
TAMRA maleimide, 6-isomer
| Catalog Number | F07-0031 |
| Category | TAMRA Dyes |
| Molecular Formula | C31H28N4O6 |
| Molecular Weight | 552.58 |
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Product Introduction
TAMRA (also known as TMR or tetramethylrhodamine) is a xanthene dye that has been used as a fluorescent label for decades. Xanthene dyes are available as two isomers (called 5- and 6-isomers) that have almost identical fluorescent properties, but need to be separated to avoid doubling and smearing of labeled product peaks or bands during chromatography or electrophoresis. This is a pure 6-isomer of TAMRA maleimide, used for the labeling of proteins and peptides via thiol (SH) groups.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Purity | NMR 1H, HPLC-MS (95%) |
| IUPAC Name | 3',6'-bis(dimethylamino)-N-[2-(2,5-dioxopyrrol-1-yl)ethyl]-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxamide |
| SMILES | CN(C)C1=CC2=C(C=C1)C3(C4=C(O2)C=C(C=C4)N(C)C)C5=C(C=CC(=C5)C(=O)NCCN6C(=O)C=CC6=O)C(=O)O3 |
| InChI | InChI=1S/C31H28N4O6/c1-33(2)19-6-9-22-25(16-19)40-26-17-20(34(3)4)7-10-23(26)31(22)24-15-18(5-8-21(24)30(39)41-31)29(38)32-13-14-35-27(36)11-12-28(35)37/h5-12,15-17H,13-14H2,1-4H3,(H,32,38) |
| InChIKey | LLYYNGSVFARFNI-UHFFFAOYSA-N |
| Solubility | Good in DMSO, DMF |
| Appearance | Dark colored solid |
Product Specification
| CF260 | 0.32 |
| CF280 | 0.19 |
| Fluorescence Quantum Yield | 0.1 |
| Mass Spec M+ Increment | 551.2 |
| Excitation | 541 |
| Emission | 567 |
| Storage | Storage: 12 months after receival at -20 °C in the Dark. Transportation: at room temperature for up to 3 weeks. Avoid prolonged exposure to light. Desiccate. |
Application
TAMRA maleimide, 6-isomer is a thiol-reactive TAMRA (carboxytetramethylrhodamine) dye provided as a maleimide functional handle for rapid, covalent labeling of sulfhydryl-containing biomolecules. Its bright red fluorescence supports fluorescence microscopy, flow cytometry, and fluorescence-based assay development, while the maleimide group enables straightforward conjugate construction with cysteine- or thiol-modified targets.
1. Protein Thiol Labeling
TAMRA maleimide, 6-isomer is widely used to fluorescently tag proteins and peptides that present accessible cysteine residues or have been engineered to carry a free thiol. Researchers employ the dye for labeling antibodies, affinity reagents, enzyme conjugates, and protein standards to enable visualization and quantitative fluorescence readouts in binding and interaction studies, as well as in protein localization experiments. The covalent maleimide-thiol coupling helps produce stable fluorescent conjugates suitable for downstream imaging workflows where dye loss or exchange would otherwise complicate interpretation.
2. Fluorescence Microscopy Staining
TAMRA maleimide, 6-isomer supports fluorescence microscopy workflows that require red-channel labeling of thiol-bearing biomolecules on cells, biomaterials, or surfaces. In practice, it is used to generate fluorescent probes for tracking biomolecule distribution, monitoring surface adsorption, or labeling extracellular components in imaging experiments. Because the labeling is driven by thiol availability, it is commonly paired with sample preparation strategies that introduce or expose sulfhydryl groups on the target of interest, enabling consistent fluorescent staining for confocal and widefield imaging.
3. Flow Cytometry Conjugates
TAMRA maleimide, 6-isomer is used to prepare flow cytometry dyes and fluorescent conjugates for labeling thiol-containing reagents used in cell-surface or intracellular staining workflows. Laboratories incorporate the TAMRA maleimide conjugates into multicolor panels where red emission is needed, enabling quantification of binding or uptake readouts by fluorescence intensity. The maleimide handle supports robust conjugate generation from thiol-functionalized antibodies, ligands, or other targeting molecules, supporting reproducible staining for cytometry-based analysis.
4. Biomaterial Surface Functionalization
TAMRA maleimide, 6-isomer is frequently applied in biomaterials science to fluorescently functionalize surfaces and matrices that contain reactive thiol groups, such as thiolated polymers, hydrogels, or thiol-terminated linkers. Researchers use the dye to visualize coating uniformity, track biomolecule immobilization, and monitor surface-associated processes in materials characterization studies. This labeling approach is particularly useful when a covalent, dye-bearing surface is required for microscopy readouts or for fluorescence-based characterization of functionalized biomaterials.
Computed Properties
| XLogP3 | 2.9 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 6 |
| Exact Mass | 552.20088463 g/mol |
| Monoisotopic Mass | 552.20088463 g/mol |
| Topological Polar Surface Area | 109Ų |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Complexity | 1060 |
| 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 |
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