Characterisation of Nox4 Inhibitors from Edible Plants

Planta Medica

Volumn 79, Issue 3-4, 2013, Pages 244-252

  Kofler, Philipp A ^a   Pircher, Haymo ^a   Von Grafenstein, Susanne ^a   Diener, Thomas ^a   Höll, Monika ^a,b   Liedl, Klaus R ^b   Siems, Karsten ^c   Jansen Dürr, Pidder ^a,b  

^a UNIVERSITY OF INNSBRUCK   (Austria)

^b INNSBRUCK MEDICAL UNIVERSITY   (Austria)

^c ANALYTICON DISCOVERY GMBH   (Germany)

Author keywords

broken cell assay; dehydrogenase domain; inhibitors; NADPH oxidase 4; Nox4; ROS

Indexed keywords

ACD 005; ACD 018; ACD 042; ACD 047; ACD 053; ACD 055; ACD 056; ACD 063; ACD 066; ACD 067; ACD 069; ACD 084; ACD 174; ACD 176; ACD 212; HONOKIOL; MAGNOLOL; OXIDOREDUCTASE INHIBITOR; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE 2; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE 4; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE 4 INHIBITOR; UNCLASSIFIED DRUG; VAS 2870;

ARTICLE; CELL ASSAY; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFICACY; DRUG IDENTIFICATION; DRUG SCREENING; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HUMAN CELL; PIPER SARMENTOSUM;

CELL MEMBRANE; CELLS, CULTURED; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; HUMANS; LUMINESCENT MEASUREMENTS; MEMBRANE GLYCOPROTEINS; MEMBRANE PROTEINS; MOLECULAR STRUCTURE; NADPH OXIDASE; PLANTS, EDIBLE; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFECTION;

EID: 84874942461     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0032-1328129     Document Type: Article

References (53)

