MD-2 as the target of nonlipid chalcone in the inhibition of endotoxin LPS-induced TLR4 activity

Journal of Infectious Diseases

Volumn 203, Issue 7, 2011, Pages 1012-1020

  Roh, Eunmiri ^a   Lee, Heun Sik ^a   Kwak, Jeong Ah ^a   Hong, Jin Tae ^a   Nam, Sang Yoon ^a   Jung, Sang Hun ^b   Lee, Joo Young ^c   Kim, Nam Doo ^d   Han, Sang Bae ^a   Kim, Youngsoo ^a  

^a Chungbuk National University   (South Korea)

^b Chungnam National University   (South Korea)

^c Gwangju Institute of Science and Technology (GIST)   (South Korea)

^d Equispharm Co   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2',4 DIHYDROXY 6' ISOPENTYLOXYCHALCONE; BACTERIUM LIPOPOLYSACCHARIDE; CHALCONE DERIVATIVE; CURCUMIN; CYCLOOXYGENASE 2; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERLEUKIN 1BETA; INTERLEUKIN 6; MEMBRANE PROTEIN; MYELOID DIFFERENTIATION 2; TOLL LIKE RECEPTOR 4; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BINDING SITE; COMPETITIVE INHIBITION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DIMERIZATION; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; GENE EXPRESSION REGULATION; IMMUNOPRECIPITATION; LIGAND BINDING; MACROPHAGE; MOLECULAR DOCKING; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN DEGRADATION; PROTEIN FUNCTION; PROTEIN PHOSPHORYLATION; PROTEIN TARGETING;

ADAPTOR PROTEINS, SIGNAL TRANSDUCING; ANIMALS; CELLS, CULTURED; CHALCONE; ENDOTOXINS; IMMUNOLOGIC FACTORS; MACROPHAGES; MICE; MICE, INBRED C3H; MICE, INBRED C57BL; NF-KAPPA B; NITRIC OXIDE SYNTHASE; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; TOLL-LIKE RECEPTOR 4;

EID: 79953016293     PISSN: 00221899     EISSN: None     Source Type: Journal    
DOI: 10.1093/infdis/jiq155     Document Type: Article

References (41)

