User menu

Naphthoquinone Derivatives Exert Their Antitrypanosomal Activity via a Multi-Target Mechanism.

Bibliographic reference Pieretti, Simone ; Haanstra, Jurgen R ; Mazet, Muriel ; Perozzo, Remo ; Bergamini, Christian ; et. al. Naphthoquinone Derivatives Exert Their Antitrypanosomal Activity via a Multi-Target Mechanism.. In: PLoS Neglected Tropical Diseases, Vol. 7, no.1, p. e2012 (2013)
Permanent URL http://hdl.handle.net/2078/122558
  1. Yamey G., The world's most neglected diseases, 10.1136/bmj.325.7357.176
  2. Barrett Michael P, Burchmore Richard JS, Stich August, Lazzari Julio O, Frasch Alberto Carlos, Cazzulo Juan José, Krishna Sanjeev, The trypanosomiases, 10.1016/s0140-6736(03)14694-6
  3. Fèvre Eric M., Wissmann Beatrix v., Welburn Susan C., Lutumba Pascal, The Burden of Human African Trypanosomiasis, 10.1371/journal.pntd.0000333
  4. Stuart Ken, Brun Reto, Croft Simon, Fairlamb Alan, Gürtler Ricardo E., McKerrow Jim, Reed Steve, Tarleton Rick, Kinetoplastids: related protozoan pathogens, different diseases, 10.1172/jci33945
  5. Brun Reto, Blum Johannes, Chappuis Francois, Burri Christian, Human African trypanosomiasis, 10.1016/s0140-6736(09)60829-1
  6. Hotez Peter J., Molyneux David H., Fenwick Alan, Kumaresan Jacob, Sachs Sonia Ehrlich, Sachs Jeffrey D., Savioli Lorenzo, Control of Neglected Tropical Diseases, 10.1056/nejmra064142
  7. Collins M. H., Craft J. M., Bustamante J. M., Tarleton R. L., Oral Exposure to Trypanosoma cruzi Elicits a Systemic CD8+ T Cell Response and Protection against Heterotopic Challenge, 10.1128/iai.01080-10
  8. Castillo E., A. Dea-Ayuela M., Bolas-Fernandez F., Rangel M., E. Gonzalez-Rosende M., The Kinetoplastid Chemotherapy Revisited: Current Drugs, Recent Advances and Future Perspectives, 10.2174/092986710793205345
  9. Pink Richard, Hudson Alan, Mouriès Marie-Annick, Bendig Mary, Opportunities and Challenges in Antiparasitic Drug Discovery, 10.1038/nrd1824
  10. Renslo Adam R, McKerrow James H, Drug discovery and development for neglected parasitic diseases, 10.1038/nchembio837
  11. Priotto Gerardo, Kasparian Serena, Mutombo Wilfried, Ngouama Daniel, Ghorashian Sara, Arnold Ute, Ghabri Salah, Baudin Elisabeth, Buard Vincent, Kazadi-Kyanza Serge, Ilunga Médard, Mutangala Willy, Pohlig Gabriele, Schmid Caecilia, Karunakara Unni, Torreele Els, Kande Victor, Nifurtimox-eflornithine combination therapy for second-stage African Trypanosoma brucei gambiense trypanosomiasis: a multicentre, randomised, phase III, non-inferiority trial, 10.1016/s0140-6736(09)61117-x
  12. Cavalli Andrea, Bolognesi Maria Laura, Neglected Tropical Diseases: Multi-Target-Directed Ligands in the Search for Novel Lead Candidates againstTrypanosomaandLeishmania, 10.1021/jm9004835
  13. Cavalli Andrea, Lizzi Federica, Bongarzone Salvatore, Belluti Federica, Piazzi Lorna, Bolognesi Maria Laura, Complementary medicinal chemistry-driven strategies toward new antitrypanosomal and antileishmanial lead drug candidates, 10.1111/j.1574-695x.2009.00615.x
  14. E Jenwitheesuk, JAMA, 294, 1490 (2005)
  15. Laura Bolognesi Maria, Multi-Target-Directed Ligands as Innovative Tools to Combat Trypanosomatid Diseases, 10.2174/156802611798184391
  16. Kayser O., Kiderlen A. F., Croft S. L., Natural products as antiparasitic drugs, 10.1007/s00436-002-0768-3
  17. Ventura Pinto Antônio, Lisboa de Castro Solange, The Trypanocidal Activity of Naphthoquinones: A Review, 10.3390/molecules14114570
  18. O. Salas Cristian, Faundez Mario, Morello Antonio, Diego Maya Juan, A. Tapia Ricardo, Natural and Synthetic Naphthoquinones Active Against Trypanosoma Cruzi: An Initial Step Towards New Drugs for Chagas Disease, 10.2174/092986711793979779
  19. K Krohn, 145 (2007)
  20. Wink M (2008) Ecological Roles of Alkaloids In: Fattorusso E, Taglialatela-Scafati O, editors. Modern Alkaloids: Wiley-VCH Verlag GmbH & Co. KGaA. pp. 1–24.
