Structure-dependent activation of NR4A2 (Nurr1) by 1,1-bis(3′- indolyl)-1-(aromatic)methane analogs in pancreatic cancer cells

Biochemical Pharmacology

Volumn 83, Issue 10, 2012, Pages 1445-1455

  Li, Xi ^a   Lee, Syng Ook ^b   Safe, Stephen ^b,c  

^a TEXAS A M COLLEGE OF MEDICINE   (United States)

^b UNIVERSITY OF TEXAS   (United States)

^c TEXAS A AND M UNIVERSITY   (United States)

Author keywords

DIM analogs; NR4A2 Nurr1; Structure activity

Indexed keywords

1,1 BIS(3' INDOLYL) 1 (AROMATIC)METHANE DERIVATIVE; 4 BROMOPHENYL DERIVATIVE; METHANE; NUCLEAR RECEPTOR RELATED FACTOR 1; PHENYL GROUP; UNCLASSIFIED DRUG; VASOACTIVE INTESTINAL POLYPEPTIDE;

AMINO TERMINAL SEQUENCE; ARTICLE; CANCER CELL CULTURE; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; HUMAN; HUMAN CELL; IMMUNOHISTOCHEMISTRY; PANCREAS CANCER; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN STRUCTURE; WESTERN BLOTTING;

BASE SEQUENCE; CELL LINE, TUMOR; DNA PRIMERS; HUMANS; INDOLES; NUCLEAR RECEPTOR SUBFAMILY 4, GROUP A, MEMBER 2; PANCREATIC NEOPLASMS; REAL-TIME POLYMERASE CHAIN REACTION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84862812311     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2012.02.021     Document Type: Article

References (35)

