Synthesis and structure-activity relationships of new quinolone-type molecules against trypanosoma brucei

Journal of Medicinal Chemistry

Volumn 55, Issue 6, 2012, Pages 2538-2548

  Hiltensperger, Georg ^a   Jones, Nicola G ^a   Niedermeier, Sabine ^a   Stich, August ^b   Kaiser, Marcel ^c,d   Jung, Jamin ^a   Puhl, Sebastian ^a   Damme, Alexander ^a   Braunschweig, Holger ^a   Meinel, Lorenz ^a   Engstler, Markus ^a   Holzgrabe, Ulrike ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b Medical Mission Institute   (Germany)

^c SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^d UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

4 QUINOLONE DERIVATIVE; ANTITRYPANOSOMAL AGENT; CIPROFLOXACIN; DNA TOPOISOMERASE (ATP HYDROLYSING);

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; KINETOPLAST; MACROPHAGE; MITOCHONDRION; NONHUMAN; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA; TRYPANOSOMA BRUCEI;

ACUTE DISEASE; ANIMALS; CELL LINE; DNA TOPOISOMERASES, TYPE II; DNA, KINETOPLAST; MICE; MICROSCOPY, FLUORESCENCE; MITOCHONDRIA; MODELS, MOLECULAR; MORPHOLINES; QUINOLONES; STRUCTURE-ACTIVITY RELATIONSHIP; TOPOISOMERASE II INHIBITORS; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI GAMBIENSE; TRYPANOSOMA BRUCEI RHODESIENSE; TRYPANOSOMIASIS, AFRICAN;

EID: 84858714296     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101439s     Document Type: Article

References (45)

