메뉴 건너뛰기




Volumn 24, Issue 5, 2011, Pages 687-697

Reaction between peroxynitrite and boronates: EPR spin-trapping, HPLC analyses, and quantum mechanical study of the free radical pathway

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; ACETONITRILE; ALKANE DERIVATIVE; ASCORBIC ACID; BORONIC ACID DERIVATIVE; FREE RADICAL; GLUTATHIONE; HYDROGEN; NITRITE; OXYGEN; PEROXYNITRITE; PHENOL; PYRROLINE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; TYROSINE;

EID: 84962440502     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx100439a     Document Type: Article
Times cited : (86)

References (35)
  • 1
    • 0025189864 scopus 로고
    • Apparent hydroxyl radical production by peroxynitrite: Implications for endothelial injury from nitric oxide and superoxide
    • Beckman, J. S., Beckman, T. W., Chen, J., Marshall, P. A., and Freeman, B. A. (1990) Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide Proc. Natl. Acad. Sci. U.S.A. 87, 1620-1624
    • (1990) Proc. Natl. Acad. Sci. U.S.A. , vol.87 , pp. 1620-1624
    • Beckman, J.S.1    Beckman, T.W.2    Chen, J.3    Marshall, P.A.4    Freeman, B.A.5
  • 2
    • 0028970801 scopus 로고
    • The role of the reactions of NO with superoxide and oxygen in biological systems: A kinetic approach
    • Czapski, G. and Goldstein, S. (1995) The role of the reactions of NO with superoxide and oxygen in biological systems: a kinetic approach Free Radical Biol. Med. 19, 785-794
    • (1995) Free Radical Biol. Med. , vol.19 , pp. 785-794
    • Czapski, G.1    Goldstein, S.2
  • 3
    • 64749101531 scopus 로고    scopus 로고
    • Chemical biology of peroxynitrite: Kinetics, diffusion, and radicals
    • Ferrer-Sueta, G. and Radi, R. (2009) Chemical biology of peroxynitrite: kinetics, diffusion, and radicals ACS Chem. Biol. 4, 161-177
    • (2009) ACS Chem. Biol. , vol.4 , pp. 161-177
    • Ferrer-Sueta, G.1    Radi, R.2
  • 4
    • 33846863589 scopus 로고    scopus 로고
    • Nitric oxide and peroxynitrite in health and disease
    • DOI 10.1152/physrev.00029.2006
    • Pacher, P., Beckman, J. S., and Liaudet, L. (2007) Nitric oxide and peroxynitrite in health and disease Physiol. Rev. 87, 315-424 (Pubitemid 46217686)
    • (2007) Physiological Reviews , vol.87 , Issue.1 , pp. 315-424
    • Pacher, P.1    Beckman, J.S.2    Liaudet, L.3
  • 5
    • 64749109634 scopus 로고    scopus 로고
    • Peroxynitrite and reactive nitrogen species: The contribution of ABB in two decades of research
    • Radi, R. (2009) Peroxynitrite and reactive nitrogen species: the contribution of ABB in two decades of research Arch. Biochem. Biophys. 484, 111-113
    • (2009) Arch. Biochem. Biophys. , vol.484 , pp. 111-113
    • Radi, R.1
  • 6
    • 70350028730 scopus 로고    scopus 로고
    • Direct oxidation of boronates by peroxynitrite: Mechanism and implications in fluorescence imaging of peroxynitrite
    • Sikora, A., Zielonka, J., Lopez, M., Joseph, J., and Kalyanaraman, B. (2009) Direct oxidation of boronates by peroxynitrite: mechanism and implications in fluorescence imaging of peroxynitrite Free Radical Biol. Med. 47, 1401-1407
    • (2009) Free Radical Biol. Med. , vol.47 , pp. 1401-1407
    • Sikora, A.1    Zielonka, J.2    Lopez, M.3    Joseph, J.4    Kalyanaraman, B.5
  • 7
    • 77951988104 scopus 로고    scopus 로고
    • Peroxynitrite is the major species formed from different flux ratios of co-generated nitric oxide and superoxide: Direct reaction with boronate-based fluorescent probe
    • Zielonka, J., Sikora, A., Joseph, J., and Kalyanaraman, B. (2010) Peroxynitrite is the major species formed from different flux ratios of co-generated nitric oxide and superoxide: direct reaction with boronate-based fluorescent probe J. Biol. Chem. 285, 14210-14216
