Lucifer yellow

Lucifer yellow
Names
	IUPAC name dilithium 6-Amino-2-(hydrazinecarbonyl)-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonate
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:52104 ;
ChemSpider	20137740 ;
PubChem CID	20835957;
CompTox Dashboard (EPA)	DTXSID70999134 ;
	InChI InChI=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 Key: DLBFLQKQABVKGT-UHFFFAOYSA-L ; InChI=1/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 Key: DLBFLQKQABVKGT-NUQVWONBAD;
	SMILES c1c(cc2c3c1c(c(cc3c(=O)n(c2=O)C(=O)NN)S(=O)(=O)[O-])N)S(=O)(=O)[O-].[Li+].[Li+];
Properties
Chemical formula	C13H10Li2N4O9S2
Molar mass	444.24 g·mol−1
	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

Lucifer yellow is a fluorescent dye used in cell biology.[1] 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.[2]

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.[3]

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.

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Hanani, Menachem (January 2012). "Lucifer yellow – an angel rather than the devil". Journal of Cellular and Molecular Medicine. 16 (2): 22–31. doi:10.1111/j.1582-4934.2011.01378.x. PMC 3823090. PMID 21740513.
Patent description
"Lucifer Yellow CH, Lithium Salt". Molecular Probes. Retrieved 17 March 2014.

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