Overcoming drug resistance to heme-targeted antimalarials by systematic side chain variation of 7-chloro-4-aminoquinolines

Journal of Medicinal Chemistry

Volumn 51, Issue 7, 2008, Pages 1995-1998

  Yearick, Kimberly ^a   Ekoue Kovi, Kekeli ^a   Iwaniuk, Daniel P ^a   Natarajan, Jayakumar K ^a,b   Alumasa, John ^a   De Dios, Angel C ^a   Roepe, Paul D ^a,b   Wolf, Christian ^a  

^a GEORGETOWN UNIVERSITY   (United States)

^b GEORGETOWN UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOQUINOLINE DERIVATIVE; AMODIAQUINE; ANTIMALARIAL AGENT; CHLOROQUINE; MEFLOQUINE; QUININE; SONTOQUINE;

ANTIMALARIAL ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; MALARIA; PLASMODIUM FALCIPARUM; STRUCTURE ACTIVITY RELATION;

AMINOQUINOLINES; ANIMALS; ANTIMALARIALS; DRUG EVALUATION, PRECLINICAL; DRUG RESISTANCE; PARASITIC SENSITIVITY TESTS; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 41849132118     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800106u     Document Type: Article

References (39)

1. De, D.; Byers, L. D.; Krogstad, D. J. Antimalarials: synthesis of 4-aminoquinolines that circumvent drug resistance in malaria parasites. J. Hetercycl. Chem. 1997, 34, 315-320.
2. O'Neill, P. M.; Bray, P. G.; Hawley, S. R.; Ward, S. A.; Park, B. K. 4-Aminoquinolines - past, present, and future: a chemical perspective. Pharmacol. Ther. 1998, 77, 29-58.
3. Dominguez, J. N. Chemotherapeutic agents against malaria: What next after chloroquine? Curr. Top. Med. Chem. 2002, 2, 1173-1185.
4. Pagola, S.; Stephens, P. W.; Bohle, D. S.; Kosar, A. D.; Madsen, S. K. The structure of malaria pigment β-haematin. Nature 2000, 404, 307-310.
5. Ridley, R. G. Medical need, scientific opportunity and the drive for antimalarial drugs. Nature 2002, 415, 686-693.
6. Leed, A.; DuBay, K.; Ursos, L. M.; Sears, D.; de Dios, A. C.; Roepe, P. D. Solution structures of antimalarial drug-heme complexes. Biochemistry 2002, 41, 10245-10255.
7. Chong, C. R.; Sullivan, D. J., Jr. Inhibition of heme crystal growth by antimalarials and other compounds: implications for drug discovery. Biochem. Pharmacol. 2003, 66, 2201-2212.
8. de Dios, A. C.; Casablanca, L. B.; Kosar, A.; Roepe, P. D. Structure of the amodiaquine-FPIX μ-oxo dimer solution complex at atomic resolution. Inorg. Chem. 2004, 43, 8078-8084.
9. de Dios, A. C.; Tycko, R.; Ursos, L. M. B.; Roepe, P. D. NMR studies of chloroquine-ferriprotoporphyrin IX complex. J. Phys. Chem. A 2003, 107, 5821-5825.
10. a, hematin binding, inhibition of hermozoin formation, and parasite growth. J. Med. Chem. 2003, 46, 3166-3169.
11. Egan, T. J.; Hunter, R.; Kaschula, C. H.; Marques, H. M.; Misplon, A.; Walden, J. Structure-function relationships in aminoquinolines: effect of amino and chloro groups on quinoline-hematin complex formation, inhibition of β-hematin formation, and antiplasmodial activity. J. Med. Chem. 2000, 43, 283-291.
12. Martin, S. K.; Oduola, A. M.; Milhous, W. K. Reversal of chloroquine resistance in Plasmodium falciparum by verapamil. Science 1987, 235, 899-901.
13. Burgess, S. J.; Selzer, A.; Kelly, J. X.; Smilkstein, M. J.; Riscoe, M. K.; Peyton, D. H. A chloroquine-like molecule designed to reverse resistance in Plasmodium falciparum. J. Med. Chem. 2006, 49, 5623-5625.
