메뉴 건너뛰기




Volumn 36, Issue 3, 2004, Pages 278-287

Coelenterazine: A two-stage antioxidant in lipid micelles

Author keywords

Aminopyrazine; Coelenteramine; Coelenterazine; Free radicals; Imidazolopyrazinone; Lipid peroxidation

Indexed keywords

AMINE; AMINOPYRAZINE; ANTIOXIDANT; COELENTERAMINE; COELENTERAZINE; LIPID; LUCIFERIN; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 1642481242     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2003.11.008     Document Type: Article
Times cited : (10)

References (44)
  • 1
    • 0034682381 scopus 로고    scopus 로고
    • The crystal structure of the photoprotein aequorin at 2.3 Å resolution
    • Head J.F., Inouye S., Teranishi K., Shimomura O. The crystal structure of the photoprotein aequorin at 2.3 Å resolution. Nature. 405:2000;372-376.
    • (2000) Nature , vol.405 , pp. 372-376
    • Head, J.F.1    Inouye, S.2    Teranishi, K.3    Shimomura, O.4
  • 2
    • 77957077055 scopus 로고
    • Origins of the luciferins, the ecology of bioluminescence in marine fishes
    • P.W. Hochachka, & T.P. Mommsen. Amsterdam/New York: Elsevier
    • Thompson E.M., Rees J.F. Origins of the luciferins, the ecology of bioluminescence in marine fishes. Hochachka P.W., Mommsen T.P. Biochemistry and molecular biology of fishes. 1994;435-466 Elsevier, Amsterdam/New York.
    • (1994) Biochemistry and Molecular Biology of Fishes , pp. 435-466
    • Thompson, E.M.1    Rees, J.F.2
  • 3
    • 37049085775 scopus 로고
    • Chemiluminescence of Cypridina luciferin analogs. 2. Kinetic studies on the reaction of 2-methyl-6-phenylimidazo[1,2-a]pyrazin-3(7h)-one (CLA) with superoxide-hydroperoxyl radical is an actual active species used to initiate the reaction
    • Akutsu K., Nakajima H., Katoh T., Kino S., Fujimori K. Chemiluminescence of Cypridina luciferin analogs. 2. Kinetic studies on the reaction of 2-methyl-6-phenylimidazo[1,2-a]pyrazin-3(7h)-one (CLA) with superoxide- hydroperoxyl radical is an actual active species used to initiate the reaction. J. Chem. Soc. Perkin Trans. 2:1995;1699-1706.
    • (1995) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 1699-1706
    • Akutsu, K.1    Nakajima, H.2    Katoh, T.3    Kino, S.4    Fujimori, K.5
  • 4
    • 0028341285 scopus 로고
    • Measurement of superoxide reaction by chemiluminescence
    • Gotoh N., Niki E. Measurement of superoxide reaction by chemiluminescence. Methods Enzymol. 233:1994;154-160.
    • (1994) Methods Enzymol. , vol.233 , pp. 154-160
    • Gotoh, N.1    Niki, E.2
  • 6
    • 0026148581 scopus 로고
    • Measurement of rate constants for quenching singlet oxygen with a Cypridina luciferin analog (2-methyl-6-[p-methoxyphenyl]-3,7-dihydroimidazo [1,2-a]pyrazin-3-one) and sodium azide
    • Mashiko S., Suzuki N., Koga S., Nakano M., Goto T., Ashino T., Mizumoto I., Inaba H. Measurement of rate constants for quenching singlet oxygen with a Cypridina luciferin analog (2-methyl-6-[p-methoxyphenyl]-3,7-dihydroimidazo [1,2-a]pyrazin-3-one) and sodium azide. J. Biolumin. Chemilumin. 6:1991;69-72.
    • (1991) J. Biolumin. Chemilumin. , vol.6 , pp. 69-72
    • Mashiko, S.1    Suzuki, N.2    Koga, S.3    Nakano, M.4    Goto, T.5    Ashino, T.6    Mizumoto, I.7    Inaba, H.8
  • 7
    • 0004909356 scopus 로고
    • Antioxidative activity of some biologically active compounds with active oxygen species
    • Suzuki N. Antioxidative activity of some biologically active compounds with active oxygen species. Spectrum. 6:1993;21-25.
