A SAR study on a series of synthetic lipophilic chalcones as Inhibitor of transcription factor NF-κB

European Journal of Medicinal Chemistry

Volumn 54, Issue , 2012, Pages 379-386

  Venkateswararao, Eeda ^a   Sharma, Vinay K ^a   Lee, Ki Cheul ^a   Sharma, Niti ^a   Park, Sun Hong ^b   Kim, Youngsoo ^b   Jung, Sang Hun ^a  

^a Center for Nano bio Engineering and Spintronics   (South Korea)

^b Chungbuk National University   (South Korea)

Author keywords

Chalcones; Inflammation; LPS induced NF B inhibition; Sepsis

Indexed keywords

1 [2 (2 HEXYLDECYLOXY) 6 HYDROXYPHENYL] 3 [4 (METHOXYMETHOXY)PHENYL]PROP 2 EN 1 ONE; 1 [2 (BENZYLOXY) 6 HYDROXYPHENYL] 3 (4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 (CYCLOHEXYLMETHOXY) 6 HYDROXYPHENYL] 3 (4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 (DEC 4 ENYLOXY) 6 HYDROXYPHENYL] 3 [4 (METHOXYMETHOXY)PHENYL]PROP 2 EN 1 ONE; 1 [2 (DECYLOXY) 6 HYDROXYPHENYL] 3 (2 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 (DECYLOXY) 6 HYDROXYPHENYL] 3 (3 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 (DECYLOXY) 6 HYDROXYPHENYL] 3 (3,4 DICHLOROPHENYL)PROP 2 EN 1 ONE; 1 [2 (DECYLOXY) 6 HYDROXYPHENYL] 3 (4 HYDROXY 3,5 DIMETHOXYPHENYL)PROP 2 EN 1 ONE; 1 [2 (DECYLOXY) 6 HYDROXYPHENYL] 3 (4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 (DECYLOXY) 6 HYDROXYPHENYL] 3 (4 METHOXYPHENYL)PROP 2 EN 1 ONE; 1 [2 (DECYLOXY) 6 HYDROXYPHENYL] 3 (4 TOLYL)PROP 2 EN 1 ONE; 1 [2 (DODECYLOXY) 6 HYDROXYPHENYL] 3 (4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 (HEXADECYLOXY) 6 HYDROXYPHENYL] 3 (4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 (HEXYLOXY) 6 HYDROXYPHENYL] 3 (4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 (HEXYLOXY) 6 HYDROXYPHENYL] 3 [4 (HEXYLOXY)PHENYL]PROP 2 EN 1 ONE; 1 [2 HYDROXY 4 (TETRADECYLOXY)PHENYL] 3 (4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 HYDROXY 6 (OCTADECYLOXY)PHENYL] 3 (4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 HYDROXY 6 (OCTYLOXY)PHENYL] 3 (4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 HYDROXY 6 (TETRADECYLOXY)PHENYL] 3 (4 HYDROXYPHENYL)PROP 2 EN 1 ONE; 1 [2 HYDROXY 6 (TETRADECYLOXY)PHENYL] 3 [4 (TETRADECYLOXY)PHENYL]PROP 2 EN 1 ONE; 3 (3 CHLORO 4 HYDROXYPHENYL) 1 [2 (DECYLOXY) 6 HYDROXYPHENYL]PROP 2 EN 1 ONE; ANTIINFLAMMATORY AGENT; CHALCONE DERIVATIVE; HYDROXYL GROUP; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; CELL LINE; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; IC 50; LIPOPHILICITY; STRUCTURE ACTIVITY RELATION;

ALKALINE PHOSPHATASE; ANIMALS; CELL LINE; CHALCONE; DRUG DESIGN; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INHIBITORY CONCENTRATION 50; LIPOPOLYSACCHARIDES; MICE; NF-KAPPA B; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84864413623     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.05.019     Document Type: Article

References (34)

