Lucifer yellow

Lucifer yellow

Names
IUPAC name dilithium 6-Amino-2-(hydrazinecarbonyl)-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonate
Identifiers
ChEBI	CHEBI:52104 Y
ChemSpider	20137740 N
Jmol interactive 3D	Image
PubChem	20835957
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 N Key: DLBFLQKQABVKGT-UHFFFAOYSA-L N 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).
N verify (what is YN ?)
Infobox references

Lucifer yellow is a fluorescent dye used in cell biology.^[1] The key property of Lucifer yellow is that it can 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.

References

1. ↑ 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. PMID 21740513. 
2. ↑ Patent description
3. ↑ "Lucifer Yellow CH, Lithium Salt". Molecular Probes. Retrieved 17 March 2014. 

External links

• Invitrogen's manual for Lucifer yellow
• Molecular structure and spectra of Lucifer yellow CH (lithium salt)