A chloroquine-like molecule designed to reverse resistance in Plasmodium falciparum

Journal of Medicinal Chemistry

Volumn 49, Issue 18, 2006, Pages 5623-5625

  Burgess, Steven J ^a   Selzer, Audrey ^a   Kelly, Jane Xu ^b   Smilkstein, Martin J ^b   Riscoe, Michael K ^b   Peyton, David H ^a  

^a PORTLAND STATE UNIVERSITY   (United States)

^b PORTLAND VA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROQUINE; IMIPRAMINE; N' (7 CHLOROQINOLIN 4 YL) N [3 (10,11 DIHYDRODIBENZO[B,F]AZEPIN 5 YL)PROPYL] N METHYLPROPANE 1,3 DIAMINE; UNCLASSIFIED DRUG; VERAPAMIL;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG EFFECT; DRUG EFFICACY; DRUG RESISTANCE; DRUG SAFETY; FEMALE; IC 50; MALARIA; MOUSE; NONHUMAN; PHARMACOPHORE; PLASMODIUM FALCIPARUM; SYNTHESIS;

ANIMALS; ANTIMALARIALS; CHLOROQUINE; DIBENZAZEPINES; DRUG RESISTANCE; FEMALE; MALARIA; MICE; PLASMODIUM CHABAUDI; PLASMODIUM FALCIPARUM;

EID: 33748520577     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060399n     Document Type: Article

References (28)

