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Issue 30, 2012
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Vinyl-triphenylamine dyes, a new family of switchable fluorescent probes for targeted two-photon cellular imaging: from DNA to protein labeling

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Abstract

On the basis of our previous work on vinyl-triphenylamine derived DNA fluorophores we explored the structure space around this core by coupling it to diverse cationic, anionic and zwitterionic groups in the aim of targeting different classes of biomolecules. In parallel core modifications were performed to optimize the photophysical properties (quantum yield, two-photon absorption). The resulting water soluble π-conjugated molecules are called TP dyes and display an exceptional combination of optical properties: high two-photon absorption cross-section, high photostability, no self-quenching, and switchable fluorescence emission when bound to a biopolymer matrix. The linear and nonlinear optical properties of the TP dyes were studied in vitro in presence of DNA and in presence of a model protein (human serum albumin) using complementary absorption and fluorescence spectroscopy characterization tools. Structure modifications enabled to switch from DNA probes (cationic TP-pyridinium series) to protein probes (anionic TP-rhodanine series) without affecting the optical properties. Finally most TP compounds appear cell-permeant and show an intracellular localization consistent with their in vitro target specificity.

Graphical abstract: Vinyl-triphenylamine dyes, a new family of switchable fluorescent probes for targeted two-photon cellular imaging: from DNA to protein labeling

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Publication details

The article was received on 09 Mar 2012, accepted on 01 May 2012, published on 21 May 2012 and first published online on 21 May 2012


Article type: Paper
DOI: 10.1039/C2OB25515D
Citation: Org. Biomol. Chem., 2012,10, 6054-6061
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    Vinyl-triphenylamine dyes, a new family of switchable fluorescent probes for targeted two-photon cellular imaging: from DNA to protein labeling

    B. Dumat, G. Bordeau, A. I. Aranda, F. Mahuteau-Betzer, Y. E. Harfouch, G. Metgé, F. Charra, C. Fiorini-Debuisschert and M. Teulade-Fichou, Org. Biomol. Chem., 2012, 10, 6054
    DOI: 10.1039/C2OB25515D

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