5-Carboxytetramethylrhodamine-PEG3-Azide (5-TAMRA-PEG3-Azide)

Product Information

An orange-red fluorophore for precision for all click chemistry applications

5-Carboxytetramethylrhodamine-PEG3-Azide (5-TAMRA-PEG3-Azide) is an orange red fluorescent dye widely used for the labeling of biomolecules using click chemistry. With excitation and emission maxima at approximately λ_ex ≈ 555 nm and λ_em ≈ 580 nm, it provides bright, photostable fluorescence compatible with Alexa Fluor® 555, DyLight® 549, and TRITC filter sets. Its reliable performance under physiological conditions makes it well suited for imaging, molecular tracking, and advanced bioconjugation workflows.

5-TAMRA-PEG3-Azide is a derivative of 5-TAMRA-Azide that incorporates a hydrophilic PEG3 spacer between the azide functional group and the fluorophore core. This spacer reduces steric hindrance during conjugation while significantly increasing water solubility. The PEG3 linker is particularly advantageous for labeling bulky biomolecules or sensitive biological systems, as it minimizes nonspecific interactions and reduces the need for organic solubilizing additives such as DMSO.

Key features that make 5‑TAMRA‑PEG3-Azide in bioorthogonal labeling

• High fluorescence intensity: Strong, reliable orange-red signal for imaging and detection.
• Fast, efficient click reactions: CuAAC labeling completes in under an hour with high yield.
• Bio‑orthogonal reaction: Selective azide–alkyne conjugation ensures maximal selectivity.
• Stability and durability: Triazole linkage remains intact under almost all conditions.
• Biologically inert: No interference with native cellular processes.
• Reduced steric interference: The PEG3 spacer minimizes steric interactions between the dye and the target molecule.
• Multiplexing capability: Works with other fluorophores for multi‑parameter analysis; can act as a quencher for FAM in dual‑labeled probes. For molecular beacons usually 5-TAMRA-Azide is used because there is no need for the additional spacer.

Applications in Research and Industry

Click Chemistry & Bioorthogonal Reactions:

Copper‑catalyzed azide–alkyne cycloaddition (CuAAC): enables the formation of stable, bio inert conjugates with reduced steric hindrance.

Copper‑free SPAAC labeling:

Compatible with DBCO and other strained alkyne derivatives, allowing labeling of sensitive biological systems.

FRET & Reaction Kinetics Studies:

TAMRA dyes can serve as fluorescence acceptors in Fluorescence Resonance Energy Transfer (FRET) assays, enhancing sensitivity in DNA sequencing, molecular interaction studies, and protein synthesis analysis. 5-TAMRA-PEG3-Azide can also be applied in reaction kinetics studies.

DNA & Protein Labeling:

Widely used in post synthetic DNA labeling, 5‑TAMRA-PEG3‑Azide facilitates efficient incorporation of multiple labels via CuAAC click chemistry, applicable in molecular diagnostics and nanotechnology. It has demonstrated strong fluorescent signals, can be applied to peptides, proteins, polysaccharides, viruses, and cells, extending its utility across various biological research areas. For example 5-Carboxytetramethylrhodamine-PEG3-Azide is used as detection reagent in all 555 variants of baseclick´s EdU cell proliferation detection kits.

With its versatile labeling capabilities, high selectivity, and robust fluorescence properties, 5‑TAMRA‑PEG3-Azide remains in combination with its mother dye 5-TAMRA-Azide a powerful tool for biomolecule detection, protein synthesis tracking, drug localization studies, and biomedical research.

LITERATURE

Postsynthetic DNA Modification through the Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction, P. M. E. Gramlich et al., 2008, Angew. Chemie Int. Ed., Vol. 47, p. 8350–8358.

https://doi.org/10.1002/anie.200802077

Click–Click–Click: Single to Triple Modification of DNA, P. M. E. Gramlich et al., 2008, Angew. Chemie Int. Ed., Vol. 47, p. 3442-3444.

https://doi.org/10.1002/anie.200705664

A chemical method for fast and sensitive detection of DNA synthesis in vivo, A. Salic et al., 2008, Proc. Natl. Acad. Sci. U. S. A., Vol. 105, p. 2415–2420.

https://doi.org/10.1073/pnas.0712168105

Chemoenzymatic Preparation of Functional Click-Labeled Messenger RNA, S. Croce et al., 2020, ChemBioChem, Vol. 21(11), p. 1641-1646.

https://doi.org/10.1002/cbic.201900718

Synthesis and biological evaluation of anthracene-9,10 dione derivatives as CK2 inhibitors, P. López-Rojas et al., 2023, Results in Chemistry, Vol. 6, p. 100997.

https://doi.org/10.1016/j.rechem.2023.100997