10356. Rhodamine 123

Nomenclature

CAS number: 62669-70-9
3,6-Diamino-9-[2-(methoxycarbonyl)phenyl]xanthylium chloride (1:1); 2-(6-amino-3-imino-3H-xanthen-9-yl)benzoic acid methyl ester hydrochloride; rhodamine 110 methyl ester; Rh 123.
C21H17ClN2O3; mol wt 380.82.
C 66.23%, H 4.50%, Cl 9.31%, N 7.36%, O 12.60%.

Description and references

Mitochondrial specific fluorescent dye for living cells. Substrate for P-glycoprotein. Prepd as methyl ester of rhodamine 110: P. Pal et al., Photochem. Photobiol. 63, 161 (1996) DOI PubMed; J. A. Ross et al., Synth. Commun. 36, 1745 (2006) DOI. Mitochondrial staining applications: L. V. Johnson et al., Proc. Natl. Acad. Sci. USA 77, 990 (1980) DOI PubMed; L. B. Chen et al., Cold Spring Harbor Symp. Quant. Biol. 46, 141 (1982) PubMed; R. K. Emaus et al., Biochim. Biophys. Acta 850, 436 (1986) DOI PubMed. Photophysical and photochemical properties: A. Chow et al., Photobiochem. Photobiophys. 11, 139 (1986); M. W. Ferguson et al., Phys. Chem. Chem. Phys. 1, 261 (1999) DOI. Binding studies with P-glycoprotein: B. Nare et al., Mol. Pharmacol. 45, 1145 (1994) PubMed; with multidrug resistance protein: R. Daoud et al., Biochemistry 39, 15344 (2000) DOI PubMed. Flow cytometric assessment of P-glycoprotein function: J. Petríz, J. García-López, Leukemia 11, 1124 (1997) DOI PubMed. HPLC detection in cell lysate: T. Iqbal et al., J. Chromatogr. B 814, 259 (2005) DOI.

Chemical structure

Properties

Brownish-red solid. Abs max: 500 nm (ε 75000, water); 507 nm (methanol). Excitation max: 511 nm (ethanol). Emission max: 529 nm (methanol); 530 nm (ethanol). Fluorescence emission: green (excitation at 485 nm); red (excitation at 546 nm). Sol in ethanol, ether, DMF, methanol, and water.

Use

Mitochondrial stain. Laser dye. In measurement of membrane potential. In flow cytometric analysis of P-glycoprotein function. In assays for assessment of multidrug resistance of cancer cells.