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R8004

Sigma-Aldrich

Rhodamine 123

mitochondrial specific fluorescent dye

Synonym(s):
2-(6-Amino-3-imino-3H-xanthen-9-yl)benzoic acid methyl ester
Linear Formula:
C21H17ClN2O3
CAS Number:
Molecular Weight:
380.82
Beilstein:
6030951
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.47

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.

Packaging

5, 25, 100 mg in glass bottle

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

13 - Non 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

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What are the excitation and emission wavelengths for Rhodamine 123, (Product Nos. 83702 and R8004)?

    Using ethanol as the solvent, the excitation maximum is  511 nm and the emission maximum is 534 nm.  The recommended excitation and emission wavelengths in PBS are 488 and 515-575 nm, respectively.

  6. Why would one select Rhodamine 123, products 83702 and R8004, instead of other rhodamine compounds?

    Due to is comparatively low toxicity, Rhodamine 123 is the dye of choice for visualizing mitochondria or for cell viability measurements.

  7. What is the solubility of Rhodamine 123, products 83702 and R8004?

    Rhodamine 123 is soluble in ethanol at 20 mg/mL, and has been reported soluble in ether, various fats and lipids, and has limited solubility in water (no concentration given).

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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
BAG5 Interacts with DJ-1 and Inhibits the NeuroprotectiveEffects of DJ-1 to Combat Mitochondrial Oxidative Damage
Li-xia Qin
Oxidative Medicine and Cellular Longevity (2017)
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)
Role of Mitochondrial Metabolism in the Control of
Early Lineage Progression and Aging Phenotypes in
Adult Hippocampal Neurogenesis
Ruth Beckervordersandforth
Neuron (2016)

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