Tetra-O-methyl nordihydroguaiaretic acid (Terameprocol) inhibits the NF-κB-dependent transcription of TNF-α and MCP-1/CCL2 genes by preventing RelA from binding its cognate sites on DNA

Journal of Inflammation

Volumn 7, Issue , 2010, Pages

  Oyegunwa, Akinbolade O ^a   Sikes, Michael L ^a   Wilson, Jason R ^a   Scholle, Frank ^a   Laster, Scott M ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFLAMMATORY AGENT; I KAPPA B ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LIPOPOLYSACCHARIDE; LUCIFERASE; MONOCYTE CHEMOTACTIC PROTEIN 1; RESIQUIMOD; TERAMEPROCOL; TOLL LIKE RECEPTOR 3; TOLL LIKE RECEPTOR 4; TOLL LIKE RECEPTOR 8; TRANSCRIPTION FACTOR RELA; TUMOR NECROSIS FACTOR ALPHA;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; AUTORADIOGRAPHY; CELL STRAIN HEK293; CHEMOLUMINESCENCE; CHROMATIN IMMUNOPRECIPITATION; CONTROLLED STUDY; CYTOKINE PRODUCTION; DNA PURIFICATION; DNA TEMPLATE; DRUG MECHANISM; ENZYME ACTIVITY; FLUORESCENCE MICROSCOPY; GEL MOBILITY SHIFT ASSAY; GENE OVEREXPRESSION; IN VITRO STUDY; IN VIVO STUDY; POLYACRYLAMIDE GEL ELECTROPHORESIS; POLYMERASE CHAIN REACTION; PROMOTER REGION; PROTEIN CROSS LINKING; PROTEIN DNA BINDING; PROTEIN PHOSPHORYLATION; SIGNAL TRANSDUCTION; WESTERN BLOTTING;

LARREA TRIDENTATA; ORTHOMYXOVIRIDAE; TETRA;

EID: 78649733443     PISSN: None     EISSN: 14769255     Source Type: Journal    
DOI: 10.1186/1476-9255-7-59     Document Type: Article

References (45)

