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Pure Appl. Chem., 1984, Vol. 56, No. 9, pp. 1179-1190

http://dx.doi.org/10.1351/pac198456091179

Generation of electronically excited triplet species in biochemical systems

Giuseppe Cilento

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  • Almeida Eduardo A., Martinez Glaucia R., Klitzke Clecio F., Medeiros Marisa H. G., Mascio Paolo Di: Oxidation of melatonin by singlet molecular oxygen (O2(1Deltag)) produces N1-acetyl-N2-formyl-5-methoxykynurenine. J Pineal Res 2003, 35, 131. <http://dx.doi.org/10.1034/j.1600-079X.2003.00066.x>
  • Nery Ana L. P., Quina Frank H., Moreira, Jr Paulo F., Medeiros Carlos E. R., Baader Wilhelm J., Shimizu Karina, Catalani Luiz H., Bechara Etelvino J. H.: Does the Photochemical Conversion of Colchicine into Lumicolchicines Involve Triplet Transients? A Solvent Dependence Study¶. Photchem Photbio 2001, 73, 213. <http://dx.doi.org/10.1562/0031-8655(2001)073<0213:DTPCOC>2.0.CO;2>
  • de Oliveira Silva Sueli, Ximenes Valdecir F., Catalani Luiz Henrique, Campa Ana: Myeloperoxidase-Catalyzed Oxidation of Melatonin by Activated Neutrophils. Biochemical and Biophysical Research Communications 2000, 279, 657. <http://dx.doi.org/10.1006/bbrc.2000.3993>
  • Brennan Thomas M., Lee Esther, Battaglia Paul R.: Participation of the Photosensitizer Alpha-terthienyl in thePeroxidase-catalyzed Oxidation of Indole-3-acetic acid†. Photchem Photbio 2000, 71, 355. <http://dx.doi.org/10.1562/0031-8655(2000)071<0355:POTPAT>2.0.CO;2>
  • Ximenes Valdecir F., Campa Ana, Baader Wilhelm J., Catalani Luiz H.: Facile chemiluminescent method for alkaline phosphatase determination. Analytica Chimica Acta 1999, 402, 99. <http://dx.doi.org/10.1016/S0003-2670(99)00550-4>
  • Chen Xi, Chen Wei, Jiang Yaqi, Jia Li, Wang Xiaoru: Electrogenerated Chemiluminescence Based on Tris(2,2′-bipyridyl) Ruthenium(II) with Hydroxyl Carboxylic Acid. Microchim J 1998, 59, 427. <http://dx.doi.org/10.1006/mchj.1998.1628>
  • Hug Gordon L., Bobrowski Krzysztof, Kozubek Halina, Marciniak Bronislaw: Photooxidation of Methionine Derivatives by the 4-Carboxybenzophenone Triplet State in Aqueous Solution. Intracomplex Proton Transfer Involving the Amino Group. Photchem Photbio 1998, 68, 785. <http://dx.doi.org/10.1111/j.1751-1097.1998.tb05285.x>
  • Sharov Victor S., Driomina Elena S., Briviba Karlis, Sies Helmut: Sensitization of Peroxynitrite Chemiluminescence by the Triplet Carbonyl Sensitizer Coumarin-525. Effect of CO2. Photchem Photbio 1998, 68, 797. <http://dx.doi.org/10.1111/j.1751-1097.1998.tb05286.x>
  • Karatani Hajime, Shizuki Takahiro: Luminescent electrooxidation of methanol in aqueous alkaline media. Electrochimica Acta 1996, 41, 1667. <http://dx.doi.org/10.1016/0013-4686(95)00421-1>
