Parallel synthesis, evaluation, and preliminary structure-activity relationship of 2,5-diamino-1,4-benzoquinones as a novel class of bivalent anti-prion compound

Journal of Medicinal Chemistry

Volumn 53, Issue 22, 2010, Pages 8197-8201

  Bongarzone, Salvatore ^a,b   Tran, Hoang Ngoc Ai ^a   Cavalli, Andrea ^b,c   Roberti, Marinella ^c   Carloni, Paolo ^a,b,d,e   Legname, Giuseppe ^a,c   Bolognesi, Maria Laura ^c  

^a SISSA   (Italy)

^b ISTITUTO ITALIANO DI TECNOLOGIA   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

^d DEMOCRITOS NATIONAL SIMULATION CENTER   (Italy)

^e RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE DERIVATIVE; 6 CHLORO 1,2,3,4 TETRAHYDROACRIDINE; ANTIINFECTIVE AGENT; PRION PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; CELL LINE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; OXIDATIVE STRESS; STRUCTURE ACTIVITY RELATION;

ACRIDINES; AMINES; ANIMALS; BENZOQUINONES; CELL LINE; CELL SURVIVAL; MICE; OXIDATIVE STRESS; PRPSC PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78649507705     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100882t     Document Type: Article

References (33)

1. Caughey, B.; Baron, G. S. Prions and their partners in crime Nature 2006, 443, 803-810
2. Prusiner, S. B. Prions Proc. Nat. Acad. Sci. U. S. A. 1998, 95, 13363-13383
3. Mallucci, G.; Collinge, J. Rational targeting for prion therapeutics Nat. Rev. Neurosci. 2005, 6, 23-34
4. Pamplona, R.; Naudi, A.; Gavin, R.; Pastrana, M. A.; Sajnani, G.; Ilieva, E. V.; del Rio, J. A.; Portero-Otin, M.; Ferrer, I.; Requena, J. R. Increased oxidation, glycoxidation, and lipoxidation of brain proteins in prion disease Free Radical Biol. Med. 2008, 45, 1159-1166
5. Klamt, F.; Dal-Pizzol, F.; da Frota, M. L. C.; Walz, R.; Andrades, M. E.; da Silva, E. G.; Brentani, R. R.; Izquierdo, I.; Moreira, J. C. F. Imbalance of antioxidant defense in mice lacking cellular prion protein Free Radical Biol. Med. 2001, 30, 1137-1144
6. Carrell, R. W.; Lomas, D. A. Conformational disease Lancet 1997, 350, 134-138
7. Cashman, N. R.; Caughey, B. Prion diseases-close to effective therapy? Nat. Rev. Drug Discovery 2004, 3, 874-884
8. Trevitt, C. R.; Collinge, J. A systematic review of prion therapeutics in experimental models Brain 2006, 129, 2241-2265
9. Caughey, B.; Raymond, L. D.; Raymond, G. J.; Maxson, L.; Silveira, J.; Baron, G. S. Inhibition of protease-resistant prion protein accumulation in vitro by curcumin J. Virol. 2003, 77, 5499-5502
10. May, B. C. H.; Fafarman, A. T.; Hong, S. B.; Rogers, M.; Deady, L. W.; Prusiner, S. B.; Cohen, F. E. Potent inhibition of scrapie prion replication in cultured cells by bis-acridines Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3416-3421
11. Csuk, R.; Barthel, A.; Raschke, C.; Kluge, R.; Strohl, D.; Trieschmann, L.; Bohm, G. Synthesis of monomeric and dimeric acridine compounds as potential therapeutics in alzheimer and prion diseases Arch. Pharm. 2009, 342, 699-709
12. Kuwata, K.; Nishida, N.; Matsumoto, T.; Kamatari, Y. O.; Hosokawa-Muto, J.; Kodama, K.; Nakamura, H. K.; Kimura, K.; Kawasaki, M.; Takakura, Y.; Shirabe, S.; Takata, J.; Kataoka, Y.; Katamine, S. Hot spots in prion protein for pathogenic conversion Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 11921-11926
13. Kocisko, D. A.; Baron, G. S.; Rubenstein, R.; Chen, J.; Kuizon, S.; Caughey, B. New inhibitors of scrapie-associated prion protein formation in a library of 2000 drugs and natural products J. Virol. 2003, 77, 10288-10294
14. Murakami-Kubo, I.; Doh-ura, K.; Ishikawa, K.; Kawatake, S.; Sasaki, K.; Kira, J. I.; Ohta, S.; Iwaki, T. Quinoline derivatives are therapeutic candidates for transmissible spongiform encephalopathies J. Virol. 2004, 78, 1281-1288
15. Wang, H.; Duennwald, M. L.; Roberts, B. E.; Rozeboom, L. M.; Zhang, Y. X. L.; Steele, A. D.; Krishnan, R.; Su, L. J.; Griffin, D.; Mukhopadhyay, S.; Hennessy, E. J.; Weigele, P.; Blanchard, B. J.; King, J.; Deniz, A. A.; Buchwald, S. L.; Ingram, V. M.; Lindquist, S.; Shorter, J. Direct and selective elimination of specific prions and amyloids by 4,5-dianilinophthalimide and analogs Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 7159-7164
