
TAMRA maleimide, 5-isomer
| Catalog Number | F07-0030 |
| Category | TAMRA Dyes |
| Molecular Formula | C31H28N4O6 |
| Molecular Weight | 552.58 |
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Product Introduction
Maleimide derivative of TAMRA (tetramethylrhodamine) for the labeling of thiol groups. Pure 5-isomer of TAMRA.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | TAMRA maleimide |
| Purity | NMR 1H, HPLC-MS (95%) |
| IUPAC Name | 3',6'-bis(dimethylamino)-N-[2-(2,5-dioxopyrrol-1-yl)ethyl]-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxamide |
| SMILES | CN(C)C1=CC2=C(C=C1)C3(C4=C(C=C(C=C4)C(=O)NCCN5C(=O)C=CC5=O)C(=O)O3)C6=C(O2)C=C(C=C6)N(C)C |
| InChI | InChI=1S/C31H28N4O6/c1-33(2)19-6-9-23-25(16-19)40-26-17-20(34(3)4)7-10-24(26)31(23)22-8-5-18(15-21(22)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 | DAJTYOCTYAARHG-UHFFFAOYSA-N |
| Solubility | Good in DMF, DMSO |
| Appearance | Red powder |
Product Specification
| CF260 | 0.32 |
| CF280 | 0.19 |
| Fluorescence Quantum Yield | 0.1 |
| Mass Spec M+ Increment | 552.2 |
| 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, 5-isomer is a thiol-reactive TAMRA (carboxytetramethylrhodamine) labeling reagent designed for efficient conjugation to sulfhydryl-containing biomolecules. Its maleimide functional group enables stable thioether formation with cysteine residues or engineered thiols, making it widely used for fluorescent tagging in chemical biology, protein labeling, and probe construction. The TAMRA fluorophore provides a bright red/orange fluorescence readout compatible with standard fluorescence imaging and many flow cytometry workflows.
1. Protein And Peptide Labeling
TAMRA maleimide, 5-isomer is frequently used by protein chemistry and chemical biology groups to fluorescently label purified proteins, peptides, and antibody fragments through thiol-reactive tagging. Researchers commonly apply it to prepare fluorescently labeled biomolecules for binding studies, tracking of biomolecular interactions, and downstream assay development where a red-emitting dye is advantageous. The maleimide reactivity supports labeling of reduced cysteines, engineered cysteine sites, or thiol-bearing ligands, enabling construction of TAMRA-tagged conjugates used in microscopy, plate-based fluorescence assays, and fluorescence-based characterization of biomolecular samples.
2. Bioconjugation For Thiol Surfaces
TAMRA maleimide, 5-isomer is also used in biomaterials and surface functionalization workflows where thiol groups are presented on surfaces or on polymer coatings. Lab teams preparing functionalized nanoparticles, hydrogel components, or sensor materials often incorporate thiol handles to enable covalent attachment of the TAMRA fluorophore, supporting visualization of material distribution and monitoring of surface conjugation. This reagent is particularly relevant when a stable, covalent fluorescent tag is needed for materials characterization, coating verification, or fluorescence-based readouts in engineered platforms.
3. Fluorescent Probe Construction
TAMRA maleimide, 5-isomer is commonly employed in fluorescent probe development where a TAMRA dye is introduced onto a targeting scaffold, affinity reagent, or reporter module that contains thiol functionality. Researchers use the thiol-reactive handle to build modular fluorescent constructs for imaging experiments, including studies that require a consistent red fluorescent reporter for colocalization or multi-color experiments. In probe construction pipelines, the maleimide chemistry provides a practical route to generate dye-labeled reagents for microscopy workflows and fluorescence assays that track biomolecular localization or binding events using TAMRA as the optical reporter.
4. Flow Cytometry Labeling
TAMRA maleimide, 5-isomer is used by flow cytometry users to generate fluorescently labeled biomolecules for cell-associated staining strategies that rely on thiol-containing ligands. Typical workflows include preparing TAMRA-tagged binding reagents (such as thiol-modified targeting ligands) to measure fluorescence associated with cell surfaces or cell-associated complexes. The dye's red fluorescence is often leveraged for multi-parameter cytometry panels where TAMRA provides spectral separation from common green and blue fluorophores, supporting robust signal readout in instrument-based fluorescence detection.
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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