1. H. Gronemeyer, J.A. Gustafsson, and V. Laudet Principles for modulation of the nuclear receptor superfamily Nat Rev Drug Discov 3 2004 950 964 (Pubitemid 39534319)
2. N.J. McKenna, A.J. Cooney, F.J. DeMayo, M. Downes, C.K. Glass, and R.B. Lanz Minireview: evolution of NURSA, the Nuclear Receptor Signaling Atlas Mol Endocrinol 23 2009 740 746
3. A. Warnmark, E. Treuter, A.P. Wright, and J.A. Gustafsson Activation functions 1 and 2 of nuclear receptors: molecular strategies for transcriptional activation Mol Endocrinol 17 2003 1901 1909 (Pubitemid 37287610)
4. G. Benoit, A. Cooney, V. Giguere, H. Ingraham, M. Lazar, and G. Muscat International Union of Pharmacology. LXVI. Orphan nuclear receptors Pharmacol Rev 58 2006 798 836 (Pubitemid 44833747)
5. M.A. Maxwell, and G.E. Muscat The NR4A subgroup: immediate early response genes with pleiotropic physiological roles Nucl Recept Signal 4 2006 e002
6. M.A. Pearen, and G.E. Muscat Minireview: nuclear hormone receptor 4A signaling - implications for metabolic disease Mol Endocrinol 24 2010 1891 1903
7. Y. Shi Orphan nuclear receptors in drug discovery Drug Discov Today 12 2007 440 445 (Pubitemid 46783687)
8. S.O. Lee, X. Li, S. Khan, and S. Safe Targeting NR4A1 (TR3) in cancer cells and tumors Expert Opin Ther Targets 15 2011 195 206
9. Z. Wang, G. Benoit, J. Liu, S. Prasad, P. Aarnisalo, and X. Liu Structure and function of Nurr1 identifies a class of ligand-independent nuclear receptors Nature 423 2003 555 560 (Pubitemid 36648581)
10. N. Ke, G. Claassen, D.H. Yu, A. Albers, W. Fan, and P. Tan Nuclear hormone receptor NR4A2 is involved in cell transformation and apoptosis Cancer Res 64 2004 8208 8212 (Pubitemid 39491757)
11. T. Inamoto, B.A. Czerniak, C.P. Dinney, and A.M. Kamat Cytoplasmic mislocalization of the orphan nuclear receptor Nurr1 is a prognostic factor in bladder cancer Cancer 116 2010 340 346
12. Q.X. Li, N. Ke, R. Sundaram, and F. Wong-Staal NR4A1,2,3 - an orphan nuclear hormone receptor family involved in cell apoptosis and carcinogenesis Histol Histopathol 21 2006 533 540
13. H. Li, S.K. Kolluri, J. Gu, M.I. Dawson, X. Cao, and P.D. Hobbs Cytochrome c release and apoptosis induced by mitochondrial targeting of nuclear orphan receptor TR3 Science 289 2000 1159 1164 (Pubitemid 30650723)
14. B. Lin, S.K. Kolluri, F. Lin, W. Liu, Y.H. Han, and X. Cao Conversion of Bcl-2 from protector to killer by interaction with nuclear orphan receptor Nur77/TR3 Cell 116 2004 527 540 (Pubitemid 38264430)
15. S.O. Lee, M. Abdelrahim, K. Yoon, S. Chintharlapalli, S. Papineni, and K. Kim Inactivation of the orphan nuclear receptor TR3/Nur77 inhibits pancreatic cancer cell and tumor growth Cancer Res 70 2010 6824 6836
16. S. Chintharlapalli, R. Burghardt, S. Papineni, S. Ramaiah, K. Yoon, and S. Safe Activation of Nur77 by selected 1,1-bis(3′-indolyl)-1-(p- substituted phenyl)methanes induces apoptosis through nuclear pathways J Biol Chem 280 2005 24903 24914 (Pubitemid 40934582)
17. S.D. Cho, S.O. Lee, S. Chintharlapalli, M. Abdelrahim, S. Khan, and K. Yoon Activation of nerve growth factor-induced B alpha by methylene-substituted diindolylmethanes in bladder cancer cells induces apoptosis and inhibits tumor growth Mol Pharmacol 77 2010 396 404
18. S.O. Lee, S. Chintharlapalli, S. Liu, S. Papineni, S.D. Cho, and K. Yoon p21 expression is induced by activation of nuclear nerve growth factor-induced Balpha (Nur77) in pancreatic cancer cells Mol Cancer Res 7 2009 1169 1178
19. Y. Zhan, X. Du, H. Chen, J. Liu, B. Zhao, and D. Huang Cytosporone B is an agonist for nuclear orphan receptor Nur77 Nat Chem Biol 4 2008 548 556
20. J.J. Liu, H.N. Zeng, L.R. Zhang, Y.Y. Zhan, Y. Chen, and Y. Wang A unique pharmacophore for activation of the nuclear orphan receptor Nur77 in vivo and in vitro Cancer Res 70 2010 3628 3637
21. P. Ordentlich, Y. Yan, S. Zhou, and R.A. Heyman Identification of the antineoplastic agent 6-mercaptopurine as an activator of the orphan nuclear hormone receptor Nurr1 J Biol Chem 278 2003 24791 24799 (Pubitemid 37548636)
22. T. Inamoto, S. Papineni, S. Chintharlapalli, S.D. Cho, S. Safe, and A.M. Kamat 1,1-Bis(3′-indolyl)-1-(p-chlorophenyl)methane activates the orphan nuclear receptor Nurr1 and inhibits bladder cancer growth Mol Cancer Ther 7 2008 3825 3833
23. C. Dubois, B. Hengerer, and H. Mattes Identification of a potent agonist of the orphan nuclear receptor Nurr1 ChemMedChem 1 2006 955 958 (Pubitemid 44448793)
24. S. Chintharlapalli, R. Smith 3rd, I. Samudio, W. Zhang, and S. Safe 1,1-Bis(3′-indolyl)-1-(p-substituted phenyl)methanes induce peroxisome proliferator-activated receptor gamma-mediated growth inhibition, transactivation, and differentiation markers in colon cancer cells Cancer Res 64 2004 5994 6001 (Pubitemid 39129396)
25. C. Qin, D. Morrow, J. Stewart, K. Spencer, W. Porter, and R. Smith 3rd A new class of peroxisome proliferator-activated receptor gamma (PPARgamma) agonists that inhibit growth of breast cancer cells: 1,1-bis(3′-indolyl)- 1-(p-substituted phenyl)methanes Mol Cancer Ther 3 2004 247 260
26. S.Y. Kim, K.C. Choi, M.S. Chang, M.H. Kim, Y.S. Na, and J.E. Lee The dopamine D2 receptor regulates the development of dopaminergic neurons via extracellular signal-regulated kinase and Nurr1 activation J Neurosci 26 2006 4567 4576
27. M. Nordzell, P. Aarnisalo, G. Benoit, D.S. Castro, and T. Perlmann Defining an N-terminal activation domain of the orphan nuclear receptor Nurr1 Biochem Biophys Res Commun 313 2004 205 211 (Pubitemid 37524044)
28. D. Kovalovsky, D. Refojo, A.C. Liberman, D. Hochbaum, M.P. Pereda, and O.A. Coso Activation and induction of NUR77/NURR1 in corticotrophs by CRH/cAMP: involvement of calcium, protein kinase A, and MAPK pathways Mol Endocrinol 16 2002 1638 1651 (Pubitemid 34746009)
29. J. Lammi, J. Huppunen, and P. Aarnisalo Regulation of the osteopontin gene by the orphan nuclear receptor NURR1 in osteoblasts Mol Endocrinol 18 2004 1546 1557 (Pubitemid 38696932)
30. Y. Luo, L.A. Henricksen, R.E. Giuliano, L. Prifti, L.M. Callahan, and H.J. Federoff VIP is a transcriptional target of Nurr1 in dopaminergic cells Exp Neurol 203 2007 221 232 (Pubitemid 44821180)
31. E. Hermanson, L. Borgius, M. Bergsland, E. Joodmardi, and T. Perlmann Neuropilin1 is a direct downstream target of Nurr1 in the developing brain stem J Neurochem 97 2006 1403 1411 (Pubitemid 43725579)
32. X.K. Zhang Targeting Nur77 translocation Expert Opin Ther Targets 11 2007 69 79
33. M. Li, H. Yang, H. Chai, W.E. Fisher, X. Wang, and F.C. Brunicardi Pancreatic carcinoma cells express neuropilins and vascular endothelial growth factor, but not vascular endothelial growth factor receptors Cancer 101 2004 2341 2350 (Pubitemid 39458692)
34. P. Lei, M. Abdelrahim, S.D. Cho, S. Liu, S. Chintharlapalli, and S. Safe 1,1-Bis(3′-indolyl)-1-(p-substituted phenyl)methanes inhibit colon cancer cell and tumor growth through activation of c-jun N-terminal kinase Carcinogenesis 29 2008 1139 1147 (Pubitemid 351958692)
35. P. Lei, M. Abdelrahim, S.D. Cho, X. Liu, and S. Safe Structure-dependent activation of endoplasmic reticulum stress-mediated apoptosis in pancreatic cancer by 1,1-bis(3′-indoly)-1-(p-substituted phenyl)methanes Mol Cancer Ther 7 2008 3363 3372