CAPRYDAA, an anthracene dye analog to LAURDAN: a comparative study using cuvette and microscopy

Castro-Castillo, Vicente; Gajardo, Jean; Sandoval-Altamirano, Catalina; Gratton, Enrico; Sánchez, Susana A.; Malacrida, Leonel; Günther, Germán

doi:10.1039/c9tb01738k

Cited by 19 publications

(13 citation statements)

References 37 publications

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“…Thus, in contrast to HIV-Gag, the interaction of Arc with membranes is not appreciably enhanced by the presence of phosphoinositides. Hence, our initial studies of Arc-mediated effects on membrane morphology were conducted using GUVs generated from dioleoyl PC (DOPC) and labeled with LAURDAN as previously described (see, for example ( Bagatolli et al, 2003 ; Pott et al, 2008 ; Malacrida and Gratton, 2018 ; Castro-Castillo et al, 2019 )).…”

Section: Resultsmentioning

confidence: 99%

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Membrane Remodeling by Arc/Arg3.1

Hedde

Malacrida

Baryłko

et al. 2021

Front. Mol. Biosci.

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The activity-regulated cytoskeletal-associated protein (Arc, also known as Arg3.1) is an immediate early gene product induced by activity/experience and required for multiple modes of synaptic plasticity. Both long-term potentiation (LTP) and long-term depression (LTD) are impaired upon Arc deletion, as well as the ability to form long-term spatial, taste and fear memories. The best-characterized cellular function of Arc is enhancement of the endocytic internalization of AMPA receptors (AMPARs) in dendritic spines. Solution of the crystal structure of a C-terminal segment of Arc revealed a striking similarity to the capsid domain of HIV Gag. It was subsequently shown that Arc assembles into viral capsid-like structures that enclose Arc mRNA, are released into the extracellular space, and are internalized by neighboring cells. Thus, Arc is unique in participating in plasma membrane budding both into and out of the cell. In this report we study the interaction of Arc with membranes using giant unilamellar vesicles (GUVs). Using the fluorescent lipid probe LAURDAN, we find that Arc promotes the formation of smaller vesicles that penetrate into the GUV interior. Our results suggest that Arc induces negative membrane curvature and may therefore facilitate the formation of mRNA-containing extracellular vesicles from the plasma membrane.

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Section: Resultsmentioning

confidence: 99%

“…GUVs were formed by electroformation ( Angelova and Dimitrov, 1986 ) as previously reported ( Bagatolli et al, 2003 ; Pott et al, 2008 ; Hedde et al, 2017 ; Castro-Castillo et al, 2019 ). Briefly, a set of Pt wires and a Teflon growth chamber were cleaned by sonication in ethanol and in chloroform for 60 min each.…”

Section: Methodsmentioning

confidence: 99%

Membrane Remodeling by Arc/Arg3.1

Hedde

Malacrida

Baryłko

et al. 2021

Front. Mol. Biosci.

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“…21,[37][38] Indeed, in tightly packed Lo phase, characterized by lower hydration, polarity and fluidity, they show blue shifted emission compared to Ld phase. 31 A variety of solvatochromic dyes have been applied for this purpose, which includes Laurdan, 39 styrylpiridinium dyes, [40][41] 3-hydroxyflavones, 42 Nile Red, 43 push-pull anthracene, 44 pyrenes, [45][46] and dioxaborine, 34 etc. Previously, the efforts were mainly focused on targeting cell plasma membranes with solvatochromic dyes by grafting both charged and lipophilic groups, as exemplified for Di-4-ANEPPDHQ, 40 C-Laurdan, 47 Pro12A, 48 F2N12S, 33 NR12S, 43 etc.…”

Section: Introductionmentioning

confidence: 99%

Targeted Solvatochromic Fluorescent Probes for Imaging Lipid Order in Organelles under Oxidative and Mechanical Stress

2021

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Biomembranes constitute a basis for all compartments of live cells, and therefore monitoring their lipid organization is essential for understanding cell status and activity. However, sensing and imaging lipid organization specifically in different organelles of live cells remains challenging. Here, we designed an array of solvatochromic probes based on Nile Red bearing ligands for specific targeting of endoplasmic reticulum, mitochondria, lysosomes, Golgi apparatus, plasma membranes and lipid droplets. These polaritysensitive probes detected variations in the lipid order by changing their emission maximum, as evidenced by fluorescence spectroscopy in model membranes. In colocalization microscopy experiments with reference organelle markers, they exhibited good organelle selectivity. Using two-color fluorescence microscopy, the new probes enabled imaging local polarity of organelles in live cells. To exclude the biased effect of the probe design on the sensitivity to membrane properties, we calibrated all probes in model membranes under the microscope, which enabled first quantitative description of lipid order in each organelle of interest. Cholesterol extraction/enrichment confirmed capacity of the probes to sense lipid order, revealing that organelles poor in cholesterol are particularly affected by its enrichment. The probes also revealed that oxidative and mechanical stresses produced changes in the local polarity and lipid order that were characteristic for each organelle, with mitochondria and lysosomes being particularly stresssensitive. The new probes constitute a powerful toolbox for monitoring the response of the cells to physical and chemical stimuli at the level of membranes of individual organelles, which remains an underexplored direction in the cellular research.

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“…Anthracene derivatives have been widely studied as materials for organic electronics and other applications and continue to be of immense interest in various fields of materials chemistry and beyond. [1][2][3][4][5][6][7][8][9] New synthetic methods keep being developed to facilitate the preparation of known anthracene derivatives and to enable the preparation and study of new derivatives, e.g. our recently developed method for the synthesis of substituted 9,10-anthracenedicarbonitriles (also known as 9,10dicyanoanthracenes).…”

Section: Introductionmentioning

confidence: 99%

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

et al. 2020

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Anthracene derivatives have been used for a wide range of applications and many different synthetic methods for their preparation have been developed. However, despite continued synthetic efforts, introducing substituents in some positions has remained difficult. Here we present a method for the synthesis of 2,3,6,7-substituted anthracene derivatives, one of the most challenging anthracene substitution patterns to obtain. The method is exemplified by the preparation of 2,3,6,7-anthracenetetracarbonitrile and employs a newly developed, stable protected 1,2,4,5-benzenetetracarbaldehyde as the precursor. The precursor can be obtained in two scalable synthetic steps from 2,5-dibromoterephthalaldehyde and is converted into the anthracene derivative by a double intermolecular Wittig reaction under very mild conditions followed by a deprotection and intramolecular double ring-closing condensation reaction. Further modification of the precursor is expected to enable the introduction of additional substituents in other positions and may even enable the synthesis of fully substituted anthracene derivatives by the presented approach. File list (3) download file view on ChemRxiv Draft_final.pdf (351.19 KiB) download file view on ChemRxiv SI_final.pdf (550.08 KiB) download file view on ChemRxiv all.cif (559.68 KiB)

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CAPRYDAA, an anthracene dye analog to LAURDAN: a comparative study using cuvette and microscopy

Abstract: We synthesized an anthracene derivative with solvatochromic properties to be used as a molecular probe for membrane dynamics and supramolecular organization.

Cited by 19 publications

References 37 publications

Membrane Remodeling by Arc/Arg3.1

Membrane Remodeling by Arc/Arg3.1

Targeted Solvatochromic Fluorescent Probes for Imaging Lipid Order in Organelles under Oxidative and Mechanical Stress

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

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