Piperidones with activity against Plasmodium falciparum

Parasitology Research

Volumn 99, Issue 3, 2006, Pages 281-286

  Saeftel, Michael ^b   Sarite, Ramadan Salem ^b   Njuguna, Tujo ^b   Holzgrabe, Ulrike ^c   Ulmer, Daniela ^c   Hoerauf, Achim ^b   Kaiser, Annette ^a,b  

^a GERMAN UNIVERSITY IN CAIRO   (Egypt)

^b UNIVERSITY OF BONN   (Germany)

^c UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 PYRIDONE DERIVATIVE; ALKYL GROUP; AMINE; AMINO ACID; ANTIFUNGAL AGENT; ANTIMALARIAL AGENT; CARBOXYLIC ACID DERIVATIVE; CHLOROQUINE; CICLOPIROXOLAMINE; DEOXYHYPUSINE; DEOXYHYPUSINE HYDROXYLASE; DEOXYHYPUSINE SYNTHASE; INITIATION FACTOR 5A; LYSINE; MIMOSINE; OXYGENASE; PIPERIDONE DERIVATIVE; PROTEIN PRECURSOR; SPERMIDINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; GENE ISOLATION; IN VITRO STUDY; MALARIA; MAMMAL CELL; METABOLISM; MOUSE; NONHUMAN; PARASITEMIA; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SURVIVAL RATE; TREATMENT OUTCOME;

ANIMALS; ANTIMALARIALS; DISEASE MODELS, ANIMAL; MALARIA; MICE; MICE, INBRED BALB C; MIMOSINE; MOLECULAR STRUCTURE; PARASITEMIA; PIPERIDONES; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; PYRIDONES;

EUKARYOTA; MAMMALIA; PLASMODIUM FALCIPARUM;

EID: 33745760476     PISSN: 09320113     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00436-006-0173-4     Document Type: Article

References (33)

