Vargulin

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Vargulin
Vargulin.svg
Names
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
Other names
Vargulin, Cypridina luciferin, cypridinid luciferin
Identifiers
3D model (JSmol)
ChemSpider
Properties
C22H27N7O
Molar mass 405.496
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Vargulin, also called Cypridina luciferin or Vargula Luciferin, is the luciferin found in the ostracod Cypridina hilgendorfii, also named Vargula hilgendorfii.[1] 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]

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.[2] The compound was first isolated and purified to crystals by Osamu Shimomura.[3] The structure of the compound was confirmed some years later.[4] Feeding experiments suggest that the compound is synthesized in the animal from three amino-acids: tryptophan, isoleucine, and arginine.[5]

Biochemistry[edit]

Vargulin is oxidized by the Vargula luciferase,[6] a 62kDa 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]

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)

Although less stable, the Cypridina system is useful because can be used in multiplex assays with other (red-emitting) luciferin assays.

References[edit]

  1. ^ Shimomura, O. (2006). Bioluminescence: Chemical Principles and Methods. World Scientific Publishing. ISBN 978-981-256-801-4. 
  2. ^ Anderson, RS (1935). "Studies on Bioluminescence : II. the Partial Purification of Cypridina Luciferin.". The Journal of General Physiology. 19 (2): 301–5. PMC 2141430Freely accessible. PMID 19872927. doi:10.1085/jgp.19.2.301. 
  3. ^ Shimomura, O; Goto, T & Hirata, Y (1957). "Crystalline Cypridina Luciferin". Bulletin of the Chemical Society of Japan. 30 (8): 929–933. doi:10.1246/bcsj.30.929. 
  4. ^ Kishi Y, Goto; T, Hirata Y; Shiromura O & Johnson FH (1966). "Cypridina bioluminescence. I. Structure of Cypridina luciferin". Tetrahedron Lett. 7: 3427–3436. doi:10.1016/S0040-4039(01)82806-9. 
  5. ^ 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. 
  6. ^ 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. PMC 297885Freely accessible. PMID 2771943. doi:10.1073/pnas.86.17.6567.