109244-58-8

Basic information

• Product Name: DIHYDRORHODAMINE 123
• Synonyms: DIHYDRORHODAMINE 123;DHR;DHR123;2-(3,6-DIAMINO-9H-XANTHEN-9-YL)-BENZOIC ACID, METHYL ESTER;DIHYDRORHODAMINE 123, FOR FLUOR-ESCENCE;Dihydrorhodamine123(DHR123);Dihydrohodamine 123;Dihydrorhodamine
• CAS NO: 109244-58-8
• Molecular Formula: C₂₁H₁₈N₂O₃
• Molecular Weight: 346.37922
• Product Categories: AlphabeticalStains and Dyes;DFluorescent Probes, Labels, Particles and Stains;Fluorescent Enzyme Substrates;Fluorescent Enzyme Substrates for Flow Cytometry;Fluorescent Probes, Labels, Particles and Stains;Stains&Dyes, A to;Xanthene
• Mol File: 109244-58-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 163–165℃
• Boiling Point: 526.877 °C at 760 mmHg
• Flash Point: 222.398 °C
• Appearance: Light red or pinkish-white/powder
• Density: 1.313g/cm³
• Vapor Pressure: 3.43E-11mmHg at 25°C
• Refractive Index: 1.683
• Storage Temp.: −20°C
• Solubility: DMSO: >5mg/mL
• PKA: 4.70 ± 0.40, most basic, temperature: 25 °C
• BRN: 5989965
• CAS DataBase Reference: DIHYDRORHODAMINE 123(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDRORHODAMINE 123(109244-58-8)
• EPA Substance Registry System: DIHYDRORHODAMINE 123(109244-58-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 109244-58-8(Hazardous Substances Data)

Usage

Description

DHR is a cell-permeable fluorogenic probe that is used as an indicator of intracellular peroxynitrite formation. It is oxidized by peroxynitrite to the highly fluorescent product rhodamine in vitro. Neither nitric oxide, superoxide, nor hydrogen peroxide alone appear to oxidize DHR. Formation of rhodamine can be monitored by fluorescence spectroscopy using excitation and emission wavelengths of 500 and 536 nm, respectively, or by absorbance spectroscopy at 500 nm (ε = 78,800 M?1cm?1). DHR has been used to investigate reactive oxygen intermediates produced by endothelial cells, eosinophils, and reactive microglia.

Uses

Different sources of media describe the Uses of 109244-58-8 differently. You can refer to the following data:
1. Dihydrorhodamine 123 is the uncharged and nonfluorescent reduction product of the mitochondrion-selective dye rhodamine 123 used for investigation of reacitve oxygen intermediates.
2. Dihydrorhodamine 123 (DHR) has been used for the detection of free intracellular radicals or ROS (reactive oxygen species) in head kidney-derived macrophages. It has also been used in DHR assay in red blood cells and in oxidative burst assay in neutrophils.

General Description

Cell-permeable fluorogenic probe that is useful for the detection of reactive oxygen species (ROS) such as peroxide and peroxynitrite. Dihydrorhodamine is not fluorescent unless it is converted to rhodamine 123.

Biochem/physiol Actions

Cell permeable: yes

InChI:InChI=1/C21H18N2O3/c1-25-21(24)15-5-3-2-4-14(15)20-16-8-6-12(22)10-18(16)26-19-11-13(23)7-9-17(19)20/h2-11,20H,22-23H2,1H3

Upstream product

• 1250257-82-9 C₂₁H₁₇⁽²⁾HN₂O₃ 
• 62669-70-9 rhodamin 123 

Downstream Products

• 62669-70-9 rhodamin 123 
• 766473-05-6 rhodamine 123 
• 109244-61-3 4',7'-diiododihydrorhodamine 123 
• 109244-60-2 2',7'-diiododihydrorhodamine 123 
• 109244-62-4 2',4',7'-triiododihydrorhodamine 123 
• 109282-63-5 4'-iododihydrorhodamine 123 
• 109244-59-9 2'-iododihydrorhodamine 123 

Relevant articles and documents

Synthesis and Biological Studies of Iodinated (127/125I) Derivatives of Rhodamine 123

Rhodamine 123, a mitochondrial stain that preferentially accumulates in certain cancer cells, has been reduced and iodinated by using NaI in the presence of N-chlorosuccinimide.The various mono-, di-, and triiodo derivatives have been isolated and charact