Imidazoquines as antimalarial and antipneumocystis agents

Journal of Medicinal Chemistry

Volumn 52, Issue 23, 2009, Pages 7800-7807

  Vale, Nuno ^a   Prudêncio, Miguel ^b   Marques, Catarina A ^b   Collins, Margaret S ^c,d   Gut, Jiri ^e   Nogueira, Fátima ^f   Matos, Joana ^a   Rosenthal, Philip J ^e   Cushion, Melanie T ^c,d   Do Rosário, Virgílio E ^f   Mota, Maria M ^b   Moreira, Rui ^g   Gomes, Paula ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSITY OF LISBON   (Portugal)

^c VETERANS AFFAIRS MEDICAL CENTER   (United States)

^d UNIVERSITY OF CINCINNATI COLLEGE OF MEDICINE   (United States)

^e UNIVERSITY OF CALIFORNIA   (United States)

^f INSTITUTO DE HIGIENE E MEDICINA TROPICAL   (Portugal)

^g RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

1 ISOLEUCYL 3 [4 (6 METHOXYQUINOLIN 8 YLAMINO)PENTYL] 2,2 DIMETHYLIMIDAZOLIDIN 4 ONE; ANTIFUNGAL AGENT; ANTIMALARIAL AGENT; PRIMAQUINE; PRIMAQUINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANOPHELES STEPHENSI; ARTICLE; BIOASSAY; BLOOD TOXICITY; CONTROLLED STUDY; CYTOTOXICITY; DEAMINATION; DRUG ACTIVITY; DRUG STABILITY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LIVER CELL; MOUSE; NONHUMAN; OXIDATION; PLASMODIUM; PLASMODIUM BERGHEI; PLASMODIUM BERGHEI INFECTION; PNEUMOCYSTIS CARINII; PROTEIN DEGRADATION; SCHIZONT; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIMALARIALS; CELL LINE; DISEASE TRANSMISSION, INFECTIOUS; DRUG STABILITY; FEMALE; HUMANS; IMIDAZOLES; LIVER; MICE; PHYSICOCHEMICAL PROCESSES; PLASMODIUM FALCIPARUM; PNEUMOCYSTIS CARINII;

EID: 72249095184     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900738c     Document Type: Article

References (52)

