title: Vinyl-triphenylamine dyes, a new family of switchable fluorescent probes for targeted two-photon cellular imaging: from DNA to protein labeling.
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.
authors.affiliation: UMR 176 CNRS/Institut Curie, Institut Curie, Bât 110, Université Paris-Sud, F-91405 Orsay, France.
authors.forename: Blaise
authors.initials: B
authors.lastname: Dumat
authors.forename: Guillaume
authors.initials: G
authors.lastname: Bordeau
authors.forename: Ana I
authors.initials: AI
authors.lastname: Aranda
authors.forename: Florence
authors.initials: F
authors.lastname: Mahuteau-Betzer
authors.forename: Yara
authors.initials: Y
authors.lastname: El Harfouch
authors.forename: Germain
authors.initials: G
authors.lastname: Metgé
authors.forename: Fabrice
authors.initials: F
authors.lastname: Charra
authors.forename: Céline
authors.initials: C
authors.lastname: Fiorini-Debuisschert
authors.forename: Marie-Paule
authors.initials: MP
authors.lastname: Teulade-Fichou
mesh_terms: D000588:Amines / Q000737:chemistry*; D004247:DNA / Q000378:metabolism*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D019073:HT29 Cells; D006801:Humans; D057054:Molecular Imaging / Q000379:methods*; D055620:Optical Phenomena; D017785:Photons; D012709:Serum Albumin / Q000378:metabolism*; D013194:Staining and Labeling; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D000588:Amines; D005456:Fluorescent Dyes; D012709:Serum Albumin; D014753:Vinyl Compounds; D004247:DNA