Two-Factor Fluorogenicity of Tetrazine-Modified Cyanine-Styryl Dyes for Bioorthogonal Labelling of DNA. 2023

Philipp Geng, and Eileen List, and Franziska Rönicke, and Hans-Achim Wagenknecht
Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.

Two green fluorescent tetrazine-modified cyanine-styryl dyes were synthesized for bioorthogonal labelling of DNA by means of the Diels-Alder reaction with inverse electron demand. With DNA as target biopolymer the fluorescence of these dyes is released by two factors: (i) sterically by their interaction with DNA, and (ii) structurally via the conjugated tetrazine as quencher moiety. As a result, the reaction with bicyclononyne-modified DNA is significantly accelerated up to ≥284,000 M-1  s-1 , and the fluorescence turn-on is enhanced up to 560 by the two-factor fluorogenicity. These dyes are cell permeable even in low concentrations and undergo fluorogenic reactions with BCN-modified DNA in living HeLa cells. The two-factor fluorescence release improves the signal-to-noise ratio such that washing procedures prior to cell imaging are not needed, which is a great advantage for live cell imaging of DNA and RNA in the future.

UI MeSH Term Description Entries
D004247 DNA A deoxyribonucleotide polymer that is the primary genetic material of all cells. Eukaryotic and prokaryotic organisms normally contain DNA in a double-stranded state, yet several important biological processes transiently involve single-stranded regions. DNA, which consists of a polysugar-phosphate backbone possessing projections of purines (adenine and guanine) and pyrimidines (thymine and cytosine), forms a double helix that is held together by hydrogen bonds between these purines and pyrimidines (adenine to thymine and guanine to cytosine). DNA, Double-Stranded,Deoxyribonucleic Acid,ds-DNA,DNA, Double Stranded,Double-Stranded DNA,ds DNA
D005456 Fluorescent Dyes Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. Flourescent Agent,Fluorescent Dye,Fluorescent Probe,Fluorescent Probes,Fluorochrome,Fluorochromes,Fluorogenic Substrates,Fluorescence Agents,Fluorescent Agents,Fluorogenic Substrate,Agents, Fluorescence,Agents, Fluorescent,Dyes, Fluorescent,Probes, Fluorescent,Substrates, Fluorogenic
D006367 HeLa Cells The first continuously cultured human malignant CELL LINE, derived from the cervical carcinoma of Henrietta Lacks. These cells are used for, among other things, VIRUS CULTIVATION and PRECLINICAL DRUG EVALUATION assays. Cell, HeLa,Cells, HeLa,HeLa Cell
D006571 Heterocyclic Compounds Cyclic compounds that include atoms other than carbon in their ring structure. Heterocyclic Compound,Compound, Heterocyclic,Compounds, Heterocyclic
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D061565 Cycloaddition Reaction Synthetic organic reactions that use reactions between unsaturated molecules to form cyclical products. Cycloaddition,Cycloaddition Reaction Techniques,Diels-Alder Reaction,Cycloaddition Reaction Technique,Cycloaddition Reactions,Diels Alder Reaction,Reaction Technique, Cycloaddition,Reaction Techniques, Cycloaddition,Reaction, Cycloaddition,Reaction, Diels-Alder,Reactions, Cycloaddition,Technique, Cycloaddition Reaction,Techniques, Cycloaddition Reaction

Related Publications

Philipp Geng, and Eileen List, and Franziska Rönicke, and Hans-Achim Wagenknecht
February 2024, Chembiochem : a European journal of chemical biology,
Philipp Geng, and Eileen List, and Franziska Rönicke, and Hans-Achim Wagenknecht
October 2022, Natural sciences (Weinheim, Germany),
Philipp Geng, and Eileen List, and Franziska Rönicke, and Hans-Achim Wagenknecht
January 2019, Communications biology,
Philipp Geng, and Eileen List, and Franziska Rönicke, and Hans-Achim Wagenknecht
November 2013, Organic & biomolecular chemistry,
Philipp Geng, and Eileen List, and Franziska Rönicke, and Hans-Achim Wagenknecht
August 2017, ChemistryOpen,
Philipp Geng, and Eileen List, and Franziska Rönicke, and Hans-Achim Wagenknecht
January 2023, RSC advances,
Philipp Geng, and Eileen List, and Franziska Rönicke, and Hans-Achim Wagenknecht
July 2022, Molecules (Basel, Switzerland),
Philipp Geng, and Eileen List, and Franziska Rönicke, and Hans-Achim Wagenknecht
February 2015, Journal of photochemistry and photobiology. B, Biology,
Philipp Geng, and Eileen List, and Franziska Rönicke, and Hans-Achim Wagenknecht
March 2016, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy,
Philipp Geng, and Eileen List, and Franziska Rönicke, and Hans-Achim Wagenknecht
October 2023, Nature chemistry,
Copied contents to your clipboard!