Esterase-activated chromane-sydnonimine prodrug hybrids

Nitric Oxide - Biology and Chemistry

Volumn 15, Issue 4, 2006, Pages 363-369

  Vinatier, Virginie ^a   Soulère, Laurent ^a   Hoffmann, Pascal ^a  

^a Université Paul Sabatier Toulouse III   (France)

Author keywords

Peroxynitrite; SIN 1; Superoxide; Sydnone; Tocopherol; Trolox ; Vitamin E

Indexed keywords

ALPHA TOCOPHEROL DERIVATIVE; ANTIOXIDANT; BUFFER; CHROMAN DERIVATIVE; DELTA TOCOPHEROL; DELTA TOCOPHERYLOXYCARBONYL 3 MORPHOLINOSYDNONIMINE; ESTERASE; LINSIDOMINE; LIVER ENZYME; METHEMOGLOBIN; NITRIC OXIDE; OXYHEMOGLOBIN; PEROXYNITRITE; PHOSPHATE; PRODRUG; SYDNONE DERIVATIVE; TROLOX C; TROLOXOXYCARBONYL 3 MORPHOLINOSYDNONIMINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG HYDROLYSIS; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVATION; LIVER; PRIORITY JOURNAL; TEMPERATURE;

CHROMANS; ESTERASES; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MORPHOLINES; NITRIC OXIDE DONORS; PRODRUGS; SPECTROPHOTOMETRY, ULTRAVIOLET; SYDNONES;

SUIDAE;

EID: 33751035237     PISSN: 10898603     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.niox.2006.03.006     Document Type: Article

References (31)