1. The two NF-kappaB activation pathways and their role in innate and adaptive immunity. G Bonizzi M Karin, Trends Immunol 2004 25 280 288 10.1016/j.it.2004.03.008 15145317
2. NF-kappaB signaling pathways in mammalian and insect innate immunity. N Silverman T Maniatis, Genes Dev 2001 15 2321 2342 10.1101/gad.909001 11562344
3. Rel/NF-kappa B/I kappa B story. S Miyamoto IM Verma, Adv Cancer Res 1995 66 255 292 full-text 7793317
4. Enhanced I kappa B alpha degradation is responsible for constitutive NF-kappa B activity in mature murine B-cell lines. S Miyamoto PJ Chiao IM Verma, Mol Cell Biol 1994 14 3276 3282 8164680
5. NF-kappa B and Rel proteins: evolutionarily conserved mediators of immune responses. S Ghosh MJ May EB Kopp, Annu Rev Immunol 1998 16 225 260 10.1146/annurev.immunol.16.1.225 9597130
6. Structure, regulation and function of NF-kappa B. U Siebenlist G Franzoso K Brown, Annu Rev Cell Biol 1994 10 405 455 10.1146/annurev.cb.10.110194.002201 7888182
7. A MAP kinase targeted by endotoxin and hyperosmolarity in mammalian cells. J Han JD Lee L Bibbs RJ Ulevitch, Science 1994 265 808 811 10.1126/science.7914033 7914033
8. Phosphorylation meets ubiquitination: the control of NF-[kappa]B activity. M Karin Y Ben-Neriah, Annu Rev Immunol 2000 18 621 663 10.1146/annurev.immunol.18.1.621 10837071
9. Nuclear localization of I kappa B alpha promotes active transport of NF-kappa B from the nucleus to the cytoplasm. F Arenzana-Seisdedos P Turpin M Rodriguez D Thomas RT Hay JL Virelizier C Dargemont, J Cell Sci 1997 110 Pt 3 369 378 9057089
10. Larrea tridentata (Creosote bush), an abundant plant of Mexican and US-American deserts and its metabolite nordihydroguaiaretic acid. S Arteaga A Andrade-Cetto R Cardenas, J Ethnopharmacol 2005 98 231 239 10.1016/j.jep.2005. 02.002 15814253
11. Inhibition of human immunodeficiency virus type 1 transcription and replication by DNA sequence-selective plant lignans. JN Gnabre JN Brady DJ Clanton Y Ito J Dittmer RB Bates RC Huang, Proc Natl Acad Sci USA 1995 92 11239 11243 10.1073/pnas.92.24.11239 7479972
12. Antiviral activities of methylated nordihydroguaiaretic acids. 1. Synthesis, structure identification, and inhibition of tat-regulated HIV transactivation. JR Hwu WN Tseng J Gnabre P Giza RC Huang, J Med Chem 1998 41 2994 3000 10.1021/jm970819w 9685238
13. Antiviral activities of methylated nordihydroguaiaretic acids. 2. Targeting herpes simplex virus replication by the mutation insensitive transcription inhibitor tetra-O-methyl-NDGA. H Chen L Teng JN Li R Park DE Mold J Gnabre JR Hwu WN Tseng RC Huang, J Med Chem 1998 41 3001 3007 10.1021/jm980182w 9685239
14. Terameprocol, a methylated derivative of nordihydroguaiaretic acid, inhibits production of prostaglandins and several key inflammatory cytokines and chemokines. D Eads R Hansen A Oyegunwa C Cecil C Culver F Scholle I Petty S Laster, J Inflamm (Lond) 2009 6 2 10.1186/1476-9255-6-2 19133137
15. Biology and biochemistry of the chemokines: a family of chemotactic and inflammatory cytokines. MD Miller MS Krangel, Crit Rev Immunol 1992 12 17 46 1418604
16. Properties of the novel proinflammatory supergene "intercrine" cytokine family. JJ Oppenheim CO Zachariae N Mukaida K Matsushima, Annu Rev Immunol 1991 9 617 648 1910690
17. Kappa B-type enhancers are involved in lipopolysaccharide-mediated transcriptional activation of the tumor necrosis factor alpha gene in primary macrophages. AN Shakhov MA Collart P Vassalli SA Nedospasov CV Jongeneel, J Exp Med 1990 171 35 47 10.1084/jem.171.1.35 2104921
18. Small cytokine superfamily. B Sherry A Cerami, Curr Opin Immunol 1991 3 56 60 10.1016/0952-7915(91)90077-E 2054114
19. A streamlined method for rapid and sensitive chromatin immunoprecipitation. ML Sikes JM Bradshaw WT Ivory JL Lunsford RE McMillan CR Morrison, J Immunol Methods 2009 344 58 63 10.1016/j.jim.2009.03.007 19328803
20. Chromatin immunoprecipitation in the analysis of large chromatin domains across murine antigen receptor loci. DN Ciccone KB Morshead MA Oettinger, Methods Enzymol 2004 376 334 348 full-text 14975316
21. A lipopolysaccharide-specific enhancer complex involving Ets, Elk-1, Sp1, and CREB binding protein and p300 is recruited to the tumor necrosis factor alpha promoter in vivo. EY Tsai JV Falvo AV Tsytsykova AK Barczak AM Reimold LH Glimcher MJ Fenton DC Gordon IF Dunn AE Goldfeld, Mol Cell Biol 2000 20 6084 6094 10.1128/MCB.20.16.6084-6094.2000 10913190
22. Lipopolysaccharide induction of the tumor necrosis factor-alpha promoter in human monocytic cells. Regulation by Egr-1, c-Jun, and NF-kappaB transcription factors. J Yao N Mackman TS Edgington ST Fan, J Biol Chem 1997 272 17795 17801 10.1074/jbc.272.28.17795 9211933
23. A growth factor-inducible nuclear protein with a novel cysteine/histidine repetitive sequence. RN DuBois MW McLane K Ryder LF Lau D Nathans, J Biol Chem 1990 265 19185 19191 1699942
