Effect of ruthenium complexation on trypanocidal activity of 5-nitrofuryl containing thiosemicarbazones

European Journal of Medicinal Chemistry

Volumn 44, Issue 12, 2009, Pages 4937-4943

  Pagano, Mariana ^a   Demoro, Bruno ^a   Toloza, Jeanette ^b   Boiani, Lucía ^a   González, Mercedes ^a   Cerecetto, Hugo ^a   Olea Azar, Claudio ^b   Norambuena, Ester ^c   Gambino, Dinorah ^a   Otero, Lucía ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^b UNIVERSITY OF CHILE   (Chile)

^c UNIVERSIDAD METROPOLITANA DE CIENCIAS DE LA EDUCACIÓN   (Chile)

Author keywords

5 Nitrofuryl containing thiosemicarbazones; Chagas disease; Ruthenium complexes

Indexed keywords

5 NITROFURYL CONTAINING THIOSEMICARBAZONE; ANTIPROTOZOAL AGENT; RUTHENIUM COMPLEX; SCAVENGER; UNCLASSIFIED DRUG;

ANTIPROTOZOAL ACTIVITY; ARTICLE; COMPLEX FORMATION; DRUG EFFECT; DRUG SYNTHESIS; GROWTH INHIBITION; IN VITRO STUDY; LIPOPHILICITY; NONHUMAN; PHYSICAL CHEMISTRY; TRYPANOSOMA CRUZI;

LIGANDS; MOLECULAR STRUCTURE; NITROFURANS; ORGANOMETALLIC COMPOUNDS; RUTHENIUM; THIOSEMICARBAZONES; TRYPANOCIDAL AGENTS; TRYPANOSOMA CRUZI;

EID: 70450242912     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.08.008     Document Type: Article

References (26)