1. Hinz B., and Schroder H. The nitric oxide donor SIN-1 is free of tolerance and maintains its cyclic GMP stimulatory potency in nitrate-tolerant LLC-PK1 cells. Pharm. Res. 16 (1999) 633-636
2. Feelisch M., Ostrowski J., and Noack E. On the mechanism of NO release from sydnonimines. J. Cardiovasc. Pharmacol. 14 (1989) S13-S22
3. Koppenol W.H. The basic chemistry of nitrogen monoxide and peroxynitrite. Free Radic. Biol. Med. 25 (1998) 385-391
4. Szabo C., and Ohshima H. DNA damage induced by peroxynitrite: subsequent biological effects. Nitric Oxide 1 (1997) 373-385
5. Ducrocq C., Blanchard B., Pignatelli B., and Ohshima H. Peroxynitrite: an endogenous oxidizing and nitrating agent. Cell. Mol. Life Sci. 55 (1999) 1068-1077
6. Radi R., Beckman J.S., Bush K.M., and Freeman B.A. Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide. Arch. Biochem. Biophys. 288 (1991) 481-487
7. Holm P., Kankaanranta H., Metsa-Ketela T., and Moilanen E. Radical releasing properties of nitric oxide donors GEA 3162, SIN-1 and S-nitroso-N-acetylpenicillamine. Eur. J. Pharmacol. 346 (1998) 97-102
8. Masuda K., Kamiya T., Imashiro Y., and Kaneko T. Studies on mesoionic compounds. II. Synthesis of N-acyl derivatives of 3-dialkylaminosydnonimines. Chem. Pharm. Bull. 19 (1971) 72-79
9. Soulere L., Bringaud F., and Hoffmann P. Synthesis of sydnonimine derivatives as potential trypanocidal agents. J. Heterocycl. Chem. 40 (2003) 943-947
10. Murphy M.E., and Noack E. Nitric oxide assay using hemoglobin method. Methods Enzymol. 233 (1994) 240-250
11. Zijlstra W.G., and Buursma A. Spectrophotometry of hemoglobin: absorption spectra of bovine oxyhemoglobin, deoxyhemoglobin, carboxyhemoglobin, and methemoglobin. Comp. Biochem. Physiol. B 118 (1997) 743-749
12. Fridovich I. Cytochrome c. In: Greenwald R.A. (Ed). Handbook of Methods for Oxygen Radical Research (1985), CRC Press, Boca Raton, FL 213-215
13. Aggarwal B.B., and Mehta K. Determination and regulation of nitric oxide production from macrophages by lipopolysaccharides, cytokines, and retinoids. Methods Enzymol. 269 (1996) 166-171
14. Garthwaite J. Glutamate, nitric oxide and cell-cell signalling in the nervous system. Trends Neurosci. 14 (1991) 60-67
15. Azuma H., Ishikawa M., and Sekizaki S. Endothelium-dependent inhibition of platelet aggregation. Br. J. Pharmacol. 88 (1986) 411-415
16. Furlong B., Henderson A.H., Lewis M.J., and Smith J.A. Endothelium-derived relaxing factor inhibits in vitro platelet aggregation. Br. J. Pharmacol. 90 (1987) 687-692
17. Radomski M.W., Palmer R.M., and Moncada S. Modulation of platelet aggregation by an l-arginine-nitric oxide pathways. Trends Pharmacol. Sci. 12 (1991) 87-88
18. Denninger J.W., and Marletta M.A. Guanylate cyclase and the NO/cGMP signaling pathway. Biochim. Biophys. Acta 1411 (1999) 334-350
19. Lopez G.V., Batthyany C., Blanco F., Botti H., Trostchansky A., Migliaro E., Radi R., Gonzalez M., Cerecetto H., and Rubbo H. Design, synthesis, and biological characterization of potential antiatherogenic nitric oxide releasing tocopherol analogs. Bioorg. Med. Chem. 13 (2005) 5787-5796
20. Cena C., Boschi D., Tron G.C., Chegaev K., Lazzarato L., Di Stilo A., Aragno M., Fruttero R., and Gasco A. Development of a new class of potential antiatherosclerosis agents: NO-donor antioxidants. Bioorg. Med. Chem. Lett. 14 (2004) 5971-5974
21. Bogdan C. Nitric oxide and the immune response. Nat. Immunol. 2 (2001) 907-916
22. Wang P.G., Xian M., Tang X., Wu X., Wen Z., Cai T., and Janczuk A.J. Nitric oxide donors: chemical activities and biological applications. Chem. Rev. 102 (2002) 1091-1134
23. Soulere L., Hoffmann P., Bringaud F., and Perie J. Synthesis and uptake of nitric oxide-releasing drugs by the P2 nucleoside transporter in Trypanosoma equiperdum. Bioorg. Med. Chem. Lett. 10 (2000) 1347-1350
24. Noack E., and Feelisch M. Molecular aspects underlying the vasodilator action of molsidomine. J. Cardiovasc. Pharmacol. 14 (1989) S1-S5
25. Douki T., and Cadet J. Peroxynitrite mediated oxidation of purine bases of nucleosides and isolated DNA. Free Radic. Res. 24 (1996) 369-380
26. Rubbo H., Radi R., Trujillo M., Telleri R., Kalyanaraman B., Barnes S., Kirk M., and Freeman B.A. Nitric oxide regulation of superoxide and peroxynitrite-dependent lipid peroxidation. Formation of novel nitrogen-containing oxidized lipid derivatives. J. Biol. Chem. 269 (1994) 26066-26075
27. Greenacre S.A., and Ischiropoulos H. Tyrosine nitration: localisation, quantification, consequences for protein function and signal transduction. Free Radic. Res. 34 (2001) 541-581
28. Soulere L., Claparols C., Perie J., and Hoffmann P. Peroxynitrite-induced nitration of tyrosine-34 does not inhibit Escherichia coli iron superoxide dismutase. Biochem. J. 360 (2001) 563-567
29. Hogg N., Singh R.J., Goss S.P., and Kalyanaraman B. The reaction between nitric oxide and alpha-tocopherol: a reappraisal. Biochem. Biophys. Res. Commun. 224 (1996) 696-702
30. de Groot H., Hegi U., and Sies H. Loss of alpha-tocopherol upon exposure to nitric oxide or the sydnonimine SIN-1. FEBS Lett. 315 (1993) 139-142
31. Singh R.J., Hogg N., Joseph J., Konorev E., and Kalyanaraman B. The peroxynitrite generator, SIN-1, becomes a nitric oxide donor in the presence of electron acceptors. Arch. Biochem. Biophys. 361 (1999) 331-339