Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group.
Caged near-IR emitting fluorescent dyes are in high demand in optical microscopy but up to now were unavailable. We discovered that the combination of a carbopyronine dye core and a photosensitive 2-diazo-1-indanone residue leads to masked near-IR emitting fluorescent dyes. Illumination of these caged dyes with either UV or visible light (λ < 420 nm) efficiently generates fluorescent compounds with absorption and emission at 635 nm and 660 nm, respectively. A high-yielding synthetic route with attractive possibilities for further dye design is described in detail. Good photostability, high contrast, and a large fluorescence quantum yield after uncaging are the most important features of the new compounds for non-invasive imaging in high-resolution optical microscopy. For use in immunolabelling the caged dyes were decorated with a (hydrophilic) linker and an (activated) carboxyl group.
Department of NanoBiophotonics, Max Planck Institute for Biophysical Chemistry, Göttingen, Germany.
Kirill
K
Kolmakov
Christian
C
Wurm
Maksim V
MV
Sednev
Mariano L
ML
Bossi
Vladimir N
VN
Belov
Stefan W
SW
Hell
D000818:Animals; D001372:Aza Compounds / Q000737:chemistry*; D002460:Cell Line; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D007189:Indans / Q000737:chemistry*; D015394:Molecular Structure; D017319:Photosensitizing Agents / Q000737:chemistry*; D011754:Pyronine / Q000031:analogs & derivatives* / Q000737:chemistry*; D051381:Rats; D013237:Stereoisomerism
C574904:2-diazo-1-indanone; D001372:Aza Compounds; D005456:Fluorescent Dyes; D007189:Indans; D017319:Photosensitizing Agents; D011754:Pyronine