Glycosaminoglycan‐Induced Emissive J‐Aggregate Formation in a <i>meso</i>‐Ester BODIPY Dye

Kim, Dami; Lee, Uisung; Bouffard, Jean; Kim, Youngmi

doi:10.1002/adom.201902161

Cited by 28 publications

(22 citation statements)

References 55 publications

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Section: Photophysical Property Changes Of Conventional Fluorophore A...mentioning

confidence: 99%

“…The interaction with heparin, however, disrupted these spherical aggregates to J‐aggregated supramolecular assemblies, and it associated a high turn‐on response with specific interactions. [ 26 ]…”

Section: Photophysical Property Changes Of Conventional Fluorophore A...mentioning

confidence: 99%

“…Recently, Kim et al successfully developed a new meso ester BODIPY dye (6) and studied their photophysical and self-assembling properties (Figure 2C). [26] The team elegantly used these emissive J-aggregate fluorescent "light-up" probes for the selective detection of heparin. The molecular recognition event between heparin and BODIPY generated emissive J-aggregates, which were well validated by their narrow linewidths, improved emission rates, red-shifted bands, and efficiency (Figure 2C).…”

Section: 2mentioning

confidence: 99%

“…The interaction with heparin, however, disrupted these spherical aggregates to J-aggregated supramolecular assemblies, and it associated a high turn-on response with specific interactions. [26] F I G U R E 3 Chemical structure, photophysical property changes, and biological applications of fluorophore aggregates. (A) Time-lapse images of mice cerebral vasculature with carotid arterial thrombosis to the left hemisphere, after administration of the dye 9 were depicted.…”

Section: 2mentioning

confidence: 99%

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Recent trends in molecular aggregates: An exploration of biomedicine

et al. 2022

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Molecular aggregates are receiving tremendous attention, demonstrating immense potential for biomedical applications in vitro and in vivo. For instance, the molecular aggregates of conventional fluorophores influence the electronic excitation states of the aggregates, causing characteristic photophysical property changes. A fundamental understanding of this classical relationship between molecular aggregate structures and photophysics has allowed for innovative biological applications. The chemical characteristics of drug molecules generally trigger the formation of colloidal aggregates, and this is considered detrimental to the drug discovery process. Furthermore, nano-sized supramolecular aggregates have been used in biomedical imaging and therapy owing to their optimal properties for in vivo utility, including enhanced cell permeability, passive tumor targeting, and convenient surface engineering. Herein, we provide an overview of the recent trends in molecular aggregates for biomedical applications. The changes in photophysical properties of conventional fluorophores and their biological applications are discussed, followed by the effects of conventional drug molecule-aggregates on drug discovery and therapeutics development. Recent trends in the investigation of biologically important analytes with aggregation-induced emission are discussed for conventional and unconventional fluorophores. Lastly, we discuss nano-sized supramolecular aggregates used in imaging and therapeutic purposes, with a focus on in vivo utilization.

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Section: Photophysical Property Changes Of Conventional Fluorophore A...mentioning

confidence: 99%

Section: Photophysical Property Changes Of Conventional Fluorophore A...mentioning

confidence: 99%

Section: 2mentioning

confidence: 99%

Section: 2mentioning

confidence: 99%

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Recent trends in molecular aggregates: An exploration of biomedicine

et al. 2022

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“…The dramatic changes in spectral characteristics of the organic pigments from the monomeric to the aggregated form provide the basis for effective biosensing where the dye specifically interacts with the target molecules and convert from a fluorescence-quenched state to a fluorescence-active state to achieve fluorescence enhancement. These dye-aggregate probes have been investigated to selectively detect small molecules [ 46 , 47 ], proteins [ 48 ], DNA [ 49 ], and glycosaminoglycans [ 50 ]. One example demonstrated that an amphiphilic dicyanovinyl squaraine SQgl [ 49 ] could serve as a highly selective probe to detect G-quadruplexes (G4) in the parallel configuration (Fig.…”

