57
Views
3
CrossRef citations to date
0
Altmetric
Research Article

Effect of 2, 5- substituents on the stability of cyclic nitrone superoxide spin adducts: A density functional theory approach

, , , , , & show all
Pages 751-778 | Received 11 Feb 2010, Published online: 07 Apr 2010

References

  • Bonnett R, Clark VM, Giddy A, Todd, A. Experiments towards the synthesis of corings. 1. the preparation and reactions of some delta-1-pyrrolines—a novel prolixne synthesis. J Chem Soc 1959;2087–2093.
  • Haire DL, Hilborn JW, Janzen EG. A more efficient synthesis of DMPO-type (nitrone) spin traps. J Org Chem 1986;51:4298–4300.
  • Finkelstein E, Rosen GM, Rauckman EJ. Production of hydroxyl radical by decomposition of superoxide spin-trapped adducts. Mol Pharmacol 1982;21:262–265.
  • Yamazaki I, Piette LH, Grover TA. Kinetics-studies on spin trapping of superoxide and hydroxyl radicals generated in NADPH-cytochrome-P-450 reductase-paraquat systems—effect of iron chelates. J Biol Chem 1990;265:652–659.
  • Buettner GR, Oberley LW. Spin traps inhibit formation of hydrogen-peroxide via the dismutation of superoxide-implications for spin trapping the hydroxyl free-radical. Biochim Biophys Acta 1991;1075:213–222.
  • Villamena FA, Zweier JL. Superoxide radical trapping and spin adduct decay of 5-tert-butoxycarbonyl-5-methyl-1- pyrroline N-oxide (BocMPO): kinetics and theoretical analysis. J Chem Soc Perkin Trans 2 2002;2:1340–1344.
  • Frejaville C, Karoui H, Tuccio B, Lemoigne F, Culcasi M, Pietri S, Lauricella R, Tordo P. 5-Diethoxyphosphoryl-5- methyl-1-pyrroline N-oxide (DEPMPO)—a new phosphorylated nitrone for the efficient in vitro and in vivo spin trapping os oxygen-centered radicals. J Chem Soc Chem Commun 1994;15:1793–1794.
  • Frejaville C, Karoui H, Tuccio B, Lemoigne F, Culcasi M, Pietri S, Lauricella R, Tordo P. 5-(Diethoxyphosphoryl)-5-methyl-pyroline N-oxide—a new efficient phosphorylated nitrone for the in vitro and in vivo spin-trapping of oxygen-centered radicals. J Med Chem 1995;38:258–265.
  • Zhang H, Joseph J, Vasquez-Vivar J, Karoui H, Nsanzumuhire C, Martasek P, Tordo P, Kalyanaraman B. Detection of superoxide anion using an isotopically labeled nitrone spin trap: potential biological applications. FEBS Lett 2000;473:58–62.
  • Olive G, Mercier A, Moigne FL, Rockenbauer A, Tordo P. 2-Ethoxycarbonyl-2-methyl-3,4-dihydro-2H-pyrrole-1-oxide: evaluation of the spin trapping properties. Free Radic Biol Med 2000;28:403–408.
  • Tsai P, Ichikawa K., Mailer C, Pou S, Halpern HJ, Robinson BH, Nielsen R, Rosen G. Esters of 5-carboxyl-5-methyl-1-pyrroline N-oxide: a family of spin traps for superoxide. J Org Chem 2003;68:7811–7817.
  • Lauricella R, Allouch A, Roubaud V, Bouteiller JC, Tuccio B. A new kinetic approach to the evaluation of rate constants for the spin trapping of superoxide/hydroperoxyl radical by nitrones in aqueous media. Org Biomol Chem 2004;2:1304–1309.
  • Liu K, Sun J, Song YG, Liu B, Xu YK, Zhang SX, Tian Q, Liu Y. Superoxide, hydrogen peroxide and hydroxyl radical in D1/D2/cytochrome b-559 photosystem II reaction center complex. Photosyn Res 2004;81:41–47.
  • Vasquez-Vivar J, Kalyanaraman B, Martasek P, Hogg N, Masters BSS, Karoui H, Tordo P, Pritchard KA. Superoxide generation by endothelial nitric oxide synthase: the influence of cofactors. Proc Natl Acad Sci USA 1998;95:9220–9225.
  • Tordo P. Spin-trapping: recent developments and applications. Electron Paramagn Reson 1998;16:116–144.
  • Stolze K, Udilova N, Rosenau T, Hofinger A, Nohl H. Spin trapping of superoxide, alkyl- and lipid-derived radicals with derivatives of the spin trap EPPN. Biochem Pharmacol 2003;66:1717–1726.