  21. Monks Terrence J., Hanzlik Robert P., Cohen Gerald M., Ross David, Graham Doyle G., Quinone chemistry and toxicity, 10.1016/0041-008x(92)90273-u
  22. Wu Hai-Qiang, Huang Zhi-Shu, Bu Xian-Zhang, Shen Yu-Dong, Zhang Zhu-Lin, Xie Bing-Fen, Liu Zong-Chao, Gu Lian-Quan, Chan Albert S.C., The molecular mechanisms involved in the cytotoxicity of alkannin derivatives, 10.1016/j.ejmech.2005.05.004
  23. Turrens Julio F., Oxidative stress and antioxidant defenses: a target for the treatment of diseases caused by parasitic protozoa, 10.1016/j.mam.2004.02.021
  24. Bolognesi Maria Laura, Lizzi Federica, Perozzo Remo, Brun Reto, Cavalli Andrea, Synthesis of a small library of 2-phenoxy-1,4-naphthoquinone and 2-phenoxy-1,4-anthraquinone derivatives bearing anti-trypanosomal and anti-leishmanial activity, 10.1016/j.bmcl.2008.03.009
  25. Nwaka Solomon, Hudson Alan, Innovative lead discovery strategies for tropical diseases, 10.1038/nrd2144
  26. Kuettel Sabine, Mosimann Marc, Mäser Pascal, Kaiser Marcel, Brun Reto, Scapozza Leonardo, Perozzo Remo, Adenosine Kinase of T. b. rhodesiense Identified as the Putative Target of 4-[5-(4-phenoxyphenyl)-2H-pyrazol-3-yl]morpholine Using Chemical Proteomics, 10.1371/journal.pntd.0000506
  27. Králová Ivica, Rigden Daniel J., Opperdoes Fred R., Michels Paul A. M., Glycerol kinase of Trypanosoma brucei : Cloning, molecular characterization and mutagenesis, 10.1046/j.1432-1327.2000.01238.x
  28. Schelling Pierre, Folkers Gerd, Scapozza Leonardo, A Spectrophotometric Assay for Quantitative Determination of kcat of Herpes Simplex Virus Type 1 Thymidine Kinase Substrates, 10.1006/abio.2001.5191
  29. Hannaert V., Opperdoes F.R., Michels P.A.M., Glycosomal Glyceraldehyde-3-phosphate Dehydrogenase of Trypanosoma brucei and Trypanosoma cruzi: Expression in Escherichia coli, Purification, and Characterization of the Enzymes, 10.1006/prep.1995.1031
  30. Albert Marie-Astrid, Haanstra Jurgen R., Hannaert Véronique, Van Roy Joris, Opperdoes Fred R., Bakker Barbara M., Michels Paul A. M., Experimental andin SilicoAnalyses of Glycolytic Flux Control in Bloodstream FormTrypanosoma brucei, 10.1074/jbc.m502403200
