
Dihydrotetramethylrosamine | CAS 105284-17-1
| Catalog Number | A18-0067 |
| Category | Fluorescent Enzyme Substrates |
| Molecular Formula | C23H24N2O |
| Molecular Weight | 344.46 |
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Product Introduction
Dihydrotetramethylrosamine is a mitochondrial ROS indicator offering strong red fluorescence upon oxidation. It’s used for tracking mitochondrial oxidative stress in live cells.
Chemical Information
Application
Computed Properties
Patents
Chemical Information
| Synonyms | H2TMRos; 3-N,3-N,6-N,6-N-tetramethyl-9-phenyl-9H-xanthene-3,6-diamine |
| IUPAC Name | 3-N,3-N,6-N,6-N-tetramethyl-9-phenyl-9H-xanthene-3,6-diamine |
| SMILES | CN(C)C1=CC2=C(C=C1)C(C3=C(O2)C=C(C=C3)N(C)C)C4=CC=CC=C4 |
| InChI | InChI=1S/C23H24N2O/c1-24(2)17-10-12-19-21(14-17)26-22-15-18(25(3)4)11-13-20(22)23(19)16-8-6-5-7-9-16/h5-15,23H,1-4H3 |
| InChIKey | PALQHVVMLBWIDW-UHFFFAOYSA-N |
Application
Dihydrotetramethylrosamine is a xanthene-class fluorescent dye commonly used as a cell-permeable, reduced-form fluorophore that can be converted to a fluorescent species under appropriate cellular or chemical conditions. Its strong fluorescence response makes it a practical reagent for fluorescence labeling workflows where controlled activation and subsequent signal generation are advantageous for microscopy and fluorescence-based readouts.
1. Fluorescence Microscopy Labeling
Dihydrotetramethylrosamine is used as a fluorescent labeling reagent in microscopy workflows to visualize cellular fluorescence after intracellular conversion to its more strongly emissive form. Researchers employ it for imaging experiments that benefit from signal development inside cells, including studies focused on cellular fluorescence patterns, staining intensity comparisons across experimental conditions, and qualitative localization within cultured cell models. The dye's xanthene brightness supports routine widefield fluorescence imaging and can be integrated into multi-condition imaging pipelines where a robust turn-on signal is helpful for distinguishing labeled regions from background.
2. Flow Cytometry Signal Staining
Dihydrotetramethylrosamine is widely applied in flow cytometry staining workflows where fluorescence activation yields a measurable cytometric signal. In typical use, cells are incubated with the dye and analyzed by flow cytometry to quantify fluorescence intensity distributions across cell populations, enabling comparative readouts between experimental groups. This format is especially convenient for screening experiments that rely on fluorescence signal generation within cells and for monitoring shifts in fluorescence intensity that correlate with the experimental variable under study.
3. Fluorescence-Based Cell Assays
Dihydrotetramethylrosamine is also used in plate-based fluorescence assay development, where researchers monitor fluorescence output after dye activation to generate quantitative readouts. Common applications include endpoint fluorescence measurements in microplate readers for comparative studies of labeled cell samples, as well as assay formats that require a strong, easily measurable fluorescence signal following incubation. The dye's compatibility with standard fluorescence instrumentation supports its use in high-throughput experimental workflows where reproducible signal generation is required for data analysis across many conditions.
4. Fluorescent Probe Development Support
Dihydrotetramethylrosamine serves as a useful building-block fluorophore for fluorescence probe development efforts that require a reduced, activatable dye format. Chemical biology and fluorescence technology teams incorporate related rosamine/xanthene derivatives into custom staining reagents and imaging constructs where fluorescence activation after introduction into biological samples improves detectability relative to non-activated background. This makes the dye relevant for reagent optimization projects aimed at producing turn-on style fluorescent tools for cellular imaging and fluorescence readouts in research settings.
Computed Properties
| XLogP3 | 5.1 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Exact Mass | 344.188863393 g/mol |
| Monoisotopic Mass | 344.188863393 g/mol |
| Topological Polar Surface Area | 15.7Ų |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Complexity | 427 |
| 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 | 1 |
| Compound Is Canonicalized | Yes |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| WO-2021168290-A1 | Multilamellar rna nanoparticles and methods of sensitizing tumors to treatment with immune checkpoint inhibitors | 2020-02-19 |
| WO-2020119766-A1 | Nanoparticles based method for screening enzyme or microorganism | 2018-12-14 |
| EP-3893849-A1 | Nanoparticles based method for screening enzyme or microorganism | 2018-12-14 |
| US-2022056387-A1 | Nanoparticles based method for screening enzyme or microorganism | 2018-12-14 |
| US-2020080117-A1 | REAGENTS AND METHODS FOR THE EXPRESSION OF AN ACTIVE NifB PROTEIN AND USES THEREOF | 2018-09-12 |
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