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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

SMILES string

[Na+].Clc1nc(c(c3c1c(n[nH][c]3=O)[O-])N)c2ccccc2

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000329187
0000304469
0000304463
0000304469
0000304463

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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
Muthusaravanan Sivaramakrishnan et al.
Current protocols, 3(8), e869-e869 (2023-08-25)
The reactive oxygen species (ROS) burst assay is a valuable tool for studying pattern-triggered immunity (PTI) in plants. During PTI, the interaction between pathogen recognition receptors (PRRs) and pathogen-associated molecular patterns (PAMPs) leads to the rapid production of ROS in
Peishan Li et al.
Nature communications, 11(1), 4387-4387 (2020-09-03)
The role of neutrophils in solid tumor metastasis remains largely controversial. In preclinical models of solid tumors, both pro-metastatic and anti-metastatic effects of neutrophils have been reported. In this study, using mouse models of breast cancer, we demonstrate that the
Madina M Sozarukova et al.
Nanomaterials (Basel, Switzerland), 14(9) (2024-05-10)
Their unique physicochemical properties and multi-enzymatic activity make CeO2 nanoparticles (CeO2 NPs) the most promising active component of the next generation of theranostic drugs. When doped with gadolinium ions, CeO2 NPs constitute a new type of contrast agent for magnetic
I Imada et al.
Analytical biochemistry, 271(1), 53-58 (1999-06-11)
Reactive oxygen species (ROS) play important roles in the defense mechanism against infection and in the pathogenesis of various diseases. Although chemical properties of ROS generated by leukocytes have been studied extensively, methods available for their analysis are not sufficiently
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