  31. Olivier B. G., Rohwer J. M., Hofmeyr J.-H. S., Modelling cellular systems with PySCeS, 10.1093/bioinformatics/bti046
  32. Bergmeyer HU (1974) Methods of enzymatic analysis. New York: Academic Press.
  33. de Duve Christian, Principles of tissue fractionation, 10.1016/0022-5193(64)90065-7
  34. Biebinger Susanne, Elizabeth Wirtz L., Lorenz Patrick, Christine Clayton, Vectors for inducible expression of toxic gene products in bloodstream and procyclic Trypanosoma brucei, 10.1016/s0166-6851(96)02815-0
  35. R Brun, Acta Trop, 36, 289 (1979)
  36. Lamour N., Riviere L., Coustou V., Coombs G. H., Barrett M. P., Bringaud F., Proline Metabolism in Procyclic Trypanosoma brucei Is Down-regulated in the Presence of Glucose, 10.1074/jbc.m414274200
  37. Orhan I., Sener B., Atıcı T., Brun R., Perozzo R., Tasdemir D., Turkish freshwater and marine macrophyte extracts show in vitro antiprotozoal activity and inhibit FabI, a key enzyme of Plasmodium falciparum fatty acid biosynthesis, 10.1016/j.phymed.2005.10.010
  38. Brun R., Lun Z.-R., Drug sensitivity of Chinese Trypanosoma evansi and Trypanosoma equiperdum isolates, 10.1016/0304-4017(94)90033-7
  39. Räz B, Iten M, Grether-Bühler Y, Kaminsky R, Brun R, The Alamar Blue® assay to determine drug sensitivity of African trypanosomes (T.b. rhodesiense and T.b. gambiense) in vitro, 10.1016/s0001-706x(97)00079-x
  40. Vellieux F. M., Hajdu J., Verlinde C. L., Groendijk H., Read R. J., Greenhough T. J., Campbell J. W., Kalk K. H., Littlechild J. A., Watson H. C., Structure of glycosomal glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma brucei determined from Laue data., 10.1073/pnas.90.6.2355
  41. Nemethy George, Gibson Kenneth D., Palmer Kathleen A., Yoon Chang No., Paterlini Germana, Zagari Adriana, Rumsey Shirley, Scheraga Harold A., Energy parameters in polypeptides. 10. Improved geometrical parameters and nonbonded interactions for use in the ECEPP/3 algorithm, with application to proline-containing peptides, 10.1021/j100194a068
  42. Halgren Thomas A., 10.1002/(sici)1096-987x(199604)17:6<490::aid-jcc1>3.3.co;2-v
  43. Abagyan Ruben, Totrov Maxim, Kuznetsov Dmitry, ICM?A new method for protein modeling and design: Applications to docking and structure prediction from the distorted native conformation, 10.1002/jcc.540150503
  44. Totrov Maxim, Abagyan Ruben, Flexible protein–ligand docking by global energy optimization in internal coordinates, 10.1002/(sici)1097-0134(1997)1+<215::aid-prot29>3.0.co;2-q
  45. Totrov M, Abagyan R (2001) Protein-ligand docking as an energy optimization problem. In: Raffa RB, editor. Drug-receptor thermodynamics: Introduction and applications. 1st ed. New York, NY: John Wiley & Sons. pp. 603–624.
  46. Lomenick Brett, Olsen Richard W., Huang Jing, Identification of Direct Protein Targets of Small Molecules, 10.1021/cb100294v
  47. Sato Shin-ichi, Murata Asako, Shirakawa Takashi, Uesugi Motonari, Biochemical Target Isolation for Novices: Affinity-Based Strategies, 10.1016/j.chembiol.2010.05.015
  48. Shiyama Takaaki, Furuya Minoru, Yamazaki Akira, Terada Tomohiro, Tanaka Akito, Design and synthesis of novel hydrophilic spacers for the reduction of nonspecific binding proteins on affinity resins, 10.1016/j.bmc.2004.03.052
  49. Mercer Luke, Bowling Tana, Perales Joe, Freeman Jennifer, Nguyen Tien, Bacchi Cyrus, Yarlett Nigel, Don Robert, Jacobs Robert, Nare Bakela, 2,4-Diaminopyrimidines as Potent Inhibitors of Trypanosoma brucei and Identification of Molecular Targets by a Chemical Proteomics Approach, 10.1371/journal.pntd.0000956
