BODIPY/Nile‐Red‐Based Efficient FRET Pair: Selective Assay of Endoplasmic Reticulum Membrane Fluidity

Yang, Zhigang; Wi, Youngjin; Yoon, Yong Jin; Verwilst, Peter; Jang, Jin Woo; Kim, Tae Woo; Kang, Chulhun; Kim, Jong Seung

doi:10.1002/asia.201501060

Cited by 15 publications

(9 citation statements)

References 27 publications

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“…A representative atomic force microscopy image of FRET nanoparticles is shown in Figure 1B. BODIPY-FL and Nile Red were selected as the D−A pair, respectively, due to their excellent spectral overlap 44 (Figure 1C).…”

Section: Resultsmentioning

confidence: 99%

Förster Resonance Energy Transfer-Based Stability Assessment of PLGA Nanoparticles in Vitro and in Vivo

Swider

Maharjan

Houkes

et al. 2019

ACS Appl. Bio Mater.

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The knowledge of in vitro and in vivo stability of polymeric nanoparticles is vital for the development of clinical formulations for drug delivery and cell labeling applications. Förster resonance energy transfer (FRET)-based fluorescence labeling approaches are promising tools to study nanoparticle stability under different physiological conditions. Here, we present the FRET-based stability assessment of poly(lactic-co-glycolic acid) (PLGA) nanoparticles encapsulating BODIPY-FL12 and Nile Red as the donor and acceptor, respectively. The stability of PLGA nanoparticles is studied via monitoring the variations of fluorescence emission characteristics along with colloidal characterization. Accordingly, PLGA nanoparticles are colloidally stable for more than 2 weeks when incubated in aqueous buffers in situ, whereas in vitro particle degradation starts in between 24 and 48 h, reaching a complete loss of FRET at 72 h as shown with fluorescence microscopy imaging and flow cytometry analysis. PLGA nanoparticles systemically administered to mice predominantly accumulate in the liver, in which FRET no longer takes place at time points as early as 24 h postadministration as determined by ex vivo organ imaging and flow cytometry analysis. The results of this study expand our knowledge on drug release and degradation behavior of PLGA nanoparticles under different physiological conditions, which will prove useful for the rational design of PLGA-based formulations for various applications that can be translated into clinical practice.

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Section: Resultsmentioning

confidence: 99%

Förster Resonance Energy Transfer-Based Stability Assessment of PLGA Nanoparticles in Vitro and in Vivo

Swider

Maharjan

Houkes

et al. 2019

ACS Appl. Bio Mater.

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show abstract

“…Similarly, two more ER‐targeting fluorescent ratiometric probes for ER stress have been designed following the same lipophilic chain strategy ( 116 and 117 , Scheme ). Both probes anchor to the ER membrane while ratiometrically responding to changes in the ER viscosity under induced stress ,. These studies are very solid investigations into ER‐targeting fluorescent probes.…”

Section: Activatable Fluorescent Probes For Targeting the Endoplasmimentioning

confidence: 93%

Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

et al. 2016

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Principle has it that even the most advanced super-resolution microscope would be futile in providing biological insight into subcellular matrices without well-designed fluorescent tags/probes. Developments in biology have increasingly been boosted by advances of chemistry, with one prominent example being small-molecule fluorescent probes that not only allow cellular-level imaging, but also subcellular imaging. A majority, if not all, of the chemical/biological events take place inside cellular organelles, and researchers have been shifting their attention towards these substructures with the help of fluorescence techniques. This Review summarizes the existing fluorescent probes that target chemical/biological events within a single organelle. More importantly, organelle-anchoring strategies are described and emphasized to inspire the design of new generations of fluorescent probes, before concluding with future prospects on the possible further development of chemical biology.

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“…This issueas well as the scarcity of synthetically accessible nitrosophenol and 1-naphthol derivativesis likely to have discouraged the development of de novo synthesized analogues . A few examples of substituted Nile Red analogues have been reported in the literature, including 6-fluoro, 6-bromo, and 6-acyloxy derivatives and a collection of 2- and 3-alkoxy derivatives. − Indeed, the 6-position is the site of the highest frontier electron density, and the 2- or 3-oxy derivatives are straightforward due to the commercial availability of 1,6- and 1,7-naphthalenediols.…”

Section: Introductionmentioning

confidence: 99%

Substituted 9-Diethylaminobenzo[a]phenoxazin-5-ones (Nile Red Analogues): Synthesis and Photophysical Properties

et al. 2020

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Nile Red is a benzo[a]phenoxazone dye containing a diethylamino substituent at the 9-position. In recent years, it has become a popular histological stain for cellular membranes and lipid droplets due to its unrivaled fluorescent properties in lipophilic environments. This makes it an attractive lead for chemical decoration to tweak its attributes and optimize it for more specialized microscopy techniques, e.g., fluorescence lifetime imaging or two-photon excited fluorescence microscopy, to which Nile Red has never been optimized. Herein, we present synthesis approaches to a series of monosubstituted Nile Red derivatives (9-diethylbenzo[a]phenoxazin-5-ones) starting from 1-naphthols or 1,3-naphthalenediols. The solvatochromic responsiveness of these fluorophores is reported with focus on how the substituents affect the absorption and emission spectra, luminosity, fluorescence lifetimes, and two-photon absorptivity. Several of the analogues emerge as strong candidates for reporting the polarity of their local environment. Specifically, the one- and two-photon excited fluorescence of Nile Red turns out to be very responsive to substitution, and the spectroscopic features can be finely tuned by judiciously introducing substituents of distinct electronic character at specific positions. This new toolkit of 9-diethylbenzo[a]phenoxazine-5-ones constitutes a step toward the next generation of optical molecular probes for advancing the understanding of lipid structures and cellular processes.

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BODIPY/Nile‐Red‐Based Efficient FRET Pair: Selective Assay of Endoplasmic Reticulum Membrane Fluidity

Cited by 15 publications

References 27 publications

Förster Resonance Energy Transfer-Based Stability Assessment of PLGA Nanoparticles in Vitro and in Vivo

Förster Resonance Energy Transfer-Based Stability Assessment of PLGA Nanoparticles in Vitro and in Vivo

Discerning the Chemistry in Individual Organelles with Small‐Molecule Fluorescent Probes

Substituted 9-Diethylaminobenzo[a]phenoxazin-5-ones (Nile Red Analogues): Synthesis and Photophysical Properties

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