Fluorous Soluble Cyanine Dyes for Visualizing Perfluorocarbons in Living Systems

Lim, Irene; Vian, Antoine; Wouw, Heidi L. van de; Day, Rachael A.; Gómez, Carlos M. Meléndez; Liu, Yucen; Rheingold, Arnold L.; Campàs, Otger; Sletten, Ellen M.

doi:10.1021/jacs.0c07761

Cited by 53 publications

(55 citation statements)

References 61 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The dye was isolated by column chromatography in 9% yield. The synthesized fluorous Cy5 dye was then diluted in the ferrofluid at a final concentration of 25 μ M. We have previously show that the dye is biocompatible and enables robust 3D measurements of mechanical stresses 51 .…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Stress-driven tissue fluidization physically segments vertebrate somites

Shelton

et al. 2021

Preprint

Self Cite

View full text Add to dashboard Cite

Shaping functional structures during embryonic development requires both genetic and physical control. During somitogenesis, cell-cell coordination sets up genetic traveling waves in the presomitic mesoderm (PSM) that orchestrate somite formation. While key molecular and genetic aspects of this process are known, the mechanical events required to physically segment somites from the PSM remain unclear. Combining direct mechanical measurements during somite formation, live imaging of cell and tissue structure, and computer simulations, here we show that somites are mechanically sectioned off from the PSM by a large, actomyosin-driven increase in anisotropic stress at the nascent somite-somite boundary. Our results show that this localized increase in stress drives the regional fluidization of the tissue adjacent to the forming somite border, enabling local tissue remodeling and the shaping of the somite. Moreover, we find that active tension fluctuations in the tissue are optimized to mechanically define sharp somite boundaries while minimizing somite morphological defects. Altogether, these results indicate that mechanical changes at the somite-somite border and optimal tension fluctuations in the tissue are essential physical aspects of somite formation.

show abstract

Section: Methodsmentioning

confidence: 99%

“…While fluorous Rhodamine dyes have been previously used to visualize droplets 30,37 , longer wavelength dyes are preferred for full 3D reconstructions of droplets. The fluorous Cy5 was synthesized using a similar protocol as previously described 51 . Briefly, a branched fluorous ketone was reacted with phenyl hydrazine to produce a fluorous indole.…”

mentioning

confidence: 99%

Stress-driven tissue fluidization physically segments vertebrate somites

Shelton

et al. 2021

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

“…As seen in Scheme 16, cyanine dyes with perfluorocarbon chains were synthesized; these compounds were designed with the intention of being studied for nano/microdroplet studied in biological systems [70]. The fluorinated chains modify the compound to be soluble in the fluorous phase opening for application avenues.…”

Section: Fluorinated Cyanine Dyesmentioning

confidence: 99%

Synthesis and Applications of Selected Fluorine-Containing Fluorophores

Casa

Henary

2021

Molecules

View full text Add to dashboard Cite

The synthesis of fluorine-containing small molecules has had numerous benefits of improving the quality and efficiency of many applications of these compounds. For example, fluorine adds promising functionalities in various areas of imaging (MRI, PET, and NIR); gives cell-targeting properties; and has demonstrated improvements in cell permeability, solubility, and other pharmacologic properties. For these and other numerous reasons, fluorination of molecules has grown in popularity in various fields of chemistry. Many reports show the effects observed from increasing the number of fluorine atoms on a fluorophore scaffold. This report will cover the most significant applications and improvements that fluorine has contributed to in various dye scaffolds such as BODIPY, rhodamine, phthalocyanine, and cyanine in the recent decade.

show abstract

“…Surface-labeled droplets were coated with Cy5-streptavidin. Volume-labeled droplets were prepared by dissolving FCy5 dye [19] in Novec 7300 fluorocarbon oil (3M) at a 25 µM concentration. A fluorinated Krytox-PEG(600) surfactant (008-fluorosurfactant, RAN Biotechnologies) was also diluted in the fluorocarbon oil at a 2.5% (w/w) concentration.…”

Section: Imaging and Sample Preparationmentioning

confidence: 99%

“…1d). However, for droplets prepared with fluorescently labelled fluorocarbon oil [9,19,20] (Fig. 1b), which display fluorescence signal throughout the droplet, we used an attenuated sigmoid profile model that captures both the fluorescence intensity fast change at the droplet surface and the mild attenuation of fluorescence inside the droplet (due to imaging a 3D object).…”

Section: Obtaining the Point Cloudmentioning

confidence: 99%

STRESS, an automated geometrical characterization of deformable particles forin vivomeasurements of cell and tissue mechanical stresses

Gross

Shelton

Gómez

et al. 2021

Preprint

Self Cite

View full text Add to dashboard Cite

From cellular mechanotransduction to the formation of embryonic tissues and organs, mechanics has been shown to play an important role in the control of cell behavior and embryonic development. Most of our existing knowledge of how mechanics affects cell behavior comes from in vitro studies, mainly because measuring cell and tissue mechanics in 3D multicellular systems, and especially in vivo, remains challenging. Oil microdroplet sensors, and more recently gel microbeads, use surface deformations to directly quantify mechanical stresses within developing tissues, in vivo and in situ, as well as in 3D in vitro systems like organoids or multicellular spheroids. However, an automated analysis software able to quantify the spatiotemporal evolution of stresses and their characteristics from particle deformations is lacking. Here we develop STRESS (Surface Topography Reconstruction for Evaluation of Spatiotemporal Stresses), an analysis software to quantify the geometry of deformable particles of spherical topology, such as microdroplets or gel microbeads, that enables the automatic quantification of the temporal evolution of stresses in the system and the spatiotemporal features of stress inhomogeneities in the tissue. As a test case, we apply this new code to measure the temporal evolution of mechanical stresses using oil microdroplets in developing zebrafish tissues. Starting from a 3D timelapse of a droplet, the software automatically calculates the statistics of local anisotropic stresses, decouples the deformation modes associated with tissue- and cell-scale stresses, obtains their spatial features on the droplet surface and analyzes their spatiotemporal variations using spatial and temporal stress autocorrelations. The automated nature of the analysis will help users obtain quantitative information about mechanical stresses in a wide range of 3D multicellular systems, from developing embryos or tissue explants to organoids.

show abstract

Fluorous Soluble Cyanine Dyes for Visualizing Perfluorocarbons in Living Systems

Cited by 53 publications

References 61 publications

Stress-driven tissue fluidization physically segments vertebrate somites

Stress-driven tissue fluidization physically segments vertebrate somites

Synthesis and Applications of Selected Fluorine-Containing Fluorophores

STRESS, an automated geometrical characterization of deformable particles forin vivomeasurements of cell and tissue mechanical stresses

Contact Info

Product

Resources

About