Antimalarial, antitrypanosomal, and antileishmanial activities and cytotoxicity of bis(9-amino-6-chloro-2- methoxyacridines): Influence of the linker

Journal of Medicinal Chemistry

Volumn 43, Issue 14, 2000, Pages 2646-2654

  Girault, Sophie ^a   Grellier, Philippe ^b   Berecibar, Amaya ^a,d   Maes, Louis ^c   Mouray, Elisabeth ^b   Lemière, Pascal ^a   Debreu, Marie Ange ^a   Davioud Charvet, Elisabeth ^a   Sergheraert, Christian ^a  

^a UNIV LILLE   (France)

^b MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^c Tibotec ^*  (Belgium)

^d Institut de Recherche Jouveinal   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; ANTILEISHMANIAL AGENT; ANTIMALARIAL AGENT; ANTITRYPANOSOMAL AGENT; BIS 9 AMINO 6 CHLORO 2 METHOXYACRIDINE DERIVATIVE; CHLOROQUINE; MEPACRINE; N1,N2 BIS(7 CHLORO 4 QUINOLINYL) 1,2 CYCLOHEXANEDIAMINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIMALARIAL ACTIVITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; CELLULAR DISTRIBUTION; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG SENSITIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ACRIDINES; ANIMALS; ANTIMALARIALS; CELL LINE; LEISHMANIA INFANTUM; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI BRUCEI; TRYPANOSOMA CRUZI;

EID: 0034644136     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990946n     Document Type: Article

References (40)

