Tetramethylrhodamine ethyl ester perchlorate

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Tetramethylrhodamine ethyl ester perchlorate

Tetramethylrhodamine ethyl ester perchlorate | 115532-52-0

Catalog Number A16-0054
Category Mitochondrial Fluorescent Probes
Molecular Formula C26H27N2O3·ClO4
Molecular Weight 515.0
Catalog Number Size Price Quantity
A16-0054 -- $--

Product Introduction

Tetramethylrhodamine ethyl ester (TMRE) perchlorate is a cell-permeant red fluorescent probe commonly used to monitor membrane potential of mitochondria using live cell fluorescence microscopy and flow cytometry. TMRE is a lipophilic cation accumulated by mitochondria and exhibits a red shift in the emission of 575 nm. However, when the membrane is depolarized, as in apoptosis, TMRE is not accumulated in the mitochondria. Thus, the strength of the fluorescence signal in mitochondria is used to assess cell viability.

Chemical Information

Synonyms TMRE Perchlorate; TMR ethyl ester perchlorate; 3,6-bis(dimethylamino)-9-[2-(ethoxycarbonyl)phenyl]-xanthylium perchlorate
Purity ≥98%
IUPAC Name [6-(dimethylamino)-9-(2-ethoxycarbonylphenyl)xanthen-3-ylidene]-dimethylazanium;perchlorate
Canonical SMILES CCOC(=O)C1=CC=CC=C1C2=C3C=CC(=[N+](C)C)C=C3OC4=C2C=CC(=C4)N(C)C.[O-]Cl(=O)(=O)=O
InChI InChI=1S/C26H27N2O3.ClHO4/c1-6-30-26(29)20-10-8-7-9-19(20)25-21-13-11-17(27(2)3)15-23(21)31-24-16-18(28(4)5)12-14-22(24)25;2-1(3,4)5/h7-16H,6H2,1-5H3;(H,2,3,4,5)/q+1;/p-1
InChI Key NBAOBNBFGNQAEJ-UHFFFAOYSA-M
Appearance Solid Powder
  • Product Specification
  • Application
Excitation 550 nm
Emission 575 nm
Storage Store at -20°C
Signal Warning
GHS Hazard Statements H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
Precautionary Statement Codes P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.)

Tetramethylrhodamine ethyl ester perchlorate (TMRE) is a fluorescent dye commonly utilized in various biological assays. Here are four key applications of TMRE:

Mitochondrial Membrane Potential Assays: Within the realm of cellular biology, TMRE serves as a pivotal tool for quantifying the mitochondrial membrane potential in living cells. By preferentially accumulating in active mitochondria, TMRE fluorescence enables researchers to gauge mitochondrial health and functionality. This capability holds significant importance for investigations into cellular metabolism, apoptosis, and mitochondrial disorders, shedding light on the intricate workings of these vital organelles.

Flow Cytometry: In the domain of flow cytometry, TMRE emerges as a critical component for analyzing and segregating cells based on their mitochondrial membrane potential. Cells boasting a high mitochondrial membrane potential exhibit heightened TMRE fluorescence, facilitating the discrimination between healthy and compromised cellular populations. This application plays a crucial role in ensuring cellular quality control and finds widespread utility across diverse biomedical research disciplines, enriching our understanding of cellular physiology.

Live Cell Imaging: Delving into the dynamic realm of live cell imaging, TMRE takes center stage by enabling the visualization and real-time tracking of mitochondrial behavior. Through the staining of mitochondria with TMRE, researchers can witness and document alterations in mitochondrial morphology, distribution, and activity under varying physiological and pathological contexts. This technique offers valuable insights into the nuanced behavior of mitochondria within living cells, providing a deeper understanding of cellular dynamics and responses to external stimuli.

Drug Screening: Within the realm of pharmaceutical research, TMRE stands as a cornerstone in drug screening assays geared towards assessing the impact of compounds on mitochondrial function. By monitoring fluctuations in TMRE fluorescence, researchers can identify potential drug candidates that either uphold or disrupt the delicate balance of mitochondrial membrane potential. This application proves particularly instrumental in the development of mitochondria-targeted therapies and plays a pivotal role in toxicology studies, driving innovation in drug discovery and safety assessment practices.

Computed Properties

Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 8
Rotatable Bond Count 5
Exact Mass 514.1506789 g/mol
Monoisotopic Mass 514.1506789 g/mol
Topological Polar Surface Area 116Ų
Heavy Atom Count 36
Formal Charge 0
Complexity 884
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 2
Compound Is Canonicalized Yes

Literatures

PMIDPublication DateTitleJournal
5026 1975-12-01 [Effect of increasing doses of dopamine on the left ventricular function in the dog] Annales de l'anesthesiologie francaise

Patents

Publication NumberTitlePriority Date
KR-20220017557-A Stem cell having improved hypoxia adaptation and therapeutic potential by induction of BICD1 expression and method for preparing the same, and cell therapeutic composition comprising the same 2020-08-04
KR-102404092-B1 Stem cell having improved hypoxia adaptation and therapeutic potential by induction of BICD1 expression and method for preparing the same, and cell therapeutic composition comprising the same 2020-08-04
CN-110570903-B Medicine for improving activity of mesocerebral substantia nigra dopamine neurons and preventing and treating Parkinson's disease 2019-08-12
WO-2020243105-A1 Methods of culturing quiescent hematopoietic stem cells and treatment methods 2019-05-24
US-2020116734-A1 Biosensor and application of the same 2018-10-11
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