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Merck
CN

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:
109244-58-8
Molecular Weight:
346.38
NACRES:
NA.47
PubChem Substance ID:
24893337
UNSPSC Code:
12171500
MDL number:
MFCD00285712
Beilstein/REAXYS Number:
5989965

Key Documents

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Product Name

Dihydrorhodamine 123, ≥95%

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

SMILES string

COC(=O)c1ccccc1C2c3ccc(N)cc3Oc4cc(N)ccc24

InChI key

FNEZBBILNYNQGC-UHFFFAOYSA-N

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

Quality Level

200

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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.

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

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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Certificates of Analysis (COA)

Lot/Batch Number
0000508876
0000508874
0000508874
0000508876
0000487810

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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)
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)
Dihydrorhodamine 123: a fluorescent probe for superoxide generation?
HENDERSON LM and CHAPPELL JB
European Journal of Biochemistry, 217(3), 973-980 (1993)
Phosphatase Wip1 negatively regulates neutrophil development through p38 MAPK-STAT1
Liu G, et al.
Blood, 121(3), 519-529 (2013)
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)
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Articles

Mitochondrial Stress and ROS

Cellular oxidative stress is countered by enzymatic scavengers and antioxidant modulators against reactive oxygen species damage.

线粒体应激和ROS

氧化应激，在一部分上，是由多种细胞过程产生的活性氧介导，并由诸如酶清除剂或抗氧化剂调节剂等细胞抗氧化剂机制所控制的。自由基，如活性氧，会通过细胞引起细胞损伤。

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