Rhodamine 123

Base Information

• Chemical Name: Rhodamine 123
• CAS No.: 62669-70-9
• Deprecated CAS: 108608-81-7,140686-88-0,1167436-73-8
• Molecular Formula: C21H17ClN2O3
• Molecular Weight: 380.831
• Hs Code.: 32049010
• European Community (EC) Number: 263-687-8
• UNII: 1N3CZ14C5O
• DSSTox Substance ID: DTXSID90910785
• Wikipedia: Rhodamine_123
• Wikidata: Q3429577
• ChEMBL ID: CHEMBL176049
• Mol file: 62669-70-9.mol

Synonyms:Rhodamine 123

Chemical Property of Rhodamine 123

Chemical Property:

• Appearance/Colour: Red to brown powder.
• Melting Point: 235 °C
• Refractive Index: 1.6500 (estimate)
• PSA: 89.31000
• Density: 1.2224 (rough estimate)
• LogP: 5.53580
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: ethanol: 20 mg/mL, clear, red
• Water Solubility.: Partially soluble
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 380.0927701
• Heavy Atom Count: 27
• Complexity: 706

Purity/Quality:

≥99% ^*data from raw suppliers

3,6-Diamino-9-(2-(methoxycarbonyl)phenyl)xanthyliumchloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Rhodamine Dyes
• Canonical SMILES: COC(=O)C1=CC=CC=C1C2=C3C=CC(=N)C=C3OC4=C2C=CC(=C4)N.Cl
• Description: Rhodamine 123 is a membrane-permeable cationic dye that is readily accumulated within living cells. It is a substrate for the efflux pump P-glycoprotein (P-gp; also known as multidrug resistance protein 1 and ABCB1) and is rapidly exported from cells with functional P-gp. As P-gp is expressed on a population of stem cells known as the side population, rhodamine 123 is used to detect this group of stem cells. Rhodamine 123 also accumulates within mitochondria due to its positive charge and can inhibit oxidative phosphorylation. Rhodamine 123 has excitation/emission maxima of 507/529 nm.
• Uses: Rhodamine derivative, a fluoresent dye-labeled compound. Fluorescent dye most commonly used as functional reporter in flow cytometry. Rhodamine-123 lycoprotein (P-gp) functional efflux activity in vivo. Rhodamine-123 PE-Cy5 and AMCA (7-amino-4-methylcoumarin-3-acetic acid). Useful as a laser dye and to have selective cell growth effects. Mitochondrial specific fluorescent dye and substrate for P-glycoprotein. Rhodamine-123 is a fluorescent dye most commonly used in flow cytometry as functional reporter for Pgp. Rhodamine 123 (R123), as a typical of P-glycoprotein substrate, was widely used to quantify P-glycoprotein (P-gp) functional efflux activity in vivo. Rhodamine-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).

Technology Process of Rhodamine 123

There total 2 articles about Rhodamine 123 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methanol (67-56-1) + rhodamine 110 chloride (13558-31-1) → rhodamin 123 (62669-70-9)

Guidance literature:

With hydrogenchloride; 1.) reflux, 6 h, 2.) RT, overnight;

DOI:10.1111/j.1751-1097.1996.tb03008.x

Reference yield:

Dihydrorhodamine 123 (109244-58-8) → rhodamin 123 (62669-70-9)

Guidance literature:

In acetone; Electrochemical reaction;

DOI:10.1021/acs.inorgchem.5b00831

Reference yield: 100.0%

rhodamin 123 (62669-70-9) → 2'-(6-amino-4,5-dibromo-3-imino-3H-xanthen-9-yl)benzoic acid methyl ester hydrochloride

Guidance literature:

With bromine; In ethanol; for 73.5h; Ambient temperature;

DOI:10.1111/j.1751-1097.1996.tb03008.x

upstream raw materials:

methanol

rhodamine 110 chloride

Dihydrorhodamine 123

Downstream raw materials:

Dihydrorhodamine 123

4'-iododihydrorhodamine 123

Refernces

Structure-activity relationship studies on benzofuran analogs of propafenone-type modulators of tumor cell multidrug resistance

10.1021/jm960384x

The research focuses on the structure-activity relationship (SAR) studies of benzofuran analogs of propafenone-type modulators aimed at reversing multidrug resistance in tumor cells. The purpose of the study was to understand the structural features required for effective inhibition of P-glycoprotein (PGP), a membrane-bound efflux pump associated with multidrug resistance. The researchers synthesized a series of benzofurylethanolamine analogs and evaluated their activity in vitro using rhodamine-123 efflux studies and daunomycin cytotoxicity assays. The conclusions drawn from the study indicated that there is an excellent correlation between the calculated lipophilicity of the compounds and their multidrug resistance-reversing activity, with the benzofuran analogs generally having lower activity/lipophilicity ratios compared to propafenones. The study also found that the incorporation of the ether oxygen of propafenone into a benzofuran moiety led to a decrease in activity, which could be partially compensated by increasing lipophilicity.