24. Interactions of CCCH zinc finger proteins with mRNA: non-binding tristetraprolin mutants exert an inhibitory effect on degradation of AU-rich element-containing mRNAs. WS Lai EA Kennington PJ Blackshear, J Biol Chem 2002 277 9606 9613 10.1074/jbc.M110395200 11782475
25. Function and activation of NF-kappa B in the immune system. PA Baeuerle T Henkel, Annu Rev Immunol 1994 12 141 179 8011280
26. Species-specific recognition of single-stranded RNA via toll-like receptor 7 and 8. F Heil H Hemmi H Hochrein F Ampenberger C Kirschning S Akira G Lipford H Wagner S Bauer, Science 2004 303 1526 1529 10.1126/science.1093620 14976262
27. Role of adaptor TRIF in the MyD88-independent toll-like receptor signaling pathway. M Yamamoto S Sato H Hemmi K Hoshino T Kaisho H Sanjo O Takeuchi M Sugiyama M Okabe K Takeda S Akira, Science 2003 301 640 643 10.1126/science.1087262 12855817 (Pubitemid 36927946)
28. IkappaBbeta acts to inhibit and activate gene expression during the inflammatory response. P Rao MS Hayden M Long ML Scott AP West D Zhang A Oeckinghaus C Lynch A Hoffmann D Baltimore S Ghosh, Nature 466 1115 1119 10.1038/nature09283 20740013
29. Regulation and function of NF-kappaB transcription factors in the immune system. S Vallabhapurapu M Karin, Annu Rev Immunol 2009 27 693 733 10.1146/annurev.immunol.021908.132641 19302050
30. NF-kappa B controls expression of inhibitor I kappa B alpha: evidence for an inducible autoregulatory pathway. SC Sun PA Ganchi DW Ballard WC Greene, Science 1993 259 1912 1915 10.1126/science.8096091 8096091
31. Inhibition of human papillomavirus type 16 gene expression by nordihydroguaiaretic acid plant lignan derivatives. J Craigo M Callahan RCC Huang AL DeLucia, Antiviral Research 2000 47 19 28 10.1016/S0166-3542(00)00089-9 10930643
32. Inhibition of HSV-1 replication and reactivation by the mutation-insensitive transcription inhibitor tetra-O-glycyl-nordihydroguaiaretic acid. R Park PE Giza DE Mold RC Huang, Antiviral Res 2003 58 35 45 10.1016/S0166-3542(02)00165-1 12719005
33. Functional interference of Sp1 and NF-kappaB through the same DNA binding site. F Hirano H Tanaka Y Hirano M Hiramoto H Handa I Makino C Scheidereit, Mol Cell Biol 1998 18 1266 1274 9488441
34. RelA Ser276 phosphorylation is required for activation of a subset of NF-kappaB-dependent genes by recruiting cyclin-dependent kinase 9/cyclin T1 complexes. DE Nowak B Tian M Jamaluddin I Boldogh LA Vergara S Choudhary AR Brasier, Mol Cell Biol 2008 28 3623 3638 10.1128/MCB.01152-07 18362169
35. Essential role of RelA Ser311 phosphorylation by zetaPKC in NF-kappaB transcriptional activation. A Duran MT Diaz-Meco J Moscat, EMBO J 2003 22 3910 3918 10.1093/emboj/cdg370 12881425
36. Ca2+/calmodulin-dependent protein kinase IV stimulates nuclear factor-kappa B transactivation via phosphorylation of the p65 subunit. MK Jang YH Goo YC Sohn YS Kim SK Lee H Kang J Cheong JW Lee, J Biol Chem 2001 276 20005 20010 10.1074/jbc.M010211200 11274168
37. The phosphorylation status of nuclear NF-kappa B determines its association with CBP/p300 or HDAC-1. H Zhong MJ May E Jimi S Ghosh, Mol Cell 2002 9 625 636 10.1016/S1097-2765(02)00477-X 11931769
38. Duration of nuclear NF-kappaB action regulated by reversible acetylation. L Chen W Fischle E Verdin WC Greene, Science 2001 293 1653 1657 10.1126/science.1062374 11533489
39. Mechanism of action of a distal NF-kappaB-dependent enhancer. B Teferedegne MR Green Z Guo JM Boss, Mol Cell Biol 2006 26 5759 5770 10.1128/MCB.00271-06 16847329
40. Regulatory elements responsible for inducible expression of the granulocyte colony-stimulating factor gene in macrophages. M Nishizawa S Nagata, Mol Cell Biol 1990 10 2002 2011 1691438
41. Transcription factors NF-IL6 and NF-kappa B synergistically activate transcription of the inflammatory cytokines, interleukin 6 and interleukin 8. T Matsusaka K Fujikawa Y Nishio N Mukaida K Matsushima T Kishimoto S Akira, Proc Natl Acad Sci USA 1993 90 10193 10197 10.1073/pnas.90.21.10193 8234276
42. C/EBP, NF-kappa B, and c-Ets family members and transcriptional regulation of the cell-specific and inducible macrophage inflammatory protein 1 alpha immediate-early gene. M Grove M Plumb, Mol Cell Biol 1993 13 5276 5289 8355682
43. Molecular and in silico characterization of a promoter module and C/EBP element that mediate LPS-induced RANTES/CCL5 expression in monocytic cells. S Fessele S Boehlk A Mojaat NG Miyamoto T Werner EL Nelson D Schlondorff PJ Nelson, FASEB J 2001 15 577 579 11259372
44. Definition of a lipopolysaccharide-responsive element in the 5'-flanking regions of MuRantes and crg-2. HS Shin BE Drysdale ML Shin PW Noble SN Fisher WA Paznekas, Mol Cell Biol 1994 14 2914 2925 7513046
45. Chaparral-associated hepatotoxicity. NM Sheikh RM Philen LA Love, Arch Intern Med 1997 157 913 919 10.1001/archinte.157.8.913 9129552