1. Raetz CR, Whitfield C. Lipopolysaccharide endotoxins. Annu Rev Biochem 2002; 71:635-700. (Pubitemid 34800232)
2. Miyake K. Roles for accessory molecules in microbial recognition by toll-like receptors. J Endotoxin Res 2006; 12:195-204. (Pubitemid 47470163)
3. Shimazu R, Akashi S, Ogata H, et al. MD-2, a molecule that confers lipopolysaccharide responsiveness on toll-like receptor 4. J Exp Med 1999; 189:1777-82. (Pubitemid 29272694)
4. Park BS, Song DH, Kim HM, Choi BS, Lee H, Lee JO. The structural basis of lipopolysaccharide recognition by the TLR4-MD-2 complex. Nature 2009; 458:1191-5.
5. Kim HM, Park BS, Kim JI, et al. Crystal structure of the TLR4-MD-2 complex with bound endotoxin antagonist eritoran. Cell 2007; 130:906-17. (Pubitemid 47332573)
6. Ohto U, Fukase K, Miyake K, Satow Y. Crystal structures of human MD-2 and its complex with antiendotoxic lipid IVa. Science 2007; 316:1632-4. (Pubitemid 46982039)
7. Saitoh S, Akashi S, Yamada T, et al. Lipid A antagonist, lipid IVa, is distinct from lipid A in interaction with toll-like receptor 4 (TLR4)-MD-2 and ligand-induced TLR4 oligomerization. Int Immunol 2004; 16:961-9. (Pubitemid 38960874)
8. Shen H, Tesar BM, Walker WE, Goldstein DR. Dual signaling of MyD88 and TRIF is critical for maximal TLR4-induced dendritic cell maturation. J Immunol 2008; 181:1849-58.
9. Baeuerle PA, Baltimore D. IκB: a specific inhibitor of the NF-κB transcription factor. Science 1988; 242:540-6. (Pubitemid 18263193)
10. Krappmann D, Wegener E, Sunami Y, et al. The IκB kinase complex and NF-κB act as master regulators of lipopolysaccharide-induced gene expression and control subordinate activation of AP-1. Mol Cell Biol 2004; 24:6488-500. (Pubitemid 38891147)
11. DiDonato J, Mercurio F, Rosette C, et al. Mapping of the inducible IκB phosphorylation sites that signal its ubiquitination and degradation. Mol Cell Biol 1996; 16:1295-304.
12. Karin M, Ben-Neriah Y. Phosphorylation meets ubiquitination: the control of NF-κB activity. Annu Rev Immunol 2000; 18:621-63. (Pubitemid 30365393)
13. Tian B, Brasier AR. Identification of a nuclear factor κB-dependent gene network. Recent Prog Horm Res 2003; 58:95-130. (Pubitemid 37339306)
14. Yang HM, Shin HR, Cho SH, et al. The role of the hydrophobic group on ring A of chalcones in the inhibition of interleukin-5. Arch Pharm Res 2006; 29:969-76.
15. Lowenstein CJ, Alley EW, Raval P, et al. Macrophage nitric oxide synthase gene: two upstream regions mediate induction by interferon γ and lipopolysaccharide. Proc Natl Acad Sci USA 1993; 90:9730-4. (Pubitemid 23315860)
16. Yeo SJ, Yoon JG, Yi AK. Myeloid differentiation factor 88-dependent post-transcriptional regulation of cyclooxygenase-2 expression by CpG DNA: tumor necrosis factor-α receptor-associated factor 6, a diverging point in the toll-like receptor 9-signaling. J Biol Chem 2003; 278:40590-600.
17. Chung EY, Roh E, Kwak JA, et al. α-Viniferin suppresses the signal transducer and activation of transcription-1 (STAT-1)-inducible inflammatory genes in interferon-γ-stimulated macrophages. J Pharmacol Sci 2010; 112:405-14.
18. Gradisar H, Keber MM, Pristovsek P, Jerala R. MD-2 as the target of curcumin in the inhibition of response to LPS. J Leukoc Biol 2007; 82:968-74. (Pubitemid 47511057)
19. Chen J, Luo XD, Luo Q, Yin JF, Fu GJ. Direct evidence of the existence of specific LPS binding sites on vascular endothelial cells. Chin J Traumatol 2004; 7:113-7. (Pubitemid 38461306)
20. Morris GM, Huey R, Lindstrom W, et al. AutoDock4 and Auto- DockTools4: automated docking with selective receptor flexibility. J Comput Chem 2009; 30:2785-91.
21. Kim BH, Roh E, Lee HY, et al. Benzoxathiole derivative blocks lipopolysaccharide-induced nuclear factor-κB activation and nuclear factor-κB-regulated gene transcription through inactivating inhibitory κB kinase β. Mol Pharmacol 2008; 73:1309-18. (Pubitemid 351439213)
22. Moon KY, Hahn BS, Lee J, Kim YS. A cell-based assay system for monitoring NF-κB activity in human HaCat transfectant cells. Anal Biochem 2001; 292:17-21. (Pubitemid 32417717)
