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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:
6030951
EC Number:
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47

product name

Rhodamine 123, mitochondrial specific fluorescent dye

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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)
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
Severin Mairinger et al.
Nuclear medicine and biology, 39(8), 1219-1225 (2012-09-18)
With the aim to develop a PET tracer to visualize P-glycoprotein (Pgp) expression levels in different organs, the Pgp inhibitor MC113 was labeled with (11)C and evaluated using small-animal PET. [(11)C]MC113 was synthesized by reaction of O-desmethyl MC113 with [(11)C]methyl
Balabhaskar Prabhakarpandian et al.
Lab on a chip, 13(6), 1093-1101 (2013-01-25)
Current techniques for mimicking the Blood-Brain Barrier (BBB) largely use incubation chambers (Transwell) separated with a filter and matrix coating to represent and to study barrier permeability. These devices have several critical shortcomings: (a) they do not reproduce critical microenvironmental

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