Coelenterazine
Encyclopedia
Coelenterazine is the luciferin
, the light-emitting molecule, found in many aquatic organisms across seven phyla
. It is the substrate in many luciferase
s and photoprotein
s including Renilla reniformis luciferase (Rluc), Gaussia luciferase (Gluc), aequorin
, and obelin.
(Renilla reniformis) and the coelenterate Aequorea victoria
, respectively. Both groups unknowingly discovered that the same compound was used in both luminescent systems, however the name of the molecule was given after the coelenterate. Likewise, the two main metabolites - coelenteramide
and coelenteramine
- were named after their respective functional groups.
The compound has also been isolated from organisms that are not luminescent, such as the Atlantic herring
and several shrimp
species including Pandalus borealis
and Pandalus platyuros.
and visible spectrum, with peak absorption at 435 nm in methanol, giving the molecule a yellow color. The molecule spontaneously oxidizes in aerobic conditions or in some organic solvents such as dimethylformamide
and DMSO and is preferentially stored in methanol
or with an inert gas
.
Luciferin
Luciferins are a class of light-emitting biological pigments found in organisms that cause bioluminescence...
, the light-emitting molecule, found in many aquatic organisms across seven phyla
Phylum
In biology, a phylum The term was coined by Georges Cuvier from Greek φῦλον phylon, "race, stock," related to φυλή phyle, "tribe, clan." is a taxonomic rank below kingdom and above class. "Phylum" is equivalent to the botanical term division....
. It is the substrate in many luciferase
Luciferase
Luciferase is a generic term for the class of oxidative enzymes used in bioluminescence and is distinct from a photoprotein. One famous example is the firefly luciferase from the firefly Photinus pyralis. "Firefly luciferase" as a laboratory reagent usually refers to P...
s and photoprotein
Photoprotein
Photoproteins refer to bioluminescent proteins from luminous organisms. These proteins do not exhibit a luciferin-luciferase reaction, that is, a normal enzyme-substrate reaction. Instead, these proteins display luminescence proportional to the amount of the protein...
s including Renilla reniformis luciferase (Rluc), Gaussia luciferase (Gluc), aequorin
Aequorin
Aequorin is a photoprotein isolated from luminescent jellyfish and a variety of other marine organisms...
, and obelin.
History
Coelenterazine was simultaneously isolated and characterized by two groups studying the luminescent organisms sea pansySea pansy
The Sea pansy is quite frequently found washed ashore on northeast Florida beaches following northeasterly winds or rough surf conditions. It also can often be found living intertidally completely buried in the sand. Its predator is the striped sea slug, Armina tigrina.The Sea pansy is a...
(Renilla reniformis) and the coelenterate Aequorea victoria
Aequorea victoria
Aequorea victoria, also sometimes called the crystal jelly, is a bioluminescent hydrozoan jellyfish, or hydromedusa, that is found off the west coast of North America. This species is thought to be synonymous with Aequorea aequorea of Osamu Shimomura, the discoverer of green fluorescent protein . ...
, respectively. Both groups unknowingly discovered that the same compound was used in both luminescent systems, however the name of the molecule was given after the coelenterate. Likewise, the two main metabolites - coelenteramide
Coelenteramide
Coelenteramide is the oxidized product, or oxyluciferin, of the bioluminescent reactions in many marine organisms that utilize coelenterazine. It was first isolated as a blue fluorescent compound from Aequorea victoria after the animals were stimulated to emit light...
and coelenteramine
Coelenteramine
Coelenteramine is a metabolic product of the bioluminescent reactions in organisms that utilize coelenterazine. It was first isolated from Aequorea victoria along with coelenteramide after coelenterates were stimulated to emit light....
- were named after their respective functional groups.
Occurrence
Coelenterazine is widely found in marine organisms including:- radiolarianRadiolarianRadiolarians are amoeboid protozoa that produce intricate mineral skeletons, typically with a central capsule dividing the cell into inner and outer portions, called endoplasm and ectoplasm. They are found as zooplankton throughout the ocean, and their skeletal remains cover large portions of the...
s - ctenophoreCtenophoreThe Ctenophora are a phylum of animals that live in marine waters worldwide. Their most distinctive feature is the "combs", groups of cilia that they use for swimming, and they are the largest animals that swim by means of cilia – adults of various species range from a few millimeters to in size...
s - cnidarians such as Aequorea victoriaAequorea victoriaAequorea victoria, also sometimes called the crystal jelly, is a bioluminescent hydrozoan jellyfish, or hydromedusa, that is found off the west coast of North America. This species is thought to be synonymous with Aequorea aequorea of Osamu Shimomura, the discoverer of green fluorescent protein . ...
