Cytotoxicity of furoxans: Quantitative structure-activity relationships study

Farmaco

Volumn 59, Issue 5, 2004, Pages 405-412

  Boiani, Mariana ^a   Cerecetto, Hugo ^a   González, Mercedes ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIPARASITIC AGENT; FURAZAN DERIVATIVE;

AB INITIO CALCULATION; ANIMAL CELL; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; CYTOTOXICITY; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL DIVISION; CELL LINE, TUMOR; CRICETINAE; LUNG; OXADIAZOLES; OXIDATION-REDUCTION; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 2142662867     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.farmac.2003.12.011     Document Type: Article

References (42)

1. Stuart K.L. Furazans. Heterocycles. 3:1975;651-690
2. Gasco A., Boulton A.J. Furoxans and benzofuroxans. Adv. Heterocycl. Chem. 29:1981;251-340
3. Stevens J., Schweizer M., Rauhut G. Toward an understanding of the furoxan-dinitrosoethylene equilibrium. J. Am. Chem. Soc. 123:2001;7326-7333. and references therein
4. Gagneux A.R., Meier R. Aminofuroxane 1. Synthese und struktur. Helv. Chim. Acta. 53:1970;1883-1892
5. Calvino R., Gasco A., Menziani E., Serafino A. Unsymmetrically substituted furoxans. VIII (1) Chloromethylfuroxans. J. Heterocyclic Chem. 20:1983;783-785
6. Calvino R., Ferrarotti B., Serafino A., Gasco A. Unsymmetrically substituted furoxans. 10. Acetyl-methyl-furoxans. Heterocycles. 23:1985;1955-1960
7. Fruttero R., Ferrarotti B., Serafino A., Gasco A. Phenylfuroxancarboxylic acids and their derivatives. Liebigs Ann. Chem. 1990;335-338
8. Mu L., Feng S.S., Go M.L. Study of synthesis and cardiovascular activity of some furoxan derivatives as potential NO-donors. Chem. Pharm. Bull. 48:2000;808-816
9. Lolli M.L., Cena C., Medana C., Lazzarato L., Morini G., Coruzzi G., Manarini S., Fruttero R., Gasco A. A new class of Ibuprofen derivatives with reduced gastrotoxicity. J. Med. Chem. 44:2001;3463-3468
10. Cena C., Visentin S., Gasco A., Martorana P.A., Fruttero R., Gasco A. Platelet antiaggregatory effects and haemodynamic activity of two terfuroxan isomer pairs. Farmaco. 57:2002;417-420
11. Cena C., Lolli M.L., Lazzarato L., Guaita E., Morini G., Coruzzi G., McElroy S.P., Megson I.L., Fruttero R., Gasco A. Antiinflammatory, gastrosparing, and antiplatelet properties of new NO-donor esters of Aspirin. J. Med. Chem. 46:2003;747-754
12. 3-antagonists endowed with NO-donor properties. Bioorg. Med. Chem. 11:2003;1197-1205
13. 1- antagonists. J. Med. Chem. 46:2003;3762-3765
14. Ovchinnikov I.V., Kulikov A.S., Makhova N.N., Tosco P., Di Stilo A., Fruttero R., Gasco A. Synthesis and vasodilating properties of N-alkylamide derivatives of 4-amino-3-furoxancarboxylic acid and related azo derivatives. Farmaco. 58:2003;677-681
15. Cerecetto H., Porcal W. Pharmacological properties of furoxans and benzofuroxans: Recent developments. Mini-Rev. Med. Chem. 2004;. in press
16. Cerecetto H., González M., Seoane G., Stanko C., Piro O.E., Castellano E.E. Mass spectrometry of 1, 2, 5-oxadiazole N-oxide derivatives. Use of deuterated analogues in fragmentation pattern studies. J. Braz. Chem. Soc. 2004;. in press
17. Cerecetto H., Di Maio R., González M., Risso M., Saenz P., Seoane G., Denicola A., Peluffo G., Quijano C., Olea-Azar C. 1, 2, 5-Oxadiazole N-oxide derivatives and related compounds as potential antitrypanosomal drugs. Structure-activity relationship. J. Med. Chem. 42:1999;1941-1950
18. Cerecetto H., Dias E., Di Maio R., González M., Pacce S., Saenz P., Seoane G., Suescun L., Mombrú A., Fernández G., Lema M., Villalba J. Synthesis and herbicidal activity of N-oxide derivatives. J. Agric. Food Chem. 48:2000;2995-3002
19. Cerecetto H., González M. N-Oxides as bioreductive compounds. Mini-Rev. Med. Chem. 1:2001;219-231
20. Monge A., López de Ceráin A., Ezpeleta O., Cerecetto H., Dias E., Di Maio R., González M., Onetto S., Risso M., Seoane G., Zinola F., Olea-Azar C. 1, 2, 5-Oxadiazole N-oxide derivatives as hypoxia-selective cytotoxins. Structure-activity relationships. Pharmazie. 53:1998;698-702
