Design, synthesis and antimalarial activity of a new class of iron chelators

Medicinal Chemistry

Volumn 2, Issue 2, 2006, Pages 133-138

  Solomon, V Raja ^a   Haq, W ^a   Puri, Sunil K ^a   Srivastava, Kumkum ^a   Katti, Settu B ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

4 aminoquinoline; Antimalarial agents; Iron chelator

Indexed keywords

4 AMINOQUINOLINE DERIVATIVE; [2 (BISCARBOXYMETHYLAMINO)ETHYL][[[2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYLCARBAMOYL]METHYL]AMINO]ACETIC ACID; [2 (BISCARBOXYMETHYLAMINO)PROPYL][[[2 (CHLOROQUINOLIN 4 YLAMINO)ETHYLCARBAMOYL]METHYL]AMINO]ACETIC ACID; [2 (BISETHOXYCARBONYLMETHYLAMINO)ALKYL][[[2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYLCARBAMOYL]METHYL]AMINO]ACETIC ACID ETHYL ESTER; [2 (BISETHOXYCARBONYLMETHYLAMINO)ETHYL][[[2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYLCARBAMOYL]METHYL]AMINO]ACETIC ACID ETHYL ESTER; [2 (BISETHOXYCARBONYLMETHYLAMINO)PROPYL][[[2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYLCARBAMOYL]METHYL]AMINO]ACETIC ACID ETHYL ESTER; [3 (BISCARBOXYMETHYLAMINO)PROPYL][[[2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYLCARBAMOYL]METHYL]AMINO]ACETIC ACID; [3 (BISETHOXYCARBONYLMETHYLAMINO)PROPYL][[[2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYLCARBAMOYL]METHYL]AMINO]ACETIC ACID; [4 (BISCARBOXYMETHYLAMINO)BUTYL][[[2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYLCABAMOYL]METHYL]AMINO]ACETIC ACID; [4 (BISETHOXYCARBONYLMETHYLAMINO)BUTYL][[[2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYLCARBAMOYL]METHYL]AMINO]ACETIC ACID ETHYL ESTER; ANTIMALARIAL AGENT; ANTISPOROZOAL AGENT; DEFERIPRONE; DEFEROXAMINE; DRUG CARRIER; EDETIC ACID; ETHANE 1,2 BIS(N 1 AMINOETHYLBUTYL 3 THIOL; IRON CHELATING AGENT; PYRIDOXAL ISONICOTINOYLHYDRAZONE; SALICYLALDEHYDE ISONICOTINOYLHYDRAZONE; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ABSORPTION; DRUG DESIGN; DRUG HALF LIFE; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; IN VITRO STUDY; IN VIVO STUDY; LIPOPHILICITY; MEMBRANE PERMEABILITY; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

AMINOQUINOLINES; ANIMALS; ANTIMALARIALS; CELL MEMBRANE PERMEABILITY; CELLS, CULTURED; EDETIC ACID; HUMANS; INHIBITORY CONCENTRATION 50; IRON CHELATING AGENTS; MICROBIAL SENSITIVITY TESTS; MODELS, CHEMICAL; PLASMODIUM FALCIPARUM;

EID: 33746107934     PISSN: 15734064     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340606776056179     Document Type: Article

References (39)

