Engineering of BODIPY-based theranostics for cancer therapy

Mao, Zhiqiang; Kim, Ji Hyeon; Lee, Jieun; Xiong, Hao; Zhang, Fan; Kim, Jong Seung

doi:10.1016/j.ccr.2022.214908

Cited by 70 publications

(55 citation statements)

References 231 publications

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“…However, 1,2,4-triazines possessing specific photophysical properties have seldom been used in optoelectrical research. Only a few 1,2,4-triazine derivatives have been employed as building blocks for organic photoactive materials, particularly organic light-emitting diodes [ 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. However, their closed nitrogen congeners (such as triazoles, pyrimidines, and s -triazines) are an inexhaustible source of numerous photoactive substances for various applications in optoelectronics and luminescent materials [ 19 , 20 , 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

et al. 2023

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New fluorescent dyes containing an assembled 1,4-dihydroazolo[5,1-c][1,2,4]triazine (DAT) core and an isoxazole ring were synthesized through a reaction between diazopyrazole or diazoimidazoles and isoxazolyl-derived enamines in mild conditions. The photophysical characteristics (maxima absorption and emission, Stokes shifts, fluorescent quantum yields, and fluorescence lifetimes) of the new fluorophores were obtained. The prepared DATs demonstrated emission maxima ranging within 433–487 nm, quantum yields within 6.1–33.3%, and a large Stokes shift. The photophysical characteristics of representative DAT examples were studied in ten different solvents. Specific (hydrogen bonds) and non-specific (dipole–dipole) intermolecular and intramolecular interactions were analyzed using XRD data and spectral experiments. Solvatochromism was analyzed using Lippert–Mataga and Dimroth–Reichardt plots, revealing the relationship between the DAT structure and the nature of solute–solvent interactions. The significant advantages of DATs are the fluorescence of their powders (QY up to 98.7%). DAT-NMe2 10 expressed bright aggregation-induced emission (AIE) behavior in DMSO and THF as the water content increased. The numerous possible variations of the structures of the heterocycles included in the DATs, as well as substituents, create excellent prospects for adjusting their photophysical and physicochemical properties.

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Section: Introductionmentioning

confidence: 99%

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

et al. 2023

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Section: Introductionmentioning

confidence: 99%

“…41,42 However, BODIPY-based photosensitizers are limited due to high hydrophobicity, low solubility and high aggregation, which reduce ROS production and restrict the PDT efficiency. 43,44 Recently, incorporation of BODIPY in different materials (for example, porous materials, silica and nanomaterials) have been shown to effectively inhibit BODIPY agglomeration and improve PDT efficiency. 45 To develop novel and potential broad-spectrum antibacterial agents to overcome bacterial resistance, and inspired by synergism, a light-activated nano-antibiotic composite (BODIPY-ZIF-90) was designed for synergistic antibacterial therapy.…”

Section: Introductionmentioning

confidence: 99%

Design of BODIPY functional ZIF-90 towards enhanced visible-light driven antibacterial performance

Chen

et al. 2023

New J. Chem.

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“…Therefore, recent efforts have also been put into development of nonporphyrin PSs . Among them, 4,4-difluoro-4-bora-3a,4a-diaza- s -indacenes (BODIPYs) have been considered superior candidates for PSs owing to their outstanding properties such as excellent photostability and biocompatibility, high molar extinction coefficient, and facile structural variation. , Some nice examples of NIR PSs are shown in Figure . − These BODIPY PSs have already shown great potential as a proof of principle concept to link with a tumor-targeting moiety or to combine with other antitumor strategies. In this regard, BODIPY PSs with excellent antitumor efficacy are highly desired.…”

Section: Introductionmentioning

confidence: 99%

Discovery of Subcellular-Targeted Aza-BODIPY Photosensitizers for Efficient Photodynamic Antitumor Therapy

Liu

et al. 2023

J. Med. Chem.

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In this study, we linked classical organelle-targeting groups, such as triphenylphosphonium, pentafluorobenzene, and morpholine, to our previously reported potent monoiodo Aza-BODIPY photosensitizer (BDP-15). They were conveniently prepared and retained the advantages of Aza-BODIPY PS with intense NIR absorption, moderate quantum yield, potent photosensitizing efficiency, and good stability. The in vitro antitumor assessment indicated that mitochondria-targeting and lysosome-targeting groups were more effective than ER-targeting groups. Considering undesirable dark toxicity of triphenylphosphonium-modified PSs, compound 6 containing amide-linked morpholine possessed a favorable dark/phototoxicity ratio (>6900 for tumor cells) and was localized in lysosomes with Pearson’s coefficient of 0.91 to Lyso-Tracker Green DND-26. 6 exhibited significantly increased intracellular ROS production and resulted in early/late apoptosis and necrosis to disrupt tumor cells. Moreover, in vivo antitumor efficacy exploration suggested that even under a slightly low dose of light (30 J/cm2) and single-time photoirradiation, 6 retarded tumor growth dramatically and displayed much better PDT activity over BDP-15 and Ce6.

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Engineering of BODIPY-based theranostics for cancer therapy

Cited by 70 publications

References 231 publications

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

Design of BODIPY functional ZIF-90 towards enhanced visible-light driven antibacterial performance

Discovery of Subcellular-Targeted Aza-BODIPY Photosensitizers for Efficient Photodynamic Antitumor Therapy

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