1. Perry B. N., Govindarajan B., Bhandarkar S. S., Knaus U. G., Valo M., Sturk C., Carrillo C. O., Sohn A., Cerimele F., Dumont D., Losken A., Williams J., Brown L. F., Tan X. L., Ioffe E., Yancopoulos G. D., Arbiser J. L. Pharmacologic blockade of angiopoietin-2 is efficacious against model hemangiomas in mice. J Invest Dermatol: 2006; 126 2316 2322 (Pubitemid 44413180)
2. Lambeth J. D. Nox enzymes and the biology of reactive oxygen. Nat Rev Immunol: 2004; 4 181 189 (Pubitemid 38339084)
3. Lambeth J. D., Krause K. H., Clark R. A. NOX enzymes as novel targets for drug development. Sem Immunopathol: 2008; 30 339 363
4. Geiszt M. NADPH oxidases: New kids on the block. Cardiovasc Res: 2006; 71 289 299
5. Martyn K. D., Frederick L. M., von Loehneysen K., Dinauer M. C., Knaus U. G. Functional analysis of Nox4 reveals unique characteristics compared to other NADPH oxidases. Cell Signal: 2006; 18 69 82 (Pubitemid 41415716)
6. Luo Z., Chen Y., Chen S., Welch W. J., Andresen B. T., Jose P. A., Wilcox C. S. Comparison of inhibitors of superoxide generation in vascular smooth muscle cells. Br J Pharmacol: 2009; 157 935 943
7. Bedard K., Krause K. H. The NOX family of ROS-generating NADPH oxidases: Physiology and pathophysiology. Physiol Rev: 2007; 87 245 313 (Pubitemid 46209993)
8. Royerpokora B., Kunkel L. M., Monaco A. P., Goff S. C., Newburger P. E., Baehner R. L., Cole F. S., Curnutte J. T., Orkin S. H. Cloning the gene for an inherited human disorder - chronic granulomatous-disease - on the basis of its chromosomal location. Nature: 1986; 322 32 38 (Pubitemid 16061506)
9. Krause K. H. Tissue distribution and putative physiological function of NOX family NADPH oxidases. Jpn J Infect Dis: 2004; 57 S28 29
10. Chen K., Craige S. E., Keaney J. F. Jr. Downstream targets and intracellular compartmentalization in Nox signaling. Antiox Redox Signal: 2009; 11 2467 2480
11. Geiszt M., Kopp J. B., Varnai P., Leto T. L. Identification of Renox, an NAD(P)H oxidase in kidney. Proc Natl Acad Sci USA: 2000; 97 8010 8014 (Pubitemid 30460764)
12. Ago T., Kitazono T., Ooboshi H., Iyama T., Han Y. H., Takada J., Wakisaka M., Ibayashi S., Utsumi H., Iida M. Nox4 as the major catalytic component of an endothelial NAD(P)H oxidase. Circulation: 2004; 109 227 233 (Pubitemid 38114144)
13. Yang S., Madyastha P., Bingel S., Ries W., Key L. A new superoxide-generating oxidase in murine osteoclasts. J Biol Chem: 2001; 276 5452 5458
14. Ellmark S. H., Dusting G. J., Fui M. N., Guzzo-Pernell N., Drummond G. R. The contribution of Nox4 to NADPH oxidase activity in mouse vascular smooth muscle. Cardiovasc Res: 2005; 65 495 504 (Pubitemid 40082491)
15. Cucoranu I., Clempus R., Dikalova A., Phelan P. J., Ariyan S., Dikalov S., Sorescu D. NAD(P)H oxidase 4 mediates transforming growth factor-beta1-induced differentiation of cardiac fibroblasts into myofibroblasts. Circ Res: 2005; 97 900 907 (Pubitemid 41552675)
16. Gorin Y., Ricono J. M., Kim N. H., Bhandari B., Choudhury G. G., Abboud H. E. Nox4 mediates angiotensin II-induced activation of Akt/protein kinase B in mesangial cells. Am J Physiol Renal Physiol: 2003; 285 F219 229 (Pubitemid 36871194)
17. Mahadev K., Motoshima H., Wu X., Ruddy J. M., Arnold R. S., Cheng G., Lambeth J. D., Goldstein B. J. The NAD(P)H oxidase homolog Nox4 modulates insulin-stimulated generation of H2O2 and plays an integral role in insulin signal transduction. Mol Cell Biol: 2004; 24 1844 1854 (Pubitemid 38248927)
18. Li J., Stouffs M., Serrander L., Banfi B., Bettiol E., Charnay Y., Steger K., Krause K. H., Jaconi M. E. The NADPH oxidase NOX4 drives cardiac differentiation: Role in regulating cardiac transcription factors and MAP kinase activation. Mol Biol Cell: 2006; 17 3978 3988 (Pubitemid 44330881)
19. Uchizono Y., Takeya R., Iwase M., Sasaki N., Oku M., Imoto H., Iida M., Sumimoto H. Expression of isoforms of NADPH oxidase components in rat pancreatic islets. Life Sci: 2006; 80 133 139 (Pubitemid 44853977)