  • Hug G.L., Marciniak B., Bobrowski K.: Sensitized photo-oxidation of sulfur-containing amino acids and peptides in aqueous solution. J Photochem Photobiol A Chem 1996, 95, 81. <http://dx.doi.org/10.1016/1010-6030(95)04230-X>
  • Baader Wilhelm J., Gillo Virginia E.: Peroxidase-catalysed chlorophyll destruction accompanied by the formation of electronically excited states: chlorophyll emission not due to energy transfer from excited substrate metabolites. J Photochem Photobiol A Chem 1996, 101, 49. <http://dx.doi.org/10.1016/S1010-6030(96)04424-3>
  • Brennan Thomas M.: Decarboxylation of lndole-3-Acetic Acid and Inhibition of Growth in Avena sativa Seedlings by Plant-Derived Photosensitizers*. Photochemistry and Photobiology 1996, 64, 1001. <http://dx.doi.org/10.1111/j.1751-1097.1996.tb01867.x>
  • Krylov Sergey N., Krylova Svetlana M.: OpticalIy Pumped Chemiluminescence of Indole-3-Acetic Acid. Photchem Photbio 1996, 63, 621. <http://dx.doi.org/10.1111/j.1751-1097.1996.tb05665.x>
  • Nantes lseli L., Becharat Etelvino J. H., Cilento Giuseppe: Horseradish Peroxidase-Catalyzed Generation of Acetophenone and Benzophenone in the Triplet State. Photchem Photbio 1996, 63, 702. <http://dx.doi.org/10.1111/j.1751-1097.1996.tb09618.x>
  • Krylov Sergey N., Dunford H. Brian: Detailed Mechanism of Phenol-Inhibited Peroxidase-Catalyzed Oxidation of Indole-3-Acetic Acid at Neutral pH. Photchem Photbio 1996, 63, 735. <http://dx.doi.org/10.1111/j.1751-1097.1996.tb09623.x>
  • Cilento Giuseppe, Adam Waldemar: From free radicals to electronically excited species. Free Radic Biol Med 1995, 19, 103. <http://dx.doi.org/10.1016/0891-5849(95)00002-F>
  • Nantes Isbli L., Cilento Giuseppe, Bechara Etelvino J. H., Vercesi Aníbal E.: CHEMILUMINESCENT DIPHENYLACETALDEHYDE OXIDATION BY MITOCHONDRIA IS PROMOTED BY CYTOCHROMES and LEADS TO OXIDATIVE INJURY OF THE ORGANELLE. Photchem Photbio 1995, 62, 522. <http://dx.doi.org/10.1111/j.1751-1097.1995.tb02378.x>
  • Adam Waldemar, Saha-Möller Chantu R., Schönberger André, Berger Maurice, Cadet Jean: FORMATION OF 7,8-DIHYDRO-8-OXOGUANINE IN THE 1,2-DIOXETANE-INDUCED OXIDATION OF CALF THYMUS DNA: EVIDENCE FOR PHOTOSENSITIZED DNA DAMAGE BY THERMALLY GENERATED TRIPLET KETONES IN THE DARK. Photchem Photbio 1995, 62, 231. <http://dx.doi.org/10.1111/j.1751-1097.1995.tb05263.x>
  • Melo Mariza Pires DE, Cilento Giuseppe: CHEMIEXCITATION IN THE PEROXIDATIVE METABOLISM OF N- METHYLCARBAZOLE: MECHANISTIC IMPLICATIONS. Photchem Photbio 1994, 59, 677. <http://dx.doi.org/10.1111/j.1751-1097.1994.tb08237.x>
  • Melo Mariza Pires, Cilento Giuseppe: CHEMIEXCITATION IN THE PEROXIDATIVE METABOLISM OF N-METHYLCARBAZOLE: MECHANISTIC IMPLICATIONS. Photchem Photbio 1994, 59, 677. <http://dx.doi.org/10.1111/j.1751-1097.1994.tb09675.x>
  • Krylov Sergey N., Chebotareva Alla B.: Peroxidase-catalyzed co-oxidation of indole-3-acetic acid and xanthene dyes in the absence of hydrogen peroxide. FEBS Letters 1993, 324, 6. <http://dx.doi.org/10.1016/0014-5793(93)81521-Z>
