{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Geng P"],"funding":["Deutsche Forschungsgemeinschaft"],"pagination":["e202203156"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC10107640"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["29(8)"],"pubmed_abstract":["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<sup>-1</sup>  s<sup>-1</sup> , 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-"],"journal":["Chemistry (Weinheim an der Bergstrasse, Germany)"],"pubmed_title":["Two-Factor Fluorogenicity of Tetrazine-Modified Cyanine-Styryl Dyes for Bioorthogonal Labelling of DNA."],"pmcid":["PMC10107640"],"funding_grant_id":["Wa 1387/17-2 und GRK 2039/2"],"pubmed_authors":["Wagenknecht HA","Ronicke F","Geng P","List E"],"additional_accession":[]},"is_claimable":false,"name":"Two-Factor Fluorogenicity of Tetrazine-Modified Cyanine-Styryl Dyes for Bioorthogonal Labelling of DNA.","description":"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<sup>-1</sup>  s<sup>-1</sup> , 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-","dates":{"release":"2023-01-01T00:00:00Z","publication":"2023 Feb","modification":"2025-04-26T04:57:03.535Z","creation":"2025-04-06T11:21:32.454Z"},"accession":"S-EPMC10107640","cross_references":{"pubmed":["36367152"],"doi":["10.1002/chem.202203156"]}}