Lucifer yellow

Lucifer yellow
IUPAC name 6-amino-2-(hydrazinecarbonyl)-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonate de dilithium
Identifiers
PubChem	20835957
ChEBI	CHEBI:52104 Y
Jmol-3D images	Image 1
SMILES c1c(cc2c3c1c(c(cc3c(=O)n(c2=O)C(=O)NN)S(=O)(=O)[O-])N)S(=O)(=O)[O-].[Li+].[Li+]
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
Properties
Molecular formula	C13H10Li2N4O9S2
Molar mass	444.25 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lucifer yellow is a fluorescent dye used in cell biology. 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 engineered by Walter W. Stewart at NIH and patented in 1978.

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.

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

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