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Lucifer Yellow CH

(Synonyms: 萤光黄二锂盐,Lucifer Yellow carbohydrazide) 目录号 : GC44089

A fluorescent probe

Lucifer Yellow CH Chemical Structure

Cas No.:67769-47-5

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产品描述

Lucifer Yellow CH dilithium salt is a highly fluorescent dye that is useful in marking nerve cells[1]. Lucifer Yellow CH dilithium salt is assumed to be nontoxic, and it is membrane impermeable and highly dissociated at physiological pH values[2][3].
Lucifer Yellow CH dilithium salt 是一种高度荧光的染料,适用于标记神经细胞[1]。Lucifer Yellow CH dilithium salt 假定为无毒,在生理 pH 值下是膜不透性和高度解离的[2][3]。

References:
[1]. Stewart WW. Functional connections between cells as revealed by dye-coupling with a highly fluorescent naphthalimide tracer. Cell. 1978 Jul;14(3):741-59.
[2]. Klein M, et al. Transport of lucifer yellow CH into plant vacuoles--evidence for direct energization of a sulphonatedsubstance and implications for the design of new molecular probes. FEBS Lett. 1997 Dec 22;420(1):86-92.
[3]. Takeuchi K, et al. Effect of superoxide derived from lucifer yellow CH on voltage-gated currents of mouse taste budcells. Chem Senses. 2008 Jun;33(5):425-32.

Chemical Properties

Cas No. 67769-47-5 SDF
别名 萤光黄二锂盐,Lucifer Yellow carbohydrazide
化学名 6-amino-2-[(hydrazinylcarbonyl)amino]-2,3-dihydro-1,3-dioxo-1H-benz[de]isoquinoline-5,8-disulfonic acid, dilithium salt
Canonical SMILES O=C(C1=CC(S([O-])(=O)=O)=C(N)C2=C1C3=CC(S([O-])(=O)=O)=C2)N(NC(NN)=O)C3=O.[Li+].[Li+]
分子式 C13H9N5O9S2•2Li 分子量 457.2
溶解度 1mg/mL in water 储存条件 Store at -20°C, protect from light
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1 mM 2.1872 mL 10.9361 mL 21.8723 mL
5 mM 0.4374 mL 2.1872 mL 4.3745 mL
10 mM 0.2187 mL 1.0936 mL 2.1872 mL
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Research Update

Intracellular marking with Lucifer Yellow CH and horseradish peroxidase of cells electrophysiologically characterized as glia in the cerebral cortex of the cat

J Comp Neurol 1979 Jul 15;186(2):173-88.PMID:87405DOI:10.1002/cne.901860205.

Intracellular microelectrodes filled with either Lucifer Yellow CH, a highly florescent dye, or horseradish peroxidase (HRP) were used to electrophysiologically characterize and mark cells in the cerebral cortex of cat. Fifty-eight cells, characterized electrophysiologically as glia, were marked with Lucifer Yellow CH. All were identified as protoplasmic astrocytes, and included cells in the glia limitans of the molecular layer. An additional 54 cells, similarly characterized as glia, were labeled with HRP. The results were the same; only protoplasmic astrocytes were labeled. The "staining quality" of the glia labeled with HRP was superior to that of cells injected with Lucifer Yellow; greater lengths of individual processes were revealed, and they could often be followed to blood vessels where they ended on the walls of vessels with expanded perivascular end-feet. The observations indicate that the many previously reported studies on presumed glial cells in the cat cerebral cortex have characterized the behavior of protoplasmic astrocytes. Neurons were also marked during these experiments. The "staining" quality of the Lucifer Yellow filled neurons was excellent; dendritic spines, axons, and axon collaterals were clearly visible. These fine neuronal details were not as well revealed after HRP labeling. High resting membrane potentials (RMP's) were not a prerequisite for obtaining well-marked neurons (mean RMP of Lucifer Yellow filled neurons was -33.6 mV; mean RMP of HRP filled neurons was 42.3 mV). In contrast, the mean RMPs of Lucifer Yellow and HRP marked glia was -68 Mv and -75 mV respectively, and the quality of "staining" appeared to be more closely related to the RMP.

Oxygen radicals mediate cell inactivation by acridine dyes, fluorescein, and Lucifer Yellow CH

Photochem Photobiol 1987 Jul;46(1):45-53.PMID:3039547DOI:10.1111/j.1751-1097.1987.tb04734.x.

