BODIPYs revealing lipid droplets as valuable targets for photodynamic theragnosis

Tabero, Andrea; García-Garrido, Fernando; Prieto‐Castañeda, Alejandro; Palao, Eduardo; Agarrabeitia, Antonia R.; García‐Moreno, Inmaculada; Villanueva, Ángeles; Cerero, Santiago de la Moya; Ortiz, María J.

doi:10.1039/c9cc09397d

Cited by 39 publications

(18 citation statements)

References 37 publications

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“…All compounds showed a strong fluorescence signal colocalized with lipid droplets (adiposomes) and a weak fluorescence signal colocalized either with lysosomes ( 3ab , 4ab , 5ab ) or the endoplasmatic reticulum ( 2ab ). Similar localization in lipid droplets has also been reported for other lipophilic BODIPYs [ 38 , 39 ].…”

Section: Resultssupporting

confidence: 84%

Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters

et al. 2021

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The photodynamic properties of a series of non-halogenated, dibrominated and diiodinated BODIPYs with a phthalimido or amino end modification on the phenoxypentyl and phenoxyoctyl linker in the meso position were investigated. Halogen substitution substantially increased the singlet oxygen production based on the heavy atom effect. This increase was accompanied by a higher photodynamic activity against skin melanoma cancer cells SK-MEL-28, with the best compound reaching an EC50 = 0.052 ± 0.01 µM upon light activation. The dark toxicity (toxicity without light activation) of all studied dyes was not detected up to the solubility limit in cell culture medium (10 µM). All studied BODIPY derivatives were predominantly found in adiposomes (lipid droplets) with further lower signals colocalized in either endolysosomal vesicles or the endoplasmic reticulum. A detailed investigation of cell death indicated that the compounds act primarily through the induction of apoptosis. In conclusion, halogenation in the 2,6 position of BODIPY dyes is crucial for the efficient photodynamic activity of these photosensitizers.

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Section: Resultssupporting

confidence: 84%

Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters

et al. 2021

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“…4 In this context, fluorescent bio-probes able to generate cytotoxic singlet oxygen ( 1 O 2 ) under light irradiation provides a good example. 5–9 Although conceptually inspiring, their development is still at an early stage since their dual activity demands a proper balance between competing photophysical phenomena (singlet vs. triplet activity) into a single dye: high enough fluorescence signal allowing bioimaging under severe irradiation conditions and/or prolonged times, and triplet-state population enabling the efficient production of 1 O 2 .…”

Section: Introductionmentioning

confidence: 99%

Generation of multiple triplet states in an orthogonal bodipy dimer: a breakthrough spectroscopic and theoretical approach

García‐Moreno

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Rebollar

et al. 2022

Phys. Chem. Chem. Phys.

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“…The synthesis of lipid droplets is at a lower level in normal cells, whereas tumor cells actively synthesize lipid droplets owing to their high-metabolism state [42,43]. Due to the suitable metabolic activity and stability, as well as their interactions with other organelles, especially mitochondrial, LDs can be valuable targets for PDT [44,45]. Therefore, AIEgens that could dual-target mitochondria and LDs may provide long-term photodynamic effect and better outcomes in PDT treatment procedure after administration of single-dose PSs.…”

Section: Introductionmentioning

confidence: 99%

Multiple Light-Activated Photodynamic Therapy of Tetraphenylethylene Derivative with AIE Characteristics for Hepatocellular Carcinoma via Dual-Organelles Targeting

et al. 2022

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Photodynamic therapy (PDT) has emerged as a promising locoregional therapy of hepatocellular carcinoma (HCC). The utilization of luminogens with aggregation-induced emission (AIE) characteristics provides a new opportunity to design functional photosensitizers (PS). PSs targeting the critical organelles that are susceptible to reactive oxygen species damage is a promising strategy to enhance the effectiveness of PDT. In this paper, a new PS, 1-[2-hydroxyethyl]-4-[4-(1,2,2-triphenylvinyl)styryl]pyridinium bromide (TPE-Py-OH) of tetraphenylethylene derivative with AIE feature was designed and synthesized for PDT. The TPE-Py-OH can not only simultaneously target lipid droplets and mitochondria, but also stay in cells for a long period (more than 7 days). Taking advantage of the long retention ability of TPE-Py-OH in tumor, the PDT effect of TPE-Py-OH can be activated through multiple irradiations after one injection, which provides a specific multiple light-activated PDT effect. We believe that this AIE-active PS will be promising for the tracking and photodynamic ablation of HCC with sustained effectiveness.

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BODIPYs revealing lipid droplets as valuable targets for photodynamic theragnosis

Abstract: Bright BODIPY photosensitizers reveal LDs as valuable targets for PDT.

Cited by 39 publications

References 37 publications

Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters

Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins’ Little Sisters

Generation of multiple triplet states in an orthogonal bodipy dimer: a breakthrough spectroscopic and theoretical approach

Multiple Light-Activated Photodynamic Therapy of Tetraphenylethylene Derivative with AIE Characteristics for Hepatocellular Carcinoma via Dual-Organelles Targeting

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