Cytotoxicity of (2,2':6',2-terpyridine)platinum(II) complexes to Leishmania donovani, Trypanosoma cruzi, and Trypanosoma brucei

Journal of Medicinal Chemistry

Volumn 42, Issue 6, 1999, Pages 999-1006

  Lowe, Gordon ^a   Droz, Anne Sophie ^a   Vilaivan, Tirayut ^a   Weaver, George W ^a   Tweedale, Lindsay ^a   Pratt, Jonathan M ^a   Rock, Peter ^b   Yardley, Vanessa ^b   Croft, Simon L ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

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

Author keywords

[No Author keywords available]

Indexed keywords

PLATINUM DERIVATIVE; PYRIDINE DERIVATIVE;

AMASTIGOTE; ANTIPROTOZOAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG EFFECT; DRUG SCREENING; LEISHMANIA DONOVANI; LEISHMANIASIS; NONHUMAN; TRYPANOSOMA BRUCEI; TRYPANOSOMA CRUZI; TRYPANOSOMIASIS; TRYPOMASTIGOTE;

ANIMALS; INTERCALATING AGENTS; LEISHMANIA DONOVANI; ORGANOPLATINUM COMPOUNDS; PYRIDINES; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI BRUCEI; TRYPANOSOMA CRUZI;

EID: 0033602511     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm981074c     Document Type: Article

References (27)

1. Jennette, K.; Lippard, S. J.; Vassiliades, G.; Bauer, W. Metallointercalation Reagents. 2-Hydroxyethanethiolato(2,2′,2″-terpyridine)-platinum(II) Monocation Binds strongly to DNA by Intercalation. Proc. Natl. Acad. Sci. U.S.A 1974, 71, 3839-3843.
2. Bond, P. J.; Langridge, R.; Jennette, K. W.; Lippard, S. J. X-ray fiber diffraction evidence for neighbour exclusion binding of a platinum metallointercalation reagent to DNA. Proc. Natl. Acad. Sci. U.S.A. 1975, 72, 4825-4829.
3. Howe-Grant, M.; Wu, K. C.; Bauer, W. R.; Lippard, S. J. Binding of Platinum and Palladium Metallointercalation Reagents and Antitumor Drugs to Closed and Open DNAs. Biochemistry 1976, 15, 4339-4346.
4. Peyratout, C. S.; Aldridge, T. K.; Crites, D. K.; McMillin, D. R. DNA-Binding Studies of a Bifunctional Platinum Complex that is a Luminescent Intercalator. Inorg. Chem. 1995, 34, 4484-4489.
5. McCoubrey, A.; Latham, H. C.; Cook, P. R.; Rodger, A.; Lowe, G. 4-Picoline 2,2′:6′,2″-terpyridine-platinum (II) - a Potent Intercalator of DNA. FEBS Lett. 1996, 380, 73-78.
6. Lowe, G.; McCloskey, J. A.; Ni, J.; Vilaivan, T. A Mass Spectroscopic Investigation of the Reaction between 4,4′-Vinylenedipyridine Bis[2,2′:6′,2″-terpyridine-platinum (II)] and the Self-complementary Oligonucleotide d(CpGpTpApCpG). Boorg. Med. Chem. 1996, 4, 1007-1013.
7. Comess, K. M.; Lippard, S. J. Molecular Aspects of Platinum-DNA Interactions. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S., Waring, M., Eds.; The MacMillan Press: New York, 1993; pp 134-168.
8. +. J. Med. Chem. 1989, 32, 128-136.
9. +. J. Med. Chem. 1989, 32, 128-136.
10. Hartley, J.; Vilaivan, T.; Weaver, G. W.; Lowe, G. unpublished work
11. Lowe, G.; Vilaivan, T. Reaction of 4-Picoline 2,2′:6′,2″-terpyridine-platinum (II) with nucleosides. J. Chem. Soc. Perkin Trans 1, 1996, 1499-1503.
12. Williamson, J. Effects of trypanocides on the fine structure of target organisms. Pharmacol. Ther. 1979, 7, 445-512.
13. Douc-Rasy, S.; Kayser, A.; Riou, G. A specific inhibitor of type 1 DNA-topoisomerase of Trypanosoma cruzi: dimethyl-hydroxyellipticinium. Biochem. Biophys. Res. Commun. 1983, 117, 1-5.
14. Ono, T.; Nakabayashi, T. Studies on the effect of bleomycin on Trypanosoma gambiense. Biken J. 1980, 23, 143-155.
15. Farrell, N.; Williamson, J.; McLaren, D. J. M. Trypanocidal and antitumour activity of platinum-metal and platinum-metal-drug dual-function complexes. Biochem. Pharmacol. 1984, 33, 961-971.
16. Croft, S. L.; Neal, R. A.; Craciunescu, D. G.; Certad-Fombona, G. The activity of platinum, iridium and rhodium drug complexes against Leishmania donovani. Trop. Med. Parasitol. 1992, 43, 24-28.
17. Pinnow, S. L.; Brothers, H. M., II; Kostic, N. M. Selective Labeling of the Enzyme Papain with Chloro(terpyridine) platinum(II). Croatica Chem. Acta 1991, 64, 519-528.
18. Croft, S. L.; Urbina, J. A.; Brun, R. Chemotherapy of Human Leishmaniasis and Trypanosomiasis. In Trypanosomiasis and Leishmaniasis; Hide, G., Mottram, J. C., Coombs, G. H., Holmes, P. H., Eds.; CAB International: Wallingford, U.K., 1997; pp 245-257.
19. Neal, R. A.; Croft, S. L. An in vitro system for determining the activity of compounds against the intracellular amastigote form of Leishmania donovani. J. Antimicrob. Chemother. 1984, 14, 463-475.
20. Chernega, A.; Droz, A. S.; Prout, K.; Vilaivan, T.; Weaver, G. W.; Lowe, G. Structural Evidence for the Reactivity of 4-Picoline 2,2′:6′,2″-terpyridine (II) Complexes and Evidence for π-Stacking in the Crystal Lattice. J. Chem. Res. (S), 1996, 402-403.
21. Hirumi, H.; Hirumi, K. Continuous cultivation of Trypanosoma brucei bloodstream forms in a medium containing a low concentration of serum protein without feeder layer cells. J. Parasitol. 1989, 75, 985-989.
22. Constable, E. C.; Ward, M. D. Synthesis and Coordination Behaviour of 6′,6″-Bis(2-pyridyl)-2,2′:4,4″:2″,2‴- quaterpyridine-;'Back-to-back' 2,2′:6′,2″-Terpyridine. J. Chem. Soc., Dalton Trans. 1990, 1405-1409.
23. 2 Films. J. Chem. Soc. Chem. Commun. 1995, 65-66.
24. 2 Films. J. Chem. Soc. Chem. Commun. 1995, 65-66.
25. 2 Films. J. Chem. Soc. Chem. Commun. 1995, 65-66.
26. Spahni, W.; Calzaferri, G. Synthese von para-substituierten Phenyl-Terpyridin Liganden. Helv. Chim. Acta 1984, 67, 450-454.
27. Lowe, G.; Vilaivan, T. An improved method for the Synthesis of 2,2′:6′,2″-Terpyridine-platinum (II) Complexes. J. Chem. Res. (S) 1996, 386-387.