D1054

Dihydrorhodamine 123

≥95% purity, powder

• Synonym(s): DHR 123; Methyl 2-(3,6-diamino-9H-xanthen-9-yl)benzoate; Benzoic acid, 2-(3,6-diamino-9H-xanthen-9-yl)-, methyl ester
• Empirical Formula (Hill Notation): C₂₁H₁₈N₂O₃
• CAS Number: 109244-58-8
• Molecular Weight: 346.38
• Beilstein/REAXYS Number: 5989965
• MDL number: MFCD00285712
• UNSPSC Code: 12171500
• PubChem Substance ID: 24893337
• NACRES: NA.47

Properties

• Product Name: Dihydrorhodamine 123, ≥95%
• Quality Level: 200
• assay: ≥95%
• form: powder
• technique(s): titration: suitable
• color: pink
• solubility: DMSO: >5 mg/mL
• application(s): diagnostic assay manufacturing; hematology; histology
• storage temp.: −20°C
• SMILES string: COC(=O)c1ccccc1C2c3ccc(N)cc3Oc4cc(N)ccc24
• InChI: 1S/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
• InChI key: FNEZBBILNYNQGC-UHFFFAOYSA-N

Description

General description

Dihydrorhodamine 123 (DHR123) is an uncharged non-fluorescent dye and a derivative of rhodamine 123 (R123). Dihydrorhodamine 123 (DHR123) is oxidized to fluorescent R123 within cells in the presence of reactive oxygen species and it localizes in mitochondria.[1] It is an analog of 2,7-Dichlorodihydrofluorescein (DCDHF), lipophilic and diffuses through cell membrane.[2]

Application

Dihydrorhodamine 123 (DHR) has been used for the detection of free intracellular radicals or ROS (reactive oxygen species) in head kidney-derived macrophages.[3] It has also been used in DHR assay in red blood cells [4] and in oxidative burst assay in neutrophils.[5]

Biochem/physiol Actions

Dihydrorhodamine 123 detects superoxide ions at the single-cell level and is used for probing neutrophils superoxide generation[6] in a respiratory burst event.[1] It is also used for measuring oxidative stress in macrophages[2] and human spermatozoa.[1]

Dihydrorhodamine 123 is used for the detection of ROS (reactive oxygen species). Presence of ROS oxidizes dihydrorhodamine 123 to the fluorescent derivative rhodamine 123. The reaction happens in the presence of a peroxidase or a similar catalyst.[7][8]

Substrates

Peroxidase substrate

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)