Isoluminol

CAS: 3682-14-2

Ref. 3D-FI03462

Product Information

• Name: Isoluminol
• Synonyms: 4-Aminophthalhydrazine hydrate, 6-Amino-2,3-dihydro-1,4-phthalazinedione, 6-Amino-2,3-Dihydrophthalazine-1,4-Dione, 6-Amino-2,3-Dihydrophthalazine-1,4-Dione Hydrate (1:1)

Description

Isoluminol is a chromogenic molecule with a hydrophilic nature due to the location of the amino group in the phthalate ring, making it impermeable to cell membranes. It is used as a chemiluminescent probe to specifically detect extracellular reactive oxygen species (ROS) metabolites, which are known to be toxic for intra-erythrocytic parasites. Isoluminol-enhanced chemiluminescence has been employed as a sensitive method to study the release of superoxide anion from human neutrophils. Additionally, isoluminol has been utilized to measure extracellular ROS, distinguishing it from luminol, which is used to measure total ROS. Furthermore, isoluminol is suggested to detect mainly extracellular production of ROS, providing a lower chemiluminescence signal compared to luminol.
Isoluminol is used as a chemiluminescence amplifier with pronounced affinity to oxidants outside polymorphonuclear leukocytes (PMNLs). It has been reported that isoluminol is less able to traverse biological membranes, making it suitable for detecting the release of NADPH oxidase-derived superoxide ions. Moreover, isoluminol is more hydrophilic and polar than luminol, as indicated by its lower capacity to form intramolecular hydrogen bridges. The molecule's impermeability ensures that only extracellularly excreted ROS are detected in the assay. In analytical chemistry, isoluminol is used as a chemiluminescence probe for labeling proteins and biomolecules, and its chemiluminescent oxidation is enhanced in the presence of certain catalysts. Isoluminol is also employed in open-tubular capillary chromatography systems for the elution of labeled biomolecules. Additionally, isoluminol has been used in microchip chromatography for the analysis of biomolecules.

• Brand: Biosynth

Chemical properties

• Molecular weight: 177.05383
• Formula: C₈H₇N₃O₂
• Purity: Min. 95%
• InChI: InChI=1S/C8H7N3O2/c9-4-1-2-5-6(3-4)8(13)11-10-7(5)12/h1-3H,9H2,(H,10,12)(H,11,13)
• InChI key: InChIKey=HUDPLKWXRLNSPC-UHFFFAOYSA-N
• SMILES: Nc1ccc2c(=O)[nH][nH]c(=O)c2c1