203:
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26:
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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".
104:
236:
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
343:
757:
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".
226:
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)
790:
396:. These bottom dwelling ostracods emit a light stream into water when disturbed presumably to deter predation. Vargulin is also used by the midshipman fish,
252:
450:, 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
618:
493:
Although less stable, the
Cypridina system is useful because can be used in multiplex assays with other (red-emitting) luciferin assays.
217:
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to allow it to be separated from the water-soluble components. The compound was first isolated and purified to crystals by
160:
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181:
350:
928:
908:
730:, T, Hirata Y, Shiromura O, Johnson FH (1966). "Cypridina bioluminescence. I. Structure of Cypridina luciferin".
893:
510:
Campbell AK, Herring PJ (1990). "Imidazolopyrazine bioluminescence in copepods and other marine organisms".
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519:
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903:
888:
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786:"Cloning and expression of cDNA for the luciferase from the marine ostracod Vargula hilgendorfii"
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A partial extraction procedure was developed in 1935 which involved reacting the compound with
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636:"Studies on Bioluminescence : II. the Partial Purification of Cypridina Luciferin"
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suggest that the compound is synthesized in the animal from three amino-acids:
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Except where otherwise noted, data are given for materials in their
25:
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418:. The structure of the compound was confirmed some years later.
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Vargulin (with the associated luciferase) has applications in
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58:
Cypridina luciferin, cypridinid luciferin, Vargula luciferin
478:
after luciferase have been genetically introduced in cells,
260:
O=C\3N4\C=C(\c2c1ccccc1c2)N/C(=C4/N=C/3(C)CC)CCC/N=C(\N)N
518:(2). Springer Science and Business Media LLC: 219–225.
338:
485:, that is used in the vargulin/luciferase reaction (
607:Bioluminescence: Chemical Principles and Methods
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791:Proceedings of the National Academy of Sciences
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50:-imidazo[2, 1-c]pyrazin-8-yl]propyl]guanidine
8:
474:in a variety of assays, to report gene or
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692:Bulletin of the Chemical Society of Japan
683:Shimomura, O, Goto, T, Hirata, Y (1957).
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784:Thompson EM, Nagata S, Tsuji FI (1989).
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229:Key: ZWPWSXGBDMGKKS-UHFFFAOYSA-N
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239:Key: ZWPWSXGBDMGKKS-UHFFFAOYAG
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14:
685:"Crystalline Cypridina Luciferin"
640:The Journal of General Physiology
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24:
324:(at 25 °C , 100 kPa).
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1:
771:10.1016/S0040-4039(02)00257-5
744:10.1016/S0040-4039(01)82806-9
442:Vargulin is oxidized by the
611:World Scientific Publishing
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37:
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23:
924:Microbiology techniques
813:10.1073/pnas.86.17.6567
846:"Luciferase Reporters"
605:Shimomura, O. (2006).
387:Cypridina hilgendorfii
919:Laboratory techniques
634:Anderson, RS (1935).
487:cell viability assays
875:at Wikimedia Commons
652:10.1085/jgp.19.2.301
393:Vargula hilgendorfii
367:Cypridinid luciferin
46:-indol-3-yl)-3-oxo-7
804:1989PNAS...86.6567T
759:Tetrahedron Letters
705:10.1246/bcsj.30.929
524:1990MarBi.104..219C
420:Feeding experiments
371:Cypridina luciferin
314: g·mol
20:
532:10.1007/bf01313261
444:Vargula luciferase
351:Infobox references
18:
871:Media related to
765:(12): 2389–2392.
738:(29): 3427–3436.
620:978-981-256-801-4
570:(1). Wiley: 1–4.
456:Firefly luciferin
375:Vargula luciferin
359:Chemical compound
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182:CompTox Dashboard
105:Interactive image
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929:Toxicology tests
909:Imidazopyrazines
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64:Identifiers
56:Other names
47:
43:
15:
714:10069/20882
269:Properties
904:Guanidines
889:Luciferins
883:Categories
497:References
481:to detect
428:isoleucine
424:tryptophan
399:Porichthys
307:Molar mass
170:761TM14Y84
116:ChemSpider
92:3D model (
71:CAS Number
39:IUPAC name
584:1522-7235
540:0025-3162
379:luciferin
377:, is the
150:135398684
81:7273-34-9
19:Vargulin
873:Vargulin
670:19872927
592:19862683
548:84250053
432:arginine
383:ostracod
363:Vargulin
914:Lactams
899:Indoles
832:2771943
800:Bibcode
661:2141430
520:Bibcode
406:History
344:what is
342: (
312:405.506
137:PubChem
42:2--6-(1
830:
823:297885
820:
668:
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546:
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448:enzyme
430:, and
339:verify
336:
253:SMILES
125:388868
33:Names
688:(PDF)
544:S2CID
373:, or
218:InChI
94:JSmol
828:PMID
666:PMID
615:ISBN
588:PMID
580:ISSN
536:ISSN
462:Uses
161:UNII
818:PMC
808:doi
767:doi
740:doi
710:hdl
700:doi
656:PMC
648:doi
572:doi
528:doi
516:104
483:ATP
454:or
187:EPA
140:CID
885::
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530::
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334:N
300:O
297:7
294:N
288:H
282:C
189:)
185:(
96:)
48:H
44:H
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