1. Tekwani, B. L.; Walker, L. A. 8-Aminoquinolines: future role as antiprotozoal drugs. Curr. Opin. Infect. Dis. 2006, 19, 623-631.
2. Baird, K. J.; Hoffman, S. L. Primaquine therapy for malaria. Clin. Infect. Dis. 2004, 39, 1336-1345.
3. Chotivanich, K.; Sattabongkot, J.; Udomsangpetch, R.; Looareesuwan, S.; Day, N. P. J.; Coleman, R. E.; White, N. J. Transmission-Blocking Activities of Quinine, Primaquine, and Artesunate. Antimicrob. Agents Chemother. 2006, 50, 1927-1930.
4. Hill, D. R.; Baird, J. K.; Parise, M. E.; Lewis, L. S.; Ryan, E. T.; Magill, A. J. Primaquine: report from CDC expert meeting on malaria chemoprophylaxis I. Am. J. Trop. Med. Hyg. 2006, 75, 402-415.
5. Vale, N.; Moreira, R.; Gomes, P. Primaquine revisited six decades after its discovery. Eur. J. Med. Chem. 2009, 44, 937-953.
6. Redhead, S. A.; Cushion, M. T.; Frenkel, J. K.; Stringer, J. R. Pneumocystis and Trypanosoma cruzi: nomenclature and typifications. J. Eukaryot. Microbiol. 2006, 53, 2-11.
7. Hawksworth, D. L. Responsibility in naming pathogens: the case of Pneumocystis jirovecii, the causal agent of pneumocystis pneumonia. Lancet Infect. Dis. 2007, 7, 3-5.
8. Seage, G. R.; Losina, E.; Goldie, S. J.; Paltiel, A. D.; Kimmel, A. D.; Freedberg, K. A. The Relationship of Preventable Opportunistic Infections, HIV-1 RNA, and CD4 Cell Counts to Chronic Mortality. JAIDS, J. Acquired Immune Defic. Syndr. 2002, 30, 421-428.
9. Morris, A.; Lundgren, J. D.; Masur, H.; Walzer, P. D.; Hanson,D. L.; Frederick, T.; Huang, L.; Beard, C. B.; Kaplan, J. E. Current epidemiology of Pneumocystis pneumonia. Emerg. Infect. Dis. 2004, 10, 1713-1720.
10. Thomas, C. F., Jr.; Limper, A. H. Pneumocystis Pneumonia. New Engl. J. Med. 2004, 350, 2487-2498.
11. Peterson, J. C.; Cushion, M. T. Pneumocystis: not just pneumonia. Curr. Opin. Microbiol. 2005, 8, 393-398.
12. Fishman, J. A. Prevention of infection due to Pneumocystis carinii. Antimicrob. Agents Chemother. 1998, 42, 995-1004.
13. Mihaly, G. W.; Ward, S. A.; Edwards, G.; L'E Orme, M.; Breckenridge, A. M. Pharmacokinetics of primaquine in man: identification of the carboxylic acid derivative as a major plasma metabolite. Br. J. Clin. Pharmacol. 1984, 17, 441-446.
14. Constantino, L.; Paixão, P.; Moreira, R.; Portela, M. J.; Rosário, V. E.; Iley, J. Metabolism of primaquine by liver homogenate fractions. Evidence for monoamine oxidase and cytochrome P450 involvement in the oxidative deamination of primaquine to carboxyprimaquine. Exp. Toxicol. Pathol. 1999, 51, 299-303.
15. Srivastava, P.; Singh, S.; Jain, G. K.; Puri, S. K.; Pandey, V. C. A simple and rapid evaluation of methemoglobin toxicity of 8-aminoquinolines and related compounds. Ecotoxicol. Environ. Saf. 2000, 45, 236-239.
16. Haymond, S.; Cariappa, R.; Eby, C. S.; Scott, M. G. Laboratory assessment of oxygenation in methemoglobinemia. Clin. Chem. 2005, 51, 434-444.
17. Umbreit, J. Methemoglobin-it0s not just blue: a concise review. Am. J. Hematol. 2007, 82, 134-144.
18. Portela, M. J.; Moreira, R.; Valente, E.; Constantino, L.; Iley, J.; Pinto, J.; Rosa, R.; Cravo, P.; Rosário, V. E. Dipeptide derivatives of primaquine as transmission-blocking antimalarials: effect of aliphatic side-chain acylation on the gametocytocidal activity and on the formation of carboxyprimaquine in rat liver homogenates. Pharm. Res. 1999, 16, 949-955.
19. Klixbull, U.; Bundgaard, H. Prodrugs as drug delivery systems. XXX. 4-Imidazolidinones as potential bioreversible derivatives for the α-aminoamide moiety in peptides. Int. J. Pharm. 1984, 20, 273-284.
