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Optimized RNA labeling: Paired metabolic reporters

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Explore the advantages of our new vinyl-modified nucleosides, which offer in combination with our labeled Pyrimidyl tetrazines the ability as high efficient metabolic reporters in RNA expression profiling!

The efficiency of nucleoside incorporation and detection with high selectivity is essential for RNA synthesis monitoring. Thus, vinyl-modified nucleosides, such as 2-Vinyl-adenosine (2-VA) and 7-Deaza-vinyl-adenosine (7-dVA) offer many advantages in application as metabolic chemical reporters in living cells as they are cell-permeable, stable and selective substrates[1,2]. Due to the small-sized alkene-moiety they are able to undergo bioorthogonal labeling and do not inhibit cellular proliferation[1-3].

Related to more conventional CuAAC reaction, the inverse electron-demand Diels-Alder (IEDDA) reaction presents an attractive method for imaging vinyl-functionalized RNA due to
  • fast kinetics (~0.02 M-1s-1)
  • high yields
  • high efficiency
  • avoidance of cytotoxic Cu-catalyst
Pairing those special features of vinyl-nucleosides with suitable and highly reactive Pyrimidyl tetrazines containing fluorescent dyes optimizes the required reactivity and selectivity for labeling nascent RNA in cells and animals[1-3] as well as in vitro synthesized biomolecules[1,4].

Figure 1: Scheme of metabolic labeling of RNA with cell-permeable vinyl-modified nucleosides 2-VA or 7-dVA, respectively. Subsequently, nascent vinyl-functionalized RNA can be monitored by fast undergo IEDDA reaction with using fluorescent Pyrimidyl tetra

Figure 1: Scheme of metabolic labeling of RNA with cell-permeable vinyl-modified nucleosides 2-VA or 7-dVA, respectively. Subsequently, nascent vinyl-functionalized RNA can be monitored by fast undergo IEDDA reaction with using fluorescent Pyrimidyl tetrazines.

Vinyl-modified nucleosides offered from stock by Jena Bioscience:

Product Cat.-No. Amount Price
2-Vinyl-adenosine (2-VA) CLK-106-10 10 mg 115,00 €
CLK-106-50 50 mg 400,00 €
7-Deaza-vinyl-adenosine (7-dVA) CLK-107-10 10 mg 115,00 €
CLK-107-50 50 mg 400,00 €
5-Vinyl-uridine (5-VU) CLK-049-10 10 mg 114,75 €
CLK-049-50 50 mg 395,55 €
5-Vinyl-2'-deoxyuridine (5-VdU) CLK-050-10 10 mg 114,75 €
CLK-050-50 50 mg 395,55 €
Dr. Fadi Younis

Please email Fadi with any questions.

Please inquire for custom compounds!

Selected References:

[1] Kubota et al. (2019) Expanding the Scope of RNA Metabolic Labeling with Vinyl Nucleosides and Inverse Electron-Demand Diels−Alder Chemistry. ACS Chem. Biol. 14:1698.
[2] Liu et al. (2019) A Nucleoside Derivative 5‑Vinyluridine (VrU) for Imaging RNA in Cells and Animals. Bioconjugate Chem. 30:2958
[3] Rieder et al. (2014) Alkene-Tetrazine Ligation for Imaging Cellular DNA. Angew. Chem. Int. Ed. 53:9168.
[4] Busskamp et al. (2014) Efficient labeling of enzymatically synthesized vinyl-modified DNA by an inverse-electron-demand Diels-Alder reaction. Chem. Commun. (Camb). 50:10827.