    • (1993) Spectrum , vol.6 , pp. 21-25
    • Suzuki, N.1
  • 8
    • 0000473989 scopus 로고    scopus 로고
    • Chemiluminescence of Cypridina luciferin analogs. Part 3. MCLA chemiluminescence with singlet oxygen generated by the retro-diels-alder reaction of a naphthalene endoperoxide
    • Fujimori K., Komiyama T., Tabata H., Nojima T., Ishiguro K., Sawaki Y., Tatsuzawa H., Nakano M. Chemiluminescence of Cypridina luciferin analogs. Part 3. MCLA chemiluminescence with singlet oxygen generated by the retro-diels-alder reaction of a naphthalene endoperoxide. Photochem. Photobiol. 68:1998;143-149.
    • (1998) Photochem. Photobiol. , vol.68 , pp. 143-149
    • Fujimori, K.1    Komiyama, T.2    Tabata, H.3    Nojima, T.4    Ishiguro, K.5    Sawaki, Y.6    Tatsuzawa, H.7    Nakano, M.8
  • 11
    • 0025193722 scopus 로고
    • - generation in in situ lungs of rats treated with drugs to induce experimental acute respiratory distress syndrome
    • - generation in in situ lungs of rats treated with drugs to induce experimental acute respiratory distress syndrome. FEBS Lett. 261:1990;369-372.
    • (1990) FEBS Lett. , vol.261 , pp. 369-372
    • Takahashi, A.1    Nakano, M.2    Mashiko, S.3    Inaba, H.4
  • 12
    • 0026492717 scopus 로고
    • Coelenterazine is a superoxide anion-sensitive chemiluminescent probe: Its usefulness in the assay of respiratory burst in neutrophils
    • Lucas M., Solano F. Coelenterazine is a superoxide anion-sensitive chemiluminescent probe: its usefulness in the assay of respiratory burst in neutrophils. Anal. Biochem. 206:1992;273-277.
    • (1992) Anal. Biochem. , vol.206 , pp. 273-277
    • Lucas, M.1    Solano, F.2
  • 13
    • 0027129791 scopus 로고
    • - possibly generated in inner membranes for iron-induced microsomal lipid peroxidation
    • - possibly generated in inner membranes for iron-induced microsomal lipid peroxidation. Biochem. Biophys. Res. Commun. 186:1992;1087-1093.
    • (1992) Biochem. Biophys. Res. Commun. , vol.186 , pp. 1087-1093
    • Koga, S.1    Nakano, M.2
  • 14
    • 0031570749 scopus 로고    scopus 로고
    • Coelenterazine analogs as chemiluminescent probe for superoxide anion
    • Teranishi K., Shimomura O. Coelenterazine analogs as chemiluminescent probe for superoxide anion. Anal. Biochem. 249:1997;37-43.
    • (1997) Anal. Biochem. , vol.249 , pp. 37-43
    • Teranishi, K.1    Shimomura, O.2
  • 15
    • 0030934316 scopus 로고    scopus 로고
    • Stable nitroxide radicals protect lipid acyl chains from radiation damage
    • Samuni A.M., Barenholz Y. Stable nitroxide radicals protect lipid acyl chains from radiation damage. Free Radic. Biol. Med. 22:1997;1165-1174.
    • (1997) Free Radic. Biol. Med. , vol.22 , pp. 1165-1174
    • Samuni, A.M.1    Barenholz, Y.2
  • 16
    • 0032052229 scopus 로고    scopus 로고
    • The origins of marine bioluminescence: Turning oxygen defence mechanisms into deep-sea communication tools
    • Rees J.F., de-Wergifosse B., Noiset O., Dubuisson M., Janssens B., Thompson E.M. The origins of marine bioluminescence: turning oxygen defence mechanisms into deep-sea communication tools. J. Exp. Biol. 201:1998;1211-1221.