20. Klixbull, U.; Bundgaard, H. Kinetics of reversible reactions of ampicillin with various aldehydes and ketones with formation of 4-imidazolidinones. Int. J. Pharm. 1985, 23, 163-173.
21. Rasmussen, G. J.; Bundgaard,H. Prodrugs of peptides. 10. Protection of di- and tripeptides against aminopeptidase by formation of bioreversible 4-imidazolidinone derivatives. Int. J. Pharm. 1991, 71, 45-53.
22. Rasmussen, G. J.; Bundgaard, H. Prodrugs of peptides. 15. 4-Imidazolidinone prodrug derivatives of enkephalins to prevent aminopeptidase-catalyzed metabolism in plasma and absorptive mucosae. Int. J. Pharm. 1991, 76, 113-122.
23. Bak, A.; Fich, M.; Larsen, B. D.; Frokjaer, S.; Frus, G. J. N-Terminal 4-imidazolidinone prodrugs of Leu-enkephalin: synthesis, chemical and enzymatic stability studies. Eur. J. Pharm. Sci. 1999, 7, 317-323.
24. Rinnová, M.; Nefzi, A.; Houghten, R. A. An efficient approach for solid-phase synthesis of peptidomimetics based on 4-imidazolidinones. Tetrahedron Lett. 2002, 43, 2343-2346.
25. Gomes, P.; Aráujo, M. J.; Rodrigues, M.; Vale, N.; Azevedo, Z.; Iley, J.; Chambel, P.; Morais, J.; Moreira, R. Synthesis of imidazolidin-4-one and 1H-imidazo[2,1-a]isoindole-2,5(3H,9bH)-dione derivatives of primaquine: scope and limitations. Tetrahedron 2004, 60, 5551-5562.
26. Araújo, M. J.; Bom, J.; Capela, R.; Casimiro, C.; Chambel, P.; Gomes, P; Iley, J.; Lopes, F.; Morais, J.; Moreira, R.; Oliveira, E.; Rosário, V.; Vale, N. Imidazolidin-4-ones of primaquine as novel transmission-blocking antimalarials. J. Med. Chem. 2005, 48, 888-892.
27. Chambel, P.; Capela, R.; Lopes, F.; Iley, J.; Morais, J.; Gouveia, L.; Gomes, J. R. B.; Gomes, P.; Moreira, R. Reactivity of imidazolidin-4-one derivatives of primaquine: implications for prodrug design. Tetrahedron 2006, 62, 9883-9891.
28. Vale, N.; Collins, M. S.; Gut, J.; Ferraz, R.; Rosenthal, P. J.; Cushion, M. T.; Moreira, R.; Gomes, P. Anti-Pneumocystis carinii and antiplasmodial activities of primaquine-derived imidazolidin-4-ones. Bioorg. Med. Chem. Lett. 2008, 18, 485-488.
29. Vale, N.; Matos, J.; Moreira, R.; Gomes, P. Amino acids as selective acylating agents: regiosselective N1-acylation of imidazolidin-4-one derivatives of the antimalarial drug primaquine. Tetrahedron 2008, 64, 11144-11149.
30. Vale, N.; Matos, J.; Gut, J.; Nogueira, F.; do Rosário, V.; Rosenthal, P. J.; Moreira, R.; Gomes, P. Imidazolidin-4-one peptidomimetic derivatives of primaquine: synthesis and antimalarial activity. Bioorg. Med. Chem. Lett. 2008, 18, 4150-4153.
31. Schmidt, L. H. Relationships between chemical structures of 8-aminoquinolines and their capacities for radical cure of infections with Plasmodium cynomolgi in rhesus monkeys. Antimicrob. Agents Chemother. 1983, 24, 615-652.
32. Nodiff, E. A.; Chatterjee, S.; Musallam,H.A. Antimalarial activity of 8-aminoquinolines. Prog. Med. Chem. 1991, 28, 1-40.
33. Prudêncio, M.; Rodrigues, C. D.; Ataíde, R.; Mota, M. M. Dissecting in vitro host cell infection by Plasmodium sporozoites using flow cytometry. Cell. Microbiol. 2008, 10, 218-224.
34. Queener, S. F. New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii. J. Med. Chem. 1995, 38, 4739-4759.
35. Fishman, J. A. Treatment of infection due to Pneumocystis carinii. Antimicrob. Agents Chemother. 1998, 42, 1309-1314.
36. Chan, C.; Montaner, J.; Lefebvre, E. A.; Morey, G.; Dohn, M.; McIvor, R. A.; Scott, J.; Marina, R.; Caldwell, P. Atovaquone suspension compared with aerosolized pentamidine for prevention of Pneumocystis carinii pneumonia in human immunodeficiency virus-infected subjects intolerant of trimethoprim or sulfonamides. J. Infect. Dis. 1999, 180, 369-376.
