Rhodamine 110

Names

[ Name ]:
Rhodamine 110

[Synonym ]:
2-(3-amino-6-iminoxanthen-9-yl)benzoic acid,hydrochloride
Benzoic acid, 2-(6-amino-3-imino-3H-xanthen-9-yl)-, hydrochloride (1:1)
Rhodamine 110
2-(6-Amino-3-imino-3H-xanthen-9-yl)benzoic acid hydrochloride
Rhodamine 110,laser grade
Rhodamine 110 chloride
MFCD00042009
2-(6-Amino-3-imino-3H-xanthen-9-yl)benzoic acid hydrochloride (1:1)
EINECS 236-944-7

Biological Activity

[Description]:

Rhodamine 110 is a xanthene dye similar to fluorescein and eosin.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Dye Reagents

Research Areas >> Others

[In Vitro]

Rhodamine 110 accumulates in mitochondria in a cationic form, which alters the pH in this cellular compartment. Rhodamine 110 accumulates in human lymphoblastoid cells and Friend leukemia cells. No cytotoxicity to human lymphoblastoid cells is observed below 10 μM, but Rhodamine 110 causes Friend leukemia cells to die at a concentrations above 100 μM[1].

[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].

[Animal admin]

Rats[1] Adult male Sprague-Dawley rats (230±20 g) are used. After the rats recovered, Rhodamine 110 in polyethylene glycol 400 (0.3 and 1 mg/mL) is administered at 3 mg/kg and 10 mg/kg by oral gavage. Blood samples (150 μL) are collected from the right jugular vein 5, 15, 30, 60, 120, 180, 240, 300, 360, 480, and 720 min after drug administration. After each sampling, 100 μL of normal saline is administered via catheter to compensate for the loss of body fluid, and a 50 μL heparin solution (20 IU heparin/mL normal saline) is provided to prevent coagulation. Blood samples are centrifuged at 16,000g for 10 min at 4 °C to obtain plasma, which is stored at -20 °C until analysis. After surgery, Rhodamine 110 in polyethylene glycol 400 (1 mg/mL) is administered intravenously to rats at 3 mg/kg (n=6). A 150 μL blood sample is collected from the right jugular vein 5, 15, 30, 60, 120, 180, 240, 300, 360, 480, and 720 min after drug administration. Then, 100 μL of normal saline is administered via the right jugular vein to compensate for body fluid loss, and 50 μL of a heparin solution (20 IU heparin/mL normal saline) is provided to prevent blood clotting.

[References]

[1]. Jiang SH, et al. Pharmacokinetics of Rhodamine 110 and Its Organ Distribution in Rats. J Agric Food Chem. 2017 Sep 6;65(35):7797-7804.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
629.3ºC at 760 mmHg

[ Melting Point ]:
>300 °C(lit.)

[ Molecular Formula ]:
C₂₀H₁₅ClN₂O₃

[ Molecular Weight ]:
366.798

[ Flash Point ]:
334.4ºC

[ Exact Mass ]:
366.077118

[ PSA ]:
100.31000

[ LogP ]:
5.44740

[ Vapour Pressure ]:
1.06E-16mmHg at 25°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Rhodamine-based fluorogenic probe for imaging biological thiol.

Bioorg. Med. Chem. Lett. 18(7) , 2246-9, (2008)

We have developed a new fluorescent probe for biological thiol. The probe was synthesized by the modification of the 2,4-dinitrobenzenesulfonyl group with rhodamine 110. The selective detection of thi...

Early detection of apoptosis in living cells by fluorescence correlation spectroscopy.

Anal. Bioanal. Chem 396(3) , 1177-85, (2010)

Early detection of apoptotic cells via caspase activity is demonstrated with fast response time. Fluorescence correlation spectroscopy (FCS) is used to identify the presence of a cleaved fluorogenic p...

Mapping vortex-like hydrodynamic flow in microfluidic networks using fluorescence correlation spectroscopy.

Anal. Chim. Acta 651(1) , 85-90, (2009)

The ability to quickly measure flow parameters in microfluidic devices is critical for micro total analysis system (microTAS) applications. Macrofluidic methods to assess flow suffer from limitations ...