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Glowing jellyfish, luminescence and a molecule called coelenterazine
Trends in Biotechnology, 1999Luminescence has assumed an important role in analytical biochemistry and molecular biology as an extremely sensitive method for determining the concentration of specific ions and molecules. The luminescent system of the jellyfish Aequorea victoria consists of the photoprotein aequorin, which contains the molecule coelenterazine as a prosthetic group ...
K, Jones, F, Hibbert, M, Keenan
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Three Efficient Methods for Preparation of Coelenterazine Analogues
Chemistry – A European Journal, 2016AbstractThe growing popularity of bioluminescent assays has highlighted the need for coelenterazine analogues possessing properties tuned for specific applications. However, the structural diversity of known coelenterazine analogues has been limited by current syntheses. Known routes for the preparation of coelenterazine analogues employ harsh reaction
Anton Shakhmin +6 more
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Photochemistry and Photobiology, 2020
AbstractCalcium‐regulated photoproteins are found in at least five phyla of organisms. The light emitted by those photoproteins can be tuned by mutating the photoprotein and/or by modifying the substrate coelenterazine (CTZ). Thirty years ago, Shimomura observed that the luminescence activity of aequorin was dramatically reduced when the substrate CTZ ...
Bo‐Wen Ding +3 more
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AbstractCalcium‐regulated photoproteins are found in at least five phyla of organisms. The light emitted by those photoproteins can be tuned by mutating the photoprotein and/or by modifying the substrate coelenterazine (CTZ). Thirty years ago, Shimomura observed that the luminescence activity of aequorin was dramatically reduced when the substrate CTZ ...
Bo‐Wen Ding +3 more
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A biomimetic synthesis of coelenterazine analogs
Tetrahedron Letters, 2002N-(Trifluoroacetyl)dehydrodipeptides 2-3 were coupled to aminomethylene dimethylacetal derivatives 4 5. The resulting pseudo-tripeptides 6 were stepwise deprotected (carbonyl function (7) then amine function) and in situ cyclized into imidazolopyrazines 1. (C) 2002 Elsevier Science Ltd. All rights reserved.
Devillers, Ingrid +3 more
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Coelenterazine Analogs as Chemiluminescent Probe for Superoxide Anion
Analytical Biochemistry, 1997Eleven new coelenterazine analogs containing the 3,7-dihydroimidazo[1,2-alpha]pyrazin-3-one structure were synthesized. The superoxide-triggered chemiluminescence of these compounds was investigated using the hypoxanthine-xanthine oxidase system in comparison with four known compounds.
K, Teranishi, O, Shimomura
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Journal of Photochemistry and Photobiology B: Biology, 2019
Imidazopyrazinone is a typical scaffold present in marine bioluminescence, in which thermal energy is converted into excitation energy in an enzyme-catalyzed reaction. In fact, the imidazopyrazinone scaffold is a common link among organisms of eight phyla.
Carla M. Magalhães +2 more
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Imidazopyrazinone is a typical scaffold present in marine bioluminescence, in which thermal energy is converted into excitation energy in an enzyme-catalyzed reaction. In fact, the imidazopyrazinone scaffold is a common link among organisms of eight phyla.
Carla M. Magalhães +2 more
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A coelenterazine-type bioluminescent probe for nitroreductase imaging
Organic & Biomolecular Chemistry, 2018Novel coelenterazine-type bioluminescent probes have been designed and synthesized to detect nitroreductase (NTR) in hypoxic tumors.
Xingye Yang +4 more
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Light-emitters involved in the luminescence of coelenterazine
Luminescence, 2000Coelenterazine emits light by chemi-and bioluminescence reactions, decomposing into coelenteramide and CO(2). To ascertain the light emitters involved, the fluorescence of coelenteramide and five analogues were studies in four kinds of solvent. The results showed that coelenteramides can form five kinds of light emitters, ie unionized (lambda(max) 386 ...
O, Shimomura, K, Teranishi
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Biochemical and Biophysical Research Communications
Dehydrocoelenterazine (dCTZ) is a dehydrogenated form of coelenterazine (CTZ), which is well-known as the luciferin responsible for the bioluminescence reaction in marine organisms. In this report, we demonstrate for the first time that dCTZ is readily reduced to CTZ in mammalian cells.
Satoshi Inouye +4 more
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Dehydrocoelenterazine (dCTZ) is a dehydrogenated form of coelenterazine (CTZ), which is well-known as the luciferin responsible for the bioluminescence reaction in marine organisms. In this report, we demonstrate for the first time that dCTZ is readily reduced to CTZ in mammalian cells.
Satoshi Inouye +4 more
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Azide- and Dye-Conjugated Coelenterazine Analogues for Imaging Mammalian Cells
2021Coelenterazine (CTZ) is a common substrate to most marine luciferases and photoproteins. The present protocol introduces mammalian cell imaging with nine novel dye- and azide-conjugated CTZ analogues, which were synthesized by conjugating a series of fluorescent dyes or an azide group to the C-2 or C-6 position of CTZ backbone. The investigation on the
Ryo, Nishihara +4 more
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