1. K. Brandl, T. Glück, P. Hartmann, B. Salzberger, and W. Falk Innate Immun. 11 2005 197 206
2. M.P. Glauser, G. Zanetti, J.D. Baumgartner, and J. Cohen Lancet 338 1991 732 736
3. R. Medzhitov, P. Preston-Hurlburt, and C.A. Janeway Jr. Nat. 388 1997 394 397
4. R.R. Ingalls, H. Heine, E. Lien, A. Yoshimura, and D. Golenbock Infect. Dis. Clin. North Am. 13 1999 341 353
5. A.S. Baldwin Jr. Annu. Rev. Immunol. 14 1996 649 683
6. H. Nakamura, K. Nakamura, and J. Yodoi Annu. Rev. Immunol. 15 1997 351 369
7. P.G. Winyard, and D.R. Blake Adv. Pharmacol. 38 1997 403 421
8. D.E. Nelson, A.E. Ihekwaba, M. Elliott, J.R. Johnson, C.A. Gibney, B.E. Foreman, G. Nelson, V. See, C.A. Horton, D.G. Spiller, S.W. Edwards, H.P. McDowell, J.F. Unitt, E. Sullivan, R. Grimley, N. Benson, D. Broomhead, D.B. Kell, and M.R. White Sci. 306 2004 704 708
9. E. Shaulian, and M. Karin Nat. Cell. Biol. 4 2002 131 136
10. C. Zaph, A.E. Troy, B.C. Taylor, L.D. Berman-Booty, K.J. Guild, Y. Du, E.A. Yost, A.D. Gruber, M.J. May, F.R. Greten, L. Eckmann, M. Karin, and D. Artis Nat. 446 2007 552 556
11. Y.J. Liu, V. Soumelis, N. Watanabe, T. Ito, Y.H. Wang, R.W. Malefyt, M. Omori, B. Zhou, and S.F. Ziegler Annu Rev. Immunol. 25 2007 193 219
12. S.F. Liu, and A.B. Malik Am. J. Physiol. Lung Cell Mol. Physiol. 290 2006 L622 L645
13. G.R. Bernard, J.L. Vincent, P.F. Laterre, S.P. LaRosa, J.F. Dhainaut, A. Lopez-Rodriguez, J.S. Steingrub, G.E. Garber, J.D. Helterbrand, E.W. Ely, and C.J. Fisher N. Engl. J. Med. 344 2001 699 709
14. H.S. Warren, A.F. Suffredini, P.Q. Eichacker, and R.S. Munford N. Engl. J. Med. 347 2002 1027 1030
15. L.D. Hawkins, W.J. Christ, and D.P. Rossignol Curr. Top. Med. Chem. 4 2004 1147 1171
16. W.J. Christ, L.D. Hawkins, M.D. Lewis, and Y. Kishi Synthetic lipid A antagonists for sepsis treeatment C.-H. Wong, Carbohydrate-based Drug Discovery 2003 Wiley-VCH Berlin 341 355
17. W.J. Christ, O.Asano, A.L. Robidoux, M. Perez, Y. Wang, G.R. Dubuc, W.E. Gavin, L.D. Hawkins, P.D. McGuinness, and M.A. Mullarkey Sci. 268 1995 80 83
18. O. Martin, W. Zhou, X.Wu, S. Front-Deschamps, S. Moutel, K. Schindl, P. Jeandet, C. Zbaeren, and J.A. Bauer J. Med. Chem. 49 2006 6000 6014
19. D.P. Rossignol, and M. Lynn J. Endotoxin Res. 8 2002 483 488
20. M. Yamada, T. Ichikawa, M. Ii, M. Sunamoto, K. Itoh, N. Tamura, and T. Kitazaki J. Med. Chem. 48 2005 7457 7467
21. M. Ii, N.Matsunaga, K. Hazeki, K. Nakamura, K. Takashima, T. Seya, O. Hazeki, T. Kitazaki, and Y. Iizawa Mol. Pharmacol. 69 2006 1288 1295
22. D.R. Storm, and K. Rosenthal A Rev. Biochem. 46 1977 723 763
23. D.C. Morrison, and D.M. Jacobs Immunochem. 13 1976 813 818
24. K.A. Miller, E.V.K. Kumar, S.J. Wood, J.R. Cromer, A. Datta, and S.A. David J. Med. Chem. 48 2005 2589 2599
25. M.R. Burns, S.A. Jenkins, M.R. Kimbrell, R. Balakrishna, T.B. Nguyen, B.G. Abbo, and S.A. David J. Med. Chem. 50 2007 877 888
26. S.A. David, L. Perez, and M.R. Infante Bioorg. Med. Chem. Lett. 12 2002 357 360
27. E. Roh, H.-S. Lee, J.-A. Kwak, J.T. Hong, S.-Y. Nam, S.-H. Jung, J.Y. Lee, N.D. Kim, S.-B. Han, and Y. Kim J. Infect. Dis. 203 2011 1012 1020
28. P. Thanigaimalai, T.A.-L. Hoang a, K.-C. Lee, V.K. Sharma, S.-C. Bang, J.H. Yun, E. Roh, Y. Kim, and S.-H. Jung Eur. J. Med. Chem. 45 2010 2531 2536
29. A.V. Pastukhov, and I.J. Ropson Proteins 53 2003 607 615
30. M. Mancek-Keber, and R. Jerala FASEB J. 20 2006 1836 1842
31. S.L. Doyle, and L.A. O'Neill Biochem. Pharmacol. 72 2006 1102 1113
32. L.V. Rubinstein, R.H. Shoemaker, K.D. Paull, R.M. Simon, S. Toshini, P. Skehan, D.A. Scudiero, A. Monks, and M.R. Boyd J. Natl. Cancer Inst. 82 1990 1113 1118
33. P. Skehan, R. Storeng, D.A. Scudiero, A. Monks, J. McMahon, D.T. Vistica, J.T. Warren, H. Bokesch, F. Kenny, and M.R. Boyd J. Natl. Cancer Inst. 82 1990 1107 1112
34. H.-M. Yang, H.-R. Shin, S.-H. Cho, S.-C. Bang, G.-Y. Song, J.-H. Ju, M.-K. Kim, S.-H. Lee, J.-C. Ryu, Y. Kim, and S.-H. Jung Bioorg. Med. Chem. 15 2007 104 111