Marine Bioluminescence with Dehydrocoelenterazine, an Imidazopyrazinone Compound
Heterocycles play important roles in bioluminescence. Among them, the imidazopyrazinone compounds are utilized for light emission in some marine bioluminescent systems. Coelenterazine (CL) is the organic substance of aequorin, a photoprotein obtained from
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Marine Bioluminescence with Dehydrocoelenterazine, an Imidazopyrazinone Compound Masaki Kuse
Contents 1 Introduction 2 Watasenia scintillans 3 Symplectoteuthis (Sthenoteuthis) oualaniensis 4 Eucleoteuthis luminosa 5 Dosidicus gigas (The Largest Luminescent Animal in the World) 6 Pholas dactylus 7 Conclusion References
Abstract Heterocycles play important roles in bioluminescence. Among them, the imidazopyrazinone compounds are utilized for light emission in some marine bioluminescent systems. Coelenterazine (CL) is the organic substance of aequorin, a photoprotein obtained from jellyfish, that possesses green fluorescent proteins (GFP). The dehydrogenative oxidation of CL affords dehydrocoelenterazine (DCL), which is also an organic substance for marine bioluminescence. DCL cannot react directly with oxygen. Therefore, it is converted to the chromophore, which is required for light emission in a photoprotein. The chromophore directly reacts with oxygen in the presence of reactive oxygen species (ROS) to emit visible light. Symplectin, a photoprotein derived from squids, and Pholasin, a photoprotein of mollusks, utilize the DCL-derived chromophore. Pholasin, a registered trademark of Knight Scientific Ltd., is widely utilized as a highly sensitive indicator of ROS, i.e., the detection of ROS that are produced from activated neutrophils by Pholasin is the biomarker for oxidative stresses. Since there are many excellent reviews regarding CL-dependent bioluminescence, this review focuses on the bioluminescent systems, which employ DCL as an organic substance, by describing the history of the research
M. Kuse (*) Graduate School of Agricultural Science, Kobe University, Kobe, Japan e-mail: [email protected]
M. Kuse
on these systems and the bioluminescent mechanism that is related to the DCL-derived chromophores. Keywords Bioluminescence · Chromophore · Dehydrocoelenterazine · Luciferase · Luciferin · Pholasin · Photoprotein · Symplectin
Abbreviations CL DCL DTT GFP GSH GST HRP LC–MS MPO NMR PBS ROS Tris
Coelenterazine Dehydrocoelenterazine Dithiothreitol Green fluorescent protein Glutathione Glutathione S-transferase Horseradish peroxidase Liquid chromatography–mass spectrometry Myeloperoxidase Nuclear magnetic resonance Phosphate-buffered saline Reactive oxygen species Tris(hydroxymethyl)aminomethane
1 Introduction Beautiful bioluminescence, i.e., light emission from living organisms, has attracted attention since ancient times. Hence, many scientists have attempted to demystify bioluminescent systems to understand how luminous organisms emitted light. Many bioluminescent organisms are found in the ocean, and 90% of deep-sea organisms are suspected to be luminous [1, 2]. Light emission is essentially facilitated by the enzymatic/nonenzymatic oxidation of organic substances. The “burning” of organic molecules with oxygen to produce light emission in luminous organisms could be figuratively likened to the burning of a candle with fire. Although this metaphor is not scientifically correct, it would afford us an ea
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