Section: Utilization Of Dye Aggregates For Biomedical Applicationsmentioning

confidence: 99%

Interfacing DNA nanotechnology and biomimetic photonic complexes: advances and prospects in energy and biomedicine

2022

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Self-assembled photonic systems with well-organized spatial arrangement and engineered optical properties can be used as efficient energy materials and as effective biomedical agents. The lessons learned from natural light-harvesting antennas have inspired the design and synthesis of a series of biomimetic photonic complexes, including those containing strongly coupled dye aggregates with dense molecular packing and unique spectroscopic features. These photoactive components provide excellent features that could be coupled to multiple applications including light-harvesting, energy transfer, biosensing, bioimaging, and cancer therapy. Meanwhile, nanoscale DNA assemblies have been employed as programmable and addressable templates to guide the formation of DNA-directed multi-pigment complexes, which can be used to enhance the complexity and precision of artificial photonic systems and show the potential for energy and biomedical applications. This review focuses on the interface of DNA nanotechnology and biomimetic photonic systems. We summarized the recent progress in the design, synthesis, and applications of bioinspired photonic systems, highlighted the advantages of the utilization of DNA nanostructures, and discussed the challenges and opportunities they provide. Graphical Abstract

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BODIPY as a Multifunctional Theranostic Reagent in Biomedicine: Self‐Assembly, Properties, and Applications

et al. 2023

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owing to its large molar absorption coefficients, high emission quantum yields, satisfactory chemical stability, and high tunability of photophysical properties. [10,11] The conventional BODIPY core has good structural stability, in which BF 2 -chelated inhibits the rotation around the CN pyrrole bridging bonds, which enhances the structural rigidity and endows the system with fluorescence emission properties. [12] The BODIPY core has 8 covalently modified positions, which can be divided into pyrrole ring carbons, the meso-carbon, and the boron atom. [11,13,14] These abundant active sites provide lots of possibilities to expand the structure of BODIPY derivatives through functionalization and to tune their photophysical properties. [15] In the past few decades, the structural modification strategies of BODIPY units and the resulting effects have been systematically explored, [4,16] providing a solid research foundation for the current-stage design and construction of various functional BODIPY derivatives for different occasions. After decades of development, by virtue of the high molar extinction coefficient, longer wavelength absorbing, outstanding photosensitivity, satisfactory internal stability, better biocompatibility relative to inorganic dyes, high light-dark toxicity ratios, and preferable photothermal conversion efficiency (PCE), [4,[17][18][19] there has been considerable interest in exploring the application of BODIPY as photosensitizers (PSs) in the area of phototherapy, which involves the production of reactive The use of boron dipyrromethene (BODIPY) in biomedicine is reviewed. To open, its synthesis and regulatory strategies are summarized, and inspiring cutting-edge work in post-functionalization strategies is highlighted. A brief overview of assembly model of BODIPY is then provided: BODIPY is introduced as a promising building block for the formation of single-and multicomponent self-assembled systems, including nanostructures suitable for aqueous environments, thereby showing the great development potential of supramolecular assembly in biomedicine applications. The frontier progress of BODIPY in biomedical application is thereafter described, supported by examples of the frontiers of biomedical applications of BODIPY-containing smart materials: it mainly involves the application of materials based on BODIPY building blocks and their assemblies in fluorescence bioimaging, photoacoustic imaging, disease treatment including photodynamic therapy, photothermal therapy, and immunotherapy. Lastly, not only the current status of the BODIPY family in the biomedical field but also the challenges worth considering are summarized. At the same time, insights into the future development prospects of biomedically applicable BODIPY are provided.

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Glycosaminoglycan‐Induced Emissive J‐Aggregate Formation in a meso‐Ester BODIPY Dye

Cited by 28 publications

References 55 publications

Recent trends in molecular aggregates: An exploration of biomedicine

Recent trends in molecular aggregates: An exploration of biomedicine

Interfacing DNA nanotechnology and biomimetic photonic complexes: advances and prospects in energy and biomedicine

BODIPY as a Multifunctional Theranostic Reagent in Biomedicine: Self‐Assembly, Properties, and Applications

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