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SML2236

Sigma-Aldrich

L-012 sodium salt

≥98% (HPLC), powder, neurotoxin

Synonym(s):

8-Amino-5-chloro-2,3-dihydro-7-phenyl-Pyrido[3,4-d]pyridazine-1,4-dione, sodium salt, 8-Amino-5-chloro-7-phenyl-2,3-dihydro-pyrido[3,4-d]pyridazine-1,4-dione, sodium salt, L012

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About This Item

Empirical Formula (Hill Notation):
C13H8ClN4O2 · Na
CAS Number:
143556-24-5
Molecular Weight:
310.67
MDL number:
MFCD30378369
UNSPSC Code:
12352200
NACRES:
NA.77

product name

L-012 sodium salt, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

color

yellow to orange

solubility

H2O: 2 mg/mL, clear

storage temp.

−20°C

InChI

1S/C13H9ClN4O2.Na/c14-11-8-7(12(19)17-18-13(8)20)9(15)10(16-11)6-4-2-1-3-5-6;/h1-5H,15H2,(H,17,19)(H,18,20);/q;+1/p-1

InChI key

IGEUYSJHQQCEFP-UHFFFAOYSA-M

Application

L-012 has been used as a probe in a bioluminescent assay for the determination of the reactive oxygen species (ROS) levels in the isolated mouse lungs.

Biochem/physiol Actions

L-012 is a luminol analog and a widely used reactive oxygen and nitrogen species (RONS; ROS & RNS) chemiluminescence (CL) probe both in cultures and in animals in vivo. L-012 displays significantly higher CL yield and sensitivity than luminol, lucigenin and MCLA. Instead of reacting with superoxide anion (O2−) directly, L-012 (LumH2) is converted via a one-electron oxidation (catalyzed by peroxidase in the presence of H2O2) to the LumH· radical form, which then reacts with oxygen (O2) to yield O2− and L-012 quinone (q-Lum). The O2− in turn reacts with the LumH· radical, leading eventually to an endoperoxide that decomposes to emit luminescence. To a less extend, H2O2 can also react with q-Lum to yield luminescence. Although not specific to NADPH oxidase-derived RONS, L-012 is also commonly used for screening NADPH oxidase inhibitors.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Ii et al.
Biochemical and biophysical research communications, 193(2), 540-545 (1993-06-15)
An enhanced chemiluminescence reaction has been incorporated into an enzyme immunoassay (EIA) for human basic fibroblast growth factor (hbFGF). We developed a new luminol derivative, designated L-012 and a new enhancer, 4-(4-hydroxyphenyl)thiazole. Using these compounds, the detection limit of hbFGF
Andreas Daiber et al.
Redox biology, 12, 35-49 (2017-02-18)
Reactive oxygen and nitrogen species (RONS such as H2O2, nitric oxide) confer redox regulation of essential cellular functions (e.g. differentiation, proliferation, migration, apoptosis), initiate and catalyze adaptive stress responses. In contrast, excessive formation of RONS caused by impaired break-down by
Jacek Zielonka et al.
Free radical biology & medicine, 65, 1310-1314 (2013-10-02)
L-012, a luminol-based chemiluminescent (CL) probe, is widely used in vitro and in vivo to detect NADPH oxidase (Nox)-derived superoxide (O2(*-)) and identify Nox inhibitors. Yet understanding of the free radical chemistry of the L-012 probe is still lacking. We
Ning Fan et al.
Experimental eye research, 161, 71-81 (2017-06-13)
Oxidative injuries, such as those related to reactive oxygen species (ROS), have been implicated in various retinal and optic nerve disorders. Many ROS detection methods have been developed. Although widely utilized, many of these methods are useful only in post
Y Nishinaka et al.
Biochemical and biophysical research communications, 193(2), 554-559 (1993-06-15)
A sensitive chemiluminescence method for measuring the production of superoxide anion (O2-) by activated EoL-1 cells (human eosinophilic leukemia cell line) is described. Recently, we succeeded in synthesizing a new chemiluminescence probe, 8-amino-5-chloro-7-phenylpyrido[3,4-d]pyridazine-1,4(2H,3H)dione (L-012). In the presence of L-012, activated
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