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Volumn 118, Issue 4, 1996, Pages 905-906

Highly sensitive colorimetric detection and facile isolation of diamagnetic free radical adducts of novel chromotropic nitrone spin trapping agents readily derived from guaiazulene

Author keywords

[No Author keywords available]

Indexed keywords

GUAIAZULENE DERIVATIVE; NITROSO DERIVATIVE; SCAVENGER; UNCLASSIFIED DRUG;

EID: 0030020575     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952895z     Document Type: Article
Times cited : (41)

References (47)
  • 3
    • 0002394350 scopus 로고
    • Hodgson, E., Bend, J. R., Philpot, R. M., Eds.; Elsevier Biomedical: New York
    • (c) Kalyanaraman, B. In Reviews in Biochemical Toxicology; Hodgson, E., Bend, J. R., Philpot, R. M., Eds.; Elsevier Biomedical: New York, 1980; Vol. 4, p 73.
    • (1980) Reviews in Biochemical Toxicology , vol.4 , pp. 73
    • Kalyanaraman, B.1
  • 6
    • 0000842339 scopus 로고
    • Rice-Evans, C. A., Burdon, R. H., Eds.; Elsevier Science: New York
    • (f) Mason, R. P.; Chignell, C. F. In Free Radical Damage and Its Control; Rice-Evans, C. A., Burdon, R. H., Eds.; Elsevier Science: New York, 1994; p 319.
    • (1994) Free Radical Damage and Its Control , pp. 319
    • Mason, R.P.1    Chignell, C.F.2
  • 22
    • 0014740170 scopus 로고
    • Even mild biological reducing agents such as cysteine (in the presence of traces of ferric ion) and ascorbic acid will reduce nitroxides to the corresponding hydroxylamine
    • (c) Even mild biological reducing agents such as cysteine (in the presence of traces of ferric ion) and ascorbic acid will reduce nitroxides to the corresponding hydroxylamine. See: McConnell, H. M ; McFarland, B. G. Q. Rev. Biaphys. 1970, 3, 91. See also: Sentjurc, M.; Mason, R. P. Free Radical Biol. Med. 1992, 13, 151.
    • (1970) Q. Rev. Biaphys. , vol.3 , pp. 91
    • McConnell, H.M.1    McFarland, B.G.2
  • 23
    • 0026652023 scopus 로고
    • (c) Even mild biological reducing agents such as cysteine (in the presence of traces of ferric ion) and ascorbic acid will reduce nitroxides to the corresponding hydroxylamine. See: McConnell, H. M ; McFarland, B. G. Q. Rev. Biaphys. 1970, 3, 91. See also: Sentjurc, M.; Mason, R. P. Free Radical Biol. Med. 1992, 13, 151.
    • (1992) Free Radical Biol. Med. , vol.13 , pp. 151
    • Sentjurc, M.1    Mason, R.P.2
  • 24
    • 3643060735 scopus 로고
    • W. A Benjamin, Inc.: New York, and references cited therein
    • Even though nitroxides possess a visible chromophore of their own, their characteristic red color is due to an absorption with a very low extinction coefficient centered around 460 nm. For example, the visible absorption spectrum in hexane for di-tert-butylnitroxide shows a maximum at 465 nm with log ε = 0.95 The extinction coefficient for the absorption giving rise to the color of the diamagnetic azulene-containing spin adducts described herein is between 1 and 2 orders of magnitude greater. See: Smith, P. A. S. Open-Chain Nitrogen Compounds; W. A Benjamin, Inc.: New York, 1965; Vol. 2, p 105 and references cited therein.
    • (1965) Open-Chain Nitrogen Compounds , vol.2 , pp. 105
    • Smith, P.A.S.1
  • 27
    • 85033822320 scopus 로고    scopus 로고
    • note
    • + + 1) 356.2226, found 356.2230.
  • 28
    • 85033819225 scopus 로고    scopus 로고
    • note
    • + + 1) 572.3852, found 572.3853.
  • 29
    • 85033831134 scopus 로고    scopus 로고
    • note
