Park, D. H. Kim, H. S. Chung, Eur. J. Med. Chem. 2000, 35, 643-648.
29. P. Darkins, B. F. Gilmore, S. J. Hawthorne, A. Healy, H. Moncrieff, N. Mc-Carthy, M. A. McKervey, D. Brömme, M. Pagano, B. Walker, Chem. Biol. Drug Des. 2007, 69, 170-179.
30. T. Satoh, S.-i. Okamoto, J. Cui, Y. Watanabe, K. Furuta, M. Suzuki, K. Tohyama, S. A. Lipton, Proc. Natl. Acad. Sci. USA 2006, 103, 768-773.
31. R. A. Linker, D.-H. Lee, M. Stangel, R. Gold, Expert Rev. Neurother. 2008, 8, 1683-1690.
32. a) S. R. Klutchko, H. Zhou, R. T. Winters, T. P. Tran, A. J. Bridges, I. W. Althaus, D. M. Amato, W. L. Elliott, P. A. Ellis, M. A. Meade, B. J. Roberts, D. W. Fry, A. J. Gonzales, P. J. Harvey, J. M. Nelson, V. Sherwood, H.-K. Han, G. Pace, J. B. Smaill, W. A. Denny, H. D. H. Showalter, J. Med. Chem. 2006, 49, 1475-1485;
33. b) A. J. Gonzales, K. E. Hook, I. W. Althaus, P. A. Ellis, E. Trachet, A. M. Delaney, P. J. Harvey, T. A. Ellis, D. M. Amato, J. M. Nelson, D. W. Fry, T. Zhu, C.-M. Loi, S. A. Fakhoury, K. M. Schlosser, K. E. Sexton, R. T. Winters, J. E. Reed, A. J. Bridges, D. J. Lettiere, D. A. Baker, J. Yang, H. T. Lee, H. Tecle, P. W. Vincent, Mol. Cancer Ther. 2008, 7, 1880 -1889.
34. S. K. Rabindran, C. M. Discafani, E. C. Rosfjord, M. Baxter, M. B. Floyd, J. Golas, W. A. Hallett, B. D. Johnson, R. Nilakantan, E. Overbeek, M. F. Reich, R. Shen, X. Shi, H.-R. Tsou, Y.-F. Wang, A. Wissner, Cancer Res. 2004, 64, 3958-3965.
35. E. L. Kwak, R. Sordella, D. W. Bell, N. Godin-Heymann, R. A. Okimoto, B. W. Brannigan, P. L. Harris, D. R. Driscoll, P. Fidias, T. J. Lynch, S. K. Rabindran, J. P. McGinnis, A. Wissner, S. V. Sharma, K. J. Isselbacher, J. Settleman, D. A. Haber, Proc. Natl. Acad. Sci. USA 2005, 102, 7665-7670.
36. A. Wissner, E. Overbeek, M. F. Reich, M. B. Floyd, B. D. Johnson, N. Mamuya, E. C. Rosfjord, C. Discafani, R. Davis, X. Shi, S. K. Rabindran, B. C. Gruber, F. Ye, W. A. Hallett, R. Nilakantan, R. Shen, Y.-F. Wang, L. M. Greenberger, H.-R. Tsou, J. Med. Chem. 2003, 46, 49-63.
37. a) Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, pp. 1-268;
38. b) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1992.
39. O. Kaumanns, R. Lucius, H. Mayr, Chem. Eur. J. 2008, 14, 9675-9682.
40. a) T. Honda, G. W. Gribble, N. Suh, H. J. Finlay, B. V. Rounds, L. Bore, F. G. Favaloro, Y. Wang, M. B. Sporn, J. Med. Chem. 2000, 43, 1866-1877;
41. b) T. Honda, Y. Honda, F. G. Favaloro, G. W. Gribble, N. Suh, A. E. Place, M. H. Rendi, M. B. Sporn, Bioorg. Med. Chem. Lett. 2002, 12, 1027-1030.
42. S.-J. Wang, J.-F. Yan, D. Hao, X.-W. Niu, M.-S. Cheng, Molecules 2007, 12, 885-895.
43. J. Wang, S. Wang, D. Song, D. Zhao, Y. Sha, Y. Jiang, Y. Jing, M. Cheng, Chem. Biol. Drug Des. 2009, 73, 511- 514.
44. P. Yaish, A. Gazit, C. Gilon, A. Levitzki, Science 1988, 242, 933-935.
45. A. Levitzki, A. Gazit, Science 1995, 267, 1782-1788.
46. N. J. Lawrence, R. P. Patterson, L.-L. Ooi, D. Cook, S. Ducki, Bioorg. Med. Chem. Lett. 2006, 16, 5844-5848.