16. Sellarajah, S.; Lekishvili, T.; Bowring, C.; Thompsett, A. R.; Rudyk, H.; Birkett, C. R.; Brown, D. R.; Gilbert, I. H. Synthesis of analogues of Congo red and evaluation of their anti-prion activity J. Med. Chem. 2004, 47, 5515-5534
17. Bolognesi, M. L.; Tran, H. N. A.; Staderini, M.; Monaco, A.; Lopez-Cobenas, A.; Bongarzone, S.; Biarnes, X.; Lopez-Alvarado, P.; Cabezas, N.; Caramelli, M.; Carloni, P.; Menendez, J. C.; Legname, G. Discovery of a class of diketopiperazines as antiprion compounds ChemMedChem 2010, 5, 1324-1334
18. Corson, T. W.; Aberle, N.; Crews, C. M. Design and applications of bifunctional small molecules: why two heads are better than one ACS Chem. Biol. 2008, 3, 677-692
19. Kim, Y. S.; Lee, J. H.; Ryu, J.; Kim, D. J. Multivalent and multifunctional ligands to beta-amyloid Curr. Pharm. Des. 2009, 15, 637-658
20. Dollinger, S.; Lober, S.; Klingenstein, R.; Korth, C.; Gmeiner, P. A chimeric ligand approach leading to potent antiprion active acridine derivatives: design, synthesis, and biological investigations J. Med. Chem. 2006, 49, 6591-6595
21. Dolphin, G. T.; Chierici, S.; Ouberai, M.; Dumy, P.; Garcia, J. A multimeric quinacrine conjugate as a potential inhibitor of Alzheimer's beta-amyloid fibril formation ChemBioChem 2008, 9, 952-963
22. Ouberai, M.; Dumy, P.; Chierici, S.; Garcia, J. Synthesis and biological evaluation of clicked curcumin and clicked KLVFFA conjugates as inhibitors beta-amyloid fibril formation Bioconjugate Chem. 2009, 20, 2123-2132
23. Tran, H. N. A.; Bongarzone, S.; Carloni, P.; Legname, G.; Bolognesi, M. L. Synthesis and evaluation of a library of 2,5-bisdiamino-benzoquinone derivatives as probes to modulate protein-protein interactions in prions Bioorg. Med. Chem. Lett. 2010, 20, 1866-1868
24. Cope, H.; Mutter, R.; Heal, W.; Pascoe, C.; Brown, P.; Pratt, S.; Chen, B. Synthesis and SAR study of acridine, 2-methylquinoline and 2-phenylquinazoline analogues as anti-prion agents Eur. J. Med. Chem. 2006, 41, 1124-1143
25. Klingenstein, R.; Melnyk, P.; Leliveld, S. R.; Ryckebusch, A.; Korth, C. Similar structure-activity relationships of quinoline derivatives for antiprion and antimalarial effects J. Med. Chem. 2006, 49, 5300-5308
26. Tribouillard-Tanvier, D.; Beringue, V.; Desban, N.; Gug, F.; Bach, S.; Voisset, C.; Galons, H.; Laude, H.; Vilette, D.; Blondel, M. Antihypertensive drug guanabenz is active in vivo against both yeast and mammalian prions PloS One 2008, 3 e1981
27. Bolognesi, M. L.; Banzi, R.; Bartolini, M.; Cavalli, A.; Tarozzi, A.; Andrisano, V.; Minarini, A.; Rosini, M.; Tumiatti, V.; Bergamini, C.; Fato, R.; Lenaz, G.; Hrelia, P.; Cattaneo, A.; Recanatini, M.; Melchiorre, C. Novel class of quinone-bearing polyamines as multi-target-directed ligands to combat Alzheimer's disease J. Med. Chem. 2007, 50, 4882-4897
28. Bolognesi, M. L.; Cavalli, A.; Bergarmini, C.; Fato, R.; Lenaz, G.; Rosini, M.; Bartolini, M.; Andrisano, V.; Melchiorre, C. Toward a rational design of multitarget-directed antioxidants: merging memoquin and lipoic acid molecular frameworks J. Med. Chem. 2009, 52, 7883-7886
29. Milhavet, O.; Mcmahon, H. E. M.; Rachidi, W.; Nishida, N.; Katamine, S.; Mange, A.; Arlotto, M.; Casanova, D.; Riondel, J.; Favier, A.; Lehmann, S. Prion infection impairs the cellular response to oxidative stress Proc. Nat. Acad. Sci. U.S.A. 2000, 97, 13937-13942
30. Singh, N.; Singh, A.; Das, D.; Mohan, M. L. Redox control of prion and disease pathogenesis Antioxid. Redox Signaling 2010, 12, 1271-1294
31. Martin, S. F.; Buron, I.; Espinosa, J. C.; Castilla, J.; Villalba, J. M.; Torres, J. M. Coenzyme Q and protein/lipid oxidation in a BSE-infected transgenic mouse model Free Radical Biol. Med. 2007, 42, 1723-1729
32. Bolognesi, M. L.; Cavalli, A.; Melchiorre, C. Memoquin: a multi-target-directed ligand as an innovative therapeutic opportunity for Alzheimer's disease Neurotherapeutics 2009, 6, 152-162
33. Kimata, A.; Nakagawa, H.; Ohyama, R.; Fukuuchi, T.; Ohta, S.; Suzuki, T.; Miyata, N. New series of antiprion compounds: pyrazolone derivatives have the potent activity of inhibiting protease-resistant prion protein accumulation J. Med. Chem. 2007, 50, 5053-5056