Lucigenin

Names

[ Name ]:
Lucigenin

[Synonym ]:
Lucigenin nitrate
Bis(N-methylacridinium) Nitrate
10,10'-Dimethyl-9,9'-biacridinium dinitrate
N,N`-dimethyl-9,9`-biacridinium dinitrate
EINECS 219-023-4
10,10'-Dimethyl-9,9'-biacridinium nitrate
Lucigenin
Dinitrate de 10,10'-diméthyl-9,9'-biacridinium
N,N'-Dimethyl-9,9'-biacridinium dinitrate
MFCD00011925
9,9'-Bis(N-methylacridinium nitrate)
10,10'-Dimethyl-9,9'-biacridiniumdinitrat
N,N'-Dimethyl-9,9'-biacridinium dinitratein
bis-n-methylacridinium nitrate
N,N'-Dimethyl-9,9'-bisacridinium nitrate

Biological Activity

[Description]:

Lucigenin(L-6868; NSC-151912) is a chemiluminescent probe used to indicate the presence of endogenously generated superoxide anion radicals in cells.Upon single-electron reduction of Lucigenin by a radical species the subsequent form of Lucigenin presents an amplified chemiluminescence which is measurable and can be correlated to the respective amount of reactive radical species present in the system. This approach can be used to probe the natural generation of these species as well as the natural functioning of superoxide dismutase and other enzymes responsible for scavenging radicals. In addition to indicating the presence of radicals in cells, Lucigenin shows interaction with redox-active oxidoreductase enzymes. Lucigenin is shown to mediate the reduction of cytochrome C by xanthine oxidase and to increase the rate of NADPH oxidation. These observations indicate that use of Lucigenin for superoxide analysis is precluded in the presence of high levels of NAD(P)H-oxidoreductases.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Dye Reagents

Research Areas >> Others

[References]

[1]. Li Y, et al. Validation of lucigenin (bis-N-methylacridinium) as a chemilumigenic probe for detecting superoxide anion radical production by enzymatic and cellular systems. J Biol Chem. 1998 Jan 23;273(4):2015-23.

[2]. Rost M, et al. What do we measure with luminol-, lucigenin- and penicillin-amplified chemiluminescence? 1. Investigations with hydrogen peroxide and sodium hypochlorite. J Biolumin Chemilumin. 1998 Nov-Dec;13(6):355-63.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
250ºC

[ Molecular Formula ]:
C₂₈H₂₂N₄O₆

[ Molecular Weight ]:
510.497

[ Exact Mass ]:
510.153931

[ PSA ]:
145.52000

[ LogP ]:
6.18360

[ Appearance of Characters ]:
Yellow powder with orange to brown cast

[ Water Solubility ]:
acetic acid: soluble10mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
24/25

[ RIDADR ]:
1479

[ WGK Germany ]:
3

[ Packaging Group ]:
III

Articles

Synthetic ion transporters can induce apoptosis by facilitating chloride anion transport into cells.

Nature Chemistry 6(10) , 885-92, (2014)

Anion transporters based on small molecules have received attention as therapeutic agents because of their potential to disrupt cellular ion homeostasis. However, a direct correlation between a change...

Trace detection of triphenylene by surface enhanced Raman spectroscopy using functionalized silver nanoparticles with bis-acridinium lucigenine.

Langmuir 26(10) , 6977-81, (2010)

Surface enhanced raman scattering (SERS) of triphenylene (TP) has been recorded on Ag nanoparticles functionalized with the molecular assembler bis-acridinium lucigenine dication (LG) which approaches...

Hollow Au/Ag nanostars displaying broad plasmonic resonance and high surface-enhanced Raman sensitivity.

Nanoscale 7 , 13629-37, (2015)

Bimetallic Au/Ag hollow nanostar (HNS) nanoparticles with different morphologies were prepared in this work. These nanoplatforms were obtained by changing the experimental conditions (concentration of...