Multifunctional Gene Carriers Labeled by Perylene Diimide Derivative as Fluorescent Probe for Tracking Gene Delivery

Li, Qian; Hao, Xiao‐Jiang; Guo, Jintang; Ren, Xiang‐Kui; Xia, Shihai; Zhang, Wencheng; Feng, Yakai

doi:10.1002/marc.201800916

Cited by 12 publications

(5 citation statements)

References 36 publications

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“…[ 14 , 15 ] In particular, a wide range of applications of PBIs were recently explored in organic solar cells (OSCs) where they found use in interlayers, [16] as sensitizers, [17] or as non‐fullerene acceptors (NFAs). [ 18 , 19 ] Furthermore, PBIs are applied as fluorescence labels for bioimaging[ 20 , 21 ] and as fluorescence dyes for single‐molecule spectroscopy and microscopy. [22] …”

Section: Introductionmentioning

confidence: 99%

Chiral Perylene Bisimide Dyes by Interlocked Arene Substituents in the Bay Area

Renner

Mahlmeister²,

Anhalt³

et al. 2021

Chemistry A European J

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A series of perylene bisimide (PBI) dyes bearing various aryl substituents in 1,6,7,12 bay positions has been synthesized by Suzuki cross‐coupling reaction. These molecules exhibit an exceptionally large and conformationally fixed twist angle of the PBI π‐core due to the high steric congestion imparted by the aryl substituents in bay positions. Single crystal X‐ray analyses of phenyl‐, naphthyl‐ and pyrenyl‐functionalized PBIs reveal interlocked π‐π‐stacking motifs, leading to conformational chirality and the possibility for the isolation of enantiopure atropoisomers by semipreparative HPLC. The interlocked arrangement endows these molecules with substantial racemization barriers of about 120 kJ mol−1 for the tetraphenyl‐ and tetra‐2‐naphthyl‐substituted derivatives, which is among the highest racemization barriers for axially chiral PBIs. Variable temperature NMR studies reveal the presence of a multitude of up to fourteen conformational isomers in solution that are interconverted via smaller activation barriers of about 65 kJ mol−1. The redox and optical properties of these core‐twisted PBIs have been characterized by cyclic voltammetry, UV/Vis/NIR and fluorescence spectroscopy and their respective atropo‐enantiomers were further characterized by circular dichroism (CD) and circular polarized luminescence (CPL) spectroscopy.

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Section: Introductionmentioning

confidence: 99%

Chiral Perylene Bisimide Dyes by Interlocked Arene Substituents in the Bay Area

Renner

Mahlmeister²,

Anhalt³

et al. 2021

Chemistry A European J

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show abstract

“…An asymmetric 1,6,7,12-tetrachloro-PDI derivative was linked to polyethylenimine-g-poly(lactide-co-glycolide)-g-polyethylenimine ( PLGA-PEI ) polymer to obtain fluorescent multifunctional polymer. Then, a peptide sequence was grafted using the free carboxylic group to attain multifunctional micelles labelled with fluorescent PDI ( Scheme 10 ) [ 117 ]. These micelles exhibited enhanced photobleaching stability, and the fluorescent images of cellular uptake show bright red emission.…”

Section: Perylenediimide (Pdi)-based Systems For Bioimaging Ptt and Pdtmentioning

confidence: 99%

Recent Advances in Applications of Fluorescent Perylenediimide and Perylenemonoimide Dyes in Bioimaging, Photothermal and Photodynamic Therapy

Krupka

Hudhomme

2023

IJMS

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The emblematic perylenediimide (PDI) motif which was initially used as a simple dye has undergone incredible development in recent decades. The increasing power of synthetic organic chemistry has allowed it to decorate PDIs to achieve highly functional dyes. As these PDI derivatives combine thermal, chemical and photostability, with an additional high absorption coefficient and near-unity fluorescence quantum yield, they have been widely studied for applications in materials science, particularly in photovoltaics. Although PDIs have always been in the spotlight, their asymmetric counterparts, perylenemonoimide (PMI) analogues, are now experiencing a resurgence of interest with new efforts to create architectures with equally exciting properties. Namely, their exceptional fluorescence properties have recently been used to develop novel systems for applications in bioimaging, biosensing and photodynamic therapy. This review covers the state of the art in the synthesis, photophysical characterizations and recently reported applications demonstrating the versatility of these two sister PDI and PMI compounds. The objective is to show that after well-known applications in materials science, the emerging trends in the use of PDI- and PMI-based derivatives concern very specific biomedicinal applications including drug delivery, diagnostics and theranostics.