1. Abbruzzese A, Park MH, Folk JE (1986) Deoxyhypusine hydroxylase from rat testis. Partial purification and characterization. J Biol Chem 261:3085-3089
2. Abbruzzese A, Park MH, Folk JE (1988) Deoxyhypusine hydroxylase from rat testis. Partial purification and characterization. J Biol Chem 261:3085-3089
3. Abbruzzese A, Hanauske-Abel HM, Park MH, Henke S, Folk JE (1991) The active site of deoxyhypusyl hydroxylase: use of catecholpeptides and their component chelator and peptide as molecular probes. Biochim Biophys Acta 1077:159-166
4. Andrus L, Szabo P, Grady RW, Hanauske A-R, Huima-Byron T, Slowinska B, Zagulska S, Hanauske-Abel HM (1998) Antiretroviral effects of deoxyhypusyl hydroxylase inhibitors. Biochem Pharmacol 55:1807-1818
5. Ashauer-Holzgrabe U, Haller R (1986) Zur Umsetzung von N-benzylsubstituierten Piperidoncarbonsäuren mit Cer(IV) sulfat. Arch Pharm 319:1079-1083
6. Burri C, Brun R (2003) Eflornithine for the treatment of human African trypanosomiasis. Parasit Res 90:49-52
7. Clement PM, Hanauske-Abel HM, Wolff EC, Kleinmann HK, Park MH (2002) The antifungal drug ciclopirox inhibits deoxyhypusine and proline hydroxylation, endothelial cell growth and angiogenesis in vitro. Int J Cancer 100:491-498
8. Csonga R, Ettmayer P, Auer M, Eckershorn C, Eder J, Klier H (1996) Evaluation of the metal ion requirement of the human deoxyhypusine hydroxylase from HeLa cells using a novel enzyme assay. FEBS Lett 380:209-214
9. Das Gupta R, Krause-Ihle T, Bergmann B, Muller IB, Khomutov AR, Müller S, Walter RD, Luersen K (2005) 3-Aminooxy-1-aminopropane and derivatives have an antiproliferative effect on cultured Plasmodium falciparum by decreasing intracellular polyamine concentrations. Antimicrob Agents Chemother 49:2857-2864
10. Dong Z, Arnold R, Yang Y, Park MH, Hrncirova P, Mechref Y, Novotny MV, Zhang JT (2005) Modulation of differentiation-related gene-1 expression by cell cycle blocker mimosine, revealed by proteomic analysis. Mol Cell Proteomics 4:993-1001
11. Gimenez F, Barraud de Lagerie S, Fernandez C, Pino P, Mazier D (2003) Tumor necrosis factor alpha in the pathogenesis of cerebral malaria. Cell Mol Life Sci 8:1623-1635
12. Haider N, Eschbach ML, Dias Sde S, Gilberger TW, Walter RD, Luersen K (2005) The spermidine synthase of the malaria parasite Plasmodium falciparum: molecular and biochemical characterization of the polyamine synthesis enzyme. Mol Biochem Parasitol 142:224-236
13. Holzgrabe U, Piening B, Kohlmorgen R, Stoll E (1988) Synthese verschieden substituierter 5-Oxo-2,6-methano-2-benzazocine. Arch Pharm 321:917-920
14. Kaiser A, Gottwald A, Wiersch C, Lindenthal B, Maier W, Seitz HM (2001) Effect of drugs inhibiting spermidine biosynthesis and metabolism on the in vitro development of Plasmodium falciparum. Parasitol Res 87:963-972
15. Kaiser A, Gottwald A, Maier W, Seitz HM (2003) Targeting enzymes involved in spermidine metabolism of parasitic protozoa - a possible new strategy for anti-parasitic treatment. Parasitol Res 91:508-516
16. Kim KK, Hung LW, Yokata H, Kim R, Kim SH (1998) Crystal structures of eukaryotic translation initiation factor 5A from Methanococcus jannaschii at 1.8 Å resolution. Proc Natl Acad Sci 95:10419-10424
17. Kwiatkowski D, Molyneux ME, Stephens S, Curtis N, Klein N, Pointaire P, Smit M, Allan R, Brewster DR, Grau GE et al (1993) Anti-TNF therapy inhibits fever in cerebral malaria. Q J Med 86:91-98
18. Lee YB, Folk JE (1998) Branched-chain and unsaturated 1,7-diaminoheptane derivatives as deoxyhypusine synthase inhibitors. Bioorg Med Chem 3:253-270
19. Lucas R, Juillard P, Decoster R, Redard M, Burkard D, Donati Y, Giroud C, Monso-Hinard C, De Kesel T, Buurman WA, Moore MW, Dayer JM, Fiers W, Bluethmann H, Grau GE (1997) Crucial role of tumor necrosis factor (TNF) receptor 2 and membrane-bound TNF in experimental cerebral malaria. Eur J Immunol 27:1719-1725
20. Merz KW, Haller R (1963) Synthesen mit Pyridin-und Chinolinaldehyden. Pharm Acta Helv 38:442-456
21. Moloney MB, Pawluk AR, Ackland NR (1990) Plasmodium falciparum growth in deep culture. Trans R Soc Trop Med Hyg 84:516-518
22. Molitor IM, Knobel S, Dang C, Spielmann T, Allera A, König GM (2004) Translation initiation factor eIF5A from Plasmodium falciparum. Mol Biochem Parasitol 137:65-74
23. Moritz E, Seidensticker S, Gottwald A, Maier W, Hoerauf A, Njuguna TJ, Kaiser A (2004) The efficacy of inhibitors involved in spermidine metabolism in Plasmodium falciparum, Anopheles stephensi and Trypanosoma evansi. Parasitol Res 94:37-48
24. Müller S, Da'dara A, Lüersen K, Wrenger C, Das Gupta R, Madhubala R, Walter RD (2000) In the human malaria parasite Plasmodium falciparum, polyamines are synthesized by a bifunctional ornithine decarboxylase, S-adenosylmethionine decarboxylase. J Biol Chem 275:8097-8102
25. Park MH, Wolff EC (1988) Cell-free synthesis of deoxyhypusine. Separation of protein substrate and enzyme and identification of 1,3-diaminopropane as a product of spermidine cleavage. J Biol Chem 263:15264-15269
26. Park JH, Aravind L, Wolff EC, Kaevel J, Kim YS, Park MH (2006) Molecular cloning, expression, and structural prediction of deoxyhypusine hydroxylase: A HEAT-repeat-containing metalloenzyme. Proc Natl Acad Sci 103:51-56
27. Saeftel M, Krueger A, Arriens S, Heussler V, Racz P, Fleischer B, Brombacher F, Hoerauf A (2004) Mice deficient in interleukin-4 (IL-4) or IL-4 receptor alpha have higher resistance to sporozoite infection with Plasmodium berghei (ANKA) than do naive wild-type mice. Infect Immun 72:322-331
28. Singh S, Puri SK, Singh SK, Srivastava R, Das Gupta RC, Pandey VC (1997) Characterization of simian malarial parasite (Plasmodium knowlesi)-mduced putrescine transport in rhesus monkey erythrocytes. A novel putrescine conjugate arrests in vitro growth of simian malarial parasite (Plasmodium knowlesi) and cures multidrug resistant murine malaria (Plasmodium yoelii) infection in vivo. J Biol Chem 272:13506-13511
29. Sommer MN, Bevec D, Knebel B, Flicke B, Holscher K, Freudenreich T, Hauber I, Hauber J, Mett H (2004) Screening assay for the identification of deoxyhypusine synthase inhibitors. J Biomol Screen 5:434-438
30. Umland TC, Wolff TC, Park MH, Davies DR (2004) A new crystal structure of deoxyhypusine synthase reveals the configuration of the active enzyme and of an enzyme NAD inhibitor ternary complex. J Biol Chem 279:28697-28705
31. Taylor CA, Senchyna M, Flanagan J, Joyce EM, Cliche DO, Boone AN, Culp-Stewart S, Thompson JE (2004) Role of eIF5A in TNF-alpha-mediated apoptosis of lamina cribrosa cells. Invest Ophthalmol Vis Sci 45:3568-3576
32. Trager W, Williams J (1992) Extracellular (axenic) development in vitro of the erythrocytic cycle of Plasmodium falciparum. Proc Nat Acad Sci 89:5351-5355
33. Whitworth JA, Hewitt KA (2005) Effect of malaria on HIV-1 progression and transmission. Lancet 365:1-3