Rhodamine 123

Rhodamine 123 /ˈroʊdəmiːn/ is a chemical compound and a dye. It is often used as a tracer dye within water to determine the rate and direction of flow and transport. Rhodamine dyes fluoresce and can thus be detected easily and inexpensively with instruments called fluorometers. Rhodamine dyes are used extensively in biotechnology applications such as fluorescence microscopy, flow cytometry, fluorescence correlation spectroscopy and ELISA. Rhodamine fluorescence can also be used as a measure of membrane polarization in live cell assays both within mitochondria[1][2] and with bacteria. This use relies on the fact that rhodamine 123 accumulates in membranes in a manner which is dependent on membrane polarization.[3]

Rhodamine 123
Names
Preferred IUPAC name
7-Amino-10-[2-(methoxycarbonyl)phenyl]-2H-xanthene-2-iminium chloride
Other names
Rhodamine 123, EINECS 263-687-8, RH 123, LS-162564, C11190
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.057.879
EC Number
  • 263-687-8
UNII
  • InChI=1S/C21H17N2O3.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;/h2-11H,22-23H2,1H3;1H/q+1;/p-1 checkY
    Key: TUFFYSFVSYUHPA-UHFFFAOYSA-M checkY
  • InChI=1/C21H17N2O3.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;/h2-11H,22-23H2,1H3;1H/q+1;/p-1
    Key: TUFFYSFVSYUHPA-REWHXWOFAU
  • [Cl-].COC(=O)c4ccccc4c1c3ccc(N)cc3[o+]c2cc(N)ccc12
Properties
C21H17ClN2O3
Molar mass 380.824
Melting point 235 °C (455 °F; 508 K)
Solubility in ethanol 20 g/l
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P312, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The absorption of rhodamine 123 peaks around 505 nm and luminescence is tunable around 560 nm when used as a laser dye.[4] Its luminescence quantum yield is 0.90.[5]

References
  1. L. B. Chen. "Mitochondrial membrane potential in living cells."Annu Rev Cell Biol. 4 (1988) 155–181
  2. Darzynkiewicz Z, Traganos F, Staiano-Coico L, Kapuscinski J, Melamed MR. (1982) Interaction of rhodamine 123 with living cells studied by flow cytometry. Cancer Res. Mar;42(3):799-806. PMID 7059978
  3. M. Huang, A. K. S. Camara, D. F. Stowe, F. Qi, D. A. Beard. "Mitochondrial inner membrane electrophysiology assessed by rhodamine-123 transport and fluorescence" Annals of Biomedical Engineering. (2007) 35 (7)
  4. Rhodamine 123
  5. R. F. Kubin and A. N. Fletcher, "Fluorescence quantum yields of some rhodamine dyes." J. Luminescence 27 (1982) 455

See also
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