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“…Unless extensive washing procedures are used, multichannel flow cytometry cannot discriminate between extracellularly bound polyplexes and intracellularly distributed ones, rendering cell uptake measurements within the polymer library challenging. , Even if washing procedures were implemented, considerable cell loss would reduce the statistical confidence in flow cytometric comparisons. Critically, even powerful multiplexed platforms such as spectral flow cytometry are not sufficiently sensitive to changes in cell morphology and shape. , Imaging flow cytometry can address the existing shortcomings of conventional cytometry by providing accurate quantification of cellular uptake, intracellular localization of proteins and DNA, as well as cell morphological profiling. − Despite the promise of imaging flow cytometry, it has found limited application in the development of nonviral vectors, possibly due to the high investment involved. Measurement approaches, such as image cytometry, unite the high throughput of flow cytometry and mechanistic insights provided by fluorescence microscopy and could transform the in vitro evaluation of polymeric vector performance.…”

Section: High-throughput Evaluation Of Polymeric Gene Delivery In Cel...mentioning

confidence: 99%

Materiomically Designed Polymeric Vehicles for Nucleic Acids: Quo Vadis?

Kumar

2022

ACS Appl. Bio Mater.

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Despite rapid advances in molecular biology, particularly in site-specific genome editing technologies, such as CRISPR/Cas9 and base editing, financial and logistical challenges hinder a broad population from accessing and benefiting from gene therapy. To improve the affordability and scalability of gene therapy, we need to deploy chemically defined, economical, and scalable materials, such as synthetic polymers. For polymers to deliver nucleic acids efficaciously to targeted cells, they must optimally combine design attributes, such as architecture, length, composition, spatial distribution of monomers, basicity, hydrophilic−hydrophobic phase balance, or protonation degree. Designing polymeric vectors for specific nucleic acid payloads is a multivariate optimization problem wherein even minuscule deviations from the optimum are poorly tolerated. To explore the multivariate polymer design space rapidly, efficiently, and fruitfully, we must integrate parallelized polymer synthesis, high-throughput biological screening, and statistical modeling. Although materiomics approaches promise to streamline polymeric vector development, several methodological ambiguities must be resolved. For instance, establishing a flexible polymer ontology that accommodates recent synthetic advances, enforcing uniform polymer characterization and data reporting standards, and implementing multiplexed in vitro and in vivo screening studies require considerable planning, coordination, and effort. This contribution will acquaint readers with the challenges associated with materiomics approaches to polymeric gene delivery and offers guidelines for overcoming these challenges. Here, we summarize recent developments in combinatorial polymer synthesis, high-throughput screening of polymeric vectors, omics-based approaches to polymer design, barcoding schemes for pooled in vitro and in vivo screening, and identify materiomics-inspired research directions that will realize the long-unfulfilled clinical potential of polymeric carriers in gene therapy.

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Multifunctional Gene Carriers Labeled by Perylene Diimide Derivative as Fluorescent Probe for Tracking Gene Delivery

Cited by 12 publications

References 36 publications

Chiral Perylene Bisimide Dyes by Interlocked Arene Substituents in the Bay Area

Chiral Perylene Bisimide Dyes by Interlocked Arene Substituents in the Bay Area

Recent Advances in Applications of Fluorescent Perylenediimide and Perylenemonoimide Dyes in Bioimaging, Photothermal and Photodynamic Therapy

Materiomically Designed Polymeric Vehicles for Nucleic Acids: Quo Vadis?

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