    • (2010) J. Biol. Chem. , vol.285 , pp. 14210-14216
    • Zielonka, J.1    Sikora, A.2    Joseph, J.3    Kalyanaraman, B.4
  • 8
    • 34247255302 scopus 로고    scopus 로고
    • Molecular imaging of hydrogen peroxide produced for cell signaling
    • DOI 10.1038/nchembio871, PII NCHEMBIO871
    • Miller, E. W., Tulyathan, O., Isacoff, E. Y., and Chang, C. J. (2007) Molecular imaging of hydrogen peroxide produced for cell signaling Nat. Chem. Biol. 3, 263-267 (Pubitemid 46625830)
    • (2007) Nature Chemical Biology , vol.3 , Issue.5 , pp. 263-267
    • Miller, E.W.1    Tulyanthan, O.2    Isacoff, E.Y.3    Chang, C.J.4
  • 9
    • 65349102944 scopus 로고    scopus 로고
    • Lighting up H2O2: The molecule that is a "necessary evil" in the cell
    • Zhao, W. (2009) Lighting up H2O2: the molecule that is a "necessary evil" in the cell Angew. Chem., Int. Ed. 48, 3022-3024
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 3022-3024
    • Zhao, W.1
  • 10
    • 0019758243 scopus 로고
    • Free radicals in pharmacology and toxicology: Selected topics
    • Mason, R. P. and Chignell, C. F. (1981) Free radicals in pharmacology and toxicology: selected topics Pharmacol. Rev. 33, 189-211
    • (1981) Pharmacol. Rev. , vol.33 , pp. 189-211
    • Mason, R.P.1    Chignell, C.F.2
  • 11
    • 0029013876 scopus 로고
    • DEPMPO: A new efficient phophorylated nitrone for the in vitro and in vivo spin trapping of oxygen-centered radicals
    • Frejaville, C., Karoui, H., Tuccio, B., Le Moigne, F., Culcasi, M., Pietri, S., Lauricella, R., and Tordo, P. (1995) DEPMPO: A new efficient phophorylated nitrone for the in vitro and in vivo spin trapping of oxygen-centered radicals J. Med. Chem. 38, 258-265
    • (1995) J. Med. Chem. , vol.38 , pp. 258-265
    • Frejaville, C.1    Karoui, H.2    Tuccio, B.3    Le Moigne, F.4    Culcasi, M.5    Pietri, S.6    Lauricella, R.7    Tordo, P.8
  • 12
    • 0031769737 scopus 로고    scopus 로고
    • Peroxynitrite studied by stopped-flow spectroscopy
    • DOI 10.1016/S0076-6879(99)01098-8
    • Kissner, R., Beckman, J. S., and Koppenol, W. H. (1999) Peroxynitrite studied by stopped-flow spectroscopy Methods Enzymol. 301, 342-352 (Pubitemid 28489796)
    • (1998) Methods in Enzymology , vol.301 , pp. 342-352
    • Kissner, R.1    Beckman, J.S.2    Koppenol, W.H.3
  • 13
    • 0030845236 scopus 로고    scopus 로고
    • The effect of nitric oxide release rates on the oxidation of human low density lipoprotein
    • DOI 10.1074/jbc.272.34.21647
    • Goss, P. A. S., Hogg, N., and Kalyanaraman, B. (1997) The effect of nitric oxide release rates on the oxidation of human low density lipoprotein J. Biol. Chem. 272, 21647-21653 (Pubitemid 27374043)
    • (1997) Journal of Biological Chemistry , vol.272 , Issue.34 , pp. 21647-21653
    • Goss, S.P.A.1    Hogg, N.2    Kalyanaraman, B.3
  • 14
    • 33751385555 scopus 로고
    • New nitric oxide-releasing zwitterions derived from polyamines
    • Hrabie, J. A., Klose, J. R., Wink, D. A., and Keefer, L. K. (1993) New nitric oxide-releasing zwitterions derived from polyamines J. Org. Chem. 58, 1472-1476
    • (1993) J. Org. Chem. , vol.58 , pp. 1472-1476
    • Hrabie, J.A.1    Klose, J.R.2    Wink, D.A.3    Keefer, L.K.4
  • 15
    • 49749184695 scopus 로고
    • The microestimation of succinate and the extinction coefficient of cytochrome c
    • Massey, V. (1959) The microestimation of succinate and the extinction coefficient of cytochrome c Biochim. Biophys. Acta 34, 255-256
    • (1959) Biochim. Biophys. Acta , vol.34 , pp. 255-256
    • Massey, V.1
  • 16
    • 70450206724 scopus 로고    scopus 로고
    • revision A.02, Gaussian, Inc., Wallingford CT.
    • Frisch, M. J., (2009) Gaussian 09, revision A.02, Gaussian, Inc., Wallingford CT.
