An Amphiphilic Perylene Imido Diester for Selective Cellular Imaging

Heek, Timm; Nikolaus, Jörg; Schwarzer, Roland; Fasting, Carlo; Welker, Pia; Licha, Kai; Herrmann, Andreas; Haag, Rainer

doi:10.1021/bc3005655

Cited by 76 publications

(68 citation statements)

References 53 publications

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“…Similarly, Haag et al reported spherical micelles self‐assembled from perylene imino diesters (PIDEs) bearing two alkyl chains and a polyglycerol dendron of which the fluorescence quantum yield is extremely low (Figure a,b). However, PIDE 48 recovers high fluorescence in an lipophilic environment.…”

Section: Nanoparticles Based On Self‐assembled π‐Conjugated Small Molmentioning

confidence: 83%

“…a) Chemical structure of PBI 47 by Genovese et al and PIDE 48 used as b) a dye to stain membranes by Haag et al, as well as the chemical structure of Pe‐Cbl 49 and 50 by Singh et al and Zhao et al, respectively, which have been explored as c) single‐component perylene‐based drug delivery system for photocontrolled delivery of an anticancer drug. b) Reproduced with permission . Copyright 2013 , American Chemical Society.…”

Section: Nanoparticles Based On Self‐assembled π‐Conjugated Small Molmentioning

confidence: 99%

See 1 more Smart Citation

Self-Assembled Fluorescent Nanoparticles from π-Conjugated Small Molecules: En Route to Biological Applications

Schill

Schenning

Brunsveld

2015

Macromol. Rapid Commun.

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Since the development of supramolecular chemical biology, self-organised nano-architectures have been widely explored in a variety of biomedical applications. Functionalized synthetic molecules with the ability of non-covalent assembly in an aqueous environment are typically able to interact with biological systems and are therefore especially interesting for their use in theranostics. Nanostructures based on π-conjugated oligomers are particularly promising as theranostic platforms as they bear outstanding photophysical properties as well as drug loading capabilities. This Feature Article provides an overview on the recent advances in the self-assembly of intrinsically fluorescent nanoparticles from π-conjugated small molecules such as fluorene or perylene based chromophores for biomedical applications.

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Section: Nanoparticles Based On Self‐assembled π‐Conjugated Small Molmentioning

confidence: 83%

Section: Nanoparticles Based On Self‐assembled π‐Conjugated Small Molmentioning

confidence: 99%

Self-Assembled Fluorescent Nanoparticles from π-Conjugated Small Molecules: En Route to Biological Applications

Schill

Schenning

Brunsveld

2015

Macromol. Rapid Commun.

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“…However, these dyes still have aggregation‐related issues that lead to fluorescence quenching, and therefore, little success has been achieved regarding specificity . Notably, PBI absorption and emission spectral properties that are well‐matched with commonly used lipophilic probes have rarely been exploited for LD imaging either in vivo or in vitro.…”

Section: Methodsmentioning

confidence: 99%

Selective Imaging of Lipids in Adipocytes by Using an Imidazolyl Derivative of Perylene Bisimide

et al. 2018

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A small molecule, perylene bisimide imidazolyl derivative (PBI-ID), has been identified and developed as a specific marker for labelling multifunctional fat bodies in various organisms, including Drosophila and mammalian adipocytes. Interestingly, PBI-ID neither labels the plasma membranes nor cell nuclei by trapping into it. A remarkable feature of unbound PBI-ID is diminished fluorescence, which reduces the background emission noise, while contrasting the bound state effectively.

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“…1 Among the different chains used, it has been shown that branched alkyl chains tend to soften the π-conjugated materials to a greater extent than attaching linear n alkyl chains and allow to tune both the molecular-scale and bulk material properties of soft matter. 7 Additionally, due to their excellent photophysical properties, great efforts have been dedicated to the production of highly water-soluble perylene derivatives 8−10 in order to apply them in different areas such as in the field of cellular imaging, 11 in vitro staining of cells and proteins, 12 in the aqueous dispersion of single wall carbon nanotubes, 13 or in the development of multilayer films for photophysical studies. 14 On the other hand, by using suitable flexible chains as substituents in PBI derivatives, it has been possible to induce liquid crystallinity.…”

Section: ■ Introductionmentioning

confidence: 99%

Electron Transport in a Water-Soluble Liquid-Crystalline Perylene Bisimide

et al. 2014

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Perylene bisimide (PBI) derivatives are n-type semiconductor materials widely used in a variety of optoelectronic devices. Great efforts have been devoted to the synthesis of soluble PBIs to allow processing by inexpensive solution-state methods. Recently, water-soluble compounds are receiving special attention for their potential in the fields of biology and "green" organic electronics. There is also a growing interest in the development of liquid crystalline PBIs, in order to improve the supramolecular organization and hence the transport performance. This work reports the first investigation of the mobility measured by the time-of-flight technique and the photoconductive response of the perylene derivative N,N′-bis[1-(2,5,8,11-tetraoxadodec-1-yl)-3,6,9,12-tetraoxatridec-1-yl]-perylene-3,4:9,10-bis(dicarboximide) (PBI-W), which is simultaneously water-soluble and liquid-crystalline. For comparison purposes, a parallel investigation with the commercial derivative N,N′-bis(1-hexylheptyl)-perylene-3,4:9,10-bis(dicarboximide) (PBI-C6), which is neither liquid-crystal nor water-soluble, has also been carried out. The conductive spectral response and the mobility dependence on the strength of the applied electric field were studied in order to optimize mobility measurements conditions. The mobility was determined as a function of temperature from room temperature (22°C) up to 100 and 120°C, for PBI-W and PBI-C6, respectively. Results are discussed in correlation with the crystalline or liquid-crystalline character phase of the material.

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An Amphiphilic Perylene Imido Diester for Selective Cellular Imaging

Cited by 76 publications

References 53 publications

Self-Assembled Fluorescent Nanoparticles from π-Conjugated Small Molecules: En Route to Biological Applications

Self-Assembled Fluorescent Nanoparticles from π-Conjugated Small Molecules: En Route to Biological Applications

Selective Imaging of Lipids in Adipocytes by Using an Imidazolyl Derivative of Perylene Bisimide

Electron Transport in a Water-Soluble Liquid-Crystalline Perylene Bisimide

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