CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 1968, Vol. 17, No. 3-4, pp. 421-442

Chemistry of bioluminescence

Toshio Goto

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Nakamura Mitsuhiro, Suzuki Tomoko, Ishizaka Norihiro, Sato Jun-ichi, Inouye Satoshi: Identification of 3-enol sulfate of Cypridina luciferin, Cypridina luciferyl sulfate, in the sea-firefly Cypridina (Vargula) hilgendorfii. Tetrahedron 2014, 70, 2161. <>
  • Ishii Yuki, Hayashi Chihiro, Suzuki Yoshihisa, Hirano Takashi: Chemiluminescent 2,6-diphenylimidazo[1,2-a]pyrazin-3(7H)-ones: a new entry to Cypridina luciferin analogues. Photochem. Photobiol. Sci. 2014, 13, 182. <>
  • Inouye Satoshi, Sahara-Miura Yuiko: A Novel Catalytic Function of Synthetic IgG-Binding Domain (Z Domain) from Staphylococcal Protein A: Light Emission with Coelenterazine. Photochem Photobiol 2014, 90, 137. <>
  • Eremeeva Elena V., Natashin Pavel V., Song Lei, Zhou Yuguang, van Berkel Willem J. H., Liu Zhi-Jie, Vysotski Eugene S.: Oxygen Activation of Apo-obelin-Coelenterazine Complex. ChemBioChem 2013, 14, 739. <>
  • Eremeeva Elena V., Markova Svetlana V., van Berkel Willem J.H., Vysotski Eugene S.: Role of key residues of obelin in coelenterazine binding and conversion into 2-hydroperoxy adduct. Journal of Photochemistry and Photobiology B: Biology 2013, 127, 133. <>
  • Eftekhari-Sis Bagher, Zirak Maryam, Akbari Ali: Arylglyoxals in Synthesis of Heterocyclic Compounds. Chem. Rev. 2013, 113, 2958. <>
  • Hirano Takashi, Nakagawa Tatsuki, Kodaka Ai, Maki Shojiro, Niwa Haruki, Yamaji Minoru: 5-[4-(Dimethylamino)phenyl]-2-benzamidopyrazines: fluorescent dyes based on Cypridina oxyluciferin. Res Chem Intermed 2012. <>
  • Naumov Panče, Wu Chun, Liu Ya-Jun, Ohmiya Yoshihiro: Spectrochemistry and artificial color modulation of Cypridina luminescence: indirect evidence for chemiexcitation of a neutral dioxetanone and emission from a neutral amide. Photochem. Photobiol. Sci. 2012, 11, 1151. <>
  • Markova Svetlana V., Burakova Ludmila P., Golz Stefan, Malikova Natalia P., Frank Ludmila A., Vysotski Eugene S.: The light-sensitive photoprotein berovin from the bioluminescent ctenophore Beroe abyssicola: a novel type of Ca2+-regulated photoprotein : Recombinant calcium-regulated photoprotein berovin. FEBS J 2012, 279, 856. <>
  • Stepanyuk Galina A., Unch James, Malikova Natalia P., Markova Svetlana V., Lee John, Vysotski Eugene S.: Coelenterazine-v ligated to Ca2+-triggered coelenterazine-binding protein is a stable and efficient substrate of the red-shifted mutant of Renilla muelleri luciferase. Anal Bioanal Chem 2010, 398, 1809. <>
  • Fetzner Susanne, Steiner Roberto A.: Cofactor-independent oxidases and oxygenases. Appl Microbiol Biotechnol 2010, 86, 791. <>
  • Hirano Takashi, Sekiguchi Takashi, Hashizume Daisuke, Ikeda Hiroshi, Maki Shojiro, Niwa Haruki: Colorimetric and fluorometric sensing of the Lewis acidity of a metal ion by metal-ion complexation of imidazo[1,2-a]pyrazin-3(7H)-ones. Tetrahedron 2010, 66, 3842. <>
  • Hachiya Sojiro, Inagaki Takayuki, Hashizume Daisuke, Maki Shojiro, Niwa Haruki, Hirano Takashi: Synthesis and fluorescence properties of difluoro[amidopyrazinato-O,N]boron derivatives: a new boron-containing fluorophore. Tetrahetron Lett 2010, 51, 1613. <>
  • Saito Ryota: Non-CRET-Based Green Chemiluminescence of Imidazopyrazinone Modified by 2,3,6,7-Tetrahydro-1H,5H-benzo[i,j]quinolizine as a Strong Electron-Donating Unit. HETEROCYCLES 2010, 81, 2831. <>
