MitoBlue: A Nontoxic and Photostable Blue-Emitting Dye That Selectively Labels Functional Mitochondria

Sánchez, Mateo I.; Martı́nez-Costas, José; Mascareñas, José L.; Vázquez, M. Eugenio

doi:10.1021/cb500552f

Cited by 9 publications

(11 citation statements)

References 49 publications

(77 reference statements)

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“…9 However, because TPP and most therapeutic drugs are nonemissive, additional conjugation of a fluorescent moiety is usually required to enable the monitoring of mitochondria‐specific drug delivery, which may disturb interactions between drugs and molecular targets, resulting in reduced therapeutic efficacy. An alternative approach demonstrated recently is the direct use of mitochondria‐targeted fluorophores to build fluorescent theranostic probes 10. Compared with the nonfluorescent TPP tag, mitochondria‐targeted fluorophores offer the potential for direct visualization of their intracellular delivery under fluorescence microscopy.…”

Section: Introductionmentioning

confidence: 99%

“…An alternative approach demonstratedr ecently is the direct use of mitochondria-targeted fluorophores to build fluorescent theranostic probes. [10] Compared with the nonfluorescent TPP tag,m itochondria-targeted fluorophores offer the potentialf or direct visualization of their intracellulard eliveryu nder fluorescence microscopy. For example,X ie et al reported an ovel fluorescentb oron dipyrromethene (BODIPY)-platinum conjugate that proved to localize predominantly in the mitochondria, and exhibited high cellular proliferation inhibition against humanc ervical carcinoma (HeLa) and humanb reast cancer( MCF-7) cells.…”

Section: Introductionmentioning

confidence: 99%

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Fluorescent Coumarin–Artemisinin Conjugates as Mitochondria‐Targeting Theranostic Probes for Enhanced Anticancer Activities

Zhang

et al. 2015

Chemistry A European J

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Mitochondria-targeting theranostic probes that enable the simultaneously reporting of and triggering of mitochondrial dysfunctions in cancer cells are highly attractive for cancer diagnosis and therapy. Three fluorescent mitochondria-targeting theranostic probes have been developed by linking a mitochondrial dye, coumarin-3-carboximide, with a widely used traditional Chinese medicine, artemisinin, to kill cancer cells. Fluorescence images showed that the designed coumarin-artemisinin conjugates localized mainly in mitochondria, leading to enhanced anticancer activities over artemisinin. High cytotoxicity against cancer cells correlated with the strong ability to accumulate in mitochondria, which could efficiently increase the intracellular reactive oxygen species level and induce cell apoptosis. This study highlights the potential of using mitochondria-targeting fluorophores to selectively trigger and directly visualize subcellular drug delivery in living cells.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fluorescent Coumarin–Artemisinin Conjugates as Mitochondria‐Targeting Theranostic Probes for Enhanced Anticancer Activities

Zhang

et al. 2015

Chemistry A European J

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“…[9,20,21] Bisbenzamidines are known to bind to the minor grooves of adenine/thymine-rich double-strandD NA. [22,23] Moreover,b enzamidine moieties present prominenta rgininem imetics and have often been used to address the S1 binding site of trypsin-like serine proteases. [24][25][26] In particular,d ibasic compounds containing at least one benzamidine substructure have been reported as potent inhibitors of trypsin, thrombin, factor Xa, matriptase and matriptase-2, indicating that severalb inding pockets within the active sites of these enzymes can be addressedb yb asic moieties.…”

Section: Introductionmentioning

confidence: 99%

Limiting the Number of Potential Binding Modes by Introducing Symmetry into Ligands: Structure‐Based Design of Inhibitors for Trypsin‐Like Serine Proteases