    • (2009) Gaussian 09
    • Frisch, M.J.1
  • 17
    • 33646464890 scopus 로고    scopus 로고
    • Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions
    • Zhao, Y., Schultz, N. E., and Truhlar, D. G. (2006) Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions J. Chem. Theory Comput. 2, 364-382
    • (2006) J. Chem. Theory Comput. , vol.2 , pp. 364-382
    • Zhao, Y.1    Schultz, N.E.2    Truhlar, D.G.3
  • 18
    • 40549127108 scopus 로고    scopus 로고
    • Density functionals with broad applicability in chemistry
    • Zhao, Y. and Truhlar, D. G. (2008) Density functionals with broad applicability in chemistry Acc. Chem. Res. 41, 157-167
    • (2008) Acc. Chem. Res. , vol.41 , pp. 157-167
    • Zhao, Y.1    Truhlar, D.G.2
  • 19
    • 33748545144 scopus 로고
    • The influence of polarization functions on molecular orbital hydrogenation energies
    • Hariharan, P. C. and Pople, J. A. (1973) The influence of polarization functions on molecular orbital hydrogenation energies Theor. Chim. Acta 28, 213-222
    • (1973) Theor. Chim. Acta , vol.28 , pp. 213-222
    • Hariharan, P.C.1    Pople, J.A.2
  • 20
    • 33645949559 scopus 로고
    • Self-consistent molecular orbital methods. XXIII. A polarization-type basis set for second-row elements
    • Francl, M. M., Pietro, W. J., Hehre, W. J., Binkley, J. S., Gordon, M. S., DeFrees, D. J., and Pople, J. A. (1982) Self-consistent molecular orbital methods. XXIII. A polarization-type basis set for second-row elements J. Chem. Phys. 77, 3654-3665
    • (1982) J. Chem. Phys. , vol.77 , pp. 3654-3665
    • Francl, M.M.1    Pietro, W.J.2    Hehre, W.J.3    Binkley, J.S.4    Gordon, M.S.5    Defrees, D.J.6    Pople, J.A.7
  • 21
    • 84946893847 scopus 로고
    • Electrostatic interaction of a solute with a continuum. A direct utilizaion of ab initio molecular potentials for the prevision of solvent effects
    • Miertus, S., Scrocco, E., and Tomasi, J. (1981) Electrostatic interaction of a solute with a continuum. A direct utilizaion of ab initio molecular potentials for the prevision of solvent effects Chem. Phys. 55, 117-129
    • (1981) Chem. Phys. , vol.55 , pp. 117-129
    • Miertus, S.1    Scrocco, E.2    Tomasi, J.3
  • 22
    • 3342906428 scopus 로고
    • Self-consistent orbitals for radicals
    • Pople, J. A. and Nesbet, R. K. (1954) Self-consistent orbitals for radicals J. Chem. Phys. 22, 571-572
    • (1954) J. Chem. Phys. , vol.22 , pp. 571-572
    • Pople, J.A.1    Nesbet, R.K.2
  • 23
    • 0024729553 scopus 로고
    • Spectroscopic studies of cutaneous photosensitizing agents - XIV. The spin trapping of free radicals formed during the photolysis of halogenated salicylanilide antibacterial agents
    • Chignell, C. F. and Sik, R. H. (1989) Spectroscopic studies of cutaneous photosensitizing agents - XIV. The spin trapping of free radicals formed during the photolysis of halogenated salicylanilide antibacterial agents Photochem. Photobiol. 50, 287-295
    • (1989) Photochem. Photobiol. , vol.50 , pp. 287-295
    • Chignell, C.F.1    Sik, R.H.2
  • 24
    • 0029939154 scopus 로고    scopus 로고
    • Characterization of sulfur-centered radical intermediates formed during the oxidation of thiols and sulfite by peroxynitrite: ESR-spin trapping and oxygen uptake studies
    • DOI 10.1074/jbc.271.11.6000
    • Karoui, H., Hogg, N., Fréjaville, C., Tordo, P., and Kalyanaraman, B. (1996) Characterization of sulfur-centered radical intermediates formed during the oxidation of thiols and sulfite by peroxynitrite. ESR-spin trapping and oxygen uptake studies J. Biol. Chem. 271, 6000-6009 (Pubitemid 26095401)
    • (1996) Journal of Biological Chemistry , vol.271 , Issue.11 , pp. 6000-6009
    • Karoui, H.1    Hogg, N.2    Frejaville, C.3    Tordo, P.4    Kalyanaraman, B.5
  • 26
    • 37049081504 scopus 로고
    • Pulse radiolysis of aryl bromides in aqueous solutions: Some properties of aryl and arylperoxyl radicals
    • Fang, X., Mertens, R., and von Sonntag, C. (1995) Pulse radiolysis of aryl bromides in aqueous solutions: some properties of aryl and arylperoxyl radicals J. Chem. Soc., Perkin Trans. 2, 1033-1036