, Obelia geniculata and Renilla reniformis - squidSquidSquid are cephalopods of the order Teuthida, which comprises around 300 species. Like all other cephalopods, squid have a distinct head, bilateral symmetry, a mantle, and arms. Squid, like cuttlefish, have eight arms arranged in pairs and two, usually longer, tentacles...
such as Watasenia scintillans and Vampyroteuthis infernalis - shrimpShrimpShrimp are swimming, decapod crustaceans classified in the infraorder Caridea, found widely around the world in both fresh and salt water. Adult shrimp are filter feeding benthic animals living close to the bottom. They can live in schools and can swim rapidly backwards. Shrimp are an important...
such as Systellaspis debilis and Oplophorus gracilirostris - copepodCopepodCopepods are a group of small crustaceans found in the sea and nearly every freshwater habitat. Some species are planktonic , some are benthic , and some continental species may live in limno-terrestrial habitats and other wet terrestrial places, such as swamps, under leaf fall in wet forests,...
s such as Pleuromamma xiphias and Gaussia princepsGaussia princeps (copepod)Gaussia princeps is a mesopelagic copepod found in the tropical waters worldwide. They have been known to display bioluminescence.-References:... - chaetognaths
- fishFishFish are a paraphyletic group of organisms that consist of all gill-bearing aquatic vertebrate animals that lack limbs with digits. Included in this definition are the living hagfish, lampreys, and cartilaginous and bony fish, as well as various extinct related groups...
including some NeoscopelidaeNeoscopelidaeThe Neoscopelidae are a small family of deep sea fish closely related to the lanternfish. They are found in tropical and subtropical marine waters worldwide....
and Myctophidae - echinodermEchinodermEchinoderms are a phylum of marine animals. Echinoderms are found at every ocean depth, from the intertidal zone to the abyssal zone....
s such as Amphiura filiformis
The compound has also been isolated from organisms that are not luminescent, such as the Atlantic herring
Atlantic herring
Atlantic herring is a fish in the family Clupeidae. It is one of the most abundant fish species on earth. Herring can be found on both sides of the Atlantic Ocean, congregating in large schools. They can grow up to in length and weigh more than...
and several shrimp
Shrimp
Shrimp are swimming, decapod crustaceans classified in the infraorder Caridea, found widely around the world in both fresh and salt water. Adult shrimp are filter feeding benthic animals living close to the bottom. They can live in schools and can swim rapidly backwards. Shrimp are an important...
species including Pandalus borealis
Pandalus borealis
Pandalus borealis is a species of shrimp found in cold parts of the Atlantic and Pacific Oceans. Many different common names are used, including pink shrimp, deepwater prawn, deep-sea prawn, great northern prawn, and northern shrimp.-Distribution:P...
and Pandalus platyuros.
Properties
Coelenterazine can be crystallized into orange-yellow crystals. The molecule absorbs light in the ultravioletUltraviolet
Ultraviolet light is electromagnetic radiation with a wavelength shorter than that of visible light, but longer than X-rays, in the range 10 nm to 400 nm, and energies from 3 eV to 124 eV...
and visible spectrum, with peak absorption at 435 nm in methanol, giving the molecule a yellow color. The molecule spontaneously oxidizes in aerobic conditions or in some organic solvents such as dimethylformamide
Dimethylformamide
Dimethylformamide is an organic compound with the formula 2NCH. Commonly abbreviated as DMF , this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions...
and DMSO and is preferentially stored in methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
or with an inert gas
Inert gas
An inert gas is a non-reactive gas used during chemical synthesis, chemical analysis, or preservation of reactive materials. Inert gases are selected for specific settings for which they are functionally inert since the cost of the gas and the cost of purifying the gas are usually a consideration...
.
External links
- Bioluminescence Page showing major luciferin types