Furtmann

Häußler

Scheidt

et al. 2015

Chemistry A European J

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In the absence of X-ray data, the exploration of compound binding modes continues to be a challenging task. For structure-based design, specific features of active sites in different targets play a major role in rationalizing ligand binding characteristics. For example, dibasic compounds have been reported as potent inhibitors of various trypsin-like serine proteases, the active sites of which contain several binding pockets that can be targeted by cationic moieties. This results in several possible orientations within the active site, complicating the binding mode prediction of such compounds by docking tools. Therefore, we introduced symmetry in bi- and tribasic compounds to reduce conformational space in docking calculations and to simplify binding mode selection by limiting the number of possible pocket occupations. Asymmetric bisbenzamidines were used as starting points for a multistage and structure-guided optimization. A series of 24 final compounds with either two or three benzamidine substructures was ultimately synthesized and evaluated as inhibitors of five serine proteases, leading to potent symmetric inhibitors for the pharmaceutical drug targets matriptase, matriptase-2, thrombin and factor Xa. This study underlines the relevance of ligand symmetry for chemical biology.

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“…Another derivative of bis(4-aminostyryl) naphthalene exhibits a pronounced fluorescence and strong affinity for fibers and for that reason it was used as an optical brightener for improving the whiteness of materials [33]. The literature reports also indicate applications of fluorescent naphthylamines and aminidonaphthalic derivatives as fluorescent dyes in cell imaging [34,35].…”

Section: Introductionmentioning

confidence: 99%

Highly Fluorescent Distyrylnaphthalene Derivatives as a Tool for Visualization of Cellular Membranes

et al. 2020

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Fluorescent imaging, which is an important interdisciplinary field bridging research from organic chemistry, biochemistry and cell biology has been applied for multi-dimensional detection, visualization and characterization of biological structures and processes. Especially valuable is the possibility to monitor cellular processes in real time using fluorescent probes. In this work, conjugated oligoelectrolytes and neutral derivatives with the distyrylnaphthalene core (SN-COEs) were designed, synthetized and tested for biological properties as membrane-specific fluorescent dyes for the visualization of membrane-dependent cellular processes. The group of tested compounds includes newly synthesized distyrylnaphthalene derivatives (DSNNs): a trimethylammonium derivative (DSNN-NMe3+), a phosphonate derivative (DSNN-P), a morpholine derivative (DSNN-Mor), a dihydroxyethylamine derivative (DSNN-DEA), a phosphonate potassium salt (DSNN-POK), an amino derivative (DSNN-NH2) and pyridinium derivative (DSNN-Py+). All compounds were tested for their biological properties, including cytotoxicity and staining efficiency towards mammalian cells. The fluorescence intensity of SN-COEs incorporated into cellular structures was analyzed by fluorescence activated cell sorting (FACS) and photoluminescence spectroscopy. The cytotoxicity results have shown that all tested SN-COEs can be safely used in the human and animal cell studies. Fluorescence and confocal microscopy observations confirm that tested COEs can be applied as fluorescent probes for the visualization of intracellular membrane components in a wide range of different cell types, including adherent and suspension cells. The staining procedure may be performed under both serum free and complete medium conditions. The presented studies have revealed the interesting biological properties of SN-COEs and confirmed their applicability as dyes for staining the membranous structures of eukaryotic cells, which may be useful for visualization of wide range of biological processes dependent of the extra-/intracellular communications and/or based on the remodeling of cellular membranes.

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MitoBlue: A Nontoxic and Photostable Blue-Emitting Dye That Selectively Labels Functional Mitochondria

Cited by 9 publications

References 49 publications

Fluorescent Coumarin–Artemisinin Conjugates as Mitochondria‐Targeting Theranostic Probes for Enhanced Anticancer Activities

Fluorescent Coumarin–Artemisinin Conjugates as Mitochondria‐Targeting Theranostic Probes for Enhanced Anticancer Activities

Limiting the Number of Potential Binding Modes by Introducing Symmetry into Ligands: Structure‐Based Design of Inhibitors for Trypsin‐Like Serine Proteases

Highly Fluorescent Distyrylnaphthalene Derivatives as a Tool for Visualization of Cellular Membranes

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