Amphiphilic pyridinium salts block TNFα/NFκB signaling and constitutive hypersecretion of interleukin-8 (IL-8) from cystic fibrosis lung epithelial cells

Biochemical Pharmacology

Volumn 70, Issue 3, 2005, Pages 381-393

  Tchilibon, Susanna ^a   Zhang, Jian ^b   Yang, QingFeng ^b   Eidelman, Ofer ^b   Kim, Haksung ^a   Caohuy, Hung ^b   Jacobson, Kenneth A ^a   Pollard, Bette S ^c   Pollard, Harvey B ^b  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b Uniformed Services University of the Health Sciences and the Walter Reed National Military Medical Center   (United States)

^c US Equal Employment Opportunity Commission   (United States)

Author keywords

AP 1; Cystic fibrosis; Epithelium; Inflammation; Interleukin 8; Lung; NF B

Indexed keywords

8 (3 CARBOXAMIDOPYRIDINIUM)OCTYL ALPHA METHYL 2 [4 (2 METHYLPROPYL)PHENYL] ACETATE IODIDE; 8 (4 PROPYLPYRIDINIUM) OCTYL ALPHA METHYL 2 [4 (2 METHYLPROPYL)PHENYL] ACETATE BROMIDE; 8 (N METHYLMORPHOLINIUM)OCTYL ALPHA METHYL 2 [4 (2 METHYLPROPYL)PHENYL] ACETATE BROMIDE; 8 [4 (2 HYDROXYETHYL)PYRIDINIUM]OCTYL ALPHA METHYL 2 [4 (2 METHYLPROPYL)PHENYL]ACETATE BROMIDE; 8 PYRIDINIUM BUTYL ALPHA METHYL 2 PHENYLACETATE; 8 PYRIDINIUM DECYL ALPHA METHYL 2 PHENYLACETATE; 8 PYRIDINIUM HEXYL ALPHA METHYL 2 PHENYLACETATE; 8 PYRIDINIUM OCTYL 2 [4 (2 METHYLPROPYL)BENZENE]ACETATE BROMIDE; 8 PYRIDINIUM OCTYL 2 BENZYLOXYPROPIONATE IODIDE; 8 PYRIDINIUM OCTYL 2 HYDROXY 3 PHENYLPROPIONATE IODIDE; 8 PYRIDINIUM OCTYL ALPHA ETHYL 2 PHENYLACETATE IODIDE; 8 PYRIDINIUM OCTYL ALPHA HYDROXYMETHYL 2 PHENYLACETATE; 8 PYRIDINIUM OCTYL ALPHA METHOXY 2 PHENYLACETATE IODIDE; 8 PYRIDINIUM OCTYL ALPHA METHYL 2 [4 (2 METHYLPROPYL)PHENYL]ACETATE IODIDE; 8 PYRIDINIUM OCTYL ALPHA METHYL 2 [4 (AMMONIUM TRIFLUOROACETATE)PHENYL] ACETATE IODIDE; 8 PYRIDINIUM OCTYL ALPHA METHYL 2 [4 (N TERT BUTYLOXYCARBONYLAMINO)PHENYL] ACETATE IODIDE; 8 PYRIDINIUM OCTYL ALPHA METHYL 2 PHENYLACETATE; 8 PYRIDINIUM OCTYLBENZOATE IODIDE; 8 PYRIDINIUM OCTYLPROPIONATE IODIDE; I KAPPA B ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INTERLEUKIN 8; MRS 2481; PHENYLPROPIONIC ACID DERIVATIVE; PYRIDINIUM DERIVATIVE; STRESS ACTIVATED PROTEIN KINASE; TRANSCRIPTION FACTOR AP 1; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYSTIC FIBROSIS; CYTOKINE RELEASE; DRUG ACTIVITY; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; LUNG ALVEOLUS EPITHELIUM; ONCOGENE C FOS; PHOSPHORYLATION; PRIORITY JOURNAL; PROMOTER REGION; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

CYSTIC FIBROSIS; DOSE-RESPONSE RELATIONSHIP, DRUG; HELA CELLS; HUMANS; INTERLEUKIN-8; NF-KAPPA B; PYRIDINIUM COMPOUNDS; RESPIRATORY MUCOSA; SALTS; SIGNAL TRANSDUCTION; SURFACE-ACTIVE AGENTS; TUMOR NECROSIS FACTOR-ALPHA;

EID: 21344457045     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2005.05.002     Document Type: Article

References (35)

