Enhancement of fluorescent properties of near-infrared dyes using clickable oligoglycerol dendrons

Abstract

Near-infrared (NIR) fluorescent dyes are gaining increased attention due to their potential to serve as molecular probes for in vivo imaging. Here, we demonstrate that oligoglycerol dendrons effectively enhance the fluorescence properties of an NIR dye by increasing the solubility in water and the prevention of aggregate formation. First- and second-generation oligoglycerol dendrons were conjugated to an NIR dye via a dipolar-cycloaddition (click) reaction. The two new dye conjugates exhibited enhanced NIR fluorescent emission and considerably higher fluorescent quantum yields than the dye alone. The high photostability measured for one of the oligoglycerol-linked dyes, in comparison to commonly used fluorogenic dyes such as Cy5 and Cy7, was validated using fluorescence microscopy of macrophages.

Fluorescent and lasing whispering gallery mode microresonators for sensing applications

“…Fluorescent dyes are the most common gain media used for active microresonators, providing a broad range of emission bands stretching from the UV , to the visible and through to the near infrared as shown in Table .…”

Molecular Insight into Long‐Wavelength Fluorogenic Dye Design: Hydrogen Bond Induces Activation of a Dormant Acceptor

“…[7][8][9] Such molecules should have ah igh physiological stability,h igh quantum yields of fluorescence, long emission wavelengths, large Stokes shifts, and ag ood photostability. [10][11][12] We have recently developed an ovel class of turn-ONc yanine-based probesw ith al ongwavelength fluorescence emission. [13] The probesa re based on the fluorochromeQ Cy7, which is generated upon removal of as pecifict rigger moiety by an analyte of interest.…”

“…Thus, there is a demand for more sensitive, more specific, and more versatile fluorescent molecules that can be used for in vitro and in vivo applications 7–9. Such molecules should have a high physiological stability, high quantum yields of fluorescence, long emission wavelengths, large Stokes shifts, and a good photostability 10–12. We have recently developed a novel class of turn‐ON cyanine‐based probes with a long‐wavelength fluorescence emission 13.…”

Highly Photostable and Fluorescent Microporous Solids Prepared via Solid-State Entrapment of Boron Dipyrromethene Dyes in a Nascent Metal–Organic Framework

“…The enhanced photostability of PM605 within ZIF-8 may be due to partial shielding of the dye excited state by the framework, with reduced molecular mobility and hindered encounters with solvent and/or O 2 molecules minimizing the rates of photochemical (e.g., rearrangements) and photophysical (e.g., sensitization of singlet oxygen followed by chromophore oxidation) processes related to dye photobleaching . Similar mechanisms have been suggested for dyes complexed to supramolecular hosts , or linked to dendrimers. − …”