Addressable Cholesterol Analogs for Live Imaging of Cellular Membranes

Rakers, Lena; Grill, David; Matos, Anna Lívia Linard; Wulff, Stephanie; Da, Wang; Börgel, Jonas; Körsgen, Martin; Arlinghaus, Heinrich F.; Galla, Hans‐Joachim; Gerke, Volker; Glorius, Frank

doi:10.1016/j.chembiol.2018.04.015

Cited by 23 publications

(35 citation statements)

References 60 publications

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“…Cholesterol analogs CHIM and CHIM-L were synthesized as previously described 9 . The synthesis was performed starting from commercially available cholesterol that was converted into the corresponding 2,3-cholestandione in five steps.…”

Section: Methodsmentioning

confidence: 99%

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CHIMs are versatile cholesterol analogs mimicking and visualizing cholesterol behavior in lipid bilayers and cells

et al. 2021

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Cholesterol is an essential component of cellular membranes regulating the structural integrity and fluidity of biological bilayers and cellular processes such as signal transduction and membrane trafficking. However, tools to investigate the role and dynamics of cholesterol in live cells are still scarce and often show limited applicability. To address this, we previously developed a class of imidazolium-based cholesterol analogs, CHIMs. Here we confirm that CHIM membrane integration characteristics largely mimic those of cholesterol. Computational studies in simulated phospholipid bilayers and biophysical analyses of model membranes reveal that in biologically relevant systems CHIMs behave similarly to natural cholesterol. Importantly, the analogs can functionally replace cholesterol in membranes, can be readily labeled by click chemistry and follow trafficking pathways of cholesterol in live cells. Thus, CHIMs represent chemically versatile cholesterol analogs that can serve as a flexible toolbox to study cholesterol behavior and function in live cells and organisms.

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Section: Methodsmentioning

confidence: 99%

“…We therefore developed a class of imidazolium-based lipids including cholesterol analogs that integrate into model and cellular membranes 9 – 14 . These include cholesterol analogs (Fig.…”

Section: Introductionmentioning

confidence: 99%

CHIMs are versatile cholesterol analogs mimicking and visualizing cholesterol behavior in lipid bilayers and cells

et al. 2021

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“…Apart from their activity in the hydrogenation of aromatics, as they are derived from cholesterol, these new nanosystems could have interesting possibilities as biological recognition systems. Another interesting ligand effect, this time involving NHCs derived from cholesterol [98], was reported by Rakers et al in 2018 ( Figure 21) [99]. These Ru NPs showed remarkable activity in the hydrogenation of arene derivatives, and a noticeable influence of the ligand due to their steric differences.…”

Section: Modifying the Catalytic Propertiesmentioning

confidence: 70%

Organometallic Nanoparticles Ligated by NHCs: Synthesis, Surface Chemistry and Ligand Effects

2020

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Over the last 20 years, the use of metallic nanoparticles (MNPs) in catalysis has awakened a great interest in the scientific community, mainly due to the many advantages of this kind of nanostructures in catalytic applications. MNPs exhibit the characteristic stability of heterogeneous catalysts, but with a higher active surface area than conventional metallic materials. However, despite their higher activity, MNPs present a wide variety of active sites, which makes it difficult to control their selectivity in catalytic processes. An efficient way to modulate the activity/selectivity of MNPs is the use of coordinating ligands, which transforms the MNP surface, subsequently modifying the nanoparticle catalytic properties. In relation to this, the use of Nheterocyclic carbenes (NHC) as stabilizing ligands has been demonstrated to be an effective tool to modify the size, stability, solubility and catalytic reactivity of MNPs. Although NHC-stabilized MNPs can be prepared by different synthetic methods, this review is centered on those prepared by an organometallic approach. Here, an organometallic precursor is decomposed under H2 in the presence of non-stoichiometric amounts of the corresponding NHC-ligand. The resulting organometallic nanoparticles present a clean surface, which makes them perfect candidates for catalytic applications and surface studies. In short, this revision study emphasizes the great versatility of NHC ligands as MNP stabilizers, as well as their influence on catalysis.

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“…Rakers et al [5] . reported the synthesis of several cholesterol‐derived IMs (Figure 6) which behave like cholesterol analogues while passing through cell membrane and when internalized by living cells.…”

Section: Cellular and Intracellular Imagingmentioning

confidence: 99%

“…In the living world, the use of fluorescent probes to investigate the behavior of biological membranes, liposomes, proteins, and nucleic acids is fundamental. For instance, it is possible to evaluate the fluidity of lipid bilayers with or without cholesterol, whose thickening role is well known [4,5] . Thus, the electrostatic, and more generally, non‐covalent character of weak interactions that can be engaged by molecular salts constitutes a key element to obtain remarkably diverse biological activities.…”

Section: Introductionmentioning

confidence: 99%

Luminescent Imidazolium Salts as Bright Multi‐Faceted Tools for Biology

2021

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Light and cognate phenomena, e. g., luminescence are powerful tools endowed with great sensitivity to explore the infinitely small. Molecular salts, especially those based on imidazolium units, are granted with original properties and structural versatility. Associated with fluorophores, they constitute highly bioavailable platforms. Their interactions with negatively charged species and biological membranes as well as their controllable cytotoxicity imparted their applications as anion receptors, but also a promising potential as antibacterial and anticancer agents whose mechanism of action can be observed using luminescence, opening the possibility of theranostics (therapy and diagnosis). One of the other assets of imidazolium salts is their flexible amphipathic character which promotes their self‐organizations into liquid‐crystal mesophases and their ability to mimic lipids. Combining luminescence to these amphipathic properties opens new prospects, e. g., following gene or drug delivery inside cells. These salts, all‐in‐one, should lead to new tools for biologists, as well as active theranostic molecules.

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Addressable Cholesterol Analogs for Live Imaging of Cellular Membranes

Cited by 23 publications

References 60 publications

CHIMs are versatile cholesterol analogs mimicking and visualizing cholesterol behavior in lipid bilayers and cells

CHIMs are versatile cholesterol analogs mimicking and visualizing cholesterol behavior in lipid bilayers and cells

Organometallic Nanoparticles Ligated by NHCs: Synthesis, Surface Chemistry and Ligand Effects

Luminescent Imidazolium Salts as Bright Multi‐Faceted Tools for Biology

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