Silicon functionalization expands the repertoire of Si-rhodamine fluorescent probes

Rao, Desaboini Nageswara; Ji, Xincai; Miller, Stephen J.

doi:10.1039/d2sc01821g

Cited by 13 publications

(7 citation statements)

References 46 publications

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“…By now, no SiR dyes (or precursors suitable for SiR synthesis) with alkoxy substituents or with a tert -butyl-substituent have been published, and most of the published SiR dyes show a symmetrical (mainly dimethyl) substitution pattern. Recently, Miller et al achieved the synthesis of a library of Si-bridge-modified SiRs with, in part, two different substituents such as aromatics, alkyl chains, and linkers suitable for ligation (e.g., HaloTag, halogen propyl, azidopropyl, NHS ester) [ 29 ].…”

Section: Resultsmentioning

confidence: 99%

Efforts toward PET-Activatable Red-Shifted Silicon Rhodamines and Silicon Pyronine Dyes

et al. 2023

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Tracers for bimodal optical imaging and positron emission tomography unite multiple advantages in a single molecule. Their tumor-specific uptake can be visualized after their PET activation by radiofluorination via PET/CT or PET/MRI allowing for staging or therapy planning, while their non-radioactive moiety additionally facilitates the visualization of malignant tissue during intraoperative fluorescence-guided surgery or in histological assessments. The silicon-bridged xanthene core offers the opportunity for radiofluorination with SiFA isotope exchange to obtain a small-molecule, PET-activatable NIR dye that can be linked to different target vectors. Herein, we demonstrate for the first time the PET-activation of a fluorinated silicon pyronine, belonging to a class of low-molecular-weight fluorescence dyes with a large Stokes shift (up to 129 nm) and solvent-dependent NIR dye properties, with a successful radiochemical conversion of 70%. The non-fluorinated pyronine precursor is easily accessible by a three-step sequence from commercially starting material with a 12% overall yield. Moreover, a library of seven unusually functionalized (by approximately 15 nm), red-shifted silicon rhodamines were synthesized in three- to four-step sequences and the optical properties of the novel dyes were characterized. It was also shown that the synthesized silicon rhodamine dyes can be easily conjugated by amide bond formation or ‘click-reaction’ approaches.

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Section: Resultsmentioning

confidence: 99%

Efforts toward PET-Activatable Red-Shifted Silicon Rhodamines and Silicon Pyronine Dyes

et al. 2023

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“…However, it was recently shown that replacement of the methyl groups on the central Si atom of SiR could result in a small red-shift and increase in brightness while providing an alternative position to append functional groups including the HaloTag ligand. [36] Simple structural modifications can also improve fluorophore photostability, a key requirement for extended and quantitative imaging. Although the photobleaching mechanisms of rhodamines are complex and not fully understood, [37] several dye ligands with improved photostability have been reported.…”

Section: Rhodamine-based Ligandsmentioning

confidence: 99%

“…Alkylation at other positions on rhodamines has been scarcely reported. However, it was recently shown that replacement of the methyl groups on the central Si atom of SiR could result in a small red‐shift and increase in brightness while providing an alternative position to append functional groups including the HaloTag ligand [36] . Simple structural modifications can also improve fluorophore photostability, a key requirement for extended and quantitative imaging.…”

Section: Fluorescent and Fluorogenic Ligands For Halotag Protein Labe...mentioning

confidence: 99%

HaloTag‐Based Reporters for Fluorescence Imaging and Biosensing

2023

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Visualizing the structure and dynamics of biomolecules is critical to understand biological function, and requires methods to fluorescently label targets of interest in their cellular context. Self‐labelling proteins, which combine a genetically encoded tag with a small‐molecule fluorophore, have attracted considerable attention for this purpose, as they can overcome limitations of fluorescent proteins. Among them, the HaloTag protein is the most broadly used, showing fast specific labelling with a small, easy to functionalize and cell‐permeant ligand. Synthetic chemistry and protein engineering have provided a portfolio of powerful imaging tools exploiting HaloTag, along with general methods to optimize and adapt them to specific applications. Here, we provide an overview of fluorescent reporters based on the HaloTag protein for imaging and biosensing, highlighting engineering strategies and general applications.

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“…Rationally designed 'Si' substituted rhodamines, popularly known as Si-rhodamines have become popular nowadays for bioimaging studies including realtime in vivo imaging, as they possess much longer excitation wavelength (NIR) which can offer the potential for enhanced optical tissue-penetration apart from enabling increased signal to noise ratios (SNRs) and minimized photo-damage. 72,73 In recent times, rhodamine dyes are effectively conjugated with biomolecules and other tags to ensure precise intracellular targeting ability. Apart from possessing excellent photophysical properties, rhodamine dyes can endure spontaneous switching between spirocyclic/open-ring structures which has been exploited recently to perform many super-resolution imaging experiments (discussed in details later).…”

Section: Xanthene/rhodaminementioning

confidence: 99%

Xanthene, cyanine, oxazine and BODIPY: the four pillars of the fluorophore empire for super-resolution bioimaging

Samanta,

Lai,

et al. 2023

Chem. Soc. Rev.

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Silicon functionalization expands the repertoire of Si-rhodamine fluorescent probes

Abstract: Fluorescent dyes such as rhodamines are widely used to assay the activity and image the location of otherwise invisible molecules. Si-rhodamines, in which the bridging oxygen of rhodamines is replaced...

Cited by 13 publications

References 46 publications

Efforts toward PET-Activatable Red-Shifted Silicon Rhodamines and Silicon Pyronine Dyes

Efforts toward PET-Activatable Red-Shifted Silicon Rhodamines and Silicon Pyronine Dyes

HaloTag‐Based Reporters for Fluorescence Imaging and Biosensing

Xanthene, cyanine, oxazine and BODIPY: the four pillars of the fluorophore empire for super-resolution bioimaging

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