1. Wiesner, J.; Ortmann, R.; Schlitzer, M. Angew. Chem. Int. Ed. 2003, 42, 5274.
2. Ridley, R.G. Nature 2002, 415, 686.
3. Warhurst, D.C. Biochem. Pharmacol. 1981, 30, 3323.
4. Goldberg, D.E.; Slater, A.F.G.; Cerami, A.; Henderson, G.B. Proc.Natl. Acad. Sci. USA 1990, 87, 2931.
5. Ridley, R.G. J. Pharm. Pharmacol. 1997, 49, 43.
6. Gordeuk, V. R.; Thuma, P. E.; Brittenham, G. M. Adv. Exp. Med. Biol. 1994, 356, 371.
7. Rouault, T. A.; Klausner, R. D. Curr. Top. Cell. Reg. 1997, 35, 1.
8. Cabantchik, Z.I; Glickstein, H.; Golenser, J.; Loyevsky, M.; Tsafack, A. Acta Haematol. 1996, 95, 70.
9. Nyholm, S.; Mann, G. I.; Johanson, A. G.; Bergerson, R. J.; Graslund, A.; Thelander, L. J. Biol. Chem. 1993, 268, 26200.
10. Lytton, S. D.; Mester, B.; Dayan, L; Glickstein, H.; Libman, J.; Shanzer, A.; Cabantchik, Z. I. Blood 1993, 81, 214.
11. Cabantchik, Z. I. Parasitol. Today 1995, 11, 74.
12. Cabantchik, Z. I.; Moody-Haupt, S.; Gordeuk, V. R. FEMS Immunol. Med. Microbiol. 1999, 26, 289.
13. Richardson, D. R. Exp. Opin. Invest. Drugs 1999, 8, 2141.
14. Raventos-Suarez, C.; Pollack, S.; Nagel R. L. Am. J. Trop. Med. Hyg. 1982, 31, 919.
15. Peto, T. E.; Thompson, J. L. Br. J. Haematol. 1986, 63, 273.
16. Loyevsky, M.; Lytton, S. D.; Mester, B.; Libman, J.; Shanzer, A.; Cabantchik, Z. I. J. Clin. Invest. 1993, 91, 218.
17. Heppner, D. G.; Hallaway, P. E.; Kontoghiorghes, G. J.; Eaton, J. W. Blood. 1988, 72, 358.
18. Hershko, C.; Theanacho, E. N.; Spira, D. T.; Peter, H. H.; Dobin, P.; Hider, R. C. Blood 1991, 77, 637.
19. Clarke, C. J.; Eaton, J. M. Clin. Res. 1990, 38, 300A.
20. Tsafack, A.; Loyevsky, M.; Ponka, P.; Cabantchik, Z. I. J. Lab. Clin. Med. 1996, 127, 575.
21. Loyevsky, M.; John, C.; Zaloujnyi, L; Gordeuk, V. Biochem. Pharmacol. 1997, 54, 451.
22. Modell, B.; Berdoukas, V. The Clinical Approach to Thalasemia. Grune & Stratton, London, 1984.
23. Skoog, D.A.; West, D. M. Fundamentals of Analytical Chemistry, 3rd edn.; Reinhart and Winston, New York, 1983, p272.
24. Welcher, F. J. The Analytical use of Ethylene diamine tetraacetic acid. EDTA, its salts and complexes in chemical analysis. D. Van Nostrand company Inc, Princeton, New Jersey, 1958, 1.
25. Zheng, H.; Weiner, L.M.; Bar-Am, O.; Epsztejn, Z.; Cabantchik, Z. I.; Warshawsky, A.; Youdim, M.B.H.; Fridkin, M. Bioorg. Med. Chem. 2005, 13, 773.
26. Aikawa, M. Am. J. Pathol. 1972, 67, 277.
27. Solomon, V. R.; Puri, S. K.; Srivastava, K.; Katti, S. B. Bioorg. Med. Chem. 2005, 13, 2157.
28. Hay, R. W.; Nolan, K. B. J. Chem. Soc. Dalton Trans. 1974, 1348.
29. Pradines, B.; Rolain, J. M.; Ramiandrasoa, F.; Fusai, T.; Mosnier, J.; Rogier, C.; Daries, W.; Baret, E.; Kunesch, G.; Le Bras, J.; Parzy, D. J. Antimicrob, Chemother. 2002, 50, 177.
30. Egan, T.J.; Hunter R.; Kaschula, C.H.; Marques, H.M.; Misplon, A.; Waldon, J.C. J. Med. Chem. 2000, 43, 283.
31. Dorn, A.; Vippagunta, S.R.; Matile, H.; Jaquet, C.; Vennerstrom, J.L.; Ridley, R. Biochem. Pharmacol. 1998, 55, 727.
32. Egan, T.J. Targets 2003, 2, 115.
33. Trager, W.; Jensen, J.B. Science 1979, 193, 673.
34. Lambros, C.; Vanderberg, J. P. J. Parasitol 1979, 65, 418.
35. Pallas 2.0, Compu-Drug Chemistry Ltd. San Francisco, CA.
36. Egan, T. J.; Mavuso, W. W.; Ross, D. C.; Marques, H. M. J. Inorg. Biochem. 1997, 68, 137.
37. Egan, T. J.; Marques, H. M. Coord. Chem. Rev. 1999, 190, 493.
38. Egan, T. J.; Hunter, R.; Kaschula, C.H.; Marques, H. M.; Misplon, A.; Walden, J. J. Med. Chem. 2000, 43, 283.
39. Tripathi, A. K; Khan, S. I.; Walker, L. A.; Tekwani, B. L. Anal. Chem. 2004, 325, 85.