21. Monge A., López de Ceráin A., Ezpeleta O., Cerecetto H., Dias E., Di Maio R., González M., Onetto S., Seoane G., Suescun L., Mariezcurrena R. Synthesis and biological evaluation of 1, 2, 5-oxadiazole N-oxide derivatives as hypoxia-selective cytotoxins. Pharmazie. 53:1998;758-764
22. Cerecetto H., González M., Risso M., Seoane G., López de Ceráin A., Ezpeleta O., Monge A., Suescun L., Mombrú A., Bruno A.M. Synthesis and biological evaluation of 1, 2, 5-oxadiazole N-oxide derivatives as potential hypoxic cytotoxins and DNA-binders. Arch. Pharm. 333:2000;387-393
23. Boiani M., Cerecetto H., González M., Risso M., Olea-Azar C., Piro O.E., Castellano E.E., López de Ceráin A., Ezpeleta O., Monge A. 1, 2, 5-Oxadiazole N-oxide derivatives as potential anti-cancer agents: Synthesis and biological evaluation. Part IV. Eur. J. Med. Chem. 36:2001;771-782
24. Hansch C., Leo A. Exploring QSAR. Fundamentals and Applications in Chemistry and Biology. 1995;Ed. American Chemical Society, Washington
25. Cronin M.T.D. Prediction of drug toxicity. Farmaco. 56:2001;149-151. and references therein
26. Maynard A.T., Pederon L.G., Posner H.S., McKinney J.D. An ab initio study of the relationship between nitroarene mutagenicity and electron affinity. Mol. Pharmacol. 29:1986;629-636
27. López de Compadre R.L., Shusterman A.J., Hansch C. The role of hydrophobicity in the Ames test. The correlation of the mutagenicity of nitropolycyclic hydrocarbons with partition coefficients and molecular orbital indices. Int. J. Quant. Chem. 34:1988;91-101
28. López de Compadre R.L., Debnath A.K., Shusterman A.J., Hansch C. LUMO energies and hydrophobicity as determinants of mutagenicity by nitroaromatic compounds in Salmonella typhimurium. Environ. Mol. Mut. 15:1990;44-55
29. Kontogiorgis C.A., Hadjipavlou-Litina D. Current trends in QSAR on NO donors and inhibitors of Nitric Oxide Synthase (NOS). Med. Res. Rev. 22:2002;385-418
30. See supplementary material.
31. Hehre W.J., Radom L., v P., Schleyer R., Pople J.A. Ab initio molecular orbital theory. 1986;Wiley, New York
32. Hehre W.J., Shusterman A.J., Huang W.W. A laboratory book of computational organic chemistry. 1996;Wavefunction Inc. California
33. Wavefunction, Inc. 18401 Von Karman Avenue, Suite 370. Irvine, California 92612 USA.
34. Myers R.H. Classical and Modern Regression with Application. 1986;P.W.S. Publishers, Boston
35. Daniel C., Wood F.S. Fitting Equations to Data. 2nd. Ed:1980;Ed. Wiley, New York
36. Draper N.R., Smith H. Applied Regression Analysis. 2nd. Ed:1981;Ed. Wiley, New York
37. Ifa D.R., Rodrigues C.R., de Alencastro R.B., Fraga C.A.M., Barreiro E.J. A possible molecular mechanism for the inhibition of cysteine proteases by salicylaldehyde N-acylhydrazones and related compounds. J. Mol. Struc. (Theochem). 505:2000;11-17
38. Paton R.M. Comprehensive Heterocyclic Chemistry II. An Extended and Updated Review of the Literature (1982-1995). eds A.R., Katritzky C.W., Rees E.F.V., Scriven. 1996;Pergamon Press, Oxford
39. Feelisch M., Schönafinger K., Noack E. Thiol-mediated generation of nitric oxide accounts for the vasodilator action of furoxans. Biochem. Pharmacol. 44:1992;1149-1157
40. Medana C., Ermondi G., Fruttero R., Di Stilo A., Ferretti C., Gasco A.A. Furoxans as nitric oxide donors. 4-Phenyl-3-furoxancarbonitrile: Thiol-mediated nitric oxide release and biological evaluation. J. Med. Chem. 37:1994;4412-4416
41. Di Stilo A., Cena C., Gasco A.M., Gasco A., Ghigo D., Bosia A. Glutathione potentiates cGMP synthesis induced by the two phenylfuroxancarbonitrile isomers in RFL-6 cells. Bioorg.Med.Chem.Lett. 6:1996;2607-2612
42. Sorba G., Medana C., Fruttero R., Cena C., Di Stilo A., Galli U., Gasco A. Water soluble furoxan derivatives as NO prodrugs. J. Med. Chem. 40:1997;463-469