14. Weisman, J. L.; Liou, A. P.; Shelat, A. A.; Cohen, F. E.; Guy, R. K.; DeRisi, J. L. Searching for new antimalarial therapeutics amongst known drugs. Chem. Biol. Drug Des. 2006, 67, 409-116.
15. Tang, Y.; Dong, Y.; Wittlin, S.; Charman, S. A.; Chollet, J.; Chiu, F. C.; Charman, W. N.; Matile, H.; Urwyler, H.; Dorn, A.; Bajpai, S.; Wang, X.; Padmanilayam, M.; Karle, J. M.; Brun, R.; Vennerstrom, J. L. Weak base dispiro-1,2,4-trioxolanes: potent antimalarial ozonides. Bioorg. Med. Chem. Lett. 2007, 17, 1260-1265.
16. Dong, Y.; Tang, Y.; Chollet, J.; Matile, H.; Wittlin, S.; Charman, S. A.; Charman, W. N.; Tomas, J. S.; Scheurer, C.; Snyder, C.; Scorneaux, B.; Bajpai, S.; Alexander, S. A.; Wang, X.; Padmanilayam, M.; Cheruku, S. R.; Brun, R.; Vennerstrom, J. L. Effect of functional group polarity on the antimalarial activity of spiro and dispiro-1,2,4-trioxolanes. Bioorg. Med. Chem. 2006, 14, 6368-6382.
17. Posner, G. H.; Paik, I. H.; Chang, W.; Borstnik, K.; Sinishtaj, S.; Rosenthal, A. S.; Shapiro, T. A. Malaria-infected mice are cured by a single dose of novel artemisinin derivatives. J. Med. Chem. 2007, 50, 2516-2519.
18. Paik, I. H.; Xie, S.; Shapiro, T. A.; Labonte, T.; Narducci Sarjeant, A. A.; Baege, A. C.; Posner, G. H. Second generation, orally active, antimalarial, artemisinin-derived trioxane dimers with high stability, efficacy, and anticancer activity. J. Med. Chem. 2006, 49, 2731-2734.
19. Vennerstrom, L.; Arbe-Barnes, S.; Brun, R.; Charman, S. A.; Chiu, F. C.; Chollet, J.; Dong, Y.; Dorn, A.; Hunziker, D.; Matile, H.; McIntosh, K.; Padmanilayam, M.; Santo Tomas, J.; Scheurer, C.; Scorneaux, B.; Tang, Y.; Urwyler, H.; Wittlin, S.; Charman, W. N. Identification of an antimalarial synthetic trioxolane drug development candidate. Nature 2004, 430 (7002), 900-904.
20. O'Neill, P. M.; Posner, G. H. A medicinal chemistry perspective on artmeisinin and related endoperoxides. J. Med. Chem. 2004, 47, 2945-2964.
21. Jambou, R.; Legrand, E.; Niang, M.; Khim, N.; Lim, P.; Volney, B.; Ekala, M. T.; Bouchier, C.; Esterre, P.; Fandeur, T.; Mercereau-Puijalon, O. Resistance of Plasmodium falciparum field isolates to in-vitro artemether and point mutations of the SERCA-type PfATPase 6. Lancet 2005, 366, 1960-1963.
22. Delarue, S.; Girault, S.; Maes, L.; Debreu-Fontaine, M. A.; Labaeid, M.; Grellier, P.; Sergheraert, C. Synthesis and in vitro and in vivo antimalarial activity of new 4-anilinoquinolines. J. Med. Chem. 2001, 44, 2827-2833.
23. O'Neill, P. M.; Willock, D. J.; Hawley, S. R.; Bray, P. G.; Storr, R. C.; Ward, S. A.; Park, B. K. Synthesis, antimalarial activity, and molecular modeling of tebuquine analogues. J. Med. Chem. 1997, 40, 437-148.
24. Madrid, P. B.; Liou, A. P.; DeRisi, J. L.; Guy, R. K. Incorporation of an intramolecular hydrogen-bonding motif in the side chain of 4-aminoquinolines enhances activity against drug-resistant P. falciparum. J. Med. Chem. 2006, 49, 4535-1543.
25. Riccio, E. S.; Lee, P. S.; Winegar, R. A.; Krogstad, D. J.; De, D.; Mirsalis, J. C. Genetic toxicology testing of the antimalarial drugs chloroquine and a new analog, AQ-13. Environ. Mol. Mutagen. 2001, 38, 69-79.
