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RHODAMINE 110

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RHODAMINE 110 Basic information

Product Name:
RHODAMINE 110
Synonyms:
  • R110
  • RHODAMINE 110
  • RHODAMINE 110 CHLORIDE
  • RHODAMINE 560
  • RHODAMINE 110 CHLORIDE, FOR FLUOR-ESCENC E
  • Rhodamine 110, laser grade, pure, 99%
  • 2-(6-Amino-3-imino-3H-xanthen-9-yl)-benzoic acid hydrochloride
  • Exciton Rhodamine 560 Chloride
CAS:
13558-31-1
MF:
C20H15ClN2O3
MW:
366.8
EINECS:
236-944-7
Product Categories:
  • Amines
  • Fluorescent Labels & Indicators
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Q-R
  • Stains and Dyes
  • Stains&Dyes, A to
Mol File:
13558-31-1.mol
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RHODAMINE 110 Chemical Properties

Melting point:
>300 °C(lit.)
Density 
1.2504 (rough estimate)
refractive index 
1.6470 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
ethanol: soluble
form 
Crystalline Powder
color 
White to light yellow
λmax
499nm (MeOH); 496nm (H2O)
BRN 
4631860
Stability:
Hygroscopic, Light Sensitive
Major Application
Color filters; liquid crystal displays; dye lasers;electroluminescent displays;inks;light-emitting diode (LED);papermaking process; recording materials; solar cells; silica thin films;sol–gel titania films;waveguides
Biological Applications
Detecting risk of Alzheimer’s disease and stroke;evaluating/testing sperm quality; identifying bacteria; as a substrate for measuring aromatase activity, azoreductase activity,phospholipase activity, proteases activity (caspase activity, cathepsin C activity, elastase activity proteinase activity);implantable drug-delivery devices
InChI
InChI=1S/C20H14N2O3.ClH/c21-11-5-7-15-17(9-11)25-18-10-12(22)6-8-16(18)19(15)13-3-1-2-4-14(13)20(23)24;/h1-10H,21-22H2;1H
InChIKey
MYIOYATURDILJN-UHFFFAOYSA-N
SMILES
C(C1C=CC=CC=1C1C2=CC=C(N)C=C2[O+]=C2C=C(N)C=CC=12)(=O)O.[Cl-]
CAS DataBase Reference
13558-31-1(CAS DataBase Reference)
EPA Substance Registry System
Xanthylium, 3,6-diamino-9-(2-carboxyphenyl)-, chloride (13558-31-1)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
22-24/25-36/37/39-26
WGK Germany 
3
HS Code 
29329990

MSDS

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RHODAMINE 110 Usage And Synthesis

Description

Rhodamine 110 is a green fluorescent cationic dye with excitation and emission maxima of 496 and 520 nm, respectively. When incorporated with a hydrolytic substrate (e.g., proteinase or peptidase substrates), it can be used as a highly sensitive detection reagent in fluorescence-based enzyme assays. Rhodamine 110 has also been used in a fluorescence quenching method for determining trace nitrite and as a probe for cytochrome P450 activity.

Chemical Properties

red to bordeaux crystals or crystalline powder

Uses

Rhodamine 110 is a fluorescent dye used as AP- and exopeptidase substrates for flow cytometric measurements. Dyes and metabolites.

in vivo

Rhodamine 110 is less toxic than the parent molecule based on the intravenous LD50 acute toxicity values of 89.5 mg/kg and 140.0 mg/kg for Rhodamine B and Rhodamine 110, respectively. Both molecules induce liver and kidney enlargement after ingestion, and male rats show more significant increases than female rats after Rhodamine 110 exposure. In addition, testis weight increased in male rats dosed with Rhodamine 110. The pharmacokinetics of Rhodamine 110 are assessed following oral administration at two dosages (3 and 10 mg/kg) and intravenous administration at one dosage (3 mg/kg). Pharmacokinetic parameters are calculated using an extravascular input and IV-bolus input, noncompartmental model analysis conducted with WinNonlin Standard Edition. The pharmacokinetic parameters of Rhodamine 110 indicates that the maximum plasma concentrations (Cmax) of the two oral dosages are 283.4 and 657.0 ng/mL, which are reached at 140 and 210 min, respectively. This indicates that Rhodamine 110 absorption is not rapid after ingestion, as it took over 2 h to be absorbed from the intestines into the blood. The areas under the concentration–time curves (AUCs) for the two dosages are 138.1±20.3 and 444.0±170.8 h ng/mL. The pharmacokinetic data demonstrate that the AUC is proportional to the administered oral dose of Rhodamine 110 (3 mg/kg and 10 mg/kg). Furthermore, the clearance (Cl) of the two orally administered doses is 7.94 and 8.61 mL/min/kg, respectively[1].

References

[1] HEMANT S THATTE PHD . Acidosis-induced apoptosis in human and porcine heart[J]. Annals of Thoracic Surgery, 2004, 77 4: Pages 1376-1383. DOI: 10.1016/j.athoracsur.2003.07.047
[2] HUBERT HUG. Rhodamine 110-Linked Amino Acids and Peptides as Substrates To Measure Caspase Activity upon Apoptosis Induction in Intact Cells?[J]. Biochemistry Biochemistry, 1999, 38 42: 13906-13911. DOI: 10.1021/bi9913395
[3] XIAN ZHANG. A fluorescence quenching method for the determination of nitrite with Rhodamine 110[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2003, 59 8: Pages 1667-1672. DOI: 10.1016/s1386-1425(02)00404-3
[4] MELISSA M. YATZECK . A highly sensitive fluorogenic probe for cytochrome P450 activity in live cells[J]. Bioorganic & Medicinal Chemistry Letters, 2008, 18 22: Pages 5864-5866. DOI: 10.1016/j.bmcl.2008.06.015

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