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
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About This Item
Empirical Formula (Hill Notation):
C21H18N2O3
CAS Number:
Molecular Weight:
346.38
NACRES:
NA.47
PubChem Substance ID:
UNSPSC Code:
12171500
MDL number:
Beilstein/REAXYS Number:
5989965
Product Name
Dihydrorhodamine 123, ≥95%
Quality Level
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
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. It is an analog of 2,7-Dichlorodihydrofluorescein (DCDHF), lipophilic and diffuses through cell membrane.
Peroxidase substrate
Application
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.
Biochem/physiol Actions
Dihydrorhodamine 123 detects superoxide ions at the single-cell level and is used for probing neutrophils superoxide generation in a respiratory burst event. It is also used for measuring oxidative stress in macrophages and human spermatozoa.
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.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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DHR123: an alternative probe for assessment of ROS in human spermatozoa
Kiani-Esfahani A, et al.
Systems Biology in Reproductive Medicine, 58(3), 168-174 (2012)
Chronic granulomatous disease (CGD) and complete myeloperoxidase deficiency both yield strongly reduced dihydrorhodamine 123 test signals but can be easily discerned in routine testing for CGD.
Mauch L, et al.
Clinical Chemistry, 53, 890-896 (2007)
Dichlorodihydrofluorescein and dihydrorhodamine 123 are sensitive indicators of peroxynitrite in vitro: implications for intracellular measurement of reactive nitrogen and oxygen species
Crow JP
Nitric Oxide, 1(2), 145-157 (1997)