Lucifer yellow
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 410367079
| ImageFile = Lucifer yellow.svg
| ImageSize = 200px
| PIN = Dilithium 6-amino-2-(hydrazinecarbonyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-5,8-disulfonate
|Section1={{Chembox Identifiers
| CASNo = 77944-88-8
| CASNo_Ref = {{Cascite|changed|CAS}}
| PubChem = 20835957
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 52104
| ChEMBL = 1650069
| UNII = 9654F8OVKE
| SMILES = c1c(cc2c3c1c(c(cc3c(=O)n(c2=O)C(=O)NN)S(=O)(=O)[O-])N)S(=O)(=O)[O-].[Li+].[Li+]
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 20137740
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C13H10N4O9S2.2Li/c14-10-5-1-4(27(21,22)23)2-6-9(5)7(3-8(10)28(24,25)26)12(19)17(11(6)18)13(20)16-15;;/h1-3H,14-15H2,(H,16,20)(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = DLBFLQKQABVKGT-UHFFFAOYSA-L
}}
|Section2={{Chembox Properties
| C=13 | H=10 | Li=2 | N=4 | O=9 | S=2
}}
}}
Lucifer yellow is a fluorescent dye used in cell biology.{{cite journal|last=Hanani|first=Menachem|title=Lucifer yellow – an angel rather than the devil|journal=Journal of Cellular and Molecular Medicine|date=January 2012|volume=16|issue=2|pages=22–31|doi=10.1111/j.1582-4934.2011.01378.x|pmid=21740513|pmc=3823090}} The key property of Lucifer yellow is that it can be readily visualized in both living and fixed cells using a fluorescence microscope. Lucifer yellow was invented by Walter W. Stewart at the National Institutes of Health and patented in 1978.[http://www.freepatentsonline.com/4473693.html Patent description]
Preparations
For common usage it is compounded with carbohydrazide (CH) and prepared as a lithium salt. The CH group allows it to be covalently linked to surrounding biomolecules during aldehyde fixation.{{cite web|title=Lucifer Yellow CH, Lithium Salt|url=http://www.lifetechnologies.com/order/catalog/product/L453|work=Molecular Probes|accessdate=17 March 2014}}
Other cations such as ammonium or potassium can be used when lithium is undesirable, but the resulting salts are less soluble in water.
Lucifer yellow can also be compounded as a vinyl sulfone, with ethylenediamine, or with cadaverine. {{what|date=January 2016}}
References
External links
- [https://web.archive.org/web/20110516164133/http://probes.invitrogen.com/media/pis/mp00453.pdf Invitrogen's manual for Lucifer yellow]
- [http://omlc.ogi.edu/spectra/PhotochemCAD/html/luciferyellowCH.html Molecular structure and spectra of Lucifer yellow CH (lithium salt)]
Category:Heterocyclic compounds with 3 rings