    • (1998) J. Exp. Biol. , vol.201 , pp. 1211-1221
    • Rees, J.F.1    De-Wergifosse, B.2    Noiset, O.3    Dubuisson, M.4    Janssens, B.5    Thompson, E.M.6
  • 17
    • 0032479471 scopus 로고    scopus 로고
    • The antioxidant action of 2-methyl-6-(p-methoxyphenyl)-3,7- dihydroimidazo[1,2-alpha]pyrazin-3-one (MCLA), a chemiluminescence probe to detect superoxide anions
    • Tampo Y., Tsukamoto M., Yonaha M. The antioxidant action of 2-methyl-6-(p-methoxyphenyl)-3,7-dihydroimidazo[1,2-alpha]pyrazin-3-one (MCLA), a chemiluminescence probe to detect superoxide anions. FEBS Lett. 430:1998;348-352.
    • (1998) FEBS Lett. , vol.430 , pp. 348-352
    • Tampo, Y.1    Tsukamoto, M.2    Yonaha, M.3
  • 18
    • 0035058128 scopus 로고    scopus 로고
    • Protection against nitrofurantoin-induced oxidative stress by coelenterazine analogues and their oxidation products in rat hepatocytes
    • Dubuisson M.L.N., de-Wergifosse B., Kremers P., Marchand-Brynaert J., Trouet A., Rees J.F. Protection against nitrofurantoin-induced oxidative stress by coelenterazine analogues and their oxidation products in rat hepatocytes. Free Radical Res. 34:2003;285-296.
    • (2003) Free Radical Res. , vol.34 , pp. 285-296
    • Dubuisson, M.L.N.1    De-Wergifosse, B.2    Kremers, P.3    Marchand-Brynaert, J.4    Trouet, A.5    Rees, J.F.6
  • 19
    • 0034664190 scopus 로고    scopus 로고
    • Antioxidative properties of natural coelenterazine and synthetic methyl coelenterazine in rat hepatocytes subjected to tert-butyl hydroperoxide-induced oxidative stress
    • Dubuisson M.L.N., de-Wergifosse B., Trouet A., Baguet F., Marchand-Brynaert J., Rees J.F. Antioxidative properties of natural coelenterazine and synthetic methyl coelenterazine in rat hepatocytes subjected to tert-butyl hydroperoxide-induced oxidative stress. Biochem. Pharmacol. 60:2000;471-478.
    • (2000) Biochem. Pharmacol. , vol.60 , pp. 471-478
    • Dubuisson, M.L.N.1    De-Wergifosse, B.2    Trouet, A.3    Baguet, F.4    Marchand-Brynaert, J.5    Rees, J.F.6
  • 20
    • 0036023306 scopus 로고    scopus 로고
    • Protection of peroxide-treated fish erythrocytes by coelenterazine and coelenteramine
    • Janssens B.J., Marchand-Brynaert J., Rees J.F. Protection of peroxide-treated fish erythrocytes by coelenterazine and coelenteramine. Free Radical Res. 36:2002;967-974.
    • (2002) Free Radical Res. , vol.36 , pp. 967-974
    • Janssens, B.J.1    Marchand-Brynaert, J.2    Rees, J.F.3
  • 21
    • 0028892652 scopus 로고
    • Two luminescent intermediates of coelenterazine analog, peroxide and dioxetanone, prepared by direct photo-oxygenation at low temperature
    • Usami K., Isobe M. Two luminescent intermediates of coelenterazine analog, peroxide and dioxetanone, prepared by direct photo-oxygenation at low temperature. Tetrahedron Lett. 36:1995;8613-8616.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8613-8616
    • Usami, K.1    Isobe, M.2
  • 22
    • 0030576862 scopus 로고    scopus 로고
    • Low-temperature photooxygenation of coelenterate luciferin analog synthesis and proof of 1,2-dioxetanone as luminescence intermediate
    • Usami K., Isobe M. Low-temperature photooxygenation of coelenterate luciferin analog synthesis and proof of 1,2-dioxetanone as luminescence intermediate. Tetrahedron. 52:1996;12061-12090.
    • (1996) Tetrahedron , vol.52 , pp. 12061-12090
    • Usami, K.1    Isobe, M.2
  • 23
    • 0011723689 scopus 로고
    • Oxidation of luciferin in bioluminescence and chemiluminescence
    • W. Ando, Moro-Oka Y. Amsterdam: Elsevier
    • Goto T. Oxidation of luciferin in bioluminescence and chemiluminescence. Ando W., Moro-Oka Y. Activation of dioxygen and homogeneous catalytic oxidations. 1988;367-382 Elsevier, Amsterdam.