1. Cecchi, G.; Paone, M.; Franco, J. R.; Fevre, E. M.; Diarra, A.; Ruiz, J. A.; Mattioli, R. C.; Simarro, P. P. Towards the Atlas of human African trypanosomiasis. Int. J. Health Geogr. 2009, 8, 10.1186/1476-072X-8-15.
2. African Trypanosomiasis (Sleeping Sickness); World Health Organization Fact Sheet; World Health Organization: Geneva, 2006.
3. Hide, G. History of sleeping sickness in East Africa Clin. Microbiol. Rev. 1999, 12, 112-125 (Pubitemid 29055956)
4. Raadt, P. The history of sleeping sickness. Fourth International Cours on African Trypanosomoses, Tunis, Oct 11-28, 2005, World Health Organization: Geneva, 2005.
5. Fèvre, E. M.; Wissmann, B.; Welburn, S. C.; Lutumba, P. The burden of human African trypanosomiasis PLoS Neglected Trop. Dis. 2008, 2 10.1371/journal.pntd.0000333
6. Priotto, G.; Kasparian, S.; Mutombo, W.; Ngouama, D.; Ghorashian, S.; Arnold, U.; Ghabri, S.; Baudin, E.; Buard, V.; Kazadi-Kyanza, S.; Ilunga, M.; Mutangala, W.; Pohlig, G.; Schmid, C.; Karunakara, U.; Torreele, E.; Kande, V. Nifurtimox-eflornithine combination therapy for second-stage African Trypanosoma brucei gambiense trypanosomiasis: a multicentre, randomised, phase III, non-inferiority trial Lancet 2009, 374, 56-64
7. Cavalli, A.; Bolognesi, M. L. Neglected tropical diseases: multi-target-directed ligands in the search for novel lead candidates against trypanosoma and leishmania J. Med. Chem. 2009, 52, 7339-7359
8. Cavalcanti, D. P.; Fragoso, S. P.; Goldenberg, S.; Souza, W.; Motta, M. C. M. The effect of topoisomerase II inhibitors on the kinetoplast ultrastructure Parasitol. Res. 2004, 94, 439-448 (Pubitemid 40104523)
9. Kulikowicz, T.; Shapiro, T. A. Distinct genes encode type II topoisomerases for the nucleus and mitochondrion in the protozoan parasite Trypanosoma brucei J. Biol. Chem. 2006, 281, 3048-3056 (Pubitemid 43845914)
10. Sen, N.; Majumder, H. K. Mitochondrion of protozoan parasite emerges as potent therapeutic target: exciting drugs are on the horizon Curr. Pharm. Dis. 2008, 14, 839-846 (Pubitemid 351736416)
11. Lee, S. H.; Stephens, J. L.; Paul, K. S.; Englund, P. T. Fatty acid synthesis by elongases in trypanosomes Cell 2006, 126, 691-699 (Pubitemid 44233626)
12. Bodley, A. L.; Chakraborty, A. K.; Xie, S.; Burri, C.; Shapiro, T. A. An unusual type IB topoisomerase from African trypanosomes Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 7539-7544 (Pubitemid 36760005)
13. Nenortas, E.; Burri, C.; Shapiro, T. A. Antitrypanosomal activity of fluoroquinolones Antimicrob. Agents Chemother. 1999, 43, 2066-2068 (Pubitemid 29395212)
14. Bringmann, G.; Hoerr, V.; Holzgrabe, U.; Stich, A. Antitrypanosomal naphthylisoquinoline alkaloids and related compounds Pharmazie 2003, 58, 343-346 (Pubitemid 36604914)
15. Nenortas, E.; Kulikowicz, T.; Burri, C.; Shapiro, T. A. Antitrypanosomal activities of fluoroquinolones with pyrrolidinyl substitutions Antimicrob. Agents Chemother. 2003, 47, 3015-3017 (Pubitemid 37040291)
16. Keiser, J.; Burri, C. Evaluation of quinolone derivatives for antitrypanosomal activity Trop. Med. Int. Health 2001, 6, 369-389 (Pubitemid 32510075)
17. Ma, X.; Zhou, W.; Brun, R. Synthesis, in vitro antitrypanosomal and antibacterial activity of phenoxy, phenylthio or benzyloxy substituted quinolones Bioorg. Med. Chem. Lett. 2009, 19, 986-989
18. Gould, R. G.; Jacobs, W. A. The synthesis of certain substituted quinolines and 5, 6-benzoquinolines J. Med. Chem. Soc. 1939, 61, 2890-2895
19. Shindikar, A. V.; Viswanathan, C. L. Novel fluoroquinolones: design, synthesis and in vivo activity in mice against Mycobacterium tuberculosis H37Rv Bioorg. Med. Chem. Lett. 2005, 15, 1803-1806 (Pubitemid 40380736)
20. Niedermeier, S.; Singethan, K.; Rohrer, S. G.; Matz, M.; Kossner, M.; Diederich, S.; Maisner, A.; Schmitz, J.; Hiltensperger, G.; Baumann, K.; Holzgrabe, U.; Schneider-Schaulies, J. A small-molecule inhibitor of Nipah virus envelope protein-mediated membrane fusion J. Med. Chem. 2009, 52, 4257-4265
21. Koga, H.; Itoh, A.; Murayama, S.; Suzue, S.; Irikura, T. Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-a1kyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids J. Med. Chem. 1980, 23, 1358-1363 (Pubitemid 11164105)