  • Hirano Takashi, Takahashi Yuto, Kondo Hiroyuki, Maki Shojiro, Kojima Satoshi, Ikeda Hiroshi, Niwa Haruki: The reaction mechanism for the high quantum yield of Cypridina (Vargula) bioluminescence supported by the chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues). Photochem Photobiol Sci 2008, 7, 197. <>
  • Stepanyuk Galina A., Liu Zhi-Jie, Markova Svetlana S., Frank Ludmila A., Lee John, Vysotski Eugene S., Wang Bi-Cheng: Crystal structure of coelenterazine-binding protein from Renilla muelleri at 1.7 Å: Why it is not a calcium-regulated photoprotein. Photochem Photobiol Sci 2008, 7, 442. <>
  • Inouye Satoshi, Sasaki Satoko: Imidazole-assisted catalysis of luminescence reaction in blue fluorescent protein from the photoprotein aequorin. BIOPHYS BIOCHEM RES COMMUN 2007, 354, 650. <>
  • Takahashi Yuto, Kondo Hiroyuki, Maki Shojiro, Niwa Haruki, Ikeda Hiroshi, Hirano Takashi: Chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones in DMSO/TMG and in diglyme/acetate buffer: support for the chemiexcitation process to generate the singlet-excited state of neutral oxyluciferin in a high quantum yield in the Cypridina (Vargula) bioluminescence mechanism. Tetrahetron Lett 2006, 47, 6057. <>
  • Suzuki Mai, Fujii Takashi, Nogami Takashi, Hirano Takashi, Ishida Takayuki: Bio-inspired Materials for Electron Donors and Charge-transfer Complex Formation Based on the Imidazopyrazinone Luciferin Core. Chem Lett 2006, 35, 250. <>
  • Takamuki Yoshiharu, Maki Shojiro, Niwa Haruki, Ikeda Hiroshi, Hirano Takashi: Substituent effects on the spectroscopic properties of solvatochromic 2-phenylimidazo[1,2-a]pyrazin-3(7H)-ones: an effective control for the colorimetric sensor properties. Tetrahedron 2005, 61, 10073. <>
  • Kondo Hiroyuki, Igarashi Takayuki, Maki Shojiro, Niwa Haruki, Ikeda Hiroshi, Hirano Takashi: Substituent effects on the kinetics for the chemiluminescence reaction of 6-arylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues): support for the single electron transfer (SET)–oxygenation mechanism with triplet molecular oxygen. Tetrahetron Lett 2005, 46, 7701. <>
  • de Wergifosse Bertrand, Dubuisson Marlène, Marchand-Brynaert Jacqueline, Trouet André, Rees Jean-François: Coelenterazine: a two-stage antioxidant in lipid micelles. Free Radic Biol Med 2004, 36, 278. <>
  • Sekiguchi Takashi, Maki Shojiro, Niwa Haruki, Ikeda Hiroshi, Hirano Takashi: Metal-ion complexation of imidazo[1,2-a]pyrazin-3(7H)-ones: continuous changes in absorption spectra of complexes depending on the Lewis acidity of the metal ion. Tetrahetron Lett 2004, 45, 1065. <>
  • Fujio Shunsuke, Hashizume Daisuke, Takamuki Yoshiharu, Yasui Masanori, Iwasaki Fujiko, Maki Shojiro, Niwa Haruki, Ikeda Hiroshi, Hirano Takashi: Regioselective phenyl-substitution effects on the solvatochromism of 2-phenylimidazo[1,2-a]pyrazin-3(7H)-one derivatives: expansion of the color variation range of a visible indicator for the proton donor ability of solvents. Tetrahetron Lett 2004, 45, 8531. <>
  • Takamuki Yoshiharu, Maki Shojiro, Niwa Haruki, Ikeda Hiroshi, Hirano Takashi: Substituent Effects on the Solvatochromism of 2-Phenylimidazopyrazinones: Effective Control of the Color Variation Range and Sensitivity toward an Indication of the Proton-donor Ability of Solvents by an Electron-withdrawing Group Substitution. Chem Lett 2004, 33, 1484. <>
