Green- to far-red-emitting fluorogenic tetrazine probes – synthetic access and no-wash protein imaging inside living cells† †Electronic supplementary information (ESI) available: Synthetic procedures and spectroscopic data, details of cell experiments and imaging. See DOI: 10.1039/c6sc03879d Click here for additional data file.

نویسندگان

  • Achim Wieczorek
  • Philipp Werther
  • Jonas Euchner
  • Richard Wombacher
چکیده

Fluorogenic probes for bioorthogonal labeling chemistry are highly beneficial to reduce background signal in fluorescence microscopy imaging. 1,2,4,5-Tetrazines are known substrates for the bioorthogonal inverse electron demand Diels–Alder reaction (DAinv) and tetrazine substituted fluorophores can exhibit fluorogenic properties. Herein, we report the synthesis of a palette of novel fluorogenic tetrazine dyes derived from widely-used fluorophores that cover the entire emission range from green to far-red. We demonstrate the power of the new fluorogenic probes in fixed and live cell labeling experiments and present the first example of intracellular live cell protein imaging using tetrazine-based probes under nowash conditions.

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Green- to far-red-emitting fluorogenic tetrazine probes - synthetic access and no-wash protein imaging inside living cells.

Fluorogenic probes for bioorthogonal labeling chemistry are highly beneficial to reduce background signal in fluorescence microscopy imaging. 1,2,4,5-Tetrazines are known substrates for the bioorthogonal inverse electron demand Diels-Alder reaction (DAinv) and tetrazine substituted fluorophores can exhibit fluorogenic properties. Herein, we report the synthesis of a palette of novel fluorogenic...

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A far-red emitting probe for unambiguous detection of mobile zinc in acidic vesicles and deep tissue† †Electronic supplementary information (ESI) available: General methods, synthetic procedures, NMR spectra, kinetic data, pH profile, metal selectivity graph, cell culture and staining protocols, wide-field microscopy experiments, tissue specimen preparation, and two-photon imaging techniques. See DOI: 10.1039/c4sc03388d Click here for additional data file.

Imaging mobile zinc in acidic environments remains challenging because most small-molecule optical probes display pH-dependent fluorescence. Here we report a reaction-based sensor that detects mobile zinc unambiguously at low pH. The sensor responds reversibly and with a large dynamic range to exogenously applied Zn2+ in lysosomes of HeLa cells, endogenous Zn2+ in insulin granules of MIN6 cells...

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عنوان ژورنال:

دوره 8  شماره 

صفحات  -

تاریخ انتشار 2017