Vargulin
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| IUPAC name
2-[3-[2-[(2S)-butan-2-yl]-6-(1H-indol-3-yl)-3-oxo-7H-imidazo[2,
1-c]pyrazin-8-yl]propyl]guanidine
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| Other names
Cypridina luciferin, cypridinid luciferin, Vargula luciferin
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C22H27N7O | |
| Molar mass | 405.506 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Vargulin,[1] also called Cypridinid luciferin,[2] Cypridina luciferin, or Vargula luciferin, is the luciferin found in the ostracod Cypridina hilgendorfii, also named Vargula hilgendorfii.[3] These bottom dwelling ostracods emit a light stream into water when disturbed presumably to deter predation. Vargulin is also used by the midshipman fish, Porichthys.
History
[edit | edit source]A partial extraction procedure was developed in 1935 which involved reacting the compound with benzoyl chloride to allow it to be separated from the water-soluble components.[4] The compound was first isolated and purified to crystals by Osamu Shimomura.[5] The structure of the compound was confirmed some years later.[6] Feeding experiments suggest that the compound is synthesized in the animal from three amino-acids: tryptophan, isoleucine, and arginine.[7]
Biochemistry
[edit | edit source]Vargulin is oxidized by the Vargula luciferase,[8] a 62 kDa enzyme, to produce blue light at 462 nm (max emission, detected with a 425 to 525 nm filter). The vargulin does not cross react with luciferases using coelenterazine or Firefly luciferin.
Uses
[edit | edit source]Vargulin (with the associated luciferase) has applications in biotechnology:
- in a variety of assays, to report gene or gene expression after luciferase have been genetically introduced in cells,
- to detect ATP, that is used in the vargulin/luciferase reaction (cell viability assays).[9]
Although less stable, the Cypridina system is useful because can be used in multiplex assays with other (red-emitting) luciferin assays.
References
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External links
[edit | edit source]- Error creating thumbnail: File missing Media related to Lua error in Module:Commons_link at line 62: attempt to index field 'wikibase' (a nil value). at Wikimedia Commons
