Chemistry:Vargulin
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
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
Vargulin is oxidized by cypridina-luciferin 2-monooxygenase,[8][9][10] a 62 kDa enzyme, to produce blue light at 462 nm (max emission, detected with a 425 to 525 nm filter).
- REDIRECT Template:Chemical reaction
The vargulin does not cross react with luciferases using coelenterazine or Firefly luciferin.
Uses
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).[11]
Although less stable, the Cypridina system is useful because can be used in multiplex assays with other (red-emitting) luciferin assays.
References
- ↑ Campbell, A. K.; Herring, P. J. (1990). "Imidazolopyrazine bioluminescence in copepods and other marine organisms". Marine Biology (Springer Science and Business Media LLC) 104 (2): 219–225. doi:10.1007/bf01313261. ISSN 0025-3162. Bibcode: 1990MarBi.104..219C.
- ↑ Morin, James G. (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 (Wiley) 26 (1): 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. PMID 19872927.
- ↑ 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.
- ↑ 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.
- ↑ "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. 1989. doi:10.1073/pnas.86.17.6567. PMID 2771943. Bibcode: 1989PNAS...86.6567T.
- ↑ "The synthesis of Cypridina etioluciferamine and the proof of the structure of Cypridina luciferin". Tetrahedron 29 (23): 3761–3773. 1973. doi:10.1016/0040-4020(73)80193-0.
- ↑ "Some properties of luciferase from the bioluminescent crustacean, Cypridina hilgendorfii". Biochemistry 13 (25): 5204–5209. 1974. doi:10.1021/bi00722a024. PMID 4433517.
- ↑ "Luciferase Reporters". https://www.thermofisher.com/vn/en/home/life-science/protein-biology/protein-biology-learning-center/protein-biology-resource-library/pierce-protein-methods/luciferase-reporters.html.
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