23. Ishiyama M, Tominaga H, Shiga M, Sasamoto K, Ohkura Y, Ueno K. A combined assay of cell viability and in vitro cytotoxicity with a highly water-soluble tetrazolium salt, neutral red and crystal violet. Biol Pharm Bull 1996; 19:1518-20. (Pubitemid 26403266)
24. Pastukhov AV, Ropson IJ. Fluorescent dyes as probes to study lipid-binding proteins. Proteins 2003; 53:607-15. (Pubitemid 37352174)
25. Mancek-Keber M, Jerala R. Structural similarity between the hydrophobic fluorescent probe and lipid A as a ligand of MD-2. FASEB J 2006; 20:1836-42. (Pubitemid 44933797)
26. Poltorak A, He X, Smirnova I, et al. Defective LPS signaling in C3H/HeJ and C57BL/10ScCr mice: mutations in Tlr4 gene. Science 1998; 282:2085-8. (Pubitemid 29001265)
27. Leon CG, Tory R, Jia J, Sivak O, Wasan KM. Discovery and development of toll-like receptor 4 (TLR4) antagonists: a new paradigm for treating sepsis and other diseases. Pharm Res 2008; 25:1751-61.
28. Yao LH, Jiang YM, Shi J, et al. Flavonoids in food and their health benefits. Plant Foods Hum Nutr 2004; 59:113-22. (Pubitemid 40172010)
29. Aherne SA, O'Brien NM. Dietary flavonols: chemistry, food content, and metabolism. Nutrition 2002; 18:75-81. (Pubitemid 34097718)
30. Peluso MR, Miranda CL, Hobbs DJ, Proteau RR, Stevens JF. Xanthohumol and related prenylated flavonoids inhibit inflammatory cytokine production in LPS-activated THP-1 monocytes: structure-activity relationships and in silico binding to myeloid differentiation protein-2 (MD-2). Planta Med 2010; 76:1536-43.
31. Madan B, Batra S, Ghosh B. 2′-Hydroxychalcone inhibits nuclear factor-κB and blocks tumor necrosis factor-α- and lipopolysaccharide-induced adhesion of neutrophils to human umbilical vein endothelial cells. Mol Pharmacol 2000; 58:526-34.
32. Pandey MK, Sandur SK, Sung B, Sethi G, Kunnumakkara AB, Aggarwal BB. Butein, a tetrahydroxychalcone, inhibits nuclear factor (NF)-κB and NF-κB-regulated gene expression through direct inhibition of IκBα kinase β on cysteine 179 residue. J Biol Chem 2007; 282:17340-50. (Pubitemid 47100316)
33. Harikumar KB, Kunnumakkara AB, Ahn KS, et al. Modification of the cysteine residues in IκBα kinase and NF-κB (p65) by xanthohumol leads to suppression of NF-κB-regulated gene products and potentiation of apoptosis in leukemia cells. Blood 2009; 113:2003-13.
34. Inoue H, Tanabe T. Transcriptional role of the nuclear factor κB site in the induction by lipopolysaccharide and suppression by dexamethasone of cyclooxygenase-2 in U937 cells. Biochem Biophys Res Commun 1998; 244:143-8. (Pubitemid 28419914)
35. Hiscott J, Marois J, Garoufalis J, et al. Characterization of a functional NF-κB site in the human interleukin 1β promoter: evidence for a positive autoregulatory loop. Mol Cell Biol 1993; 13:6231-40. (Pubitemid 23292617)
36. Zhang Y, Broser M, Rom W. Activation of the interleukin 6 gene by Mycobacterium tuberculosis or lipopolysaccharide is mediated by nuclear factors NF-IL6 and NF-κB. Proc Natl Acad Sci USA 1995; 92:3632.
37. Romagne F. Current and future drugs targeting one class of innate immunity receptors: the toll-like receptors. Drug Discov Today 2007; 12:80-7. (Pubitemid 46014484)
38. Tidswell M, Tillis W, Larosa SP, et al. Phase 2 trial of eritoran tetrasodium (E5564), a toll-like receptor 4 antagonist, in patients with severe sepsis. Crit Care Med 2010; 38:72-83.
39. Wasan KM, Sivak O, Cote RA, et al. Association of the endotoxin antagonist E5564 with high-density lipoproteins in vitro: dependence on low-density and triglyceride-rich lipoprotein concentrations. Antimicrob Agents Chemother 2003; 47:2796-803. (Pubitemid 37040250)
40. Mancek-Keber M, Gradisar H, Pestana MI, Martinez de Tejada G, Jerala R. Free thiol group of MD-2 as the target for inhibition of the lipopolysaccharide-induced cell activation. J Biol Chem 2009; 284:19493-500.
41. Jeon KI, Byun MS, Jue DM. Gold compound auranofin inhibits IκB kinase (IKK) by modifying Cys-179 of IKKβ subunit. Exp Mol Med 2003; 35:61-6.