Synthesis, β-hematin inhibition studies and antimalarial evaluation of dehydroxy isotebuquine derivatives against Plasmodium berghei

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 15, 2015, Pages 4755-4762

  Romero, Angel H ^a   Acosta, María E ^b   Gamboa, Neira ^b   Charris, Jaime E ^b   Salazar, José ^a   López, Simón E ^a  

^a UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

^b UNIVERSIDAD CENTRAL DE VENEZUELA   (Venezuela)

Author keywords

4 Aminoquinoline; Antimalarial activity; Haemozoin formation; Isotebuquine; Malaria; Hematin

Indexed keywords

4 AMINOQUINOLINE; 7 CHLORO N [4' CHLORO 6 [PYRROLIDIN 1 YLMETHYL] [1,1' BIPHENYL] 3 YL]QUINOLIN 4 AMINE DIHYDROCHLORIDE; 7 CHLORO N [6 [PIPERIDIN 1 YLMETHYL] [1,1' BIPHENYL] 3 YL]QUINOLIN 4 AMINE DIHYDROCHLORIDE; 7 CHLORO N [6 [PYRROLIDIN 1 YLMETHYL] [1,1' BIPHENYL] 3 YL]QUINOLIN 4 AMINE DIHYDROCHLORIDE; ANTIMALARIAL AGENT; BETA HEMATIN; CHLOROQUINE; DEHYDROXY ISOTEBUQUINE DERIVATIVE; HEMATIN; HEMOZOIN; UNCLASSIFIED DRUG; AMINOQUINOLINE DERIVATIVE; HEMOPROTEIN; TEBUQUINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; RODENT MALARIA; ANIMAL; ANTAGONISTS AND INHIBITORS; BAGG ALBINO MOUSE; CHEMISTRY; DRUG EFFECTS; MALARIA; METABOLISM; PATHOLOGY; PRECLINICAL STUDY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; VETERINARY;

MUS; PLASMODIUM BERGHEI;

AMINOQUINOLINES; ANIMALS; ANTIMALARIALS; CHLOROQUINE; DRUG EVALUATION, PRECLINICAL; HEMEPROTEINS; MALARIA; MALE; MICE; MICE, INBRED BALB C; PLASMODIUM BERGHEI; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84937513024     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.05.040     Document Type: Article

References (39)