  • Cilento Giuseppe, Nascimento Ana Lucia T.O.: Generation of electronically excited triplet species at the cellular level: A potential source of genotoxicity. Toxicol Lett 1993, 67, 17. <http://dx.doi.org/10.1016/0378-4274(93)90043-W>
  • Surpili Marcelo José, Faijoni-Alario Adelaide, Cilento Giuseppe: PHOTON EMISSION BY BACTERIA CHALLENGED WITH PHENYLACETALDEHYDE. A POSSIBLE DISTINCTION BETWEEN GRAM-POSITIVE and GRAM-NEGATIVE BACTERIA. Photchem Photbio 1993, 57, 564. <http://dx.doi.org/10.1111/j.1751-1097.1993.tb02334.x>
  • Sundquist Alfred R., Hanusch Michael, Stahl Wilhelm, Sies Helmut: Cis/trans ISOMERIZATION OF CAROTENOIDS BY THE TRIPLET CARBONYL SOURCE 3-HYDROXYMETHYL-3,4,4-TRIMETHYL-1,2-DIOXETANE. Photchem Photbio 1993, 57, 785. <http://dx.doi.org/10.1111/j.1751-1097.1993.tb09211.x>
  • Epe Bernd, Müller Elvira, Adam Waldemar, Saha-Möller Chantu R.: Photochemical DNA modifications induced by 1,2-dioxetanes. Chemico Biological Interactions 1992, 85, 265. <http://dx.doi.org/10.1016/0009-2797(92)90067-U>
  • Watanabe Haruo, Nagoshi Toshiyuki, Suzuki Sohkichi, Kobayashi Masaki, Usa Masashi, Humio Inaba: Chemiluminescence in the crude extracts of soybean seedlings. Postulated mechanism on the formation of hydroperoxide intermediates. General Subjects 1992, 1117, 107. <http://dx.doi.org/10.1016/0304-4165(92)90066-4>
  • Knudsen Fernanda da Silva, Cilento Giuseppe: CHEMIEXCITATION IN THE PEROXIDATIVE METABOLISM OF DIETHYLSTILBESTROL. METABOLIC PRODUCTS. Photchem Photbio 1992, 55, 267. <http://dx.doi.org/10.1111/j.1751-1097.1992.tb04236.x>
  • Nagoshi Toshiyuki, Watanabe Nobuyuki, Suzuki Sohkichi, Usa Masashi, Watanabe Haruo, Ichimura Tsutomu, Inaba Humio: SPECTRAL ANALYSES OF LOW LEVEL CHEMILUMINESCENCE OF A SHORT LIFETIME USING A HIGHLY SENSITIVE POLYCHROMATIC SPECTROMETER INCORPORATING A TWO DIMENSIONAL PHOTON-COUNTING TYPE DETECTOR. Photchem Photbio 1992, 56, 89. <http://dx.doi.org/10.1111/j.1751-1097.1992.tb09607.x>
  • Watanabe Haruo, Kobayashi Masaki, Suzuki Sohkichi, Usa Masashi, Agatsuma Shin-ichi, Saeki Rie, Inaba Humio: Aldehyde-enhanced photon emission from crude extracts of soybean seedlings. Biochim Biophys Acta Bioenerg 1991, 1058, 209. <http://dx.doi.org/10.1016/S0005-2728(05)80239-7>
  • NASCIMENTO ANA LUCIA T. O., CILENTO GIUSEPPE: CHEMIEXCITATION IN THE ARACHIDONIC ACID CASCADE. Photchem Photbio 1991, 53, 379. <http://dx.doi.org/10.1111/j.1751-1097.1991.tb03644.x>
  • HIDEG ÈVA, INABA HUMIO: BIOPHOTON EMISSION (ULTRAWEAK PHOTOEMISSION) FROM DARK ADAPTED SPINACH CHLOROPLASTS. Photchem Photbio 1991, 53, 137. <http://dx.doi.org/10.1111/j.1751-1097.1991.tb08479.x>
  • Silva Eduardo, Edwards Ana M., Faljoni-Alario Adelaide: Enzymatic generation of triplet acetone by deglycosylated horseradish peroxidase. Archives of Biochemistry and Biophysics 1990, 276, 527. <http://dx.doi.org/10.1016/0003-9861(90)90754-M>