  50. Haanstra Jurgen R., Kerkhoven Eduard J., van Tuijl Arjen, Blits Marjolein, Wurst Martin, van Nuland Rick, Albert Marie-Astrid, Michels Paul A. M., Bouwman Jildau, Clayton Christine, Westerhoff Hans V., Bakker Barbara M., A domino effect in drug action: from metabolic assault towards parasite differentiation : Network-based drug target selection in T. brucei, 10.1111/j.1365-2958.2010.07435.x
  51. Copeland Robert A., Enzymes, ISBN:0471359297, 10.1002/0471220639
  52. RA Copeland, Methods Biochem Anal, 46, 1 (2005)
  53. Wissner Allan, Floyd M. Brawner, Johnson Bernard D., Fraser Heidi, Ingalls Charles, Nittoli Thomas, Dushin Russell G., Discafani Carolyn, Nilakantan Ramaswamy, Marini Joseph, Ravi Malini, Cheung Kinwang, Tan Xingzhi, Musto Sylvia, Annable Tami, Siegel Marshall M., Loganzo Frank, 2-(Quinazolin-4-ylamino)-[1,4]benzoquinones as Covalent-Binding, Irreversible Inhibitors of the Kinase Domain of Vascular Endothelial Growth Factor Receptor-2, 10.1021/jm050559f
  54. Tisdale Ellen J., Kelly Carmen, Artalejo Cristina R., Glyceraldehyde-3-phosphate Dehydrogenase Interacts with Rab2 and Plays an Essential Role in Endoplasmic Reticulum to Golgi Transport Exclusive of Its Glycolytic Activity, 10.1074/jbc.m409472200
  55. Menna-Barreto Rubem F.S., Goncalves Renata L.S., Costa Elaine M., Silva Raphael S.F., Pinto Antonio V., Oliveira Marcus F., de Castro Solange L., The effects on Trypanosoma cruzi of novel synthetic naphthoquinones are mediated by mitochondrial dysfunction, 10.1016/j.freeradbiomed.2009.06.004
  56. Cordeiro Artur T., Thiemann Otavio H., Michels Paul A.M., Inhibition of Trypanosoma brucei glucose-6-phosphate dehydrogenase by human steroids and their effects on the viability of cultured parasites, 10.1016/j.bmc.2009.01.068
  57. S Gupta, Mol Biochem Parasitol (2011)
  58. H. Gilbert Ian, Leroy Didier, A. Frearson Julie, Finding New Hits in Neglected Disease Projects: Target or Phenotypic Based Screening?, 10.2174/156802611795429176
  59. Jeffery Douglas A, Bogyo Matthew, Chemical proteomics and its application to drug discovery, 10.1016/s0958-1669(02)00010-1
  60. Terstappen Georg C., Schlüpen Christina, Raggiaschi Roberto, Gaviraghi Giovanni, Target deconvolution strategies in drug discovery, 10.1038/nrd2410
  61. Guiffant Damien, Tribouillard Déborah, Gug Fabienne, Galons Hervé, Meijer Laurent, Blondel Marc, Bach Stéphane, Identification of intracellular targets of small molecular weight chemical compounds using affinity chromatography, 10.1002/biot.200600223
  62. Verlinde Christophe L.M.J., Hannaert Véronique, Blonski Casimir, Willson Michèle, Périé Jacques J., Fothergill-Gilmore Linda A., Opperdoes Fred R., Gelb Michael H., Hol Wim G.J., Michels Paul A.M., Glycolysis as a target for the design of new anti-trypanosome drugs, 10.1054/drup.2000.0177
  63. Morello Antonio, Pavani Mario, Garbarino Juan A., Chamy maría C., Frey Cristián, Mancilla Jerson, Guerrero aníbal, Repetto Yolanda, Ferreira Jorge, Effects and mode of action of 1,4-naphthoquinones isolated from Calceolaria sessilis on tumoral cells and Trypanosoma parasites, 10.1016/0742-8413(95)02003-9
  64. Boveris Alberto, Stoppani Andrés O.M., Docampo Roberto, Cruz Fernando S., Superoxide anion production and trypanocidal action of naphthoquinones on Trypanosoma cruzi, 10.1016/0306-4492(78)90063-1
  65. Fato Romana, Bergamini Christian, Leoni Serena, Lenaz Giorgio, Mitochondrial production of reactive oxygen species: Role of Complex I and quinone analogues, 10.1002/biof.5520320105