26. Egan, T, J.; Hunter, R.; Kaschula, C. H.; Marques, H. M.; Misplon, A.; Waiden, J. C. Structure-function relationships in aminoquinolines: effect of amino and chloro groups on quinoline-hematin complex formation, inhibition of β-hematin formation, and antiplasmodial activity. J. Med. Chem. 2000, 43, 283-291.
27. Kaschula, C. H.; Egan, T. J.; Hunter, R.; Basilico, N.; Parapani, S.; Tarameli, D.; Pasini, E.; Monti, D. Structure-activity relationships in 4-aminoquinoline antiplasmodials. The role of the group at the 7-position. J. Med. Chem. 2002, 45, 3531-3539.
28. Ridley, R. G.; Hofheinz, H.; Matile, H.; Jacquet, C.; Dorn, A.; Masciadri, R.; Jolidon, S.; Richter, W. F.; Guenzi, A.; Girometta, M. A.; Urwyler, H.; Huber, W.; Thiathong, S.; Peters, W. 4-Aminoquinoline analogues of CQ with shortened side chains retain activity against CQ-resistant Plasmodium falciparum. Antimicrob. Agents Chemother. 1996, 40, 1846-1854.
29. De, D.; Krogstad, F. M.; Byers, L. D.; Krogstad, D. J. Structure-activity relationships for antiplasmodial activity among 7-substituted 4-aminoquinolines. J. Med. Chem. 1998, 41, 4918-1926.
30. Madrid, P. B.; Liou, A. P.; DeRisi, J. L.; Guy, K. Incorporation of an intramolecular hydrogen bonding motif in the side chain of 4-aminoquinolines enhances activity against drug-resistant P. falciparum. J. Med. Chem. 2006, 49, 4535-1543.
31. Hawley, S. R.; Bray, P. G.; Park, B. K.; Ward, S. A. Amodiaquine accumulation in Plasmodium falciparum as a possible explanation for its superior antimalarial activity over chloroquine. Mol. Biochem. Parasitol. 1996, 80, 15-25.
32. Stocks, P. A.; Raynes, K. J.; Bray, P. G.; Park, B. K.; O'Neill, P. M.; Ward, S. A. Novel short chain chloroquine analogues retain activity against chloroquine resistant K1 Plasmodium falciparum. J. Med. Chem. 2002, 45, 4975-1983.
33. Madrid, P. B.; Wilson, N. T.; DeRisi, J. L.; Guy, R. K. Parallel synthesis and antimalarial screening of a 4-aminoquinoline library. J. Comb. Chem. 2004, 6, 437-142.
34. Bennett, T. N.; Paguio, M.; Gligorijevic, B.; Seudieu, C.; Kosar, A. D.; Davidson, E.; Roepe, P. D. Novel, rapid, and inexpensive cell-based quantification of antimalarial drug efficacy. Antimicrob. Agents Chemother. 2004, 48, 1807-1810.
35. Smilkstein, M.; Sriwilaijaroen, N.; Kelly, J. X.; Wilairat, P.; Riscoe, M. Simple and inexpensive fluorescence-based technique for high-throughput antimalarial drug screening. Antimicrob. Agents Chemother. 2004, 48, 1803-1806.
36. Johnson, J. D.; Dennull, R. A.; Gerena, L.; Lopez-Sanchez, M.; Roncal, N. E.; Waters, N. C. Assessment and continued validation of the malaria SYBR green I-based fluorescence assay for use in malaria drug screening. Antimicrob. Agents Chemother. 2007, 51, 1926-1933.
37. Drake, N. L.; Creech, H. J.; Garman, J. A.; Haywood, S. T.; Peck, R. M.; van Hook, J. O.; Walton, E. Synthetic antimalrials. The preparation of certain 4-aminoquinolines. J. Am. Chem. Soc. 1946, 68, 1208-1213.
38. Geary, T. G.; Divo, A. A.; Jensen, J. B. Activity of quinoline-containing antimalarials against chloroquine-sensitive and -resistant strains of Plasmodium falciparum in vitro. Trans. R. Soc. Trop. Med. Hyg. 1987, 81, 499-503.
39. Geary, T. G.; Jensen, J. B. Lack of cross-resistance to 4-aminoquinolines in chloroquine-resistant Plasmodium falciparum in vitro. J. Parasitol. 1983, 69, 97-105.