  • Veselý K., Rychlý J., Kummer M., Jančář J.: Flammability of highly filled polyolefins. Polym Deg Stabil 1990, 30, 101. <http://dx.doi.org/10.1016/0141-3910(90)90120-V>
  • Villablanca Miguel, Indig Guilermi, Slawinska Danuta, Slawinski Janusz: Studies on chemiluminescence in the enzymatic and autoxidative transformation of 3,4-dihydroxyphenylalanine into eumelanins. J Biolumin Chemilumin 1989, 3, 181. <http://dx.doi.org/10.1002/bio.1170030405>
  • Cilento Giuseppe: Generation of triplet carbonyl compounds during peroxidase catalysed reactions. J Biolumin Chemilumin 1989, 4, 193. <http://dx.doi.org/10.1002/bio.1170040128>
  • Cadenas Enrique: Lipid peroxidation during the oxidation of haemoproteins by hydroperoxides. Relation to electronically excited state formation. J Biolumin Chemilumin 1989, 4, 208. <http://dx.doi.org/10.1002/bio.1170040130>
  • Salim-Hanna Marta, Campa Ana, Cilento Giuseppe: α-Oxidation of α-hydroxyfatty acids in rat brain. Possible involvement of an α-peroxylactone. Lipid 1989, 24, 750. <http://dx.doi.org/10.1007/BF02535217>
  • Monteiro Hugo P., Abdalla Dulcineia S.P., Augusto Ohara, Bechara Etelvino J.H.: Free radical generation during δ-Aminolevulinic acid autoxidation: Induction by hemoglobin and connections with porphyrinpathies. Archives of Biochemistry and Biophysics 1989, 271, 206. <http://dx.doi.org/10.1016/0003-9861(89)90271-3>
  • Nascimento Ana Lucia T.O., Cilento Giuseppe: Schiff base formation with amino acids enhances light emission and damage induced in neutrophils by phenylacetaldehyde. General Subjects 1989, 991, 50. <http://dx.doi.org/10.1016/0304-4165(89)90027-5>
  • Brunmark Anders, Cadenas Enrique: Redox and addition chemistry of quinoid compounds and its biological implications. Free Radic Biol Med 1989, 7, 435. <http://dx.doi.org/10.1016/0891-5849(89)90126-3>
  • Vanderkooi Jane M., Berger Jeffrey W.: Excited triplet states used to study biological macromolecules at room temperature. Biochim Biophys Acta Bioenerg 1989, 976, 1. <http://dx.doi.org/10.1016/S0005-2728(89)80185-9>
  • Geacintov Nicholas E., Brenner Henry C.: THE TRIPLET STATE AS A PROBE OF DYNAMICS AND STRUCTURE IN BIOLOGICAL MACROMOLECULES. Photchem Photbio 1989, 50, 841. <http://dx.doi.org/10.1111/j.1751-1097.1989.tb02916.x>
  • ENCINAS M. V., LISSI E. A., VASQUEZ M., OLEA A. F., SILVA E.: PHOTOINTERACTION OF BENZOPHENONE TRIPLET WITH LYSOZYME. Photchem Photbio 1989, 49, 557. <http://dx.doi.org/10.1111/j.1751-1097.1989.tb08424.x>
  • SCHULTE-HERBRUGGEN THOMAS, SIES HELMUT: THE PEROXIDASE/OXIDASE ACTIVITY OF SOYBEAN LIPOXYGENASE - I. TRIPLET EXCITED CARBONYLS FROM THE REACTION WITH ISOBUTANAL AND THE EFFECT OF GLUTATHIONE. Photchem Photbio 1989, 49, 697. <http://dx.doi.org/10.1111/j.1751-1097.1989.tb08443.x>
  • Cilento G.: Photobiochemistry without light. CMLS Cell Mol Life Sci 1988, 44, 572. <http://dx.doi.org/10.1007/BF01953304>
