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Revision as of 15:50, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 444242436 of page Vargulin for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'CASNo').  Latest revision as of 05:09, 8 February 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,087 edits Added bibcode. Removed 3 name-list-style attributes from cite entries that match that of "cs1 config" template to exclude the article from Category:CS1 maint: overridden setting. 
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{{cs1 config|name-list-style=vanc}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ |ImageFile=Vargulin.svg
| verifiedrevid = 470629261
⚫ |ImageSize=200px
⚫ | ImageFile=Vargulin.svg
⚫ |IUPACName=2--6-(1''H''-indol-3-yl)-3-oxo-7''H''-imidazo[2,
⚫ | ImageSize=200px
⚫ | IUPACName=2--6-(1''H''-indol-3-yl)-3-oxo-7''H''-imidazo[2,
1-c]pyrazin-8-yl]propyl]guanidine 1-c]pyrazin-8-yl]propyl]guanidine
|OtherNames=Vargulin, Cypridina luciferin, cypridinluciferin | OtherNames=Cypridina luciferin, cypridinid luciferin, Vargula luciferin
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 2043419 | ChemSpiderID = 388868
| InChI = InChI=1S/C22H27N7O/c1-3-13(2)19-21(30)29-12-18(15-11-26-16-8-5-4-7-14(15)16)27-17(20(29)28-19)9-6-10-25-22(23)24/h4-5,7-8,11-13,26-27H,3,6,9-10H2,1-2H3,(H4,23,24,25)/t13-/m0/s1 | InChI = InChI=1S/C22H27N7O/c1-3-13(2)19-21(30)29-12-18(15-11-26-16-8-5-4-7-14(15)16)27-17(20(29)28-19)9-6-10-25-22(23)24/h4-5,7-8,11-13,26-27H,3,6,9-10H2,1-2H3,(H4,23,24,25)/t13-/m0/s1
| InChIKey = ZWPWSXGBDMGKKS-UHFFFAOYAG | InChIKey = ZWPWSXGBDMGKKS-UHFFFAOYAG
| CASNo = <!-- blanked - oldvalue: 7273-34-9 --> | CASNo=7273-34-9
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 2762720
| UNII = 761TM14Y84
⚫ | StdInChI = 1S/C22H27N7O/c1-3-13(2)19-21(30)29-12-18(15-11-26-16-8-5-4-7-14(15)16)27-17(20(29)28-19)9-6-10-25-22(23)24/h4-5,7-8,11-13,26-27H,3,6,9-10H2,1-2H3,(H4,23,24,25)
⚫ | PubChem = 135398684
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChI = 1S/C22H27N7O/c1-3-13(2)19-21(30)29-12-18(15-11-26-16-8-5-4-7-14(15)16)27-17(20(29)28-19)9-6-10-25-22(23)24/h4-5,7-8,11-13,26-27H,3,6,9-10H2,1-2H3,(H4,23,24,25)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZWPWSXGBDMGKKS-UHFFFAOYSA-N | StdInChIKey = ZWPWSXGBDMGKKS-UHFFFAOYSA-N
| SMILES = O=C\3N4\C=C(\c2c1ccccc1nc2)N/C(=C4/N=C/3(C)CC)CCC/N=C(\N)N | SMILES = O=C\3N4\C=C(\c2c1ccccc1c2)N/C(=C4/N=C/3(C)CC)CCC/N=C(\N)N
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=22 | H=27 | N=7 | O=1
| Formula=C<sub>22</sub>H<sub>27</sub>N<sub>7</sub>O
| Appearance=
| MolarMass=405.496
| Appearance= | Density=
| Density= | MeltingPt=
| MeltingPt= | BoilingPt=
| BoilingPt= | Solubility=
| Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}

