All Photos(1)
Synonym(s):
6-Amino-2,3-dihydro-1,4-phthalazinedione, Isoluminol
Empirical Formula (Hill Notation):
C8H7N3O2
CAS Number:
Molecular Weight:
177.16
Beilstein:
164804
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.83
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Assay
≥98% (HPLC)
Quality Level
form
powder
mp
300 °C (lit.)
solubility
2 M NH4OH: 50 mg/mL, clear to slightly hazy
SMILES string
Nc1ccc2C(=O)NNC(=O)c2c1
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
HUDPLKWXRLNSPC-UHFFFAOYSA-N
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Application
4-Aminophthalhydrazide has been used in:
- chemiluminescence-based reactive oxygen species (ROS) assay in bone marrow (BM) neutrophils post-Yersinia pseudotuberculosis infection
- neutrophil ROS assays post-K. pneumonia exposure
- neutrophil ROS assays in response to formylated-methionine-leucine-proline
Biochem/physiol Actions
4-Aminophthalhydrazide or isoluminol is a chemiluminescent compound that comprises a phthalazine ring. It is more hydrophilic than luminol. Isoluminol is commercially used in a wide variety of in vitro immunoassays and is a chemiluminescence amplifier for studying reactive oxygen species. It is also useful as an electroluminescence (ECL) biosensor and as a probe for rapid microbial detection.
Features and Benefits
Produces chemiluminescence.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Kazuhiko Tsukagoshi et al.
Journal of chromatography. A, 1143(1-2), 288-290 (2007-02-03)
In our previous study, we developed capillary electrophoresis with an ultraviolet absorption/chemiluminescence dual detection system. Here, to demonstrate one of the possible applications of the capable system as well as confirm the advantage, migration behavior of isoluminol isothiocyanate-labeled alpha-amino acids
Viera Jancinová et al.
Redox report : communications in free radical research, 11(3), 110-116 (2006-06-30)
To address the question why isoluminol, but not luminol, failed to detect oxidants produced intracellularly, differences between these luminophores were investigated with respect to physicochemical parameters and the character of chemiluminescence signal. Our results showed the isoluminol molecule to be
Caifeng Ding et al.
Chemical communications (Cambridge, England), 46(42), 7990-7992 (2010-09-25)
A new strategy of photoelectrochemical (PEC) analysis with chemiluminescence (CL) of the isoluminol-H(2)O(2)-Co(2+) system as a light source for the determination of physiological thiols in cancer cells was reported for the first time.
B G Yushkov et al.
Bulletin of experimental biology and medicine, 150(3), 352-354 (2011-01-18)
The effects of 3-aminophthalhydrazide and carrageenan on reparative regeneration and expression of CD117 by liver cells after partial hepatectomy were studied in mice. 3-Aminophthalhydrazide stimulated regeneration of the liver and increased the count of CD117(+) hepatocytes. By contrast, carrageenan inhibited
Sundar Neelakantan et al.
Bioorganic & medicinal chemistry letters, 19(19), 5722-5726 (2009-08-25)
Rapid assays for bacteria have been developed utilizing novel LysLysLys-isoluminol (14) and GluGlu-isoluminol (16) probes that have been derived from peptides which potentially mimic bacteriophage attachment protein binding regions. Compared to two conventional methods that are widely used, namely nucleic
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