A chemiluminescent probe
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Lucigenin

Item No. 14872

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
10,10'-dimethyl-9,9'-biacridinium, dinitrate
CAS Number
2315-97-1
Synonyms
  • L-6,868
  • NSC 151912
Molecular Formula
C28H22N2 • 2NO3
Formula Weight
510.5
Purity
≥95%
Emission
505 nm
Excitation
455 nm
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.33 mg/mlDMSO: 5 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
222, 261, 369, 429 nm
SMILES
C[N+](C1=C2C=CC=C1)=C3C(C=CC=C3)=C2C4=C5C(C=CC=C5)=[N+](C)C6=CC=CC=C64.O=[N+]([O-])[O-].O=[N+]([O-])[O-]
InChi Code
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
InChi Key
KNJDBYZZKAZQNG-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    50 mg

    $36

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    100 mg

    $63

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    500 mg

    $135

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    1 g

    $236

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    Product Description

    Lucigenin is a chemiluminescent probe used to detect superoxide production and the presence of chloride.1,2 It can be used to detect superoxide production by enzymatic and cellular sources.1,3,4 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.3,5 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.6 It also reacts with hydrogen peroxide without generating free radical intermediates and has been used to detect lipid hydroperoxide in oils.7 Lucigenin is also used as a fluorescent chloride-sensitive indicator, with its fluorescence being quenched by chloride (ex/em = 455/505 nm, respectively).2,8,9 Lucigenin fluorescence is insensitive to phosphate, sulfate, and nitrate.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Li, Y., Zhu, H., Kuppusamy, P., et al. Validation of lucigenin (Bis-N-methylacridinium) as a chemilumigenic probe for detecting superoxide anion radical production by enzymatic and cellular systems. The Journal of Biological Chemisty 273(4), 2015-2023 (1998).

    2. Biwersi, J., Tulk, B., and Werkman, A.S. Long-wavelength chloride-sensitive fluorescent indicators. Anal. Biochem. 219(1), 139-143 (1994).

    3. Vladimirov, Y.A., and Proskurnina, E.V. Free radicals and cell chemiluminescence. Biochemistry (Mosc.) 74(13), 1545-1566 (2009).

    4. Skatchkov, M.P., Sperling, D., Hink, U., et al. Validation of lucigenin as a chemiluminescent probe to monitor vascular superoxide as well as basal vascular nitric oxide production. Biochem. Biophys. Res. Commun. 254(2), 319-324 (1999).

    5. Cai, H., Dikalov, S., Griendling, K.K., et al. Detection of reactive oxygen species and nitric oxide in vascular cells and tissues: Comparison of sensitivity and specificity. Methods Mol. Med. 139, 293-311 (2007).

    6. Rezende, F., Löwe, O., Helfinger, V., et al. Unchanged NADPH oxidase activity in Nox1-Nox2-Nox4 triple knockout mice – What do NADPH-stimulated chemiluminescence assays really detect? Antioxid. Redox Signal. 24(7), 392-399 (2016).

    7. Bunting, J.P., and Gray, D.A. Development of a flow injection chemiluminescent assay for the quantification of lipid hydroperoxides. J. Am. Oil Chem. Soc. 80(10), 951-955 (2003).

    8. Ferdani, R., Li, R., Pajewski, R., et al. Transport of chloride and carboxyfluorescein through phospholipid vesicle membranes by heptapeptide amphiphiles. Org. Biomol. Chem. 5(15), 2423-2432 (2007).

    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. Analyst 137(6), 1500-1508 (2012).

    Product Citations

    Agrawal, K., Bouchal, J., Das, V., et al. Laboratory techniques in cellular and molecular medicine. (2021).