Antitrypanosomal activities and cytotoxicity of 5-nitro-2-furancarbohydrazides

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 24, 2002, Pages 3601-3604

  Millet, Régis ^a   Maes, Louis ^b   Landry, Valérie ^a   Sergheraert, Christian ^a   Davioud Charvet, Elisabeth ^a  

^a UNIV LILLE   (France)

^b L11 Gen De Wittelaan ^*  (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITRYPANOSOMAL AGENT; BENZNIDAZOLE; HYDRAZIDE DERIVATIVE; MELARSOPROL; NIFURTIMOX; HYDRAZINE DERIVATIVE;

ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; NONHUMAN; TRYPANOSOMA BRUCEI; TRYPANOSOMA CRUZI; ANIMAL; CELL CULTURE; CELL SURVIVAL; DRUG EFFECT; IC 50; LEISHMANIA INFANTUM; MOUSE; PARASITOLOGY; PERITONEUM MACROPHAGE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

PROTOZOA; TRYPANOSOMA; TRYPANOSOMA BRUCEI; TRYPANOSOMA CRUZI;

ANIMALS; CELL SURVIVAL; HUMANS; HYDRAZINES; INHIBITORY CONCENTRATION 50; LEISHMANIA INFANTUM; MACROPHAGES, PERITONEAL; MICE; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOCIDAL AGENTS; TRYPANOSOMA BRUCEI BRUCEI; TRYPANOSOMA CRUZI; TUMOR CELLS, CULTURED;

EID: 0036891274     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00788-6     Document Type: Article

References (23)

1. (a) Castro J.A., Diaz de Toranzo E.G. Biomed. Environ. Sci. 1:1988;19.
2. (b) Gorla N.B., Ledesma O.S., Barbieri G.P., Larripa I.B. Mut. Res. 224:1989;263.
3. (a) Cerecetto H., Di Maio R., González M., Risso M., Saenz P., Seoane G., Denicola A., Peluffo G., Quijano C., Olea-Azar C. J. Med. Chem. 3:1999;1941.
4. (b) Cerecetto H., Di Maio R., González M., Risso M., Sagrera G., Seoane G., Denicola A., Peluffo G., Quijano C., Stoppani A.O.M., Paulino M., Olea-Azar C., Basombrio M.A. Eur. J. Med. Chem. 35:2000;343.
5. (a) Blumenstiel, K.; Schoneck, R.; Yardley, V.; Croft, S. L.; Krauth-Siegel, R. L. Biochem. Pharmacol. 1999, 58, 1791.
6. (b) Cenas, N.; Bironaite, D.; Dickancaite, E.; Anusevicius, Z.; Sarlauskas, J.; Blanchard, J. S. Biochem. Biophys. Res. Commun. 1994, 204, 224.
7. (c) Kato, Y., Inouye, T.; Jyosui, S.; Kakimoto, K.; Iyehara-Ogawa, H.; Tsuruta, T. 1984, 140, 169.
8. (d) Meltzer, R. I.; Lewis, A. D.; McMillan, F. H.; Genzer, D.; Leonard, F.; King, J. A. J. Am. Pharm. Assoc. 1953, 42, 594.
9. (e) Yale, H. L.; Losee, K.; Martins, J.; Holsing, M.; Perry, F. M.; Bernstein J. J. Am. Chem. Soc. 1953, 75, 1933.
10. Troeberg L., Chen X., Flaherty T.M., Morty R.E., Cheng M., Hua H., Springer C., McKerrow J.H., Kenyon G.L., Lonsdale-Eccles J.D., Coetzer T.H., Cohen F.E. Mol. Med. 6:2000;6609.
11. Gross, E.; Meienhofer, J. The Peptides, Analysis, Synthesis, Biology. Vols 1,2,3,5; 1979-1983. Academic Press: New York, NY.
12. (a) Coste J., Le-Nguyen D., Castro B. Tetrahedron Lett. 31:1990;205.
13. (b) Hoeg-Jensen T., Havsteen Jakobsen M., Olsen C.E., Holm A. Tetrahedron Lett. 32:1991;7617.
14. 2 and TR (0.02 U per assay).
15. Faerman C.H., Savvides S.N., Strickland C., Breidenbach M.A., Ponasik J.A., Ganem B., Ripoll D., Krauth-Siegel R.L., Karplus P.A. Biorg. Med. Chem. 4:1996;1247.
16. 3a as positive control. 4 mM Stock solutions of the compounds were prepared in DMSO and stored at -20°C. The LipDH sample used had an activity of 5.3 U/mL in the physiological forward reaction (lipoamide+NAD) and an intrinsic oxidase activity of 0.05 U/mL (the control assay contained only NADH but lacked the nitrofuran derivatives). Nitrofuran reductase assay: assay volume 90 μL in 50 mM potassium phosphate buffer, 1 mM EDTA, pH 7.5, 25°C, 100 μM NADH, 133 μM nitrofuran derivative. The nitrofuran reductase activity of LipDH was determined by following the disappearance of the NADH absorption at 340 nm.
17. (a) Krauth-Siegel R.L., Enders B., Henderson G.B., Fairlamb A.H., Schirmer R.H. Eur. J. Biochem. 164:1987;123.
18. (b) Lohrer H., Krauth-Siegel R.L. Eur. J. Biochem. 194:1990;863.
19. (a) Krauth-Siegel R.L., Schöneck R. FASEB J. 9:1995;1138.
20. (b) Henderson G.B., Ulrich P., Fairlamb A.H., Rosenberg I., Pereira M., Sela M., Cerami A. Proc. Natl. Acad. Sci. U.S.A. 85:1988;5374.
21. (c) Jockers-Scherübl M.C., Schirmer R.H., Krauth-Siegel R.L. Eur. J. Biochem. 180:1989;267.
22. (d) Salmon-Chemin L., Buisine E., Yardley V., Kohler S., Debreu M.A., Landry V., Sergheraert C., Croft S.L., Krauth-Siegel L.R., Davioud-Charvet E. J. Med. Chem. 44:2001;548.
23. Li R., Chen X., Gong B., Selzer P.M., Li Z., Davidson E., Kurzban G., Miller R.E., Nuzum E.O., McKerrow J.H., Fletterick R.J., Gillmor S.A., Craik C.S., Kuntz I.D., Cohen F.E., Kenyon G.L. Bioorg. Med. Chem. 4:1996;1421.