1. J.M. Pilewski, and R.A. Frizzell Role of CFTR in airway disease Physiol Rev 79 1999 S215 S255
2. Welsh MJ, Ramsey BW, Accurso F, Cutting GR. Cystic fibrosis. In: The metabolic and molecular bases of inherited diseases (Scriver CL, Beaudet AL, Valle D, Sly WS, eds; Childs B, Kinzler KW, Vogelstein B, Assoc Eds) 2001; eighth ed. 5121-5188, McGraw-Hill, New York.
3. T.P. Dean, Y. Dai, J.K. Shute, M.K. Church, and J.O. Warner Interleukin-8 concentrations are elevated in bronchoalveolar lavage, sputum, and sera of children with cystic fibrosis Pediatr Res 34 1993 159 161
4. J.B. Richman-Eisenstat, P.G. Jorens, C.A. Hebert, I. Ueki, and J.A. Nadel Interleukin-8: an important chemoattractant in sputum of patients with chronic inflammatory airway diseases Am J Physiol 264 1993 L413 L418
5. D.S. Armstrong, K. Grimwood, J.B. Carlin, R. Carzino, J.P. Gutierrez, and J. Hull Lower airway inflammation in infants and young children with cystic fibrosis Am J Respir Crit Care Med 156 1997 1197 1204
6. T.Z. Khan, J.S. Wagener, T. Bost, J. Martinez, F.J. Accurso, and D.W. Riches Early pulmonary inflammation in infants with cystic fibrosis Am J Respir Crit Care Med 151 1995 1075 1082
7. E. DiMango, A.J. Ratner, R. Bryan, S. Tabibi, and A. Prince Activation of NF-kappaB by adherent Pseudomonas aeruginosa in normal and cystic fibrosis respiratory epithelial cells J Clin Invest 101 1998 2598 2605
8. T.L. Bonfield, J.R. Panuska, M.W. Konstan, K.A. Hilliard, J.B. Hilliard, and H. Ghnaim Inflammatory cytokines in cystic fibrosis lungs Am J Respir Care Med 152 1995 2111 2118
9. T.L. Bonfield, M.W. Konstan, P. Burfeind, J.R. Panuska, J.B. Hilliard, and M. Berger Normal bronchial epithelial cells constitutively produce the anti-inflammatory cytokine interleukin-10, which is downregulated in cystic fibrosis Am J Respir Cell Mol Biol 13 1995 257 261
10. R. Tirouvanziam, S. de Bentzmann, C. Hubeau, J. Hinnrasky, J. Jacquot, and B. Peault Inflammation and infection in naive human cystic fibrosis airway grafts Am J Respir Cell Mol Biol 23 2000 121 127
11. J.M. Cruse, and R.E. Lewis Illustrated dictionary of immunology 1995 CRC Press Boca Raton Appendix 3
12. K.A. Roebuck Regulation of interleukin-8 gene expression J Interferon Cytokine Res 19 1999 429 438
13. E. Hoffmann, O. Dittrich-Breiholz, H. Holtmann, and M. Kracht Multiple control of interleukin-8 gene expression J Leukoc Biol 72 2002 847 855
14. S.H. Cheng, R.J. Gregory, J. Marshall, D.W. Souza, G.A. White, and C.R. O'Riordan Defective intracellular transport and processing of CFTR is the molecular basis of most cystic fibrosis Cell 63 1990 827 834
15. O. Eidelman, C. Guay-Broder, van Galen PJM, K.A. Jacobson, R.J. Turner, and Z.I. Cabantchik A1-adenosine antagonists activate chloride efflux from cystic fibrosis cells Proc Nat Acad Sci USA 89 1992 5562 5566
16. C. Guay-Broder, K.A. Jacobson, S. BarNoy, Z.I. Cabantchik, W.B. Guggino, and P.L. Zeitlin Al-Receptor antagonist 8-cyclopentyl-1,3-dipropyl-xanthine (CPX) selectively activates chloride efflux from human epithelial and mouse fibroblast cell lines expressing the CFTR (ΔF508) mutation, but not the wild type CFTR Biochemistry 34 1995 9079 9087
17. K.A. Jacobson, C. Guay-Broder, van Galen PJM, C. Gallo-Rodriguez, N. Melman, and M.A. Jacobson Stimulation of alkylxanthines of chloride efflux from CFPAC-1 cells does not involve A1-adenosine receptors Biochemistry 34 1995 9088 9094
18. C.M. Haws, I. Nepomuceno, M.E. Krause, H. Wakelen, T. Law, and Y. Xia ΔF508-CFTR channels: kinetics, activation by forskolin, and potentiation by xanthines Am J Physiol 270 1996 C1544 C1555