Acridine dyes, fluorescein and Lucifer Yellow CH are fluorescent photosensitizers used experimentally to selectively stain and photodynamically destroy eukaryotic cells and subcellular structures. We have determined that the mechanism of light- and oxygen-dependent inactivation of E. coli by these dyes involves oxygen radicals and hydrogen peroxide. All of the dyes oxidized NAD(P)H+ under illumination. Superoxide (O2), detected as the superoxide dismutase (SOD)-inhibitable reduction of ferricytochrome c, was a major product of the dye sensitized photooxidation. Cationic acridine dyes penetrated the membranes of E. coli and were photoreduced intracellularly. Reduced dyes diffused back into the medium and mediated the reduction of extracellular ferricytochrome c. The anionic dyes fluorescein and Lucifer Yellow CH were unable to mediate extracellular cytochrome c reduction, indicating that these dyes were impermeable to the E. coli membrane. Acridine dyes, when illuminated, inhibited the growth of E. coli in a rich medium, and induced the synthesis of SOD. Fluorescein and Lucifer Yellow CH did not inhibit growth or induce SOD synthesis because they were unable to enter the cells. Superoxide (O2) and hydrogen peroxide (H2O2), generated by the enzyme xanthine oxidase were toxic to E. coli B. Inactivation by xanthine oxidase was partially inhibited by exogenous SOD and completely inhibited by exogenous catalase or SOD plus catalase. Similarly, exogenous SOD plus catalase protected against inactivation by acridines and fluorescein-NADH or lucifer yellow CH-NADH mixtures. Prior induction of superoxide dismutase and catalase in E. coli B significantly protected cells against a subsequent challenge by illuminated acridine dyes. SOD and catalases preinduction combined with additions of exogenous SOD and catalase completely protected E. coli B against photodynamic inactivation by acridine yellow. The hydroxyl radical scavengers, dimethyl sulfoxide, sodium benzoate and thiourea, protected E. coli B against photodynamic inactivation by acridine orange. The results implicate O2, H2O2, and the hydroxyl radical (OH) as underlying molecular agents of the phototoxicity mediated by acridine orange, acridine yellow, fluorescein and Lucifer Yellow CH.

Microinjection of Lucifer Yellow CH into sea urchin eggs and embryos

Cell Tissue Res 1983;234(2):309-18.PMID:6640624DOI:10.1007/BF00213770.

Eggs and embryos of Arbacia punctulata were microinjected with the fluorescent dye, Lucifer Yellow CH, using a simple pressure injection system. When injected into eggs that were subsequently fertilized, the dye was distributed throughout all cells of the developing embryo. If one cell of a two-cell embryo was injected, dye did not diffuse into the uninjected blastomere. During subsequent development, all progeny of the injected cell contained dye resulting in an embryo that was half-fluorescent. Blue light irradiation of a two-cell embryo, one cell of which had been injected with Lucifer yellow, caused the injected blastomere to stop further divisions while the uninjected blastomere developed normally and was free of dye. These results indicate that the first two blastomeres of Arbacia embryos are not electrically coupled, nor up to the time of hatching, is there any coupling between cells in one half of the first cleavage plane and cells in the other half.

Effect of superoxide derived from Lucifer Yellow CH on voltage-gated currents of mouse taste bud cells

Chem Senses 2008 Jun;33(5):425-32.PMID:18319263DOI:10.1093/chemse/bjn009.

Lucifer Yellow CH (LY), a fluorescent membrane-impermeable cell marker dye, has been routinely loaded into cells through recording electrodes to visualize these cells after electrophysiological investigation, without considering its pharmacological effect. Recently, we showed that the exposure of cells loaded with LY to light for microscopy produced unidentified radical species that retarded the inactivation of voltage-gated Na+ currents irreversibly (Higure Y et al. 2003). Here, we show that superoxide dismutase, an enzyme that decomposes superoxide, reverses the retardation effect, which assures that superoxide is the unidentified radical species. The estimated mean lifetime of superoxide in recording electrodes (in the absence of cytoplasm) is approximately 6 min, and hence, the Na+ currents are retarded even in the dark, when LY is exposed to light before being loaded into the cell. Superoxide has no effect on voltage-gated Cl- currents. These results show that superoxide action on ion channels is rather selective. The breakdown of superoxide inside cells and the effect of endogenous superoxide on the superoxide-susceptible channels are discussed.

Lucifer yellow, neuronal marking and paraffin sectioning

Stain Technol 1983 Jul;58(4):189-92.PMID:6197772DOI:10.3109/10520298309066784.

An unusual procedure with the dye lucifer yellow has provided stable neuronal marking that survives paraffin embedding and sectioning. Lucifer Yellow CH was dissolved in an electrolyte containing formaldehyde and injected into the large interneurons of a cricket. Intense fluorescence in the axoplasm was retained even after conventional histological procedures.