'''Vargulin''',<ref name="Campbell Herring 1990">{{cite journal | last1=Campbell | first1=A. K. | last2=Herring | first2=P. J. | title=Imidazolopyrazine bioluminescence in copepods and other marine organisms | journal=Marine Biology | publisher=Springer Science and Business Media LLC | volume=104 | issue=2 | year=1990 | issn=0025-3162 | doi=10.1007/bf01313261 | pages=219–225| bibcode=1990MarBi.104..219C | s2cid=84250053 }}</ref> also called '''Cypridinid luciferin''',<ref name="Morin2011">{{cite journal | last=Morin | first=James G. | title=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 | journal=Luminescence | publisher=Wiley | volume=26 | issue=1 | year=2011 | issn=1522-7235 | doi=10.1002/bio.1282 | pages=1–4| pmid=19862683 }}</ref> '''Cypridina luciferin''', or '''Vargula luciferin''', is the ] found in the ] '']'', also named '']''.<ref>{{cite book |author=Shimomura, O. |year=2006 |title=Bioluminescence: Chemical Principles and Methods |publisher=] |isbn=978-981-256-801-4}}</ref> These bottom dwelling ostracods emit a light stream into water when disturbed presumably to deter predation. Vargulin is also used by the midshipman fish, ].

== History ==
A partial extraction procedure was developed in 1935 which involved reacting the compound with ] to allow it to be separated from the water-soluble components.<ref>{{cite journal | author = Anderson, RS | title = Studies on Bioluminescence : II. the Partial Purification of Cypridina Luciferin.| journal =The Journal of General Physiology| volume=19| issue=2 | pages=301–5 | year=1935 | pmid=19872927 | doi=10.1085/jgp.19.2.301 | pmc=2141430}}</ref> The compound was first isolated and purified to crystals by ].<ref>{{cite journal | author = Shimomura, O | author2 = Goto, T | author3 = Hirata, Y | title = Crystalline Cypridina Luciferin| journal =Bulletin of the Chemical Society of Japan| volume=30| issue=8 | pages=929–933 | year=1957 | doi=10.1246/bcsj.30.929| url=http://naosite.lb.nagasaki-u.ac.jp/dspace/bitstream/10069/20882/1/BullCSJ30_929.pdf| doi-access=free| hdl = 10069/20882 }}</ref> The structure of the compound was confirmed some years later.<ref>{{cite journal | author = Kishi Y, Goto | author2 = T, Hirata Y | author3 = Shiromura O | author4 = Johnson FH | author-link = Kishi Y | year = 1966 | title = Cypridina bioluminescence. I. Structure of Cypridina luciferin | journal = Tetrahedron Lett. | volume = 7 | issue = 29 | doi = 10.1016/S0040-4039(01)82806-9 | pages = 3427&ndash;3436 }}</ref> ] suggest that the compound is synthesized in the animal from three amino-acids: ], ], and ].<ref>{{cite journal | author = Oba, Y | author2 = Kato, S | author3 = Ojika, M | author4 = Inouye, S | title=Biosynthesis of luciferin in the sea firefly, Cypridina hilgendorfii: l-tryptophan is a component in Cypridina luciferin | journal = Tetrahedron Letters| volume=43| issue=12 | pages=2389–2392 | year=2002 | doi=10.1016/S0040-4039(02)00257-5 }}</ref>

== Biochemistry ==
Vargulin is oxidized by the ],<ref>{{cite journal | vauthors = Thompson EM, Nagata S, Tsuji FI | title = Cloning and expression of cDNA for the luciferase from the marine ostracod Vargula hilgendorfii | journal = ] | volume = 86 | issue = 17 | pages = 6567–71 | year = 1989 | pmid = 2771943 | pmc = 297885 | doi=10.1073/pnas.86.17.6567| bibcode = 1989PNAS...86.6567T | doi-access = free }}</ref> a 62&nbsp;kDa ], to produce blue light at 462&nbsp;nm (max emission, detected with a 425 to 525&nbsp;nm filter).
The vargulin does not cross react with luciferases using ] or ].

== Uses ==
Vargulin (with the associated luciferase) has applications in ]:
* in a variety of assays, to report gene or ] after luciferase have been genetically introduced in cells,
* to detect ], that is used in the vargulin/luciferase reaction (]).<ref>{{cite web |title=Luciferase Reporters |url=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 |website=thermofisher.com}}</ref>

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

==References==
{{Reflist}}

==External links==
*{{Commonscatinline}}

{{DEFAULTSORT:Viability Assay}}
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Misplaced Pages:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Vargulin: Difference between pages Add topic