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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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| ChemSpider | |
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.
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]
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.
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.
- ^ Campbell AK, Herring PJ (1990). "Imidazolopyrazine bioluminescence in copepods and other marine organisms". Marine Biology. 104 (2). Springer Science and Business Media LLC: 219–225. Bibcode: 1990MarBi.104..219C. doi: 10.1007/bf01313261. ISSN 0025-3162. S2CID 84250053.
- ^ Morin JG (2011). "Based on a review of the data, use of the term 'cypridinid' solves the Cypridina/Vargula dilemma for naming the constituents of the luminescent system of ostracods in the family Cypridinidae". Luminescence. 26 (1). Wiley: 1–4. doi: 10.1002/bio.1282. ISSN 1522-7235. PMID 19862683.
- ^ Shimomura, O. (2006). Bioluminescence: Chemical Principles and Methods. World Scientific Publishing. ISBN 978-981-256-801-4.
- ^ Anderson, RS (1935). "Studies on Bioluminescence : II. the Partial Purification of Cypridina Luciferin". The Journal of General Physiology. 19 (2): 301–5. doi: 10.1085/jgp.19.2.301. PMC 2141430. PMID 19872927.
- ^ Shimomura, O, Goto, T, Hirata, Y (1957). "Crystalline Cypridina Luciferin" (PDF). Bulletin of the Chemical Society of Japan. 30 (8): 929–933. doi: 10.1246/bcsj.30.929. hdl: 10069/20882.
- ^ Kishi Y, Goto, T, Hirata Y, Shiromura O, Johnson FH (1966). "Cypridina bioluminescence. I. Structure of Cypridina luciferin". Tetrahedron Lett. 7 (29): 3427–3436. doi: 10.1016/S0040-4039(01)82806-9.
- ^ Oba, Y, Kato, S, Ojika, M, Inouye, S (2002). "Biosynthesis of luciferin in the sea firefly, Cypridina hilgendorfii: l-tryptophan is a component in Cypridina luciferin". Tetrahedron Letters. 43 (12): 2389–2392. doi: 10.1016/S0040-4039(02)00257-5.
- ^ Thompson EM, Nagata S, Tsuji FI (1989). "Cloning and expression of cDNA for the luciferase from the marine ostracod Vargula hilgendorfii". Proceedings of the National Academy of Sciences. 86 (17): 6567–71. Bibcode: 1989PNAS...86.6567T. doi: 10.1073/pnas.86.17.6567. PMC 297885. PMID 2771943.
- ^ "Luciferase Reporters". thermofisher.com.
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Media related to
Vargulin at Wikimedia Commons
