TMRM

Solubility Soluble in ethanol, methanol, dimethyl sulfoxide 

CA Index Name Xanthylium, 3,6-bis(dimethylamino)-9-[2-(methoxycarbonyl)phenyl]-, perchlorate 

Other Names T 668 TMRM Tetramethylrhodamine methyl ester perchlorate 

Merck Index Number Not listed Chemical/Dye Class Xanthene Molecular Formula C25H25CIN2O7 Molecular Weight 500.93 Physical Form Dark green crystals 

Staining Applications Mitochondria cells Biological Applications Detecting mitochondrial membrane potential apoptosis assays multidrug resistance assays  

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Fig. 1 Examples of the structures of a few slow-response electric field sensitive dyes 3, 3 -dipropylthiadicarbocyanine (DiSC3(5)), tetramethylrhodamine methyl ester (TMRM), and bis-(3-propyl-5-oxoisooxazol-4-yl)pentamine oxonol (oxonol VI)...

Dye oxidation (e.g., tetrazolium reductase activity with 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide, MTT 2-[4-iodophenyl]-3-[4-nitrophenyl]-5-[2,4-disulfophenyl]-2H tetrazolium monosodium salt, WST-1 3- (4,5 -carboxymethoxyphenyl) -2-(4-sulfophenyl)-2 H-tetra-zolium, MTS 2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide inner salt, XTT 2,2 -di-p-nitrophenyl-5,5 -diphenyl-3,3 -(3,3 -dimethoxy-4,4 -diphe-nylenej-ditetrazolium chloride, NET), Alamar blue assays, ATP concentration (e.g., luciferase assay), oxygen consumption (e.g., oxygen electrodes, phosphorescent oxygen-sensitive dyes), mitochondrial protein and nucleic acid synthesis mitochondrial mass (e.g., mitotracker dyes) mitochondrial membrane potential (e.g., tetramethylrho-damine methyl ester, TMRM tetramethylrhodamine ethyl ester, TMRE)... 

Drug DILI label Nuclei count (<0.4 = positive) Nuclei area (<0.4 = positive) ROS intensity (>2.5 = positive) TMRM intensity (<0.4 = positive) Lipid intensity (>2.5 = positive) GSH content (<0.4 = positive) GSH area (<0.65 = positive) GSH average pixel intensity (<0.4 = positive) HH imaging final score (logical OR of 8 measures) Human C ax (Pg/ml)... 

Mitochondria damage Mitochondria membrane potential dyes (e.g., TMRM) [52]... 

Mitochondrial toxicity may also lead to a decrease in the mitochondrial membrane potential which can be measured by various dyes, such as Tetramethylrhodamine methyl ester (TMRM), Rhodaminel23, JC-1 (Molecular Probes), and mitochondrial membrane potential indicator (m-MPI, Codex). These dyes specifically accumulate in the matrix of the mitochondria according to the Nernst equation, with an inverse proportion to the A Pmembrane [9]. Thus, upon loss of mitochondrial membrane potential, the fluorescence intensity will decrease, as shown for TMRM in Fig. 2e, f. Notably, TMRM, is not a ratio-metric dye, which means that additional controls for mitochondrial number/ mass may be required, as in contrast to the ratio-metric dyes JC-1 and m-MPI. 

Fig. 6 Assessment of mitochondrial membrane potential by TMRM. Graph represents percentage intensity of TMRM in Panel cells exposed for 24 h to either Sorafenib alone (black) or Sorafenib+100 pM Verapamil (red), relative to vehicle control cells. Images represent nuclei stained with Hoechst 33342(blue) and mitochondria by TMRM (red) (Color figure online)...

Fio. 9. Selectivity to tmrM-decalin in the hydrogenation of tetralin at 1000 psig hydrogen pressure and 25° over mixtures of 5% metal-on-charcoal catalyst. A, Rh-Pd , Ir-Pd O, Ru-Pd. 

Our laboratory (44) has synthesized two rhodamine dyes, TMRE (Chart III) and TMRM, that are very similar to rhodamine 123 except the free amino groups are substituted with methyl substituents. This substitution makes the dyes more permeable than rhodamine 123 and also blocks any poorly reversible hydrogen-bonding interactions with anionic sites in the mitochondrial inner membrane and matrix. These qualities combined with... 

The slow dyes that change their spectral characteristics as a result of potential-dependent accumulation are well suited for cells in suspension. However, the complexity of these mechanisms makes it very difficult to interpret the change in dye fluorescence within a single cell. Accordingly, we set out to find dyes that display a rapid, reversible, potential-dependent intracellular accumulation with no accompanying spectral perturbation (44). As previously discussed, the dyes TMRE (Chart III) and TMRM emerged from this investigation and have proven useful in a wide variety of cultured cells. 

Stilbene Isothiocyanate Sulfonic Acid (SITS) 438 115532-50-8 TMRM 469... 

Tetramethylrhodamine ethyl ester perchlorate (TMRE) Tetramethylrhodamine methyl ester perchlorate (TMRM) Vita Blue... 

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