37. Bartlett, S. R.; Queener, S. F.; Tidwell, R. R.; Milhouse, W. K.; Berman, J. D.; Ellis, W. Y.; Smith, J. W. 8-Aminoquinolines from Walter Reed Army Institute for Research for treatment and prophylaxis of Pneumocystis pneumonia in rat models. Antimicrob. Agents Chemother. 1991, 35, 277-282.
38. Queener, S. F.; Bartlett, M. S.; Nasr, M.; Smith, J. W. 8-Aminoquinolines effective against Pneumocystis carinii in vitro and in vivo. Antimicrob. Agents Chemother. 1993, 37, 2166-2172.
39. Goodwin, T. E.; Boylan,C. J.;Current,W. L.; Byrd, J.C.; Fuller,D. A.; Green, J. L.; Larocca, C. D.; Raney, K.D.; Ross, A. S.; Tucker, W. A. Enhanced pneumocystis carinii activity of new primaquine analogues. Bioorg. Med. Chem. Lett. 2000, 10, 2205-2208.
40. Cushion, M. T.; Chen, F.; Kloepfer, N. A cytotoxicity assay for evaluation of candidate anti-Pneumocystis carinii agents. Antimicrob. Agents Chemother. 1997, 41, 379-384.
41. Cushion, M. T.; Walzer, P. D.; Collins, M. S.; Rebholz, S.; Vanden Eynde, J. J.; Mayence, A.; Huang, T. L. Highly active anti-Pneumocystis carinii compounds in a library of novel piperazinelinked bisbenzamidines and related compounds. Antimicrob. Agents Chemother. 2004, 48, 4209-4216.
42. Van den Eynde, J. J.; Mayence, A.; Huang, T. L.; Collins, M. S.; Rebholz, S.; Walzer, P. D.; Cushion, M. T. Novel bisbenzamidines as potential drug candidates for the treatment of Pneumocystis carinii pneumonia. Bioorg. Med. Chem. Lett. 2004, 14, 4545-4548.
43. Flipo, M.; Beghyn, T.; Leroux, V.; Florent, I.; Deprez, B. P.; Deprez-Poulain, R. F. Novel selective inhibitors of the zinc Plasmodial aminopeptidase PfA-M1 as potential antimalarial agents. J. Med. Chem. 2007, 50, 1322-1334.
44. Lipinski, C. A.; Lombardo, 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.
45. ALOGPS 2.1; Virtual Computational Chemistry Laboratory; http:// www.vcclab.org/lab/alogps/; accessed July 3, 2009.
46. OSIRIS Property Explorer; http://www.organic-chemistry.org/prog/ peo/; accessed July 3, 2009.
47. Vale, N.; Moreira, R.; Gomes, P. Characterization of primaquine imidazolidin-4-ones with antimalarial activity by electrospray ionization-ion trap mass spectrometry. Int. J. Mass Spectrom. 2008, 270, 81-93.
48. Vale, N.; Matos, J.; Moreira, R.; Gomes, P. Electrospray ionization-ion trap mass spectrometry study of PQAAPro and PQProAA mimetic derivatives of the antimalarial primaquine. J. Am. Soc. Mass Spectrom. 2008, 19, 1476-1490.
49. Rosenthal, P. J.; Olson, J. E.; Lee, G. K.; Palmer, J. T.; Klaus, J. L.; Rasnick, D. Antimalarial effects of vinyl sulfone cysteine proteinase inhibitors. Antimicrob. Agents Chemother. 1996, 40, 1600-1603.
50. Shenai, B. R.; Lee, B. J.; Alvarez-Hernandez, A.; Chong, P. Y.; Emal, C. D.; Neitz, R. J.; Roush, W. R.; Rosenthal, P. J. Structure-activity relationships for inhibition of cysteine protease activity and development of Plasmodium falciparum by peptidyl vinyl sulfones. Antimicrob. Agents Chemother. 2003, 47, 154-160.
51. Sijwali, P. S.; Rosenthal, P. J. Gene disruption confirms a critical role for the cysteine protease falcipain-2 in haemoglobin hydrolysis by Plasmodium falciparum. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 4384-4389.
52. Sijwali, P. S.; Kato, K.; Seydel, K. B.; Gut, J.; Lehman, J.; Klemba, M.; Goldberg, D. E.; Miller, L. H.; Rosenthal, P. J. Plasmodium falciparum cysteine protease falcipain-1 is not essential in erythrocytic stage malaria parasites. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 8721-8726.