    • (1988) Activation of Dioxygen and Homogeneous Catalytic Oxidations , pp. 367-382
    • Goto, T.1
  • 24
    • 12244288879 scopus 로고    scopus 로고
    • Synthesis, structure-activity relationship and in vitro evaluation of coelenterazine and coelenteramine derivatives as inhibitors of lipid peroxidation
    • Burton M., De-Tollenaere C., Cavalier J.F., Marchand C., Dussart F., Marchand-Brynaert J., Rees J.F. Synthesis, structure-activity relationship and in vitro evaluation of coelenterazine and coelenteramine derivatives as inhibitors of lipid peroxidation. Free Radical Res. 37:2003;145-158.
    • (2003) Free Radical Res. , vol.37 , pp. 145-158
    • Burton, M.1    De-Tollenaere, C.2    Cavalier, J.F.3    Marchand, C.4    Dussart, F.5    Marchand-Brynaert, J.6    Rees, J.F.7
  • 26
    • 0000758183 scopus 로고    scopus 로고
    • Highly efficient and flexible total synthesis of coelenterazine
    • Keenan M., Jones K., Hibbert F. Highly efficient and flexible total synthesis of coelenterazine. J. Chem. Soc. Chem. Commun. 1997;323-324.
    • (1997) J. Chem. Soc. Chem. Commun. , pp. 323-324
    • Keenan, M.1    Jones, K.2    Hibbert, F.3
  • 27
    • 0027521196 scopus 로고
    • Mass-spectrometric studies on chemiluminescence of coelenterate luciferin analogs
    • Hirano T., Nishibuchi S., Yoneda M., Tsujimoto K., Ohashi M. Mass-spectrometric studies on chemiluminescence of coelenterate luciferin analogs. Tetrahedron. 49:1993;9267-9276.
    • (1993) Tetrahedron , vol.49 , pp. 9267-9276
    • Hirano, T.1    Nishibuchi, S.2    Yoneda, M.3    Tsujimoto, K.4    Ohashi, M.5
  • 28
    • 0345127796 scopus 로고
    • Chemiluminescence and bioluminescence of coelenterazine analogs with phenyl homologs at the C-2 position
    • Qi C.F., Gomi Y., Hirano T., Ohashi M., Ohmiya Y., Tsuji F.I. Chemiluminescence and bioluminescence of coelenterazine analogs with phenyl homologs at the C-2 position. J. Chem. Soc. Perkin Trans. 1:1992;1607-1611.
    • (1992) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 1607-1611
    • Qi, C.F.1    Gomi, Y.2    Hirano, T.3    Ohashi, M.4    Ohmiya, Y.5    Tsuji, F.I.6
  • 29
    • 0000621071 scopus 로고
    • Chemical nature of the light emitter in bioluminescence of aequorin
    • Shimomura O., Johnson F.H. Chemical nature of the light emitter in bioluminescence of aequorin. Tetrahedron Lett. 31:1973;2963-2966.
    • (1973) Tetrahedron Lett. , vol.31 , pp. 2963-2966
    • Shimomura, O.1    Johnson, F.H.2
  • 31
    • 0002727536 scopus 로고
    • Spectrophotometric method for determination of lipoxidase activity
    • Surrey K. Spectrophotometric method for determination of lipoxidase activity. Physiol. Rev. 39:1964;65-70.
    • (1964) Physiol. Rev. , vol.39 , pp. 65-70
    • Surrey, K.1
  • 32
    • 0021330425 scopus 로고
    • Inhibition of oxidation of methyl linoleate in solution by vitamin e and vitamin C
    • Niki E., Saito T., Kawakami A., Kamiya Y. Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C. J. Biol. Chem. 259:1984;4177-4182.