    • 1H NMR and TLC comparison with an authentic sample) when the thermolysis is conducted in the presence of an equimolar concentration of benzophenone. In toluene solution, benzophenone is preferentially attacked by carbanions (organolithium derivatives) in the presence of equimolar concentrations of nitrone 1 (R = OEt).
  • 30
    • 0000932162 scopus 로고
    • 1H NMR spectra of the violet and green products formed at room temperature when nitrone 1 (R = OEt, 10 mg. 100 mM in benzene) is subjected to conditions for the generation of the 4-bromophenyl radical (according to the Gokel modification of the Gomberg-Bachmann reaction), their structures have been assigned as the corresponding hydroxylamine (violet) and nitrone (green) resulting from disproportionation of the expected intermediate nitroxide radical. That these products are also formed in 9:1 benzene-t-BuOH argues strongly against their being artifacts formed via the involvement of aryl carbanion intermediates. See: Beadle, J. R : Korzeniowski, S. H.; Rosenberg, D. E., Garcia-Slanga, B. J ; Gokel, G. W J. Org. Chem. 1984, 49, 1594
    • (1984) J. Org. Chem. , vol.49 , pp. 1594
    • Beadle, J.R.1    Korzeniowski, S.H.2    Rosenberg, D.E.3    Garcia-Slanga, B.J.4    Gokel, G.W.5
  • 31
    • 85033816253 scopus 로고    scopus 로고
    • note
    • -4 M) is unchanged in 98:1:1 EtOAc-HOAc-water after 10 h at 90 °C in a sealed tube. Spin trapping studies of 1 with active oxygen radicals have not yet been conducted. See also ref 18b.
  • 34
    • 0027947387 scopus 로고
    • Packer, L., Ed.; Academic Press: San Diego
    • (b) Lee, D. M. In Methods in Enzymology; Packer, L., Ed.; Academic Press: San Diego, 1994; Vol. 234, p 513. See also: Steinberg, D.; Parthasarathy, S.; Carew. T. E.; Khoo, J. C.; Witztum, J. L. N. Engl. J. Med. 1989, 320, 915.
    • (1994) Methods in Enzymology , vol.234 , pp. 513
    • Lee, D.M.1
  • 41
    • 77049308856 scopus 로고
    • (b) Chen, Q.; Fischer, A.; Reagan, J D.; Yan. L.-Y.; Ames, B. N. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 4337 See also: Harman, D. J. Gerontol. 1956, 11, 298.
    • (1956) J. Gerontol. , vol.11 , pp. 298
    • Harman, D.1
  • 45
    • 0028959058 scopus 로고
    • (d) Hiramoto, K.; Kaku, M.; Kato, T.; Kikugawa, K. Chem. Biol. Interact. 1995, 94, 21. See also: Ames, B. N. Science 1983, 221, 1256. Pryor, W. A. In Anticarcinogenesis and Radiation Protection: Cerutti, P. A., Nygaard, O. F., Simic, M. G., Eds.: Plenum Press New York, 1987: p 1.
    • (1995) Chem. Biol. Interact. , vol.94 , pp. 21
    • Hiramoto, K.1    Kaku, M.2    Kato, T.3    Kikugawa, K.4
  • 46
    • 0020508747 scopus 로고
    • (d) Hiramoto, K.; Kaku, M.; Kato, T.; Kikugawa, K. Chem. Biol. Interact. 1995, 94, 21. See also: Ames, B. N. Science 1983, 221, 1256. Pryor, W. A. In Anticarcinogenesis and Radiation Protection: Cerutti, P. A., Nygaard, O. F., Simic, M. G., Eds.: Plenum Press New York, 1987: p 1.
    • (1983) Science , vol.221 , pp. 1256
    • Ames, B.N.1
  • 47
    • 0002476544 scopus 로고
    • Cerutti, P. A., Nygaard, O. F., Simic, M. G., Eds.: Plenum Press New York
    • (d) Hiramoto, K.; Kaku, M.; Kato, T.; Kikugawa, K. Chem. Biol. Interact. 1995, 94, 21. See also: Ames, B. N. Science 1983, 221, 1256. Pryor, W. A. In Anticarcinogenesis and Radiation Protection: Cerutti, P. A., Nygaard, O. F., Simic, M. G., Eds.: Plenum Press New York, 1987: p 1.
    • (1987) Anticarcinogenesis and Radiation Protection , pp. 1
    • Pryor, W.A.1


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