Synthesis and in vitro evaluation of a PDT active BODIPY–NLS conjugate

Verwilst, Peter; David, Christophe; Leen, Volker; Hofkens, Johan; Witte, Peter de; Borggraeve, Wim M. De

doi:10.1016/j.bmcl.2013.03.128

Cited by 28 publications

(21 citation statements)

References 57 publications

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“…Many functional peptide libraries have actually been described in the literature, with different sequences and functions, offering a versatile platform of delivery agents to localize PS conjugates in different kinds of cells and tissues. 48 Covalently linked PS-peptide biohybrids can be synthesized, taking advantage of mild synthetic organic methodologies such as amide [49][50][51][52][53]77,78,81,[85][86][87]89,[91][92][93]95,97,104,105 or sulphonamide 54 bond formation, palladium-catalysed cross-coupling reactions, 55,56 click-chemistry reactions [57][58][59]81,94 and isothiocyanate chemistry, 60,82 among other strategies. Supramolecular approaches have also been used toward self-assembled peptide nanofibers, 61 nanodots, 62 vesicles, 63 light harvesting complexes, 64 arrays 65 or polymeric micelles with a peptide-decorated surface, 66 among others.…”

Section: Conjugation Of Ps To Short Peptide Sequencesmentioning

confidence: 99%

“…93 In this case, the conjugate was able to interact in vitro with low density lipoproteins (LDL) (see Section 4.1), allowing the delivery of the PS into tumorigenic cells overexpressing LDL receptors. Finally, as another interesting example, the conjugation of NLS peptides to BODIPY derivatives was carried out by De Borggraeve and co-workers, 94 through a copper catalysed azide-alkyne cycloaddition. Unfortunately, no nuclear localization was observed for such hybrids.…”

Section: 22mentioning

confidence: 99%

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Porphyrinoid biohybrid materials as an emerging toolbox for biomedical light management

et al. 2018

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The development of photoactive and biocompatible nanomaterials is a current major challenge of materials science and nanotechnology, as they will contribute to promoting current and future biomedical applications. A growing strategy in this direction consists of using biologically inspired hybrid materials to maintain or even enhance the optical properties of chromophores and fluorophores in biological media. Within this area, porphyrinoids constitute the most important family of organic photosensitizers. The following extensive review will cover their incorporation into different kinds of photosensitizing biohybrid materials, as a fundamental research effort toward the management of light for biomedical use, including technologies such as photochemical internalization (PCI), photoimmunotherapy (PIT), and theranostic combinations of fluorescence imaging and photodynamic therapy (PDT) or photodynamic inactivation (PDI) of microorganisms.

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Section: Conjugation Of Ps To Short Peptide Sequencesmentioning

confidence: 99%

Section: 22mentioning

confidence: 99%

Porphyrinoid biohybrid materials as an emerging toolbox for biomedical light management

et al. 2018

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“…noted a similar result, that no cytotoxicity was seen at 10 μM with a peptide‐conjugated dihalogenated BODIPY (Verwilst et al. , ). However, Han et al .…”

Section: Resultsmentioning

confidence: 99%

The application of water soluble, mega‐Stokes‐shifted BODIPY fluorophores to cell and tissue imaging

Moriarty

Martin

Adamson

et al. 2014

Journal of Microscopy

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SummaryBODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) fluorophores are widely used in bioimaging to label proteins, lipids and nucleotides, but in spite of their attractive optical properties they tend to be prone to self-quenching because of their notably small Stokes shift. Herein, we compare two BODIPY compounds from a recently developed family of naphthyridine substituted BODIPY derivatives, one a visible emitting derivative (BODIPY-VIS) and one a near-infrared emitting fluorophore with a Stokes shift of approximately 165 nm as contrast reagents for live mammalian cells and murine brain tissue. The compounds were rendered water soluble by their conjugation to polyethylene glycol (PEG). Both PEGylated compounds exhibited good cell uptake compared with their parent compounds and confocal fluorescence microscopy revealed all dyes explored to be nuclear excluding, localizing predominantly within the lipophilic organelles; the endoplasmic reticulum and mitochondria. Cytotoxicity studies revealed that these BODIPY derivatives are modestly cytotoxic at concentrations exceeding 10 μM where they induce apoptosis and necrosis. Although the quantum yield of emission of the visible emitting fluorophore was over an order of magnitude greater than the Mega-Stokes shifted probe, the latter showed considerably reduced tendency to self quench and less interference from autofluorescence. The near-infrared probe also showed good penetrability and staining in live tissue samples.

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“…Compound 38, found to specifically localize on ER and lesser extent to mitochondria, outperformed in photo-cytotoxicity compared to its counterpart 39, which exhibited no subcellular localization, due to oxidative sensitivity of endoplasmic reticulum (EC 50 values for HeLa, A549 and MRC-5 of 4.7, 6.8, and 18.5 mM without observable dark toxicity, respectively) [109]. In addition, Borggraeve and co-workers reported that BODIPY dye 40 and 41 co-localized in lysosome and endoplasmic reticulum of with T24 human urinary bladder carcinoma cell line; however, staining imaged of nuclear sequence localization peptide embedded 40, even though showed absence of 40 in nucleus, showed enhanced localization on ER compared to 41, explaining 2.6 times lower IC 50 value of 40 compared to control structure 41 [110]. Aforementioned studies conducted with BODIPY dyes lead to similar results in terms of higher oxidative sensitivity of endoplasmic reticulum.…”

Section: Control On Pdt Through Subcellular Localizationmentioning

confidence: 98%

Photosensitization and controlled photosensitization with BODIPY dyes

Türksoy

Yıldız

Akkaya

2019

Coordination Chemistry Reviews

330

190

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Highly versatile BODIPY dyes proved themselves to be very useful as photosensitizers. These dyes can be derivatized to absorb essentially anywhere in the visible the near IR region of the spectrum. As a result of their diverse reactivity, singlet oxygen generation efficiency can be modulated very precisely, leading to a number of selective photosensitizers for photodynamic therapy. Among the biologically relevant modulators, glutathione concentration and pH received particular attention. In this review, we highlight modulatable BODIPY-based photodynamic photosensitizers, and various synthetically useful chemical reactions triggered by singlet oxygen and other reactive oxygen species generated by BODIPY-based photosensitizers.

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Synthesis and in vitro evaluation of a PDT active BODIPY–NLS conjugate

Cited by 28 publications

References 57 publications

Porphyrinoid biohybrid materials as an emerging toolbox for biomedical light management

Porphyrinoid biohybrid materials as an emerging toolbox for biomedical light management

The application of water soluble, mega‐Stokes‐shifted BODIPY fluorophores to cell and tissue imaging

Photosensitization and controlled photosensitization with BODIPY dyes

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