1. Van Est, H. G.; Skamene, G. E.; Schurr, E. Chemotherapy of malaria: a battle against the odds? Clin. Invest. Med. 1993, 16, 285-293.
2. White, N. J. Antimalarial drug resistance: the pace quickens. J. Antimicrob. Chemother. 1992, 30, 571-585.
3. Dorn, A.; Stoffel, R.; Matile, H.; Bubendorf, A.; Ridley, R. G. Malarial haemozoin/β hematin supports haem polymerization in the absence of protein. Nature 1995, 374, 269-271.
4. 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, 727-736.
5. Ginsburg, H.; Famin, O.; Zhang, J.; Krugliak, M. Inhibition of Glutathione-dependent Degradation of Heme by Chloroquine and Amodiaquine as a Possible Basis for Their Antimalarial Mode of Action. Biochem. Pharmacol. 1998, 56, 1305-1313.
6. 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, 1283-1285.
7. Ginsburg, H.; Stein, W. D. Kinetic modeling of chloroquine uptake by malaria-infected erythrocytes. Biochem. Pharmacol. 1991, 41, 1463-1470.
8. + exchanger determines chloroquine uptake in Plasmodium falciparum. J. Cell. Biol. 1998, 140, 335-345.
9. Bray, P. G.; Janneh, O.; Raynes, K. J.; Mungthin, M.; Ginsburg, H.; Ward, S. A. Cellular uptake of chloroquine is dependent on binding to ferriprotoporphyrin IX and is dependent on NHE activity in Plasmodium falciparum. J. Cell. Biol. 1999, 145, 363-376.
10. Reed, M. B.; Saliba, K. J.; Caruana; S. R.; Kirk, K.; Cowman A. F. Pgh1 modulates sensitivity and resistance to multiple antimalarials in Plasmodium falciparum. Nature 2000, 403, 906-909.
11. Vennerstrom, J. L.; Ellis, W. Y.; Ager, A. L., Jr.; Andersen, S. L.; Gerena, L.; Milhous, W. K. Bisquinolines. 1. N,N-Bis(7-chloroquinolin-4-yl)alkanediamines with potential against cloroquine-resistant malaria. J. Med. Chem. 1992, 35, 2129-2134.
12. Raynes, K.; Galatis, D.; Cowman, A. F.; Tilley, L.; Deady, L. W. Synthesis and activity of some antimalarial Bisquinolines. J. Med. Chem. 1995, 38, 204-206.
13. 2-Bis(7-chloroquinolin-4-yl)cyclohexane1,2-diamine: comparison of two stereoisomers and detailed evaluation of the S,S enantiomer, Ro 47-7737. Antimicrob. Chemother. 1997, 41, 677-686.
14. Cowman, A. F.; Deady, L. W.; Deharo, E.; Desneves, J.; Tilley, L. Synthesis and activity of some antimalarial Bisquinolinemethanols. Aust. J. Chem. 1997, 50, 1091-1096.
15. Basco, L. K.; Ruggeri, C.; Le Bras, J. Molécules antipaludiques; Masson: Paris, 1994; pp 115-120.
16. Gamage, S. A.; Figgitt, D. P.; Wojcik, S. J.; Ralph, R. K.; Ransijn, A.; Mauel, J.; Yardley, V.; Snowdon, D.; Croft, S. L.; Denny, W. A. Structure-activity relationships for the antileishmanial and antitrypanosomal activities of 1′-substituted 9-anilinoacridines. J. Med. Chem. 1997, 40, 2634-2642.
17. Le Pecq, J.-B.; Le Bret, M.; Barbet, J.; Roques, B. P. DNA polyintercalating drugs: DNA binding of Diacridine derivatives. Proc. Natl. Acad. Sci. U.S.A. 1975, 72, 2915-2919.
18. Gaugain, B.; Markovits, J.; Le Pecq, J.-B.; Roques, B.; Hydrogen Bonding in Deoxyribonucleic Acid Recognition. 1. Proton Nuclear Magnetic Resonance Studies of Dinucleotide-Acridine Alkylamide Complexes. Biochemistry 1981, 20, 3035-3042.
19. Chen, T. K.; Fico, R.; Canellakis, E. S. Diacridines, Bifunctional Intercalators. Chemistry and Antitumor Activity. J. Med. Chem. 1978, 21, 868-874.
20. Markovits, J.; Garbay-Jaureguiberry, C.; Roques, B. P.; Le Pecq, J.-B. Acridine dimers: influence of the intercalating ring and of the linking-chain nature on the equilibrium and kinetic DNA-binding parameters. Eur. J. Biochem. 1989, 180, 359-366.
21. Denny, W. A.; Atwell, G. J.; Baguley, B. C.; Wakelin, L. P. G. Potential antitumor agents. Synthesis and antitumor activity of new classes of diacridines. The importance of linker chain rigidity for DNA binding kinetics and biological activity. J. Med. Chem. 1985, 28, 1568-1574.
22. Wakelin, L. P. G.; Romanos, M.; Chen, T. K.; Glaubiger, D.; Canellakis, E. S.; Waring, M. J. Structural limitations on the bifunctional interaction of Diacridines into DNA. Biochemistry 1978, 17, 5057-5063.
23. Wakelin, L. P. G.; Creasy, T. S.; Waring, M. J. Equilibrium constants for the binding of an homologous series of monofunctional and bifunctional intercalating diacridines to calf thymus DNA. FEBS Lett. 1979, 104, 261-265.
24. Canellakis, E. S.; Shaw, Y. H.; Hanners, W. E.; Schwartz, R. A. Diacridines: bifunctional intercalators. I. Chemistry, physical chemistry and growth inhibitor properties. Biochim. Biophys. Acta 1976, 418, 277-289.
25. Srivastava, S.; Tewari, S.; Chauhan, P. M. S.; Puri, S. K.; Bhaduri, A. P.; Pandey V. C. Synthesis of bisquinolines and their in vitro ability to produce methemoglobin in canin hemosylate. Bioorg. Med. Chem. Lett. 1999, 9, 653-658.
26. Coste, J.; Frerot, E.; Jouin, P. Coupling N-Methylated Amino Acids Using PyBroP and PyCloP Halogenophosphonium Salts: Mechanism and Fields of Application. J. Org. Chem. 1994, 59, 2437-2446.
27. Girault, S.; Davioud-Charvet, E.; Salmon, L.; Berecibar, A.; Debreu, M.-A.; Sergheraert, C. Structure-activity relationships in 2-aminodiphenylsulfides against trypanothione reductase from Trypanosoma cruzi. Bioorg. Med. Chem. Lett. 1998, 8, 1175-1180.
28. Girault, S.; Baillet, S.; Horvath, D.; Lucas, V.; Davioud-Charvet, E.; Tartar, A.; Sergheraert C. New potent inhibitors of trypanothione reductase from Trypanosoma cruzi in the 2-aminodiphenylsulfide series. Eur. J. Med. Chem. 1997, 32, 39-52.
29. Vennerstrom, J. L.; Ager, A. L., Jr.; Dorn, A.; Andersen, S. L.; Gerena, L.; Ridley, R. G.; Milhous, W. K. Bisquinolines. 2. Antimalarial N,N-Bis(7-chloroquinolin-4-yl)heteroalkanediamines. J. Med. Chem. 1998, 41, 4360-4364.
30. Crothers, D. M. Calculation of Binding Isotherms for Heterogeneous Polymers. Biopolymers 1968, 6, 575-581.
31. Bauer, W.; Vinograd, J. Interaction of Closed Circular DNA with Intercalative Dyes. II. The Free Energy of Superhelix Formation in SV40 DNA. J. Mol. Biol. 1970, 47, 419-435.
32. 1-Acetyltransferase (SSAT) and as potential Antitumor Agents. J. Med. Chem. 1993, 36, 2998-3004.
33. Weber, J. L. A Review. Molecular Biology of Malaria Parasites. Exp. Parasitol. 1988, 66, 143-170.
34. Weber, J. L. Analysis of sequences from the extremely A + T-rich genome of Plasmodium falciparum. Gene 1987, 52, 103-109.
35. Wang, C. C. Validating targets for antiparasite chemotherapy. Parasitology 1997, 114, S31-S44.
36. Trager, W.; Jensen J. B. Human malarial parasites in continuous culture. Science 1976, 193, 673-677.
37. Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob. Agents Chemother. 1979, 16, 710-718.
38. Mossman, T. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to proliferation and Cytotoxicity Assays. J. Immunol. Methods 1983, 65, 55-63.
39. Hirumi, H.; Hirumi, K. Continuous cultivation of Trypanosoma brucei blood stream forms in a medium containing a low concentration of serum protein without feeder cell layers. J. Parasitol. 1989, 75, 985-989.
40. Camargo, E. P. Growth and differenciation in Trypanosoma cruzi: origin of metacyclic trypomastigotes in liquid media. Rev. Inst. Med. Trop. Sao Paulo 1964, 6, 63-100.