20. Serrander L., Cartier L., Bedard K., Banfi B., Lardy B., Plastre O., Sienkiewicz A., Forro L., Schlegel W., Krause K. H. NOX4 activity is determined by mRNA levels and reveals a unique pattern of ROS generation. Biochem J: 2007; 406 105 114 (Pubitemid 47264740)
21. Sampson N., Koziel R., Zenzmaier C., Bubendorf L., Plas E., Jansen-Durr P., Berger P. ROS signaling by NOX4 drives fibroblast-to-myofibroblast differentiation in the diseased prostatic stroma. Mol Endocrinol: 2011; 25 503 515
22. Schroder K., Zhang M., Benkhoff S., Mieth A., Pliquett R., Kosowski J., Kruse C., Luedike P., Michaelis U. R., Weissmann N., Dimmeler S., Shah A. M., Brandes R. P. Nox4 is a protective reactive oxygen species generating vascular NADPH oxidase. Circ Res: 2012; 110 1217 1225
23. Li Y., Mouche S., Sajic T., Veyrat-Durebex C., Supale R., Pierroz D., Ferrari S., Negro F., Hasler U., Feraille E., Moll S., Meda P., Deffert C., Montet X., Krause K. H., Szanto I. Deficiency in the NADPH oxidase 4 predisposes towards diet-induced obesity. Int J Obes (Lond): 2012; 36 1503 1513
24. Laleu B., Gaggini F., Orchard M., Fioraso-Cartier L., Cagnon L., Houngninou-Molango S., Gradia A., Duboux G., Merlot C., Heitz F., Szyndralewiez C., Page P. First in class, potent, and orally bioavailable NADPH oxidase isoform 4 (Nox4) inhibitors for the treatment of idiopathic pulmonary fibrosis. J Med Chem: 2010; 53 7715 7730
25. Jaquet V., Scapozza L., Clark R. A., Krause K-H, Lambeth J. D. Small-molecule NOX inhibitors: ROS-generating NADPH oxidases as therapeutic targets. Antiox Redox Signal: 2009; 11 2535 2552
26. Ugusman A., Zakaria Z., Hui C. K., Nordin N. A. Piper sarmentosum inhibits ICAM-1 and Nox4 gene expression in oxidative stress-induced human umbilical vein endothelial cells. BMC Complement Alternat Med: 2011; 11 31
27. Jaquet V., Marcoux J., Forest E., Leidal K. G., McCormick S., Westermaier Y., Perozzo R., Plastre O., Fioraso-Cartier L., Diebold B., Scapozza L., Nauseef W. M., Fieschi F., Krause K. H., Bedard K. NADPH oxidase (NOX) isoforms are inhibited by celastrol with a dual mode of action. Br J Pharmacol: 2011; 164 507 520
28. Jiang J. X., Chen X., Serizawa N., Szyndralewiez C., Page P., Schroder K., Brandes R. P., Devaraj S., Torok N. J. Liver fibrosis and hepatocyte apoptosis are attenuated by GKT137831, a novel NOX4/NOX1 inhibitor in vivo. Free Radic Biol Med: 2012; 53 289 296
29. Doussiere J., Gaillard J., Vignais P. V. The heme component of the neutrophil NADPH oxidase complex is a target for aryliodonium compounds. Biochemistry: 1999; 38 3694 3703
30. ODonnell B. V., Tew D. G., Jones O. T., England P. J. Studies on the inhibitory mechanism of iodonium compounds with special reference to neutrophil NADPH oxidase. Biochem J: 1993; 290 41 49 (Pubitemid 23081198)
31. Kim J. A., Neupane G. P., Lee E. S., Jeong B. S., Park B. C., Thapa P. NADPH oxidase inhibitors: a patent review. Expert Opin Ther Pat: 2011; 21 1147 1158
32. Borbely G., Szabadkai I., Horvath Z., Marko P., Varga Z., Breza N., Baska F., Vantus T., Huszar M., Geiszt M., Hunyady L., Buday L., Orfi L., Keri G. Small-molecule inhibitors of NADPH oxidase 4. J Med Chem: 2010; 53 6758 6762
33. Wind S., Beuerlein K., Eucker T., Muller H., Scheurer P., Armitage M. E., Ho H., Schmidt H., Wingler K. Comparative pharmacology of chemically distinct NADPH oxidase inhibitors. Br J Pharmacol: 2010; 161 885 898
34. Gaggini F., Laleu B., Orchard M., Fioraso-Cartier L., Cagnon L., Houngninou-Molango S., Gradia A., Duboux G., Merlot C., Heitz F., Szyndralewiez C., Page P. Design, synthesis and biological activity of original pyrazolo-pyrido-diazepine, -pyrazine and -oxazine dione derivatives as novel dual Nox4/Nox1 inhibitors. Bioorg Med Chem: 2011; 19 6989 6999
35. Borbely G., Huszar M., Varga A., Futosi K., Mocsai A., Orfi L., Idei M., Mandl J., Keri G., Vantus T. Optimization of important early ADME(T) parameters of NADPH oxidase-4 inhibitor molecules. Med Chem: 2012; 8 174 181
