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Key Documents

R8004

Sigma-Aldrich

Rhodamine 123

Powder

Synonym(s):

2-(6-Amino-3-imino-3H-xanthen-9-yl)benzoic acid methyl ester

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About This Item

Linear Formula:
C21H17ClN2O3
CAS Number:
Molecular Weight:
380.82
Beilstein/REAXYS Number:
6030951
EC Number:
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47

product name

Rhodamine 123, mitochondrial specific fluorescent dye

Quality Level

form

powder

solubility

ethanol: 1 mg/mL

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

Cl[H].COC(=O)c1ccccc1C2=C3C=CC(=N)C=C3Oc4cc(N)ccc24

InChI

1S/C21H16N2O3.ClH/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;/h2-11,22H,23H2,1H3;1H

InChI key

MYFATKRONKHHQL-UHFFFAOYSA-N

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Application

Rhodamine 123 is useful as a laser dye and to have selective cell growth effects. It has also been used to measure mitochondrial membrane potential.

Biochem/physiol Actions

Rhodamine 123 is a fluorescent dye most commonly used in flow cytometry as functional reporter for P-glycoprotein (Pgp). It is part of the rhodamine family of flurone dyes. The dye is mostly used to assess mitochondrial bioenergetics in living cells. Functional assays for multi-drug resistance (MDR) proteins are better prognostic indicators in cancer therapy than levels of MDR protein expression. Rh 123 can be used in multiparameter analyses without fluorescence interference in combination with common protein labeling dyes such as PE-Cy5 and AMCA (7-amino-4-methylcoumarin-3-acetic acid). Recent reports indicate Rh 123 may also be a substrate of multi-drug resistance protein-1 (MRP1).
Fluorescent dye most commonly used in flow cytometry as functional reporter for Pgp. Functional assays for MDR proteins are better prognostic indicators in cancer therapy than levels of MDR protein expression. Rh 123 can be used in multiparameter analyses without fluorescence interference in combination with common protein labeling dyes such as PE-Cy5 and AMCA (7-amino-4-methylcoumarin-3-acetic acid). Recent reports indicate Rh 123 may also be a substrate of MRP1.

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)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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S D Bernal et al.
Science (New York, N.Y.), 218(4577), 1117-1119 (1982-12-10)
Rhodamine-123, a cationic laser dye, markedly reduced the clonal growth of carcinoma cells but had little effect on nontumorigenic epithelial cells in vitro. This selective inhibitory effect of Rhodamine-123 on some carcinomas is unusual since known anticancer drugs, such as
Advances in Pharmacology (1999)
Role of Mitochondrial Metabolism in the Control of
Early Lineage Progression and Aging Phenotypes in
Adult Hippocampal Neurogenesis
Ruth Beckervordersandforth
Neuron (2016)
Paul E Abraham et al.
The Plant journal : for cell and molecular biology, 103(2), 869-888 (2020-04-22)
Crassulacean acid metabolism (CAM) is a specialized mode of photosynthesis that offers the potential to engineer improved water-use efficiency (WUE) and drought resilience in C3 plants while sustaining productivity in the hotter and drier climates that are predicted for much
Characterization of Rhodamine-123 as a Tracer Dye for Use In In vitro Drug Transport Assays
Samantha
PLoS ONE (2012)

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