  • Villamena FA, Hadad CM, Zweier JL. Theoretical study of the spin trapping of hydroxyl radical by cyclic nitrones: A density functional theory approach. J Am Chem Soc 2004;126:1816–1829.
  • Villamena FA, Hadad CM, Zweier JL. Comparative DFT study of the spin trapping of methyl, mercapto, hydroperoxy, superoxide, and nitric oxide radicals by various substituted cyclic nitrones. J Phys Chem A 2005;109:1662–1674.
  • Han YB, Tuccio B, Lauricella R, Rockenbauer R, Zweier JL, Villamena FA. Improved spin trapping properties by beta-cyclodextrin-cyclic nitrone conjugate. J Org Chem 2008;73:2533–2541.
  • Liu YP, Wang LF, Nie Z, Ji YQ, Liu Y, Liu KJ, Tian Q. Effect of the phosphoryl substituent in the linear nitrone on the spin trapping of superoxide radical and the stability of the superoxide adduct: Combined experimental and theoretical studies. J Org Chem 2006;71:7753–7762.
  • Finkelstein E, Rosen GM, Rauckman EJ. Spin trapping kinetics of the reaction of superoxide and hydroxyl radicals with nitrones. J Am Chem Soc 1980;102:4994–4999.
  • Janzen EG, Zhang YK. EPR spin trapping alkoxyl radicals with 2-substituted 5,5-dimethylpyrroline-N-oxides(2-XM2POS). J Magn Reson B 1993;101:91–93.
  • Barasch D, Krishna MC, Russo A, Katzhendler J, Samuni A. Novel DMPO-derived C-13-labeled spin traps yield identifiable stable nitroxides. J Am Chem Soc 1994;116:7319–7324.
  • Xu YK, Sun J, Liu K, Chen ZW, Zhang XK, Liu Y. Structural analysis on superoxide spin adducts trapped by DEPMPO analogues. Chem J Chin Univ 2001;22:1732–1734.
  • Berthold DA, Babcock GT, Yocum CF. A highly resolved, oxygen-evolving photosystem-II preparation from spinach thylakoid membranesp-electron-paramagnetic-res and electron-transport properties. FEBS Lett 1981;134:231–234.
  • Yruela I, Montoya G, Alonso PA, Picorel R. Identification of the pheophytin-QA-FE domain of the reducing side of the photosystem-II as the Cu(II)-inhibitory binding-dite. J Biol Chem 1991;266:22847–22850.
  • Buettner GR. Spin trapping: ESR parameters of spin adduct. Free Radic Res 1999;10:11–15.
  • Liu K, Sun J, Liu Y, Zhang QY, Kuang TY. ESR studies on the superoxide radicals generated in photosystem II of higher plant. Prog Biochem Biophys 2001;28:372–374.
  • Song YG, Liu B, Wang LF, Li MH, Liu Y. Damage to the oxygen-evolving complex by superoxide anion, hydrogen peroxide, and hydroxyl radical in photoinhibition of photosystem II. Photosynth. Res 2006;90:67–78.
  • Labanowski JW, Andzelm J. Density functional methods in chemistry. New York: Springer; 1991.
  • Parr RG, Yang W. Density functional theory in atoms and molecules. New York: Oxford University Press; 1989.
  • Scott AP, Radom L. Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Moller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors. J Phys Chem 1996;100:16502–16513.
  • Barone V, Cossi M. Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model. J Phys Chem A 1998;102:1995–2001.
  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Jr, Stratmann RE, Burant JC, Dapprich S, Millam J M, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, revision A. 11. Pittsburgh, PA: Gaussian, Inc; 2001.
  • Roubaud V, Mercier A, Olive G, Moigne FL, Tordo P. 5-(Diethoxyphosphorylmethyl)-5-methyl-4,5-dihydro-3H-pyrrole N-oxide: synthesis and evaluation of spin trapping properties. J Chem Soc Perkin Trans 2 1997;9:1827–1830.
  • Villamena FA, Merle JK, Hadad CM, Zweier JL. Superoxide radical anion adduct of 5,5-dimethyl-1-pyrroline N-oxide (DMPO). 1. The thermodynamics of formation and its acidity. J Phys Chem A 2005;109:6083–6088.
  • Tsuzuki S, Uchimaru T, Tanabe K, Hirano T. Conformational-analysis of 1,2-dimethoxyethane by abinoton molecular-orbital and molecular mechanics calculations-stabilization of the TGG' rotamer by the 1,5-CH3/O nonbonding attractive interaction. J Phys Chem 1993;97:1346–1350.
  • Villamena FA, Merle JK, Hadad CM, Zweier JL. Superoxide radical anion adduct of 5,5-dimethyl-1-pyrroline N-oxide (DMPO). 2. The thermodynamics of decay and EPR spectral properties. J Phys Chem A 2005;109:6089–6098.