36. Lener B., Koziel R., Pircher H., Hutter E., Greussing R., Herndler-Brandstetter D., Hermann M., Unterluggauer H., Jansen-Durr P. The NADPH oxidase Nox4 restricts the replicative lifespan of human endothelial cells. Biochem J: 2009; 423 363 374
37. Stockl P., Hutter E., Zwerschke W., Jansen-Durr P. Sustained inhibition of oxidative phosphorylation impairs cell proliferation and induces premature senescence in human fibroblasts. Exp Gerontol: 2006; 41 674 682 (Pubitemid 43866356)
38. Caldwell S. E., McCall C. E., Hendricks C. L., Leone P. A., Bass D. A., McPhail L. C. Coregulation of NADPH oxidase activation and phosphorylation of a 48-kD protein(s) by a cytosolic factor defective in autosomal recessive chronic granulomatous disease. J Clin Invest: 1988; 81 1485 1496
39. Grant J. A., Gallardo M., Pickup B. A fast method of molecular shape comparison: A simple application of a Gaussian description of molecular shape. J Computat Chem: 1996; 17 1653 1666 (Pubitemid 126535414)
40. Mills J. E., Dean P. M. Three-dimensional hydrogen-bond geometry and probability information from a crystal survey. J Comput Aided Mol Des: 1996; 10 607 622 (Pubitemid 126712453)
41. Stielow C., Catar R. A., Muller G., Wingler K., Scheurer P., Schmidt H. H., Morawietz H. Novel Nox inhibitor of oxLDL-induced reactive oxygen species formation in human endothelial cells. Biochem Biophys Res Commun: 2006; 344 200 205
42. ten Freyhaus H., Huntgeburth M., Wingler K., Schnitker J., Baumer A. T., Vantler M., Bekhite M. M., Wartenberg M., Sauer H., Rosenkranz S. Novel Nox inhibitor VAS2870 attenuates PDGF-dependent smooth muscle cell chemotaxis, but not proliferation. Cardiovasc Res: 2006; 71 331 341
43. Stefanska J., Pawliczak R. Apocynin: molecular aptitudes. Mediators Inflamm: 2008; 10.1155/2008/106507
44. Liou K. T., Shen Y. C., Chen C. F., Tsao C. M., Tsai S. K. The anti-inflammatory effect of honokiol on neutrophils: mechanisms in the inhibition of reactive oxygen species production. Eur J Pharmacol: 2003; 475 19 27
45. Banfi B., Tirone F., Durussel I., Knisz J., Moskwa P., Molnar G. Z., Krause K. H., Cox J. A. Mechanism of Ca2+ activation of the NADPH oxidase 5 (NOX5). J Biol Chem: 2004; 279 18583 18591 (Pubitemid 38623279)
46. Foti M. C., Amorati R. Non-phenolic radical-trapping antioxidants. J Pharm Pharmacol: 2009; 61 1435 1448
47. Fato R., Bergamini C., Bortolus M., Maniero A. L., Leoni S., Ohnishi T., Lenaz G. Differential effects of mitochondrial complex I inhibitors on production of reactive oxygen species. Biochim Biophys Acta: 2009; 1787 384 392
48. Helmcke I., Heumuller S., Tikkanen R., Schroder K., Brandes R. P. Identification of structural elements in Nox1 and Nox4 controlling localization and activity. Antiox Redox Signal: 2009; 11 1279 1287
49. Lyle A. N., Deshpande N. N., Taniyama Y., Seidel-Rogol B., Pounkova L., Du P., Papaharalambus C., Lassegue B., Griendling K. K. Poldip2, a novel regulator of Nox4 and cytoskeletal integrity in vascular smooth muscle cells. Circ Res: 2009; 105 249 259
50. Zhang L., Nguyen M. V., Lardy B., Jesaitis A. J., Grichine A., Rousset F., Talbot M., Paclet M. H., Qian G., Morel F. New insight into the Nox4 subcellular localization in HEK293 cells: first monoclonal antibodies against Nox4. Biochimie: 2011; 93 457 468
51. Nisimoto Y., Jackson H. M., Ogawa H., Kawahara T., Lambeth J. D. Constitutive NADPH-dependent electron transferase activity of the Nox4 dehydrogenase domain. Biochemistry: 2010; 49 2433 2442
52. Kleinschnitz C., Grund H., Wingler K., Armitage M. E., Jones E., Mittal M., Barit D., Schwarz T., Geis C., Kraft P., Barthel K., Schuhmann M. K., Herrmann A. M., Meuth S. G., Stoll G., Meurer S., Schrewe A., Becker L., Gailus-Durner V., Fuchs H., Klopstock T., de Angelis M. H., Jandeleit-Dahm K., Shah A. M., Weissmann N., Schmidt H. H. Post-stroke inhibition of induced NADPH oxidase type 4 prevents oxidative stress and neurodegeneration. PLoS Biol: 2010; 8 e1000479
53. Lipinski C. A., Lombardo F., Dominy B. W., Feeney P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev: 2001; 46 3 26 (Pubitemid 33653411)