  • Adamczyk Maciej, Akireddy Srinivasa Rao, Johnson Donald D, Mattingly Phillip G, Pan You, Reddy Rajarathnam E: Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties. Tetrahedron 2003, 59, 8129. <>
  • Teranishi Katsunori, Nishiguchi Tatsuya, Ueda Haruhisa: Enhanced chemiluminescence of 6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one by attachment of a cyclomaltooligosaccharide (cyclodextrin). Attachment of cyclomaltononaose (δ-cyclodextrin). Carbohydrates Research 2003, 338, 987. <>
  • Nakai Shunichiro, Yasui Masanori, Nakazato Masaki, Iwasaki Fujiko, Maki Shojiro, Niwa Haruki, Ohashi Mamoru, Hirano Takashi: Fundamental Studies on the Structures and Spectroscopic Properties of Imidazo[1,2-a]pyrazin-3(7H)-one Derivatives. Bull Chem Soc Jpn 2003, 76, 2361. <>
  • Wakasugi Takeshi, Fujimori Ken, Matsumoto Masakatsu: Kinetics of Base Catalyzed Chemiluminescence Reaction of Spiro[adamantane -1,3′-(4′-(m-hydroxyphenyl)-4′-methoxy-1′,2′-dioxetane)]. Chem Lett 2002, 762. <>
  • Teranishi Katsunori: Effect of conformation on the chemiluminescence efficiency of light-producing 2-methyl-6-(4-methoxyphenyl)imidazo[1,2-α]pyrazin-3(7H)-ones. formerly the Journal of Bioluminescence and Chemiluminescence 2001, 16, 367. <>
  • Imai Yuko, Shibata Takuya, Maki Shojiro, Niwa Haruki, Ohashi Mamoru, Hirano Takashi: Fluorescence properties of phenolate anions of coelenteramide analogues: the light-emitter structure in aequorin bioluminescence. J Photochem Photobiol A Chem 2001, 146, 95. <>
  • Fischer Frank, Fetzner Susanne: Site-directed mutagenesis of potential catalytic residues in 1H-3-hydroxy-4-oxoquinoline 2,4-dioxygenase, and hypothesis on the catalytic mechanism of 2,4-dioxygenolytic ring cleavage. FEMS Microbiol Lett 2000, 190, 21. <>
  • Teranishi Katsunori, Hisamatsu Makoto, Yamada Tetsuya: Chemiluminescence of 2-methyl-6-arylimidazo­[1,2-a]pyrazin-3(7H)-one in protic solvents: electron-donating substituent effect on the formation of the neutral singlet excited-state molecule. formerly the Journal of Bioluminescence and Chemiluminescence 1999, 14, 297. <<297::AID-BIO574>3.0.CO;2-Y>
  • Teranishi Katsunori, Tanabe Saori, Hisamatsu Makoto, Yamada Tetsuya: Investigation of cyclomaltooligosaccharide-bound 6-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one for enhanced chemiluminescence. formerly the Journal of Bioluminescence and Chemiluminescence 1999, 14, 303. <<303::AID-BIO575>3.0.CO;2-C>
  • Okajima Takeyoshi, Tokuda Koichi, Ohsaka Takeo: Electrochemical behavior of a Cypridina luciferin analogue in acetonitrile solutions in the presence of proton acceptors. Journal of Electroanalytical Chemistry 1999, 476, 46. <>
  • Tampo Yoshiko, Tsukamoto Maki, Yonaha Masanori: The antioxidant action of 2-methyl-6-(p-methoxyphenyl)-3,7-dihydroimidazo[1,2-α]pyrazin-3-one (MCLA), a chemiluminescence probe to detect superoxide anions. FEBS Letters 1998, 430, 348. <>
  • Substituent Effects on the Chemiluminescent Properties of Coelenterazine Analogues. Chem Lett 1998, 95. <>
  • Hisamatsu Makoto, Yamada Tetsuya, Teranishi Katsunori: Synthesis and chemiluminescent properties of the peroxy acid compound as an intermediate of coelenterate luciferin luminescence. Tetrahetron Lett 1997, 38, 2689. <>
  • Usami Ken, Isobe Minoru: Low-temperature photooxygenation of coelenterate luciferin analog synthesis and proof of 1,2-dioxetanone as luminescence intermediate. Tetrahedron 1996, 52, 12061. <>
