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SML2236

Sigma-Aldrich

L-012 sodium salt

≥98% (HPLC)

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

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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Julian Jehle et al.
Archives of medical science : AMS, 13(4), 930-936 (2017-07-20)
Multidrug resistance-associated protein 1 (MRP1) is an anion transporter which is implicated in the efflux of the intracellular antioxidant anion glutathione as well as leukotrienes. Pharmacological inhibition of MRP1 exhibits antioxidative and anti-atherosclerotic effects both in vitro and in vivo.
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
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
Andreas Daiber et al.
Free radical biology & medicine, 36(1), 101-111 (2004-01-21)
In the present study we sought to determine the ability of the chemiluminescence dye 8-amino-5-chloro-7-phenylpyridol[3,4-d]pyridazine-1,4-(2H,3H)dione sodium salt (L-012) to detect superoxide in different biological systems. In human whole blood or isolated leukocytes, the sensitivity of the luminol analogue L-012 to
Markus Albert et al.
Methods in molecular biology (Clifton, N.J.), 1621, 69-76 (2017-06-02)
The oxidative burst or the production of reactive oxygen species (ROS) is a typical cellular response of both plants and animals to diverse abiotic and biotic stresses. Mainly, the (re-)active oxygen species include the superoxide anion (O2-), hydrogen peroxide (H2O2)
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