  • Epe Bernd, Mützel Petra, Adam Waldemar: DNA damage by oxygen radicals and excited state species: A comparative study using enzymatic probes in vitro. Chemico Biological Interactions 1988, 67, 149. <http://dx.doi.org/10.1016/0009-2797(88)90094-4>
  • Nassi L., Schiffmann D., Favre A., Adam W., Fuchs R.: Induction of the SOS function sfiA in E. coli by systems which generate triplet ketones. Mutat Res Fundam Mol Mech Mutagen 1988, 198, 53. <http://dx.doi.org/10.1016/0027-5107(88)90039-5>
  • ROJAS JORGE, SILVA EDUARDO: PHOTOCHEMICAL-LIKE BEHAVIOUR OF RIBOFLAVIN IN THE DARK PROMOTED BY ENZYME-GENERATED TRIPLET ACETONE. Photchem Photbio 1988, 47, 467. <http://dx.doi.org/10.1111/j.1751-1097.1988.tb02753.x>
  • Bohne Cornelia, Faljoni-Alario Adelaide, Cilento Giuseppe: INTERACTION OF ENZYME-GENERATED SPECIES WITH CHLOROPHYLL-a AND PROBES BOUND TO SERUM ALBUMINS. Photchem Photbio 1988, 48, 341. <http://dx.doi.org/10.1111/j.1751-1097.1988.tb02831.x>
  • Cilento Giuseppe, Adam Waldemar: PHOTOCHEMISTRY and PHOTOBIOLOGY WITHOUT LIGHT. Photchem Photbio 1988, 48, 361. <http://dx.doi.org/10.1111/j.1751-1097.1988.tb02835.x>
  • Indig Guilherme L., Campa Ana, Bechara Etelvino J. H., Cilento Giuseppe: CONJUGATED DIENE FORMATION PROMOTED BY TRIPLET ACETONE ACTING UPON ARACHIDONIC ACID. Photchem Photbio 1988, 48, 719. <http://dx.doi.org/10.1111/j.1751-1097.1988.tb02886.x>
  • Durán Nelson, Cadenas Enrique: The role of singlet oxygen and triplet carbonyls in biological systems. Res Chem Intermed 1987, 8, 147. <http://dx.doi.org/10.1007/BF03156138>
  • Indig Guilherme L., Cilento Giuseppe: Peroxidase-promoted aerobic oxidation of 2-nitropropane: mechanism of excited state formation. General Subjects 1987, 923, 347. <http://dx.doi.org/10.1016/0304-4165(87)90042-0>
  • Villablanca Miguel, Cilento Giuseppe: Oxidation of phenylpyruvic acid. General Subjects 1987, 926, 224. <http://dx.doi.org/10.1016/0304-4165(87)90207-8>
  • Brunmark Anders, Cadenas Enrique: Electronically excited state generation during the reaction of p-benzoquinone with H2O2. Free Radic Biol Med 1987, 3, 169. <http://dx.doi.org/10.1016/0891-5849(87)90002-5>
  • Catalani Luiz H., Wilson Thérèse, Bechara Etelvino J. H.: TWO WATER-SOLUBLE FLUORESCENCE PROBES FOR CHEMIEXCITATION STUDIES: SODIUM 9,10-DIBROMO- AND 9, 10-DIPHENYLANTHRACENE-2-SULFONATE. SYNTHESIS, PROPERTIES AND APPLICATION TO TRIPLET ACETONE AND TETRAMETHYLDIOXETANE. Photchem Photbio 1987, 45, 273. <http://dx.doi.org/10.1111/j.1751-1097.1987.tb05375.x>
  • Salim-Hanna Marta, Campa Ana, Cilento Giuseppe: THE α-OXIDASE SYSTEM OF YOUNG PEA LEAVES (Pisum sativum) AS GENERATOR OF ELECTRONICALLY EXCITED STATES. EXCITATION IN THE DARK UNDER NATURAL CONDITIONS. Photchem Photbio 1987, 45, 849. <http://dx.doi.org/10.1111/j.1751-1097.1987.tb07894.x>
