Heterocyclic chalcone activators of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) with improved in vivo efficacy

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 17, 2015, Pages 5352-5359

  Lounsbury, Nicole ^a   Mateo, George ^a   Jones, Brielle ^b   Papaiahgari, Srinivas ^b   Thimmulappa, Rajash K ^c   Teijaro, Christiana ^d   Gordon, John ^a   Korzekwa, Kenneth ^a   Ye, Min ^a   Allaway, Graham ^b   Abou Gharbia, Magid ^a   Biswal, Shyam ^c   Childers, Wayne ^a  

^a TEMPLE UNIVERSITY   (United States)

^b Cureveda LLC   (United States)

^c JOHNS HOPKINS BLOOMBERG SCHOOL OF PUBLIC HEALTH   (United States)

^d Temple University   (United States)

Author keywords

Bioavailability; Chalcone; Keap1; Nrf2; Solubility

Indexed keywords

1 (2 METHOXYPHENYL) 3 [2 (TRIFLUOROMETHYL)PYRIDINE 3 YL]PROP 2 EN 1 ONE; 1 (2 METHOXYPHENYL) 3 [3 (TRIFLUOROMETHYL)PYRIDIN 2 YL]PROP 2 EN 1 ONE; 1 (2 METHOXYPHENYL) 3 [3 (TRIFLUOROMETHYL)PYRIDIN 4 YL]PROP 2 EN 1 ONE; 1 (2 METHOXYPHENYL) 3 [4 (TRIFLUOROMETHYL)PYRIDIN 4 YL]PROP 2 EN 1 ONE; 1 (3 METHOXYPYRIDIN 2 YL) 3 [2 (TRIFLUOROMETHYL)PHENYL] PROP 2 EN 1 ONE; 1 (3 METHOXYPYRIDIN 4 YL) 3 [2 (TRIFLUOROMETHYL)PHENYL] PROP 2 EN 1 ONE; CHALCONE DERIVATIVE; HETEROCYCLIC COMPOUND; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG; ANTIOXIDANT; CHALCONE; HEME OXYGENASE 1; NFE2L2 PROTEIN, HUMAN; NFE2L2 PROTEIN, MOUSE;

ANIMAL CELL; ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG EFFECT; DRUG EFFICACY; DRUG HALF LIFE; DRUG METABOLISM; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; IN VITRO STUDY; IN VIVO STUDY; LIPOPHILICITY; LIVER MICROSOME METABOLISM; MOUSE; NONHUMAN; PHARMACODYNAMICS; AGONISTS; ANIMAL; C57BL MOUSE; CACO 2 CELL LINE; CELL LINE; CHEMISTRY; DRUG EFFECTS; GENE EXPRESSION REGULATION; GENETICS; HUMAN; METABOLISM; ORAL DRUG ADMINISTRATION; OXIDATIVE STRESS; SOLUBILITY;

ADMINISTRATION, ORAL; ANIMALS; ANTIOXIDANTS; CACO-2 CELLS; CELL LINE; CHALCONE; FEMALE; GENE EXPRESSION REGULATION; HEME OXYGENASE-1; HUMANS; MICE; MICE, INBRED C57BL; NF-E2-RELATED FACTOR 2; OXIDATIVE STRESS; SOLUBILITY;

EID: 84946492697     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.07.056     Document Type: Article

References (41)

