A novel synthetic compound 4-Acetyl-3-methyl-6-(2-bromophenyl)pyrano[3,4-c] pyran-1,8-dione inhibits the production of nitric oxide and proinflammatory cytokines Via the NF-κB pathway in lipopolysaccharide-activated microglia cells

Neurochemical Research

Volumn 38, Issue 4, 2013, Pages 807-814

  Chung, Hwan Suck ^a   Kim, Sae Noon ^a   Jeong, Jin Hyun ^b   Bae, Hyunsu ^a  

^a Kyung Hee University   (South Korea)

^b Yonsei University   (South Korea)

Author keywords

4 Acetyl 3 methyl 6 (2 bromophenyl)pyrano 3,4 c pyran 1,8 dione; Lipopolysaccharide; Microglia; NF B; Nitric oxide

Indexed keywords

4 ACETYL 3 METHYL 6 (2 BROMOPHENYL)PYRANO[3,4 C]PYRAN 1,8 DIONE; ANTIINFLAMMATORY AGENT; AUTACOID; CYTOKINE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERLEUKIN 6; LIPOPOLYSACCHARIDE; NITRIC OXIDE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL ACTIVATION; CELL NUCLEUS; CONTROLLED STUDY; CYTOKINE PRODUCTION; CYTOKINE RELEASE; DRUG STRUCTURE; DRUG SYNTHESIS; METABOLIC INHIBITION; MICROGLIA; MOUSE; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN EXPRESSION; PROTEIN INDUCTION; PROTEIN PHOSPHORYLATION; PROTEIN SYNTHESIS INHIBITION; PROTEIN TRANSPORT; SIGNAL TRANSDUCTION;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BICYCLO COMPOUNDS, HETEROCYCLIC; CYTOKINES; INTERLEUKIN-6; LIPOPOLYSACCHARIDES; MICE; MICROGLIA; NF-KAPPA B; NITRIC OXIDE; NITRIC OXIDE SYNTHASE TYPE II; PHOSPHORYLATION; PYRONES; TUMOR NECROSIS FACTOR-ALPHA;

VITEX ROTUNDIFOLIA;

EID: 84876179150     PISSN: 03643190     EISSN: 15736903     Source Type: Journal    
DOI: 10.1007/s11064-013-0983-6     Document Type: Article

References (36)