1. Krogstad, D. J. Malaria as a reemerging disease. Epidemiol. Rev. 1996, 18 (1), 77-89.
2. Greenwood, B. M.; Bojang, K.; Whitty, C. J.; Targett, G. A. Malaria. Lancet 2005, 365 (9469), 1487-98.
3. Ashley, E. A.; White, N. J. Artemisinin-based combinations. Curr. Opin. Infect. Dis. 2005, 18 (6), 531-6.
4. Schellenberg, D.; Abdulla, S.; Roper, C. Current Issues for Anti-Malarial Drugs to Control P. falciparum Malaria. Curr. Mol. Med. 2006, 6 (2), 253-60.
5. Zhang, H.; Paguio, M.; Roepe, P. D. The antimalarial drug resistance protein Plasmodium falciparum chloroquine resistance transporter binds chloroquine. Biochemistry (Mosc). 2004, 43 (26), 8290-6.
6. Bennett, T. N.; Kosar, A. D.; Ursos, L. M.; Dzekunov, S.; Singh Sidhu, A. B.; Fidock, D. A.; Roepe, P. D. Drug resistance-associated pfCRT mutations confer decreased Plasmodium falciparum digestive vacuolar pH. Mol. Biochem. Parasitol. 2004, 133 (1), 99-114.
7. Martin, R. E.; Kirk, K. The malaria parasite's chloroquine resistance transporter is a member of the drug/metabolite transporter superfamily. Mol. Biol. Evol. 2004, 21 (10), 1938-49.
8. Ginsburg, H. Should chloroquine be laid to rest? Acta Trop. 2005, 96 (1), 16-23.
9. Martin, S. K.; Oduola, A. M.; Milhous, W. K. Reversal of chloroquine resistance in Plasmodium falciparum by verapamil. Science 1987, 255 (4791), 899-901.
10. Krogstad, D. J.; Gluzman, I. Y.; Kyle, D. E.; Oduola, A. M.; Martin, S. K.; Milhous, W. K.; Schlesinger, P. H. Efflux of chloroquine from Plasmodium falciparum: mechanism of chloroquine resistance. Science 1987, 238 (4831), 1283-5.
11. van Schalkwyk, D. A.; Walden, J. C.; Smith, P. J. Reversal of chloroquine resistance in Plasmodium falciparum using combinations of chemosensitizers. Antimicrob. Agents Chemother. 2001, 45 (11), 3171-4.
12. Millet, J.; Torrentino-Madamet, M.; Alibert, S.; Rogier, C.; Santelli-Rouvier, C.; Mosnier, J.; Baret, E.; Barbe, J.; Parzy, D.; Pradines, B. Dihydroethanoanthracene derivatives as in vitro malarial chloroquine resistance reversal agents. Antimicrob. Agents Chemother. 2004, 48 (7), 2753-6.
13. Bhattacharjee, A. K.; Kyle, D. E.; Vennerstrom, J. L.; Milhous, W. K. A 3D QSAR pharmacophore model and quantum chemical structure-activity analysis of chloroquine(CQ)-resistance reversal. J. Chem. Inf. Comput. Sci. 2002, 42 (5), 1212-20.
14. Morphy, R.; Rankovic, Z. Designed multiple ligands. An emerging drug discovery paradigm. J. Med. Chem. 2005, 48 (21), 6523-43.
15. Egan, T. J.; Mavuso, W. W.; Ross, D. C.; Marques, H. M. Thermodynamic factors controlling the interaction of quinoline antimalarial drugs with ferriprotoporphyrin IX. J. Inorg. Biochem. 1997, 68 (2), 137-45.
16. Bhattacharjee, A. K.; Kyle, D. E.; Vennerstrom, J. L. Structural analysis of chloroquine resistance reversal by imipramine analogs. Antimicrob. Agents Chemother. 2001, 45 (9), 2655-7.
17. Menezes, C. M.; Kirchgatter, K.; Di Santi, S. M.; Savalli, C.; Monteiro, F. G.; Paula, G. A.; Ferreira, E. I. Antimalarial effect in vitro and lack of modulating effect of desipramine and imipramine. Trans. R. Soc. Trop. Med. Hyg. 1997, 91 (6), 697-700.
18. Miki, A.; Tanabe, K.; Nakayama, T.; Kiryon, C.; Ohsawa, K. Plasmodium chabaudi: association of reversal of chloroquine resistance with increased accumulation of chloroquine in resistant parasites. Exp. Parasitol. 1992, 74, (2), 134-42.
19. Dorn, A.; Vippagunta, S. R.; Matile, H.; Jaquet, C.; Vennerstrom, J. L.; Ridley, R. G. An assessment of drug-haematin binding as a mechanism for inhibition of haematin polymerisation by quinoline antimalarials. Biochem. Pharmacol. 1998, 55, (6), 727-36.
20. Xu Kelly, J.; Winter, R.; Riscoe, M.; Peyton, D. H. A spectroscopic investigation of the binding interactions between 4,5- dihydroxyxanthone and heme. J. Inorg. Biochem. 2001, 86, (2-3), 617-25.
21. Hunt, P.; Cravo, P. V.; Donleavy, P.; Carlton, J. M.; Walliker, D. Chloroquine resistance in Plasmodium chabaudi: are chloroquine-resistance transporter (crt) and multi-drug resistance (mdr1) orthologues involved? Mol. Biochem. Parasitol. 2004, 133, (1), 27-35.
22. Bolte, J.; Demuynck, C.; Lhomme, J. Synthetic models of DNA complexes with antimalarial compounds. 2. The problem of guanine specificity in chloroquine binding. J. Med. Chem. 1977, 20, 0, (1), 106-13.
23. Fujita, M.; Seki, T. Syntheses and bioactivities of novel carbamates combining platelet activating factor (PAF) receptor antagonist with thromboxane synthase inhibitor (TxSI). Bioorg. Med. Chem. Lett. 2002, 12, (10), 1383-6.
24. 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, (5), 1803-6.
25. Peters, W. The chemotherapy of rodent malaria, XXII. The value of drug-resistant strains of P. berghei in screening for blood schizontocidal activity. Ann. Trop. Med. Parasitol. 1975, 69, (2), 155-71.
26. Mackinnon, M. J.; Read, A. F. Virulence in malaria: an evolutionary viewpoint. Philos. Trans. R. Soc. London B Biol. Sci. 2004, 359, (1446), 965-86.
27. Mackinnon, M. J.; Walker, P. R.; Rowe, J. A. Plasmodium chabaudi: rosetting in a rodent malaria model. Exp. Parasitol. 2002, 101, (2-3), 121-8.
28. Hommel, M. Diagnostic methods in malaria, 4th ed.; Arnold: London, New York, 2002; pp 35-58.