Abstract
Far-red cyanine fluorophores find extensive use in modern microscopy despite modest quantum yields. To improve the photon output of these molecules, we report a synthetic strategy that blocks the major deactivation pathway: excited-state trans-to-cis polyene rotation. In the key transformation, a protected dialdehyde precursor undergoes a cascade reaction to install the requisite tetracyclic ring system. The resulting molecules exhibit the characteristic features of conformational restraint, including improved fluorescence quantum yield and extended lifetime. Moreover, these compounds recover from hydride reduction with dramatically improved efficiency. These observations enable efficient single-molecule localization microscopy in oxygenated buffer without addition of thiols. Enabled by modern organic synthesis, these studies provide a new class of far-red dyes with promising spectroscopic and chemical properties.
🔬 Techniques
✨ Fluorophores
🔬 Cell Lines
🏛️ Research Organizations (ROR)
Affiliated research institutions:
📊 Figures
Figure 1.
(A) Conformational restraint applied to trimethine cyanines,(B) application to far-red cyanines (these studies), and (C) retrosynthesis.
Figure 2.
(A) Key structures and (B) their spectroscopic properties. (C) Absorbance/emission curves for 4 and 10 (750 nM in MeOH). (D) Temperature Dependence of the Emission of 4 (red u25a0) and 10 (black u25cf...
Figure 3.
Left : High quality 3D TRABI-BP SMLM image of F-Actin in a U2OS cell with 9 -phalloidin in PBS buffer. Right : (A) Lateral (x: black, y: red) and axial (blue) localization precisions calculated from t...
Scheme 1.
Synthetic Route to 4 (A) and 9 (B)
Figure images are served from the NIH/NLM PubMed Central Open Access Subset or Europe PMC; copyright remains with the publishers and authors.
💬 Discussion
0 commentsNo comments yet. Be the first to start a discussion!
Leave a Comment