  • Finkelstein E, Rosen GM, Rauckman EJ. Production of hydroxyl radical by decomposition of superoxide spin-trapping adducts. Mol Pharm 1982;21:262–265.
  • Villamena FA, Hadad CM, Zweier J. Kinetic study and theoretical analysis of hydroxyl radical trapping and spin adduct decay of alkoxycarbonyl and dialkoxyphosphoryl nitrones in aqueous media. J Phys Chem A 2003;107:4407–4414.
  • Kocherginsky N, Swartz HM. Nitroxide spin labels. Reaction in biology and chemistry. New York, London, Tokyo: CRC Press: Boca Raton; 1995.
  • Wertz JE, Bolton JR. Electron spin resonance elementary theory and practical applications. New York, London: Chapman and Hall; 1986.
  • Villamena FA, Liu YP, Zweier JL. Superoxide radical anion adduct of 5, 5-dimethyl-1-pyrroline N-Oxide. 4. Conformational effects on the EPR hyperfine splitting constants. J Phys Chem A 2008;112:12607–12615.
  • Cirujeda J, Vidal-Gancedo J, Jürgens O, Mota F, Movoa JJ, Rovira C, Veciana J. Spin density distribution of a-nitronyl aminoxyl radicals from experimental and ab initio calculated ESR isotropic hyperfine coupling constants. J Am Chem Soc 2000;122:11393–11405.
  • Tordo P, Chalier F. 5-Diisopropoxyphosphoryl-5-methyl-1-pyrroline N-oxide, DIPPMPO, a crystalline analog of the nitrone DEPMPO: synthesis and spin trapping properties. J Chem Soc Perkin Trans 2 2002;2110–2113.
  • Villamena FA, Rockenbauer A, Gallucci J, Velayutham M, Hadad CM, Zweier JL. Spin trapping by 5-carbamoyl-5-methyl-1-pyrroline N-oxide (AMPO): theoretical and experimental studies. J Org Chem 2004;69:7994–8004.
  • Hardy M, Rockenbauer A, Vasquez-Vivar J, Felix C, Lopez M, Srinivasan S, Avadhani N, Tordo P, Kalyanaraman B. Detection, characterization, and decay kinetics of ROS and thiyl adducts of Mito-DEPMPO spin trap. Chem Res Toxicol 2007;20:1053–1060.
  • Han Y, Tuccio B, Lauricella R, Rockenbauer A, Zweier JL, Villamena FA. Synthesis and spin-trapping properties of a new spirolactonyl nitrone. J Org Chem 2008;73:2533–2541.
  • Finkelstein E, Rosen GM, Rauckman EJ. Spin trapping of superoxide. Mol Pharm 1979;16:676–685.
  • Briere R, Rassat A. Nitroxides . 68. synthesis and konetic dtudy of decomposition of T-butyl isopropyl nitroxide -isotope effect. Tetrahedron 1976;32:2891–2898.
  • Villamena FA, Dickman MH, Crist DR. Stabilization of a nitroxide with a beta-hydrogen by metals: Structure and magnetic properties of adducts of N-oxy-N-tert-butyl-(2-pyridyl)phenylmethanamine with Mn(II), Ni(II), and Co(II) hexafluoroacetylacetonates. Inorg Chem 1998;37:1454–1457.
  • Karoui H, Tordo P. ESR-spin trapping in the presence of cyclodextrins. Detection of PBN-superoxide spin adduct. Tetrahedron Lett 2004;45:1043–1406.
  • Khramtsov V, Berliner LJ, Clanton TL. NMR spin trapping: detection of free radical reactions using a phosphorus-containing nitrone spin trap. Magn Reson Med 1999;42:228–234.
  • Tuccio B, Lauricella R, Fréjaville C, Bouteiller JC, Tordo P. Decay of the hydroperoxyl spin adduct of 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxode - an EPR kinetic-study. J Chem Soc Perkin Trans 2 1995;295–298.
  • Gaffney BJ. Spin labeling theory and application. New York: Academic Press; 1976. 183.
  • Smith ICP. Biological applications of electron spin resonance. New York: Wiley-Interscience; 1972. 483.
  • Tuccio B, Bouteiller JC, Cerri V, Tordo P. Spin-trapping of free radicals by PBN-type beta-phosphorylated nitrones in the presence of SDS micelles. J Chem Soc Perkin Trans 2 1997;2507–2512.
  • Karoui H, Clément JL, Rockenbauer A, Siri D, Tordo P. Synthesis and structure of 5,5-diethoxycarbonyl-l-pyrroline N-oxide (DECPO). Application to superoxide radical trapping. Tetrahedron Lett 2004;45:149–152.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.