Vinyl-pyridinium triphenylamines: novel far-red emitters with high photostability and two-photon absorption properties for staining DNA.
A series of mono-, bis- and trisvinyl-pyridinium triphenylamines (TP-py) has been synthesised and evaluated for its one- and two-photon absorption (2PA) induced-fluorescence properties under biological conditions. Interestingly, these compounds are only weakly fluorescent in water, whereas their fluorescence emissions are strongly restored (exaltation factors of 20-100) upon binding to double-stranded DNA. Additional measurements in glycerol indicate that the fluorescence increases are the result of immobilisation of the dyes in the DNA matrix, which inhibits rotational de-excitation modes. This particular feature is especially remarkable in the case of the bis and tris derivatives (TP-2 py, TP-3 py), which each display a high affinity (K(d) ~ microM) for dsDNA. TPIF measurements have shown that TP-2 py and TP-3 py each have a large 2PA cross section (delta up to 700 GM) both in glycerol and in the presence of DNA, which ranks them amongst the best 2PA biological fluorophores. Finally, one- and two-photon confocal imaging in cells revealed that these compounds perform red staining (lambda(em)=660-680 nm) of nuclear DNA with excellent contrast. The remarkable optical properties of the TP-py series, combined with their high photostability and their easy synthetic access, make these compounds extremely attractive for use in confocal and 2PA microscopy.
Allain
Clémence
C
Institut Curie UMR 176, Centre Universitaire, Bâtiment 110, 91405 Orsay, France.
Schmidt
Falk
F
Lartia
Rémy
R
Bordeau
Guillaume
G
Fiorini-Debuisschert
Céline
C
Charra
Fabrice
F
Tauc
Patrick
P
Teulade-Fichou
Marie-Paule
MP
D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D004247:DNA / Q000737:chemistry / Q000378:metabolism*; D007364:Intercalating Agents / Q000737:chemistry*; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D018613:Microscopy, Confocal; D036641:Microscopy, Fluorescence, Multiphoton; D017785:Photons; D011726:Pyridinium Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000814:Aniline Compounds; D007364:Intercalating Agents; D011726:Pyridinium Compounds; D014753:Vinyl Compounds; D004247:DNA