    • (1995) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1033-1036
    • Fang, X.1    Mertens, R.2    Von Sonntag, C.3
  • 27
    • 0029343433 scopus 로고
    • Formation and reactions of halogenated phenylperoxyl radicals in aqueous alcohol solutions
    • Khaikin, G. I., Alfassi, Z. B., and Neta, P. (1995) Formation and reactions of halogenated phenylperoxyl radicals in aqueous alcohol solutions J. Phys. Chem. 99, 11447-11451
    • (1995) J. Phys. Chem. , vol.99 , pp. 11447-11451
    • Khaikin, G.I.1    Alfassi, Z.B.2    Neta, P.3
  • 28
    • 0029640426 scopus 로고
    • Inter- and intramolecular redox reactions of substituted phenylperoxyl radicals in aqueous solutions
    • Khaikin, G. I., Alfassi, Z. B., and Neta, P. (1995) Inter- and intramolecular redox reactions of substituted phenylperoxyl radicals in aqueous solutions J. Phys. Chem. 99, 16722-16726
    • (1995) J. Phys. Chem. , vol.99 , pp. 16722-16726
    • Khaikin, G.I.1    Alfassi, Z.B.2    Neta, P.3
  • 29
    • 0029635991 scopus 로고
    • Arylperoxyl radicals. Formation, absorption spectra, and reactivity in aqueous alcohol solutions
    • Alfassi, Z. B., Khaikin, G. I., and Neta, P. (1995) Arylperoxyl radicals. Formation, absorption spectra, and reactivity in aqueous alcohol solutions J. Phys. Chem. 99, 265-268
    • (1995) J. Phys. Chem. , vol.99 , pp. 265-268
    • Alfassi, Z.B.1    Khaikin, G.I.2    Neta, P.3
  • 30
    • 0028493343 scopus 로고
    • Formation and reactivity of phenylperoxyl radicals in aqueous solutions
    • Alfassi, Z. B., Marguet, S., and Neta, P. (1994) Formation and reactivity of phenylperoxyl radicals in aqueous solutions J. Phys. Chem. 98, 8019-8023
    • (1994) J. Phys. Chem. , vol.98 , pp. 8019-8023
    • Alfassi, Z.B.1    Marguet, S.2    Neta, P.3
  • 31
    • 0000803231 scopus 로고
    • Radiation chemistry of aqueous solutions of simple RCN [hydrogen or alkyl cyanide] compounds
    • Draganic, I., Draganic, Z., Petkovic, Lj., and Nikolic, A. (1973) Radiation chemistry of aqueous solutions of simple RCN [hydrogen or alkyl cyanide] compounds J. Am. Chem. Soc. 95, 7193-7199
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 7193-7199
    • Draganic, I.1    Draganic, Z.2    Petkovic, Lj.3    Nikolic, A.4
  • 32
    • 0000370082 scopus 로고
    • Absolute rate constants for reactions of phenyl radicals
    • Madhavan, V., Schuler, R. H., and Fessenden, R. W. (1978) Absolute rate constants for reactions of phenyl radicals J. Am. Chem. Soc. 100, 888-893
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 888-893
    • Madhavan, V.1    Schuler, R.H.2    Fessenden, R.W.3
  • 33
    • 22644438390 scopus 로고    scopus 로고
    • Rate constants for reactions of phenoxyl radicals in solution
    • DOI 10.1063/1.1797812
    • Neta, P. and Grodkowski, J. (2005) Rate constants for reactions of phenoxyl radicals in solution J. Phys. Chem. Ref. Data 34, 109-199 (Pubitemid 41025519)
    • (2005) Journal of Physical and Chemical Reference Data , vol.34 , Issue.1 , pp. 109-199
    • Neta, P.1    Grodkowski, J.2
  • 34
    • 0343089547 scopus 로고
    • Nitrogen dioxide and related free radicals: Electron-transfer reactions with organic compounds in solutions containing nitrite or nitrate
    • Forni, L. G., Mora-Arellano, V. O., Packer, J. E., and Willson, R. L. (1986) Nitrogen dioxide and related free radicals: electron-transfer reactions with organic compounds in solutions containing nitrite or nitrate J. Chem. Soc., Perkin Trans. 2, 1-6
    • (1986) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1-6
    • Forni, L.G.1    Mora-Arellano, V.O.2    Packer, J.E.3    Willson, R.L.4
  • 35
    • 33845185172 scopus 로고
    • A new population analysis based on atomic polar tensors
    • Cioslowski, J. (1989) A new population analysis based on atomic polar tensors J. Am. Chem. Soc. 111, 8333-8336
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8333-8336
    • Cioslowski, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.