1. B.M. Hybertson, B. Gao, S.K. Bose, and J.M. McCord Mol. Aspects Med. 32 2011 234
2. P. Moi, K. Chan, I. Asunis, A. Cao, and Y.W. Kan Proc. Natl. Acad. Sci. U.S.A. 91 1994 9926
3. R. Venugopal, and A.K. Jaiswal Proc. Natl. Acad. Sci. U.S.A. 93 1996 14960
4. K. Itoh, N. Wakabayashi, Y. Katoh, T. Ishii, K. Igarashi, J.D. Engel, and M. Yamamoto Genes Dev. 13 1999 76
5. S.K. Niture, R. Khatri, and A.K. Jaiswal Free Radical Biol. Med. 66 2014 36
6. A. Kobayashi, M.-I. Kang, H. Okawa, M. Ohtsuji, Y. Zenke, T. Chiba, I. Kazuhiko, and M. Yamamoto Mol. Cell. Biol. 24 2004 7130
7. T.E. Sussan, T. Rangasamy, D.J. Blake, D. Malhotra, H. El-Haddad, D. Bedja, M.S. Yates, P. Kombairaju, M. Yamamoto, K.T. Liby, M.b. Sporn, K.L. Gabrielson, H.C. Champoin, R.M. Tuder, T.W. Knesler, and S. Biswal Proc. Natl. Acad. Sci. U.S.A. 106 2009 250
8. T.W. Kensler, N. Wakabayashi, and S. Biswal Annu. Rev. Pharmacol. Toxicol. 47 2007 89
9. T. Rangasamy, J. Guo, W.A. Mitzner, J. Roman, A. Singh, A.D. Fryer, M. Yamamoto, T.W. Kensler, R.M. Tuder, S.N. Georas, and S. Biswal J. Exp. Med. 202 2005 47
10. R.K. Thimmulappa, K.H. Mai, S. Srisuma, T.W. Kensler, M. Yamamoto, and S. biswal Cancer Res. 62 2002 5196
11. Ii.M. Copple Adv. Pharmacol. 63 2012 43
12. T. Suzuki, H. Motohashi, and M. Yamamoto Trends Pharmacol. Sci. 34 2013 340
13. K.R. Sekhar, G. Rschakonda, and M.L. Freeman Toxicol. Appl. Pharmacol. 244 2010 21
14. W. Hur, and N.S. Gray Curr. Opin. Chem. Biol. 15 2011 162
15. T.W. Kensler, P.A. Egner, A.S. Agyeman, K. Visvanathan, J.D. Groopman, J.-G. Chen, T.-Y. Chen, J.W. Fahey, and P. Talalay Top Curr. Chem. 329 2013 163
16. M.S. Yates, M. Tauchi, F. Katsouda, K.C. Flanders, K.T. Liby, T. Honda, G.W. Gribble, D.A. Johnson, J.A. Johnson, N.C. Burton, T.R. Builarte, M. Yamamoto, M.B. Sporn, and T.W. Kensler Mol. Cancer Ther. 6 2007 154
17. Center for Drug Evaluation and Research. New Drug Application # 204063Orig1s000. Clinical Pharmacology and Biopharmaceutics Review. Reference ID: 3123618. US Food and Drug Administration. Rockville, MD. Dated 4/29/2012. Available from: http://www.accessdata.fda.gov/drugsatfda-docs/nda/2013/204063Orig1s000TOC.cfm. Last accessed 09/03/2014.
18. V. Kumar, S. Kumar, M. Hassan, H. Wu, R.K. Thimmulappa, A. Kumar, S.K. Sharma, V.S. Parmar, S. Biswal, and S.V. Malhotra J. Med. Chem. 54 2011 4147
19. S. Bhagat, R. Sharma, D.M. Sawant, L. Sharma, and A.K. Chakraborty J. Mol. Catal. A: Chem. 244 2006 20
20. B.-C. Kao, H. Doshi, H. Reyes-Rivera, D.D. Titus, M. Yin, and D.R. Dalton J. Heterocycl. Chem. 28 1991 1315
21. A. Ashimori, T. Ono, T. Uchida, Y. Ohtaki, C. Fukaya, M. Watanabe, and K. Yokoyama Chem. Pharm. Bull. 38 1990 2446
22. J.L. LaMattina J. Heterocycl. Chem. 20 1983 533
23. E. Busto, V. Gotor-Fernandez, and V. Gotor Adv. Synth. Catal. 348 2006 2626
24. F. Trecourt, F. Marsais, T. Gungor, and G. Queguiner J. Chem. Soc. Perkin Trans. 1 1990 2409
25. X.-L. Chen, and C. Kunsch Curr. Pharm. Design 10 2004 879
26. J. Alam, D. Stewart, C. Touchard, S. Bonapally, A.M.K. Choi, and J.L. Cook J. Biol. Chem. 274 1999 26071
27. S. Kumar, B.K. Kingh, A.K. Prasad, V.S. Parmer, S. Biswal, and B. Ghosh Eur. J. Pharmacol. 700 2013 32
28. Y. Kuzuya, T. Adachi, H. Hara, A. Anan, K. Izuhara, and H. Nagai IUBMB Life 56 2004 355
29. F. Bois, C. Beney, A. Boumendjel, A.-M. Mariotte, G. Conseil, and A. DiPietro J. Med. Chem. 41 1998 4161
30. X.-L. Liu, H.-W. Tee, and M.-L. Go Bioorg. Med. Chem. 16 2008 171
31. Z. Parveen, G. Brunhofer, I. Jabeen, T. Erker, P. Chiba, and G.F. Ecker Bioorg. Med. Chem. 22 2014 2311
32. G.L. Amidon, H. Lennernas, V.P. Shah, and J.R. Crison Pharm. Res. 12 1995 413
33. Szegezdi, J. P. Scizmadia, F. Prediction of distribution coefficient using microconstants. Poster presented at the 227th ACS National Meeting, March 28-April 1, 2004, Anaheim, CA. Available on the world wide web at: http://www.chemaxon.com/conf/Prediction-of-distribution-coefficient-using-microconstants.pdf. Last accessed 09/16/2014.
34. V.N. Viswanadhan, A.K. Ghose, G.R. Revankar, and R.K. Robins J. Chem. Inf. Comput. Sci. 3 1989 163
35. P. Ertl, B. Rohde, and P. Selzer J. Med. Chem. 43 2000 3714
36. MOE Version 2013.08, Chemical Computing Group (Montreal, CA), available at: http://www.chemcomp.com/MOE-Molecular-Operating-Environment.htm. Last accessed 10/02/2014.
37. T.A. Halgren J. Comput. Chem. 17 1996 490
38. J.J.P. Stewart J. Comput. Chem. 10 1989 209
39. I.J. Hidalgo, T.J. Raub, and R.T. Borchart Gastroenterology 96 1989 736
40. I. Hubatsch, E.G.E. Ragnarsson, and P. Artursson Nat. Protocols 2 2007 2111
41. C.J. Kochansky, D.R. McMasters, P. Lu, K.A. Koeplinger, H.H. Kerr, M. Shou, and K.R. Korzekwa Mol. Pharm. 5 2008 438