22. Heravi, M. M.; Jaddi, Z. S.; Oskooie, H. A.; Khaleghi, S.; Ghassemzadeh, M. Regioselective synthesis of quinolone antibacterials via borate complex of quinolone carboxylic acid J. Chem. Res. 2005, 578-579 (Pubitemid 41494374)
23. Miyaura, M.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds Chem. Rev. 1995, 95, 2457-2483
24. Austin, W. B.; Bilow, N.; Kelleghan, W. J.; Lau, K. S. Y. Facile synthesis of ethynylated benzoic acid derivatives and aromatic compounds via ethynyltrimethylsilane J. Org. Chem. 1981, 46, 2280-2286
25. Gilligan, P. J.; Witty, M. J.; McGuirk, P. R. Substituted dihydroquinolone carboxylic acids, and antibacterial compositions containing them. Patent EP/184384/19860611, 1986.
26. Vice, S.; Bara, T.; Bauer, A.; Fort, J.; Josien, H.; McCombie, S.; Miller, M.; Nazareno, A. P.; Tagat, J. Concise formation of 4-benzyl piperidines and related derivatives using a Suzuki protocol J. Org. Chem. 2001, 66, 2487-2492 (Pubitemid 32867447)
27. Räz, B.; Iten, M.; Grether-Bühler, Y.; Kaminsky, R.; Brun, R. The AlamarBlue assay to determine drug sensitivity of African trypanosomes (T. brucei rhodesiense and T. brucei gambiense) in vitro Acta Trop. 1997, 68, 139-147 (Pubitemid 27438330)
28. Baltz, T.; Baltz, D.; Giroud, C.; Crocket, J. Cultivation in a semi-defined medium of animal infective forms of Trypanosoma brucei, T. equiperdum, T. evansi, T. rhodesiense and T. gambiense EMBO J. 1985, 4, 1273-1277
29. 3H]thymidine incorporation assay J. Immunol. Methods 1994, 170, 211-224 (Pubitemid 24122510)
30. Alptüzün, V.; Prinz, M.; Hörr, V.; Scheiber, J.; Radacki, K.; Fallarero, A.; Vuorela, P.; Engels, B.; Braunschweig, H.; Erciyas, E.; Holzgrabe, U. Interaction of (benzylidene-hydrazono)-1,4-dihydropyridines with β-amyloid, acetylcholine, and butyrylcholine esterases Bioorg. Med. Chem. 2010, 18, 2049-2059
31. Lipinski, C. A.; Lombard, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 2001, 46, 3-26 (Pubitemid 33653411)
32. Tenjarla, S. Microemulsions: an overview and pharmaceutical applications Crit. Rev. Ther. Drug Carrier Syst. 1999, 16, 461-521 (Pubitemid 30004629)
33. Date, A. A.; Nagarsnker, M. S. Parenteral microemulsions: an overview Int. J. Pharm. 2008, 355, 19-30
34. Benita, S. Submicron Emulsion in Drug Targeting and Delivery; Harwood Academic Publishers: Amsterdam, 1998.
35. Wang, Z.; Englund, P. T. RNA interference of a trypanosome topoisomerase II causes progressive loss of mitochondrial DNA EMBO J. 2001, 20, 4674-4683 (Pubitemid 32848621)
36. Lindsay, M. E.; Gluenz, E.; Gull, K.; Englund, P. T. A new function of Trypanosoma brucei mitochondrial topoisomerase II is to maintain kinetoplast DNA network topology Mol. Microbiol. 2008, 70, 1465-1476
37. Wohlkonig, A.; Chan, P. F.; Fosberry, A. P.; Homes, P.; Huang, J.; Kranz, M.; Leydon, V. R.; Miles, T. J.; Pearson, N. D.; Perera, R. L.; Shillings, A. J.; Gwynn, M. N.; Bax, B. D. Structural basis of quinolone inhibition of type IIA topoisomerases and target-mediated resistance Nature Struct. Mol. Biol. 2010, 17, 1152-1153
38. Hansch, C.; Leo, A.; Hoekman, D. Exploring QSAR: Volume 2: Hydrophobic, Electronic and Steric Constants; American Chemical Society: Waschington DC, 1995.
39. Clarke, J.; Cunliffe, A. E. Rapid spectrophotometric measurement of ionisation constants in aqueous solution Chem. Ind. (London) 1973, 281
40. Albert, A.; Serjeant, E. P. Ionisation constants of acids and bases. Wiley Inc.: New York, 1962.
41. Box, K.; Comer, J. E.; Gravestock, T.; Stuart, M. New ideas about the solubility of drugs Chem. Biodiversity 2009, 6, 1767-1788
42. Rasband, W. S. ImageJ; National Institutes of Health: Bethesda, MD, 1997-2008; http://rsb.info.nih.gov/ij/.
43. Strauss, P. R.; Wang, J. C. The TOP2 gene of Trypanosoma brucei: a single-copy gene that shares extensive homology with other TOP2 genes encoding eukaryotic DNA topoisomerase II Mol. Biochem. Parasitol. 1990, 38, 141-150 (Pubitemid 20008194)
44. Wickstead, B.; Ersfeld, K.; Gull, K. Targeting of a tetracycline- inducible expression system to the transcriptionally silent minichromosomes of Trypanosoma brucei Mol. Biochem. Parasitol. 2002, 125, 211-216 (Pubitemid 35449262)
45. Kaiser, M.; Bray, M. A.; Cal, M.; Bourdin Trunz, B.; Torreele, E.; Brun, R. Antitrypanosomal activity of fexinidazole, a new oral nitroimidazole drug candidate for treatment of sleeping sickness Antimicrob. Agents Chemother. 2011, 55 (12) 5602-5608