71550-19-1

Basic information

• Product Name: 1-Amino-4-[(2,5-dimethylphenyl)amino]-9,10-dihydro-9,10-dioxo-2-anthracenesulfonic acid sodium salt
• Synonyms: 1-Amino-4-[(2,5-dimethylphenyl)amino]-9,10-dihydro-9,10-dioxo-2-anthracenesulfonic acid sodium salt
• CAS NO: 71550-19-1
• Molecular Formula: C₂₂H₁₇N₂O₅S*Na
• Molecular Weight: 444.44
• Mol File: 71550-19-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Amino-4-[(2,5-dimethylphenyl)amino]-9,10-dihydro-9,10-dioxo-2-anthracenesulfonic acid sodium salt(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Amino-4-[(2,5-dimethylphenyl)amino]-9,10-dihydro-9,10-dioxo-2-anthracenesulfonic acid sodium salt(71550-19-1)
• EPA Substance Registry System: 1-Amino-4-[(2,5-dimethylphenyl)amino]-9,10-dihydro-9,10-dioxo-2-anthracenesulfonic acid sodium salt(71550-19-1)

Safety Data

• Hazardous Substances Data: 71550-19-1(Hazardous Substances Data)

Usage

General Description

"1-Amino-4-[(2,5-dimethylphenyl)amino]-9,10-dihydro-9,10-dioxo-2-anthracenesulfonic acid sodium salt" is a chemical compound that belongs to the class of anthraquinone dyes. It is commonly used as a fluorescent dye in various applications such as in the textile industry for dyeing and printing fabrics, and in the medical field for staining cells and tissues in laboratory experiments. This chemical is also used in the manufacturing of colored inks, paints, and coatings, as well as in the production of colorants for food and cosmetic products. Due to its ability to fluoresce under certain conditions, it is also utilized as a dye tracer in scientific research and industrial processes.

InChI:InChI=1/C22H18N2O5S.Na/c1-11-7-8-12(2)15(9-11)24-16-10-17(30(27,28)29)20(23)19-18(16)21(25)13-5-3-4-6-14(13)22(19)26;/h3-10,24H,23H2,1-2H3,(H,27,28,29);/q;+1/p-1

Upstream product

• 95-78-3 2,5-Dimethylaniline 
• 6258-06-6 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 

Relevant articles and documents

Development of Potent and Selective Antagonists for the UTP-Activated P2Y4 Receptor

P2Y4 is a Gq protein-coupled receptor activated by uridine-5′-triphosphate (UTP), which is widely expressed in the body, e.g., in intestine, heart, and brain. No selective P2Y4 receptor antagonist has been described so far. Therefore, we developed and optimized P2Y4 receptor antagonists based on an anthraquinone scaffold. Potency was assessed by a fluorescence-based assay measuring inhibition of UTP-induced intracellular calcium release in 1321N1 astrocytoma cells stably transfected with the human P2Y4 receptor. The most potent compound of the present series, sodium 1-amino-4-[4-(2,4-dimethylphenylthio)phenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (PSB-16133, 61) exhibited an IC50 value of 233 nM, selectivity versus other P2Y receptor subtypes, and is thought to act as an allosteric antagonist. A receptor homology model was built and docking studies were performed to analyze ligand-receptor interactions. Compound 64 (PSB-1699, sodium 1-amino-4-[4-(3-pyridin-3-ylmethylthio)phenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate) represents the most selective P2Y4 receptor antagonist known to date. Compounds 61 and 64 are therefore anticipated to become useful tools for studying this scarcely investigated receptor.

Combinatorial synthesis of anilinoanthraquinone derivatives and evaluation as non-nucleotide-derived P2Y2 receptor antagonists

A library of anilinoanthraquinone derivatives was synthesized by parallel Ullmann coupling reaction of bromaminic acid with aniline derivatives in solution using a compact parallel synthesizer. The products were purified by HPLC and evaluated as antagonists at mouse and human P2Y2 receptors. 4-Phenylamino-substituted 1-amino-2-sulfoanthraquinones, for example, 1-amino-4-(2-methoxyphenyl)-2-sulfoanthraquinone (PSB-716), were potent P2Y2 antagonists with IC50 values in the low micromolar range.