  • Bohne Cornelia, Campa Ana, Cilento Giuseppe, Nassi Lilian, Villablanca Miguel: Chlorophyll: An efficient detector of electronically excited species in biochemical systems. Analytical Biochemistry 1986, 155, 1. <http://dx.doi.org/10.1016/0003-2697(86)90215-0>
  • de Medeiros Marisa H.G., Bechara Etelvino J.H.: Chemiluminescent aerobic oxidation of protein adducts with glycolaldehyde catalyzed by horseradish peroxidase. Archives of Biochemistry and Biophysics 1986, 248, 435. <http://dx.doi.org/10.1016/0003-9861(86)90441-8>
  • Sargentini Neil J., Smith Kendric C.: Mutagenesis by normal metabolites in Escherichia coli: phenylalanine mutagenesis is dependent on error-prone DNA repair. Mutat Res Fundam Mol Mech Mutagen 1986, 161, 113. <http://dx.doi.org/10.1016/0027-5107(86)90002-3>
  • Menck Carlos F.M., Cabral-Neto Janu��rico B., Faljoni-Al��rio A., Alcantara-Gomes Roberto, Franklin William A., Haseltine William A., Ochi Takafumi, Ishiguro Tohru, Oshawa Motoyasu: Damages induced in �� phage DNA by enzyme-generated triplet acetone. Mutation Research/DNA Repair Reports 1986, 165, 9. <http://dx.doi.org/10.1016/0167-8817(86)90003-9>
  • Adam Waldemar, Baader Wilhelm J., Cilento Giuseppe: Enols of aldehydes in the peroxidase/oxidase-promoted generation of excited triplet species. General Subjects 1986, 881, 330. <http://dx.doi.org/10.1016/0304-4165(86)90023-1>
  • Nascimento Ana Lucia T.O., da Fonseca Luis Marcos, Brunetti Iguatemy L., Cilento Giuseppe: Intracellular generation of electronically excited states. Polymorphonuclear leukocytes challenged with a precursor of triplet acetone. General Subjects 1986, 881, 337. <http://dx.doi.org/10.1016/0304-4165(86)90024-3>
  • Guillo Lidia A., Faljoni-Alário Adelaide, Cilento Giuseppe: Interaction between enzyme-generated triplet carbonyls and molecules intercalated into DNA. General Subjects 1986, 884, 39. <http://dx.doi.org/10.1016/0304-4165(86)90224-2>
  • Baader W.J., Bohne C., Cilento G., Nassi L., Wood E.J.: Enzymatic generation of triplet acetone: A window to photobiochemistry without light. Biochemical Education 1986, 14, 190. <http://dx.doi.org/10.1016/0307-4412(86)90216-5>
  • do Nascimento Ana Lucia T.O., Cilento Giuseppe: Induction of chemiluminescent processes in the fungus Blastocladiella emersonii by exposure to enzyme-generated triplet benzaldehyde. General Subjects 1985, 843, 254. <http://dx.doi.org/10.1016/0304-4165(85)90146-1>
  • Adam Waldemar, Baader Wilhelm J., Catalani Luiz H., Cilento Giuseppe, Rychlá Lyda: ENERGY TRANSFER FROM CHEMIEXCITED ACETONE TO SUBSTANCES THAT DISPLAY ANOMALOUS FLUORESCENCE. Photchem Photbio 1985, 42, 587. <http://dx.doi.org/10.1111/j.1751-1097.1985.tb01614.x>
  • Villablanca Miguel, Cilento Giuseppe: ENZYMATIC GENERATION OF ELECTRONICALLY EXCITED STATES BY ELECTRON TRANSFER. Photchem Photbio 1985, 42, 591. <http://dx.doi.org/10.1111/j.1751-1097.1985.tb01615.x>