  • Teranishi Katsunori, Hisamatsu Makoto, Yamada Tetsuya: Studies on the mechanism of chemiluminescence: Synthesis and chemiluminescent properties of the 5-hydroperoxide analogue of coelenterate luciferin. Tetrahetron Lett 1996, 37, 8425. <>
  • OKAJIMA T, TOKUDA K, OHSAKA T: Chemiluminescence of a luciferin analogue by electrogenerated superoxide ion. Bioelectrochem Bioenerg 1996, 41, 205. <>
  • Shimomura Osamu: The roles of the two highly unstable components F and P involved in the bioluminescence of euphausiid shrimps. J Biolumin Chemilumin 1995, 10, 91. <>
  • Mitani Motohiro, Yokoyama Yuko, Ichikawa Syuji, Sawada Hideo, Matsumoto Takeo, Fujimori Ken, Kosugi Masanori: Determination of horserdish peroxidase concentration using the chemiluminescence ofCypridina luciferin analogue, 2 methyl-6-(p-methyoxyphenyl)-3,7-dihydroimidazo[1,2-a]pyrazin-3-one. J Biolumin Chemilumin 1994, 9, 355. <>
  • Teranishi Katsunori, Isobe Minoru, Yamada Tetsuya: Synthesis of silyl peroxide of coelenterazine (oplophorus luciferin) analogue for precursor of luminescence. Tetrahetron Lett 1994, 35, 2565. <>
  • Hirano Takashi, Nisbibuchi Sadatoshi, Yoneda Michiaki, Tsujimoto Kazuo, Ohashi Mamoru: Mass spectrometric studies on chemiluminescence of coelenterate luciferin analogues. Tetrahedron 1993, 49, 9267. <>
  • Takahashi Hiroyuki, Isobe Minoru: Symplectoteuthis bioluminescence (1) Structure and binding form of chromophore in photoprotein of a luminous squid. Biorg Med Chem Lett 1993, 3, 2647. <>
  • Toya Yoshiaki, Kayano Toshimasa, Sato Kyoko, Goto Toshio: Synthesis and Chemiluminescence Properties of 6-(4-Methoxyphenyl)-2-methylimidazo(1,2-a)pyrazin-3(7H)-one and 2-Methyl-6-(2-naphthyl)imidazo(1,2-a)pyrazin-3(7H)-one. Bull Chem Soc Jpn 1992, 65, 2475. <>
  • Nakano Minoru, Sugioka Katsuaki, Ushijima Yoshio, Goto Toshio: Chemiluminescence probe with Cypridina luciferin analog, 2-methyl-6-phenyl-3,7-dihydroimidazo[1,2-a]pyrazin-3-one, for estimating the ability of human granulocytes to generate O2−. Analytical Biochemistry 1986, 159, 363. <>
  • Toya Yoshiaki, Nakatsuka Shin-ichi, Goto Toshio: Structure of biluciferyl, a dimer of luciferyl radical having bioluminescent activity. Tetrahetron Lett 1985, 26, 239. <>
  • Wada Naohisa, Honda Mitsuo, Suzuki Hideo: Theory of D-(-)-Luciferin and Dehydroluciferin in Acidic or Basic Solution. J. Phys. Soc. Jpn. 1985, 54, 4851. <>
  • Inoue Shoji, Kakoi Hisae, Goto Toshio: Squid bioluminescence III. Isolation and structure of Watasenia luciferin. Tetrahetron Lett 1976, 17, 2971. <>
  • Goto T., Isobe M., Kishi Y., Inoue S., Sugiura S.: Cypridina bioluminescence—IX. Tetrahedron 1975, 31, 939. <>
  • Shimomura Os'amu, Johnson Frank H.: Exchange of oxygen between solvent H2O and the CO2 produced in bioluminescence. BIOPHYS BIOCHEM RES COMMUN 1973, 51, 558. <>
  • Goto T., Isobe M., Coviello D.A., Kishi Y., Inoue S.: Cypridina bioluminescence—VII. Tetrahedron 1973, 29, 2035. <>
  • Karpetsky T.P., White E.H.: The synthesis of cypridina etioluciferamine and the proof of structure of cypridina luciferin. Tetrahedron 1973, 29, 3761. <>
  • Shimomura Osamu, Johnson Frank H.: Mechanism of the luminescent oxidation of luciferin. BIOPHYS BIOCHEM RES COMMUN 1971, 44, 340. <>
  • Goto Toshio, Fukatsu Hiroshi: Cypridina bioluminescence VII. chemiluminescence in micelle solutions — a model system for cypridina bioluminescence. Tetrahetron Lett 1969, 10, 4299. <>