LUCIGENIN Chemical Properties

Melting point:

250°C

storage temp. 

room temp

solubility 

acetic acid: soluble10mg/mL

form 

powder

color 

Yellow powder with orange to brown cast

λmax

455nm

BRN 

3901768

Biological Applications

Chloride indicator; diagnosis of hemostatic disorders; detecting bacteria,nucleicacids,proteins,pathogens; identifying respiratory infections; generating and detecting reactive oxygen species; chemiluminescent indicator

InChI

InChI=1S/C28H22N2.2NO3/c1-29-23-15-7-3-11-19(23)27(20-12-4-8-16-24(20)29)28-21-13-5-9-17-25(21)30(2)26-18-10-6-14-22(26)28;2*2-1(3)4/h3-18H,1-2H3;;/q+2;2*-1

InChIKey

KNJDBYZZKAZQNG-UHFFFAOYSA-N

SMILES

C1(=C2C=CC=CC2=[N+](C)C2=CC=CC=C12)C1=C2C=CC=CC2=[N+](C)C2=CC=CC=C12.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O

Safety Information

Safety Statements 

24/25

RIDADR 

1479

WGK Germany 

3

HazardClass 

5.1

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

LUCIGENIN Usage And Synthesis

Description

Lucigenin is a chemiluminescent probe used to detect superoxide production and the presence of chloride. It can be used to detect superoxide production by enzymatic and cellular sources. It is a sensitive method that has been applied to the monitoring of superoxide production from xanthine oxidase, microsomal NADPH cytochrome reductase, and NADPH oxidases of phagocytes, endothelial cells, fibroblasts, and smooth muscle cells of blood vessel walls. However, it produces similar chemiluminescence signals in isolated aortic and cardiac tissues from wild-type and Nox1-Nox2-Nox4 triple knockout mice, suggesting that it is not selective for NADPH-based ROS production. It also reacts with hydrogen peroxide without generating free radical intermediates and has been used to detect lipid hydroperoxide in oils. Lucigenin is also used as a fluorescent chloride-sensitive indicator, with its fluorescence being quenched by chloride (ex/em = 455/505 nm, respectively). Lucigenin fluorescence is insensitive to phosphate, sulfate, and nitrate.

Chemical Properties

Dark yellow powder

Uses

Lucigenine, is used as chemiluminescence. It exhibits a bluish-green fluorescence. Dyes and metabolites.

Uses

Chemiluminescent probe for the detection of peroxides in biological systems.

Mechanism of action

In the case of lucigenin it is first reduced to a cation radical. Then it reacts in its univalently reduced form with ROS to produce dioxetane, which breaks down to generate photons. These probes cannot measure the individual free radicals but measure global ROS levels in the sample. Luminescence signals are expressed in relative light units (RLU), a direct measure of free radicals produced.

References

[1] Y LI. Validation of lucigenin (bis-N-methylacridinium) as a chemilumigenic probe for detecting superoxide anion radical production by enzymatic and cellular systems.[J]. The Journal of Biological Chemistry, 1998, 273 4: 2015-2023. DOI: 10.1074/jbc.273.4.2015
[2] BIWERSI J.  Verkman A S  Tulk B. Long-Wavelength Chloride-Sensitive Fluorescent Indicators[J]. Analytical biochemistry, 1994, 219 1: Pages 139-143. DOI: 10.1006/abio.1994.1242
[3] YU. A. VLADIMIROV  E. V P. Free radicals and cell chemiluminescence[J]. Biochemistry (Moscow), 2010, 74 13: 1545-1566. DOI: 10.1134/s0006297909130082
[4] MIKHAIL P. SKATCHKOV . Validation of Lucigenin as a Chemiluminescent Probe to Monitor Vascular Superoxide as Well as Basal Vascular Nitric Oxide Production[J]. Biochemical and biophysical research communications, 1999, 254 2: Pages 319-324. DOI: 10.1006/bbrc.1998.9942
[5] HUA CAI. Detection of reactive oxygen species and nitric oxide in vascular cells and tissues: comparison of sensitivity and specificity.[J]. Methods in molecular medicine, 2007, 139: 293-311. DOI: 10.1007/978-1-59745-571-8_20
[6] FLáVIA REZENDE. Unchanged NADPH Oxidase Activity in Nox1-Nox2-Nox4 Triple Knockout Mice: What Do NADPH-Stimulated Chemiluminescence Assays Really Detect?[J]. Antioxidants & redox signaling, 2016, 24 7: 392-399. DOI: 10.1089/ars.2015.6314
[7] JOHN P. BUNTING  David A G. Development of a flow injection chemiluminescent assay for the quantification of lipid hydroperoxides[J]. Journal of the American Oil Chemists Society, 2003, 80 10: 951-955. DOI: 10.1007/s11746-003-0802-1
[8] FERDANI R, LI R, PAJEWSKI R, et al. Transport of chloride and carboxyfluorescein through phospholipid vesicle membranes by heptapeptide amphiphiles[J]. Organic & Biomolecular Chemistry, 2007, 15: 2423-2432. DOI: 10.1039/b705544g
[9] RUEDAS-RAMA M J, ORTE A, HALL E A H, et al. A chloride ion nanosensor for time-resolved fluorimetry and fluorescence lifetime imaging?[J]. Analyst, 2012, 6: 1500-1508. DOI: 10.1039/c2an15851e

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