Synthesis of some cryptolepine analogues, assessment of their antimalarial and cytotoxic activities, and consideration of their antimalarial mode of action

Journal of Medicinal Chemistry

Volumn 48, Issue 7, 2005, Pages 2701-2709

  Onyeibor, Onyeka ^a,d   Croft, Simon L ^b   Dodson, Hilary I ^a   Feiz Haddad, Mohammad ^a   Kendrick, Howard ^b   Millington, Nicola J ^a   Parapini, Silvia ^c   Phillips, Roger M ^a   Seville, Scott ^a   Shnyder, Steven D ^a   Taramelli, Donatella ^c   Wright, Colin W ^a  

^a UNIVERSITY OF BRADFORD   (United Kingdom)

^b LONDON SCHOOL OF HYGIENE AND TROPICAL MEDICINE   (United Kingdom)

^c UNIVERSITY OF MILAN   (Italy)

^d Emzor Pharmaceutical Industries Ltd   (Nigeria)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICHLOROCRYPTOLEPINE; 2 BROMO 7 NITROCRYPTOLEPINE; 2,8 DICHLOROCRYPTOLEPINE; 7 BROMO 2 CHLOROCRYPTOLEPINE; 7 BROMO 2 FLUOROCRYPTOLEPINE; 7 BROMO 3 CHLOROCRYPTOLEPINE; ANTIMALARIAL AGENT; CRYPTOLEPINE DERIVATIVE; HALOGEN; HEMOZOIN; INDOLE DERIVATIVE; NITRO DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CORRELATION ANALYSIS; DOSE RESPONSE; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG SYNTHESIS; EVALUATION; IC 50; IN VITRO STUDY; MOUSE; NONHUMAN; PARASITEMIA; PLASMODIUM FALCIPARUM; PREDICTION; STRUCTURE ACTIVITY RELATION;

ALGORITHMS; ALKALOIDS; ANIMALS; ANTIMALARIALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; FEMALE; HEMEPROTEINS; INDOLES; MALARIA; MICE; MICE, INBRED BALB C; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 20244383747     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040893w     Document Type: Article

References (25)

1. Fidock, D. A.; Rosenthal, P. J.; Croft, S. L.; Brun, R.; Nwaka, S. Antimalarial drug discovery: Efficacy models for compound screening. Nat. Rev. Drug Discovery 2004, 3, 509-520.
2. Boye, G. L.; Ampofo, O. Clinical uses of Cryptolepis sanguinolenta. Proceedings of the First International Seminar on Cryptolepine, July 27-30, 1983; University of Science and Technology: Kumasi, Ghana, 1983; pp 37-40.
3. Wright, C. W.; Addae-Kyereme, J.; Breen, A. G.; Brown, J. E.; Cox, M. F. et al. Synthesis and evaluation of cryptolepine analogues for their potential as new antimalarial agents. J. Med. Chem. 2001, 44, 3187-3194.
4. Lisgarten, J. N.; Coll, M.; Portugal, J.; Wright, C. W.; Aymami, J. The antimalarial and cytotoxic drug cryptolepine intercalates into DNA at cytosine-cytosine sites. Nat. Struct. Biol. 2002, 9, 57-60.
5. Bonjean, K.; De Pauw-Gillet, M. C.; Defresne, M. P.; Colson, P.; Houssier, C. et al. The DNA intercalating alkaloid cryptolepine interferes with topoisomerase II and inhibits primarily DNA synthesis in B16 melanoma cells. Biochemistry 1998, 37, 5136-5146.
6. Kaschula, C. H.; Egan, T. J.; Hunter, R.; Basilico, N.; Parapini, S. et al. Structure-activity relationships in 4-aminoquinoline antiplasmodials. The role of the group at the 7-position. J. Med. Chem. 2002, 45, 3531-3539.
7. Pagola, S.; Stephens, P. W.; Bohle, D. S.; Kosar, A. D.; Madsen, S. K. The structure of malaria pigment beta-haematin. Nature 2000, 404, 307-310.
8. Egan, T. J.; Ross, D.; Adams, P. A. Quinoline anti-malarial drugs inhibit spontaneous formation of β-haematin (malaria pigment). FEBS Lett. 1994, 352, 54-57.
9. Raileanu, D.; Constantinescu-Simon, O.; Mosanu, E.; Nenitzescu, C. D. Improved preparatory method for N,O-diacetylindoxyl and N-acetylindoxyl. Rev. Rom. Chim. 1967, 12, 105-108.
10. Holt, S. J.; Petrow, V. Carbazoles, carbolines, and related compounds. Part 1. J. Chem. Soc. 1947, 607-611.
11. Peters, W.; Portus, J. H.; Robinson, B. L. The chemotherapy of rhodent malaria XXII. The value of drug resistant strains of Plasmodium berghei in screening for blood schizontocidal activity. Ann. Trop. Med. Parasitol. 1975, 69, 155-171.
12. Krogstad, D. J.; Dibyendu, D. Chloroquine: modes of action and resistance and the activity of chloroquine analogs. Malaria; ASM Press: Washington, D.C., 1998; pp 331-339.
13. Arzel, E.; Rocca, P.; Grellier, P.; Labaeid, M.; Frappier, F. et al. New synthesis of benzo-delta-carbolines, cryptolepines, and their salts: In vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of delta-carbolines, benzo-delta-carbolines, and cryptolepines. J. Med. Chem. 2001, 44, 949-960.
14. Sandmeyer, T. Uberisonitrosacetanilide und deren Kondensation zu Isatinen. Helvetica Chimica Acta 1919, 2, 234-242.
15. Marvel, C. S.; Hiers, G. S. Isatin. In: Blatt, A. H. Ed. Organic Syntheses Collective; Wiley: New York, 1941; pp 327-330.
16. Goodwin, B. L. Hazardous reactions. Chem. Br. 1988, 24, 336.
17. Gandy, R.; Hill, M. G. Hazardous reactions. Chem. Br. 1988, 24, 336
18. Sadler, P. W. Separation of isomeric isatins. J. Org. Chem. 1956, 21, 169-170.
19. Trager, W.; Jensen, J. B. Human malaria parasites in continuous culture. Science 1976, 193, 673.
20. Fairlamb, A. H.; Warhurst, D. C.; Peters, W. An Improved Technique for the Cultivation of Plasmodium falciparum In vitro without Daily Medium Change. Ann. Trop. Med. Parasitol. 1985, 79, 379-384.
21. Makler, M. T.; Ries, J. M.; Williams, J. A.; Bancroft, J. E.; Piper, R. C. et al. Parasite Lactate-Dehydrogenase as an Assay for Plasmodium falciparum Drug-Sensitivity. Am. J. Trop. Med. Hyg. 1993, 48, 739-741.
22. Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival - Application to Proliferation and Cyto-Toxicity Assays. J. Immun. Methods 1983, 65, 55-63.
23. Diem, K. Documenta Geigy. Scientific tables; Geigy Pharmaceuticals Company Limited: Manchester, 1962.
24. Basilico, N.; Pagani, E.; Monti, D.; Olliaro, P.; Taramelli, D. A microtitre-based method for measuring the haem polymerisation inhibitory activity (HPIA) of antimalarial drugs. J. Antimicrob. Chemother. 1998, 42, 55-60.
25. Parapini, S.; Basilico, N.; Pasini, E.; Egan, T. J.; Olliaro, P.; Taramelli, D.; Monti, D. Standardisation of the physicochemical parameters to assess in vitro the beta-hematin inhibitory activity of antimalarial drugs. Exp. Parasitol. 2000, 96, 249-256.