1. WHO. World Malaria Report 2014, http://www.who.int/malaria/world-malaria-report-2014/en/index.html (accessed 03.03.2015).
2. J.K. Baird Trends Parasitol. 23 2007 533
3. World Health Organisation (WHO) Conquering, Suffering and Enriching Humanity: The World Health Report 1997 World Health Organisation Publishers Geneva
4. W.M. Watkins, D.G. Sixsmith, H.G. Spencer, D.A. Boriga, D.M. Karjuki, T. Kipingor, and D.K. Koech Lancet 323 1984 357
5. N.J. White Lancet 348 1996 1184
6. P. Olliaro, C. Nevill, J. Lebras, P. Ringwald, P. Mussano, P. Garner, and P. Brasseur Lancet 348 1996 1196
7. P.M. O'Neill, A. Mukhtar, P.A. Stocks, L.E. Randle, S. Hindley, S.A. Ward, R.C. Storr, J.F. Bickley, I.A. O'Neil, J.L. Maggs, R.H. Hughes, P.A. Winstanley, P.G. Bray, and B.K. Park J. Med. Chem. 46 2003 4933
8. B. Pradines, A. Tall, D. Prazzy, A. Spiegel, T. Fusai, R. Hienne, J.F. Trape, and J.C. Doury J. Antimicrob. Chemother. 42 1998 333
9. K.A. Neftel, W. Woodtly, M. Schmid, P.G. Frick, and J. Fehr Br. Med. J. 292 1986 721
10. D.E. Lind, J.A. Levi, and P.C. Vincent Br. Med. J. 1 1973 458
11. D.J. Naisbitt, D.P. Williams, P.M. O'Neill, J.L. Maggs, D.J. Willock, M. Pirmohamed, and B.K. Park Chem. Res. Toxicol. 11 1998 1586
12. A.C. Harrison, N.R. Kitteringham, J.B. Clarke, and B.K. Park Biochem. Pharmacol. 43 1992 1421
13. J.L. Maggs, N.R. Kitteringham, and B.K. Park Biochem. Pharmacol. 37 1988 303
14. J.E. Ruscoe, M.D. Tingle, P.M. O'Neill, S.A. Ward, and B.K. Park Antimicrob. Agents Chemother. 42 1998 2410
15. D.J. Naisbitt, J.E. Ruscoe, D. Williams, P.M. O'Neill, M. Pirmohamed, and B.K. Park J. Pharmacol. Exp. Ther. 280 1997 884
16. S. Delarue-Cochin, E. Paunescu, L. Maes, E. Mouray, C. Sergheraert, P. Grellier, and P. Melnyk Eur. J. Med. Chem. 43 2008 252
17. O.V. Miroshnikova, T.H. Hudson, L. Gerena, D.E. Kyle, and A.J. Lin J. Med. Chem. 50 2007 889
18. P.M. O'Neill, B.K. Park, A.E. Shone, J.L. Maggs, P. Roberts, P.A. Stocks, G.A. Biagini, P.G. Bray, P. Gibbons, N. Berry, P.A. Winstanley, A. Mukhtar, R. Bonar-Law, S. Hindley, R.B. Bambal, C.B. Davis, M. Bates, T.K. Hart, S.L. Gresham, R.M. Lawrence, R.A. Brigandi, F.M. Gomez-delas-Heras, D.V. Gargallo, and S.A. Ward J. Med. Chem. 52 2009 1408
19. R. Banerjee, J. Liu, W. Beatly, L. Pelosof, M. Klemba, and D.E. Goldberg Proc. Natl. Acad. Sci U.S.A. 99 2002 990
20. N.D. Gamboa de Dominguez, and P.J. Rosenthal Blood 87 1996 4448
21. P. Loria, S. Miller, M. Foley, and L. Tilley Biochem. J. 339 1999 363
22. C.D. Fitch, R. Chevli, P. Kanyoananggulpan, P. Dotta, K. Chevli, and A.C. Chou Blood 62 1983 1165
23. A.P. Gorka, A. de Dios, and P.D. Roepe J. Med. Chem. 56 2013 5231
24. T. Egan, R. Hunter, C.H. Kaschula, H.M. Marques, A. Miplon, and J. Walden J. Med. Chem. 43 2000 283
25. J.M. Combrinck, T.E. Mabotha, K.K. Ncokazi, M.A. Ambele, D. Taylor, P.J. Smith, H.C. Hoppe, and J.J. Egan ACS Chem. Biol. 8 2013 133
26. A. Leed, K. DuBay, L.M. Ursos, D. Sears, A.C. de Dios, and P.D. Roepe Biochemistry 41 2002 10245
27. A.C. De Dios, L.B. Casabianca, A. Kosar, and P.D. Roepe Inorg. Chem. 43 2004 8078
28. D. Kater, K. Chibale, and T.J. Egan J. Inorg. Biochem. 105 2011 684
29. S. Kapishnikov, A. Weiner, E. Shimoni, P. Guttmann, G. Schneider, N. Dahan-Pasternak, R. Dzikowski, L. Leiserewitz, and M. Elbaum Proc. Natl. Acad. Sci. U.S.A. 109 2012 11188
30. R. Buller, M.L. Peterson, O. Almarsson, and L. Leiserowitz Cryst. Growth Des. 2 2002 553
31. A.P. Gorka, J.N. Alumasa, K.S. Sharlach, L.M. Jacobs, K.B. Nicle, J.P. Brower, A.C. De-Dios, and P.D. Roepe Antimicrob. Agents Chemother. 57 2013 356
32. A.P. Gorka, K.S. Sharlach, A.C. de Dios, and P.D. Roepe Antimicrob. Agents Chemother. 57 2013 365
33. M.F. Paquio, K.L. Bogle, and P.D. Roepe Mol. Biochem. Parasitol. 178 2011 1
34. R. Baelmans, E. Deharo, V. Muñoz, M. Sauvain, and H. Ginsburg Exp. Parasitol. 96 2000 243
35. http://www.cambridgesoft.com/Ensemble-for-Chemistry/ChemBioDraw/ChemBioDrawUltra14Suite.
36. W. Peters Chemotherapy and Drug Resistance in Malaria 1970 Academic Press New York
37. http://clinicaltrials.gov/ct2/show/NCT01614964?term = aq13.
38. J.M. Pezzuto, C.V. Angerhofer, and H. Mehdi In Vitro Models of Human Disease States Atta-ur-Rahman Natural Products Chemistry Vol. 20 1998 Elsevier Science B.V. 507 560
39. S. Nwaka, and A. Hudson Nat. Rev. Drug Disc. 5 2006 941