1. World Health Organization: http://www.who.int/ctd/chagas/burdens/.
2. Paulino M., Iribarne F., Dubin M., Aguilera-Morales S., Tapia O., and Stoppani A.O.M. The chemotherapy of Chagas disease: an overview. Mini-Rev. Med. Chem. 5 (2005) 499-519
3. Maya J.D., Cassels B., Iturriaga-Vásquez P., Ferreira J., Faúndez M., Galanti N., Ferreira A., and Morello A. Mode of action of natural and synthetic drugs against Trypanosoma cruzi and their interaction with the mammalian host. Comp. Biochem. Physiol. A 146 4 (2007) 601-620
4. Cerecetto H., and González M. Chemotherapy of Chagas disease: status and new developments. Curr. Top. Med. Chem. 2 (2002) 1185-1190
5. Schofield C., Jannin J., and Salvatella R. The future of Chagas disease control. Trends Parasitol. 22 (2006) 583-588
6. Sánchez-Delgado R.A., and Anzellotti A. Metal complexes as chemotherapeutic agents against tropical diseases: trypanosomiasis, malaria and leishmaniasis. Mini-Rev. Med. Chem. 4 (2004) 23-30
7. Fricker S.P., Mosi R.M., Cameron B.R., Baird I., Zhu Y., Anastassov V., Cox J., Doyle P.S., Hansell E., Lau G., Langille J., Olsen M., Qin L., Skerlj R., Wong R.S.Y., Santucci Z., and McKerrow J.H. Metal compounds for the treatment of parasitic diseases. J. Inorg. Biochem. 102 (2008) 1839-1845
8. Otero L., Noblía P., Gambino D., Cerecetto H., González M., Ellena J.A., and Piro O.E. Synthesis and characterization of new ruthenium complexes with active ligands against Chagas' disease. Inorg. Chim. Acta 344 (2003) 85-94
9. 3)(3-(5-Nitrofuryl)acroleine semicarbazone). Z. Anorg. Allg. Chem. 629 (2003) 1033-1036
10. Otero L., Aguirre G., Boiani L., González M., Denicola A., Rigol C., Olea-Azar C., Maya J.D., Morello A., Gambino D., and Cerecetto H. Nitrofurylsemicarbazone rhenium and ruthenium complexes as anti-trypanosomal agents. Eur. J. Med. Chem. 41 (2006) 1231-1239
11. Otero L., Vieites M., Boiani L., Denicola A., Rigol C., Opazo L., Olea-Azar C., Maya J.D., Morello A., Krauth-Siegel R.L., Piro O.E., Castellano E., González M., Gambino D., and Cerecetto H. Novel antitrypanosomal agents based on palladium nitrofurylthiosemicarbazone complexes: DNA and redox metabolism as potential therapeutic targets. J. Med. Chem. 49 (2006) 3322-3331
12. Vieites M., Otero L., Santos D., Gajardo D., Toloza J., Figueroa R., Norambuena E., Olea-Azar C., Aguirre G., Cerecetto H., González M., Morello A., Maya J.D., Garat B., and Gambino D. Platinum (II) metal complexes as potential anti-Trypanosoma cruzi agents. J. Inorg. Biochem 102 (2008) 1033-1043
13. Vieites M., Otero L., Santos D., Olea-Azar C., Norambuena E., Aguirre G., Cerecetto H., González M., Kemmerling U., Morello A., Maya J.D., and Gambino D. Platinum-based complexes of bioactive 3-(5-nitrofuryl)acroleine thiosemicarbazones showing anti-Trypanosoma cruzi activity. J. Inorg. Biochem 103 (2009) 411-418
14. Allardyce C.S., Dorcier A., Scolaro C., and Dyson P.J. Development of organometallic (organo-transition metal) pharmaceuticals. Appl. Organometal. Chem. 19 (2005) 1-10
15. Gambino D., Otero L., Vieites M., Boiani M., González M., Baran E.J., and Cerecetto H. Vibrational spectra of palladium 5-nitrofuryl thiosemicarbazone complexes: experimental and theoretical study. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 68 (2007) 341-348
16. Olea-Azar C., Atria A.M., Mendizábal F., Di Maio R., Seoane G., and Cerecetto H. Electrón spin resonance and cyclic voltammetry studies of nitrofurane and nitrothiophene analogues of nifurtimox. Spectrosc. Lett. 31 (1998) 99-109
17. Otero L., Folch C., Barriga G., Rigol C., Opazo L., Vieites M., Gambino D., Cerecetto H., Norambuena E., and Olea-Azar C. ESR, electrochemical and reactivity studies of antitrypanosomal palladium thiosemicarbazone complexes. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 70 (2008) 519-523
18. Aguirre G., Boiani L., Cerecetto H., Fernández M., González M., Denicola A., Otero L., Gambino D., Rigol C., Olea-Azar C., and Faundez M. In vitro activity and mechanism of action against the protozoan parasite Trypanosoma cruzi of 5-nitrofuryl containing thiosemicarbazones. Bioorg. Med. Chem. 12 (2004) 4885-4893
19. Otero L., Maya J.D., Morello A., Rigol C., Barriga G., Rodriguez J., Folch C., Norambuena E., Gonzalez M., Olea-Azar C., Cerecetto H., and Gambino D. Insight into the bioreductive mode of action of antitrypanosomal 5-nitrofuryl containing thiosemicarbazones. Med. Chem. 4 (2008) 11-17
20. Stephenson J.A., and Wilkinson G. New complexes of ruthenium(II) and (III) with triphenylfosfine, triphenylarsine, trichlorostannate, pyridine and other ligands. J. Inorg. Nucl. Chem. 28 (1966) 945-956
21. Evans I., Spencer A., and Wilkinson G.J. Dichlorotetrakis(dimethylsulfoxide)ruthenium(II) and its use as a source material for some new ruthenium(II) complexes. Chem. Soc. Dalton Trans. (1973) 204-209
22. 3). Inorg. Chim. Acta 203 (1993) 205-217
23. Cerecetto H., Di Maio R., González M., Risso M., Saenz P., Seoane G., Denicola A., Peluffo G., Quijano C., and Olea-Azar C. 1,2,5-Oxadiazole N-oxide derivatives and related compounds as potential antitrypanosomal drugs. Structure-activity relationships. J. Med. Chem. 42 (1999) 1941-1950
24. Huang L., Lee A., and Ellman J.A. Identification of potent and selective mechanism-based inhibitors of the cysteine protease cruzain using solid-phase parallel synthesis. J. Med. Chem. 45 (2002) 676-684
25. Ou B., Hampsch-Woodill M., and Prior R.L. Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe. J. Agric. Food Chem. 49 (2001) 4619-4626
26. Dávalos A., Gómez-Cordovés C., and Bartolomé B. Extending applicability of the oxygen radical absorbance capacity (ORAC - Fluorescein) assay. J. Agric. Food Chem. 52 (2004) 48-54