1. Yang I, Han SJ, Kaur G, Crane C, Parsa AT (2010) The role of microglia in central nervous system immunity and glioma immunology. J Clin Neurosci 17:6-10
2. Wyss-Coray T, Mucke L (2002) Inflammation in neurodegenerative disease - a double-edged sword. Neuron 35:419-432 (Pubitemid 34879943)
3. Nathan CF, Hibbs JB Jr (1991) Role of nitric oxide synthesis in macrophage antimicrobial activity. Curr Opin Immunol 3:65-70
4. Akiyama H, Barger S, Barnum S, Bradt B, Bauer J, Cole GM, Cooper NR, Eikelenboom P, Emmerling M, Fiebich BL et al (2000) Inflammation and alzheimer's disease. Neurobiol Aging 21:383-421 (Pubitemid 30349107)
5. McGeer PL, McGeer EG (2004) Inflammation and neurodegeneration in parkinson's disease. Parkinsonism Relat Disord 10(Suppl 1):S3-S7 (Pubitemid 38510423)
6. Danton GH, Dietrich WD (2003) Inflammatory mechanisms after ischemia and stroke. J Neuropathol Exp Neurol 62:127-136 (Pubitemid 36176947)
7. Chao CC, Hu S, Peterson PK (1995) Glia, cytokines, and neurotoxicity. Crit Rev Neurobiol 9:189-205
8. Tracey KJ, Fong Y, Hesse DG, Manogue KR, Lee AT, Kuo GC, Lowry SF, Cerami A (1987) Anti-cachectin/tnf monoclonal antibodies prevent septic shock during lethal bacteraemia. Nature 330:662-664 (Pubitemid 18005583)
9. Baker SJ, Reddy EP (1998) Modulation of life and death by the tnf receptor superfamily. Oncogene 17:3261-3270 (Pubitemid 29043978)
10. Vilcek J, Lee TH (1991) Tumor necrosis factor. New insights into the molecular mechanisms of its multiple actions. J Biol Chem 266:7313-7316 (Pubitemid 21906368)
11. Sweet MJ, Hume DA (1996) Endotoxin signal transduction in macrophages. J Leukoc Biol 60:8-26 (Pubitemid 26248877)
12. Kuprash DV, Udalova IA, Turetskaya RL, Rice NR, Nedospasov SA (1995) Conserved kappa b element located downstream of the tumor necrosis factor alpha gene: distinct nf-kappa b binding pattern and enhancer activity in lps activated murine macrophages. Oncogene 11:97-106
13. Lee H, Han AR, Kim Y, Choi SH, Ko E, Lee NY, Jeong JH, Kim SH, Bae H (2009) A new compound, 1h,8h-pyrano[3,4-c]pyran-1,8-dione, suppresses airway epithelial cell inflammatory responses in a murine model of asthma. Int J Immunopathol Pharmacol 22:591-603
14. Blasi E, Barluzzi R, Bocchini V, Mazzolla R, Bistoni F (1990) Immortalization of murine microglial cells by a v-raf/v-myc carrying retrovirus. J Neuroimmunol 27:229-237 (Pubitemid 20146292)
15. Saura J, Tusell JM, Serratosa J (2003) High-yield isolation of murine microglia by mild trypsinization. Glia 44:183-189 (Pubitemid 37484470)
16. Cory AH, Owen TC, Barltrop JA, Cory JG (1991) Use of an aqueous soluble tetrazolium/formazan assay for cell growth assays in culture. Cancer Commun 3:207-212
17. Xie QW, Cho HJ, Calaycay J, Mumford RA, Swiderek KM, Lee TD, Ding A, Troso T, Nathan C (1992) Cloning and characterization of inducible nitric oxide synthase from mouse macrophages. Science 256:225-228
18. Bal-Price A, Brown GC (2001) Inflammatory neurodegeneration mediated by nitric oxide from activated glia-inhibiting neuronal respiration, causing glutamate release and excitotoxicity. J Neurosci 21:6480-6491 (Pubitemid 32781092)
19. Woo MS, Jung SH, Hyun JW, Kim HS (2004) Differential regulation of inducible nitric oxide synthase and cytokine gene expression by forskolin and dibutyryl-camp in lipopolysaccharide-stimulated murine bv2 microglial cells. Neurosci Lett 356:187-190 (Pubitemid 38186683)
20. Fiebich BL, Schleicher S, Butcher RD, Craig A, Lieb K (2000) The neuropeptide substance p activates p38 mitogen-activated protein kinase resulting in il-6 expression independently from nf-kappa b. J Immunol 165:5606-5611
21. Rao A (1994) Nf-atp: a transcription factor required for the co-ordinate induction of several cytokine genes. Immunol Today 15:274-281 (Pubitemid 24170521)
22. Stoll G, Jander S (1999) The role of microglia and macrophages in the pathophysiology of the cns. Prog Neurobiol 58:233-247 (Pubitemid 29193056)
23. Kreutzberg GW (1996) Microglia: a sensor for pathological events in the cns. Trends Neurosci 19:312-318 (Pubitemid 26349059)
24. Vila M, Jackson-Lewis V, Guegan C, Wu DC, Teismann P, Choi DK, Tieu K, Przedborski S (2001) The role of glial cells in parkinson's disease. Curr Opin Neurol 14:483-489 (Pubitemid 32703541)
25. Sriram K, Matheson JM, Benkovic SA, Miller DB, Luster MI, O'Callaghan JP (2006) Deficiency of tnf receptors suppresses microglial activation and alters the susceptibility of brain regions to mptp-induced neurotoxicity: role of tnf-alpha. Faseb J 20:670-682 (Pubitemid 44933311)
26. Lawrence T, Gilroy DW, Colville-Nash PR, Willoughby DA (2001) Possible new role for nf-kappab in the resolution of inflammation. Nat Med 7:1291-1297 (Pubitemid 34007932)
27. Makarov SS (2001) Nf-kappa b in rheumatoid arthritis: a pivotal regulator of inflammation, hyperplasia, and tissue destruction. Arthritis Res 3:200-206 (Pubitemid 32621955)
28. Boje KM, Arora PK (1992) Microglial-produced nitric oxide and reactive nitrogen oxides mediate neuronal cell death. Brain Res 587:250-256
29. Majumder S, Zhou LZ, Chaturvedi P, Babcock G, Aras S, Ransohoff RM (1998) P48/stat-1alpha-containing complexes play a predominant role in induction of ifn-gamma-inducible protein, 10 kDa (ip-10) by ifn-gamma alone or in synergy with tnf-alpha. J Immunol 161:4736-4744 (Pubitemid 28492049)
30. Piao HZ, Choi IY, Park JS, Kim HS, Cheong JH, Son KH, Jeon SJ, Ko KH, Kim WK (2008) Wogonin inhibits microglial cell migration via suppression of nuclear factor-kappa b activity. Int Immunopharmacol 8:1658-1662
31. Sparkman NL, Buchanan JB, Heyen JR, Chen J, Beverly JL, Johnson RW (2006) Interleukin-6 facilitates lipopolysaccharide-induced disruption in working memory and expression of other proinflammatory cytokines in hippocampal neuronal cell layers. J Neurosci 26:10709-10716
32. Chakrabarty P, Jansen-West K, Beccard A, Ceballos-Diaz C, Levites Y, Verbeeck C, Zubair AC, Dickson D, Golde TE, Das P (2010) Massive gliosis induced by interleukin-6 suppresses a beta deposition in vivo: evidence against inflammation as a driving force for amyloid deposition. FASEB J 24:548-559
33. Chakrabarty P, Herring A, Ceballos-Diaz C, Das P, Golde TE (2011) Hippocampal expression of murine tnfalpha results in attenuation of amyloid deposition in vivo. Mol Neurodegener 6:16
34. Weitz TM, Town T (2012) Microglia in alzheimer's disease: it's all about context. Int J Alzheimers Dis 2012:314185
35. Jimenez S, Baglietto-Vargas D, Caballero C, Moreno-Gonzalez I, Torres M, Sanchez-Varo R, Ruano D, Vizuete M, Gutierrez A, Vitorica J (2008) Inflammatory response in the hippocampus of ps1m146 l/app 751sl mouse model of alzheimer's disease: age-dependent switch in the microglial phenotype from alternative to classic. J Neurosci 28:11650-11661
36. Meda L, Cassatella MA, Szendrei GI, Otvos L Jr, Baron P, Villalba M, Ferrari D, Rossi F (1995) Activation of microglial cells by beta-amyloid protein and interferon-gamma. Nature 374:647-650