    • (1984) J. Biol. Chem. , vol.259 , pp. 4177-4182
    • Niki, E.1    Saito, T.2    Kawakami, A.3    Kamiya, Y.4
  • 33
    • 33845470074 scopus 로고
    • Autoxidation of micelles and model membranes. Quantitative kinetic measurements can be made by using either water-soluble or lipid-soluble initiators with water-soluble or lipid-soluble chain-breaking antioxidants
    • Barclay L.R., Locke S.J., McNeil J.M., VanKessel J., Burton G.W., Ingold K.U. Autoxidation of micelles and model membranes. Quantitative kinetic measurements can be made by using either water-soluble or lipid-soluble initiators with water-soluble or lipid-soluble chain-breaking antioxidants. J. Am. Chem. Soc. 106:1984;2479-2481.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 2479-2481
    • Barclay, L.R.1    Locke, S.J.2    McNeil, J.M.3    Vankessel, J.4    Burton, G.W.5    Ingold, K.U.6
  • 35
    • 0026657363 scopus 로고
    • The role of lipid peroxidation and antioxidants in oxidative modification of LDL
    • Esterbauer H., Gebicki J., Puhl H., Jurgens G. The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radic. Biol. Med. 13:1992;341-390.
    • (1992) Free Radic. Biol. Med. , vol.13 , pp. 341-390
    • Esterbauer, H.1    Gebicki, J.2    Puhl, H.3    Jurgens, G.4
  • 36
    • 0021288839 scopus 로고
    • Spectrophotometric detection of lipid conjugated dienes
    • Recknagel R.O., Glende-EA J. Spectrophotometric detection of lipid conjugated dienes. Methods Enzymol. 105:1984;331-337.
    • (1984) Methods Enzymol. , vol.105 , pp. 331-337
    • Recknagel, R.O.1    Glende-Ea, J.2
  • 38
    • 0001723228 scopus 로고
    • Chemistry of bioluminescence
    • Goto T. Chemistry of bioluminescence. Pure Appl. Chem. 17:1968;421-441.
    • (1968) Pure Appl. Chem. , vol.17 , pp. 421-441
    • Goto, T.1
  • 39
    • 0032404444 scopus 로고    scopus 로고
    • Aequorea victoria bioluminescence moves into an exciting new era
    • Kendall J.M., Badminton M.N. Aequorea victoria bioluminescence moves into an exciting new era. Trends Biotechnol. 16:1998;216-224.
    • (1998) Trends Biotechnol. , vol.16 , pp. 216-224
    • Kendall, J.M.1    Badminton, M.N.2
  • 40
    • 0027960129 scopus 로고
    • Synthesis of hydroperoxide via photooxygenation for a model aequorin bioluminescence
    • Teranishi K., Ueda K., Nakano H., Hisamatsu M., Yamada T. Synthesis of hydroperoxide via photooxygenation for a model aequorin bioluminescence. Tetrahedron Lett. 35:1994;8181-8184.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8181-8184
    • Teranishi, K.1    Ueda, K.2    Nakano, H.3    Hisamatsu, M.4    Yamada, T.5
  • 41
    • 0030528338 scopus 로고    scopus 로고
    • Chemiluminescent characters of hydroperoxide and dioxetanone of coelenterate luciferin analog prepared by low-temperature photooxygenation
    • Usami K., Isobe M. Chemiluminescent characters of hydroperoxide and dioxetanone of coelenterate luciferin analog prepared by low-temperature photooxygenation. Chem. Lett. 1996;215-216.
    • (1996) Chem. Lett. , pp. 215-216
    • Usami, K.1    Isobe, M.2
  • 42
    • 0029044256 scopus 로고
    • Antioxidant activities of aminophenols against oxidation of methyl linoleate in solution
    • Iwatsuki M., Komuro E., Niki E. Antioxidant activities of aminophenols against oxidation of methyl linoleate in solution. Bull. Chem. Soc. Jpn. 68:1995;620-624.
    • (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 620-624
    • Iwatsuki, M.1    Komuro, E.2    Niki, E.3
  • 43
    • 0028356351 scopus 로고
    • Membrane peroxidation: Inhibiting effects of water-soluble antioxidants on phospholipids of different charge types
    • Barclay L.R., Vinqvist M.R. Membrane peroxidation: inhibiting effects of water-soluble antioxidants on phospholipids of different charge types. Free Radic. Biol. Med. 16:1994;779-788.
    • (1994) Free Radic. Biol. Med. , vol.16 , pp. 779-788
    • Barclay, L.R.1    Vinqvist, M.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.