19. B.E. Cohen, G. Lee, K.A. Jacobson, Y.-C. Kim, Z. Huang, and E.J. Sorscher CPX (1,3-dipropyl-8-cyclopentyl xanthine) and other alkyl-xanthines differentially bind to the wild type and ΔF508 mutant first nucleotide binding fold (NBF-1) domains of the cystic fibrosis transmembrane conductance regulator (CFTR) Biochemistry 36 1997 6455 6461
20. N. Arispe, J. Ma, K.A. Jacobson, and H.B. Pollard Direct activation of cystic fibrosis transmembrane conductance regulator by 8-cyclopentyl-1,3- dipropylxanthine and 1,3-diallyl-8-cyclohexylxanthine J Biol Chem 273 1998 5724 5734
21. N.A. McCarty, T.A. Standaert, M. Teresi, C. Tuthill, J. Launspach, and T.J. Kelley A phase I randomized, multicenter trial of CPX in adult subjects with mild cystic fibrosis Pediatr Pulmonol 33 2002 90 98
22. O. Eidelman, M. Srivastava, J. Zhang, J. Murthy, E. Heldman, and K.A. Jacobson Genes from the TNFαR/NFκB pathway control the pro-inflammatory state in cystic fibrosis epithelial cells Mol Med 7 2001 523 534
23. M. Srivastava, O. Eidelman, J. Zhang, C. Paweletz, H. Caohuy, and Q-F. Yang Digitoxin mimics CFTR-gene therapy, and suppresses hypersecretion of proinflammatory interleukin-8 (IL-8) from cystic fibrosis lung epithelial cells Proc Nat Acad Sci USA 101 2004 7693 7698
24. M.L. Drumm, D.J. Wilkinson, L.S. Smit, R.T. Worrell, T.V. Strong, and R.A. Frizzell Chloride conductance expressed by ΔF508 and other mutant CFTR's in Xenopus oocytes Science 254 1991 1797 1799
25. T.-C. Hwang, F. Wang, I. Yang, and W.W. Reenstra Genistein potentiates wild-type and ΔF508-CFTR channel activity Am J Physiol 273 1997 C988 C998
26. C. Andersson, Z. Servetnyk, and G.M. Roomans Activation of CFTR by genistein in human airway epithelial cell lines Biochem Biophys Res Commun 308 2003 518 522
27. F. Becq, Y. Mettey, M.A. Gray, L.J. Galietta, R.L. Dormer, and M. Merten Development of substituted Benzo[c]quinolizinium compounds as novel activators of the cystic fibrosis chloride channel J Biol Chem 274 1999 27415 27425
28. R.C. Rubenstein, and P.L. Zeitlin Sodium 4-phenylbutyrate downregulates Hsc70: implications for intracellular trafficking of ΔF508-CFTR Am J Physiol Cell Physiol 278 2000 C259 C267
29. H. Yang, A.A. Shelat, R.K. Guy, V.S. Gopinath, T. Ma, and K. Du Nanomolar affinity small molecule correctors of defective Delta F508-CFTR chloride channel gating J Biol Chem 278 2003 35079 35085
30. M.W. Konstan, P.J. Byard, C.-L. Hoppel, and P.B. Davis Effect of high dose ibuprofen in patients with cystic fibrosis New Eng J Med 332 1995 848 854
31. F.J. Accurso, S.D. Sagel, M.K. Sontag, and J.S. Wegener Anti-inflammatory endpoints in cystic fibrosis (CF): lessons from clinical trials Pediatr Pulmonol S25 2003 104 105
32. P.L. Zeitlin, L. Lu, T.-C. Hwang, J. Rhim, G.R. Cutting, and K.A. Keiffer A cystic fibrosis bronchial epithelial cell line: immortalization by adeno12-SV40 infection Am J Respir Cell Mol Biol 4 1991 313 319
33. T.R. Flotte, S.A. Afione, R. Solow, M.L. Drumm, D. Markakis, and W.B. Guggino Expression of the cystic fibrosis transmembrane conductance regulator from a novel adeno-associated virus promoter J Biol Chem 268 1993 3781 3790
34. Y. Karton, B.J. Bradbury, J. Baumgold, R. Paek, and K.A. Jacobson Functionalized congener approach to muscarinic antagonists: analogues of pirenzepine J Med Chem 34 1991 2133 2145
35. S.K. Davidsen, J.B. Summers, D.H. Albert, J.H. Holms, H.R. Heyman, and T.J. Magoc N-(Acyloxyalkyl)pyridinium salts as soluble prodrugs of a potent platelet activating factor antagonist J Med Chem 37 1994 4423 4429